Updated on 2024/03/29

写真a

 
TERAGUCHI Masahiro
 
Organization
Academic Assembly Institute of Science and Technology SEISAN DESIGN KOUGAKU KEIRETU Associate Professor
Graduate School of Science and Technology Advanced Materials Science and Technology Associate Professor
Faculty of Engineering Department of Engineering Associate Professor
Title
Associate Professor
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Degree

  • Doctor(Engineering) ( 2000.3   Kyoto University )

  • Master(Engineering) ( 2000.3   Kyoto University )

  • Bachelor(Science) ( 1995.3   Kochi University )

Research Interests

  • separation membrane

  • substituted polyacetylene

  • conjugated polymer

  • helical polymer

  • optical active polymer

  • functional polymer

Research Areas

  • Nanotechnology/Materials / Polymer materials

  • Life Science / Bioorganic chemistry

  • Nanotechnology/Materials / Organic functional materials

  • Nanotechnology/Materials / Nanomaterials

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

  • Nanotechnology/Materials / Polymer chemistry

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Research History (researchmap)

  • Niigata University   Faculty of Engineering Department of Engineering   Assistant Professor

    2017.4

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  • Niigata University   Graduate School of Science and Technology Advanced Materials Science and Technology   Assistant Professor

    2007.4

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  • Niigata University   Faculty of Engineering Department of Chemistry and Chemical Engineering   Assistant Professor

    2007.4 - 2017.3

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  • Niigata University   Faculty of Engineering   Assistant

    2006.6 - 2007.3

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Research History

  • Niigata University   Institute of Science and Technology, Academic Assembly   Associate Professor

    2024.1

  • Niigata University   Advanced Materials Science and Technology, Graduate School of Science and Technology   Associate Professor

    2024.1

  • Niigata University   Department of Engineering, Faculty of Engineering   Associate Professor

    2024.1

  • Niigata University   Faculty of Engineering Department of Engineering   Assistant Professor

    2017.4 - 2023.12

  • Niigata University   Graduate School of Science and Technology Advanced Materials Science and Technology   Assistant Professor

    2007.4

  • Niigata University   Graduate School of Science and Technology Advanced Materials Science and Technology   Assistant Professor

    2007.4

  • Niigata University   Faculty of Engineering Department of Chemistry and Chemical Engineering   Assistant Professor

    2007.4 - 2017.3

  • Niigata University   Faculty of Engineering   Research Assistant

    2006.6 - 2007.3

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Professional Memberships

 

Papers

  • Synthesis and Direct Observation of Molecules of 2D Polymers: With High Molecular Weights, Large Areas, Small Micropores, Solubility, Membrane Forming Ability, and High Oxygen Permselectivity

    Kehan Cheng, Ken‐ichi Shinohara, Osamu Notoya, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Small   2023.12

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    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    Abstract

    If ideal 2D polymer (2DP) macromolecules with small pores that are similar in size to gas molecules, large areas, small thickness, and excellent membrane‐forming ability are synthesized, ultimate gas separation membranes would be obtained. However, as far it is known, such ideal well‐characterized 2DP macromolecules are not isolated. In this study, an ideal 2DP macromolecule is synthesized by using the successive three reactions (Glaser coupling, SCAT reaction, and the introduction of octyl groups), in which the conjugated framework structure is maintained, from a fully conjugated 1D polymer. Because this exfoliated 2DP is soluble, the macromolecular structure can be fully characterized by <sup>1</sup>H‐NMR, GPC, SEM, AFM, and its dense membrane with no defects can be fabricated by the solvent cast method. This soluble 2DP macromolecule has very small micropores (6.0 Å) inside the macromolecule, a large area (30 × 68 nm by SEM and AFM), high molecular weight (Mn = 2.80 × 10<sup>5</sup> by GPC), and a small thickness (4.4 Å by AFM). This membrane shows the highest oxygen permselectivity exceeding Robeson's upper line because of the high molecular sieving effect of the controlled small micropores.

    DOI: 10.1002/smll.202308050

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  • Synthesis of a Two-dimensional Multi-functional Macromonomer and Oxygen Permselectivity of Its Supramolecular and Covalent Polymer Membranes

    Kehan Cheng, Ken-ichi Shinohara, Koichi Higashimine, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Chemistry Letters   52 ( 10 )   807 - 810   2023.10

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    Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.230341

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  • Synthesis of <i>Pure</i> Supramolecular Polymers from Poly(substituted Phenylacetylene)s by Highly Selective Photocyclic Aromatization and Their Characterization: Effect of the Structures and Properties of Precursor Covalent Polymers on those of the Resulting <i>Pure</i> Supramolecular Polymers

    Chenxi Xu, Shuaishuai Huang, Shunya Narita, Michiru Shibata, Nennei Nagaoka, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Macromolecules   56 ( 9 )   3334 - 3344   2023.4

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.macromol.2c02601

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  • Preparation and oxygen permeability of pure supramolecular polymer membranes synthesized from poly (substituted phenylacetylene)

    Chenxi Xu, Shintaro Hosono, Shunya Narita, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Polymer   267   125622 - 125622   2023.2

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    Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    DOI: 10.1016/j.polymer.2022.125622

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  • Oxygen permeability of fully conjugated polymers consisting of (di)ethynylene and phenylene groups synthesized by Glaser or Sonogashira coupling polycondensation

    Jia Shi, Taisei Yashiro, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Chemistry Letters   52 ( 3 )   160 - 162   2023.1

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    Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.230006

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  • Novel synthesis of porous one-handed helical poly(substituted phenylacetylene) bearing betulin derivatives pendant groups

    Zhichun Shi, Jiaxiang Wen, Yingnan Zhao, Jianjun Wang, Jun Li, Ming Zhao, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    Polymer Journal   55 ( 3 )   203 - 211   2023.1

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    Publishing type:Research paper (scientific journal)   Publisher:Springer Science and Business Media LLC  

    DOI: 10.1038/s41428-022-00752-7

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    Other Link: https://www.nature.com/articles/s41428-022-00752-7

  • Synthesis, characterization and application of soluble <scp>fully conjugated</scp> polyazomethine from di‐ or trifunctional monomers

    Liang Xu, Yu Zang, Kyousuke Takata, Boyu Jing, Jianjun Wang, Masahiro Teraguchi, Takashi Kaneko, Fengjuan Miao, Toshiki Aoki

    Polymer International   71 ( 11 )   1354 - 1361   2022.11

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    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/pi.6440

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/pi.6440

  • Poly(anthryleneethynylene)s Bearing Benzyl Ether Dendrimers with Peripheral Alkyl Groups and Bearing Chiral Menthoxy Groups

    Yoshinori Sato, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    Chemistry Letters   51 ( 10 )   997 - 999   2022.10

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    Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.220333

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  • Synthesis and oxygen permselectivity of multi-stranded graft copolymers

    Kehan Cheng, Takaya Ohno, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Polymer   255   125092 - 125092   2022.8

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    Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    DOI: 10.1016/j.polymer.2022.125092

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  • Synthesis and Oxygen Permeation of Well-Defined Multistranded Copolymers from Monomers Having Two Different Polymerizable Groups Reviewed

    Yu Zang, Kana Matsi, Jianjun Wang, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Macromolecules   55 ( 13 )   5699 - 5710   2022.7

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.macromol.2c00596

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  • Corrigendum to “Absolute asymmetric polymerizations in solution needing no physical chiral source” [Polymer 245 (2022) 124673] (Polymer (2022) 245, (S0032386122001604), (10.1016/j.polymer.2022.124673))

    Guanwu Yin, Takeshi Namikoshi, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Polymer   245   2022.4

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    The authors regret incorrect Table 3. The revised Table with the changes is available below. [Table presented] The authors would like to apologise for any inconvenience caused.

    DOI: 10.1016/j.polymer.2022.124726

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  • Absolute asymmetric polymerizations in solution needing no physical chiral source

    Guanwu Yin, Takeshi Namikoshi, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Polymer   245   2022.4

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    Absolute asymmetric polymerizations, which do not need chiral compounds, are very limited. In addition, they involve spontaneously formed supramolecular compounds, or they need circularly polarized light, and the resulting polymers are often insoluble showing no chiral information at the molecular level. Here we have achieved five kinds of real absolute asymmetric polymerizations of achiral acetylene monomers showing no CD in solution to yield soluble high MW chiral polymers showing CD peaks in solution. These polymerizations did not contain spontaneously formed chiral crystals of monomers or did not use circularly polarized light. A new mechanism we propose here for this new unusual polymerization will give us clues to a better understanding of the reason for the homochirality of our world.

    DOI: 10.1016/j.polymer.2022.124673

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  • Novel highly efficient <i>absolute</i> optical resolution method by serial combination of two asymmetric reactions from acetylene monomers having racemic substituents

    Yanan Tang, Lijia Liu, Junpei Suzuki, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Chirality   34 ( 3 )   450 - 461   2022.3

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    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/chir.23404

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    Other Link: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chir.23404

  • On-off reversible switching of the chirality of one-handed helical Poly(phenylacetylene)s by polarity stimuli

    Guanwu Yin, Lijia Liu, Kazuomi Mottate, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Polymer   237   124347 - 124347   2021.12

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    Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    DOI: 10.1016/j.polymer.2021.124347

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  • Macromolecular Design for Oxygen/Nitrogen Permselective Membranes—Top-Performing Polymers in 2020—

    Jianjun Wang, Zhichun Shi, Yu Zang, Hongge Jia, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Polymers   13 ( 17 )   3012 - 3012   2021.9

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    Publishing type:Research paper (scientific journal)   Publisher:MDPI AG  

    Oxygen/nitrogen permselective membranes play particularly important roles in fundamental scientific studies and in a number of applications in industrial chemistry, but have not yet fulfilled their full potential. Organic polymers are the main materials used for such membranes because of the possibility of using sophisticated techniques of precise molecular design and their ready processability for making thin and large self-supporting membranes. However, since the difference in the properties of oxygen and nitrogen gas molecules is quite small, for example, their kinetic diameters are 3.46 Å and 3.64 Å, respectively, the architectures of the membrane macromolecules should be designed precisely. It has been reported often that oxygen permeability (PO2) and oxygen permselectivity (α = PO2/PN2) have trade-off relationships for symmetric membranes made from pure polymers. Some empirical upper bound lines have been reported in (ln α − ln PO2) plots since Robeson reported an upper bound line in 1991 for the first time. The main purpose of this review is to discuss suitable macromolecular structures that produce excellent oxygen/nitrogen permselective membranes. For this purpose, we first searched extensively and intensively for papers which had reported α and PO2 values through symmetric dense membranes from pure polymers. Then, we examined the chemical structures of the polymers showing the top performances in (ln α − ln PO2) plots, using their aged performances. Furthermore, we also explored progress in the molecular design in this field by comparing the best polymers reported by 2013 and those subsequently found up to now (2020) because of the rapid outstanding growth in this period. Finally, we discussed how to improve α and PO2 simultaneously on the basis of reported results using not only symmetric membranes of pure organic polymers but also composite asymmetric membranes containing various additives.

    DOI: 10.3390/polym13173012

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  • Highly Efficient Absolute Optical Resolution with Circularly Polarized Light via Two Serial Enantioselective Reactions of Acetylene Monomers Bearing a Racemic Substituent

    Yanan Tang, Lijia Liu, Junpei Suzuki, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Chemistry Letters   50 ( 9 )   1688 - 1690   2021.9

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    DOI: 10.1246/cl.210341

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  • Synthesis and Oxygen Permeation of Novel Alternating Copolymers Containing Disiloxane and Imido Groups by Hydrosilylation Polyaddition

    Chenxi Xu, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Chemistry Letters   50 ( 9 )   1617 - 1619   2021.9

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    Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.210306

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  • Improved oxygen permeation of a multi-stranded network two-dimensional polymer synthesized by three-step polymerizations of a novel monomer bearing three different polymerizable groups followed by photoexfoliation

    Kehan Cheng, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Polymer   228   123857 - 123857   2021.7

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    Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    DOI: 10.1016/j.polymer.2021.123857

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  • Improvement of oxygen permselectivity of a rigid helical polyphenylacetylene: Effect of flexible groups, degree of polymerization, composites, thickness, orientation, and network formation

    Jia Shi, Yuka Kimura, Shohei Takeda, Chenxi Xu, Kazuki Shoji, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Polymer   228   123900 - 123900   2021.7

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    DOI: 10.1016/j.polymer.2021.123900

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  • Synthesis of Cis-Cisoid or Cis-Transoid Poly(Phenyl-Acetylene)s Having One or Two Carbamate Groups as Oxygen Permeation Membrane Materials

    Yu Zang, Yinghui Lun, Masahiro Teraguchi, Takashi Kaneko, Hongge Jia, Fengjuan Miao, Xunhai Zhang, Toshiki Aoki

    Membranes   10 ( 9 )   199 - 199   2020.8

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    Three new phenylacetylene monomers having one or two carbamate groups were synthesized and polymerized by using (Rh(norbornadiene)Cl)2 as an initiator. The resulting polymers had very high average molecular weights (Mw) of 1.4–4.8 × 106, with different solubility and membrane-forming abilities. The polymer having two carbamate groups and no hydroxy groups in the monomer unit showed the best solubility and membrane-forming ability among the three polymers. In addition, the oxygen permeability coefficient of the membrane was more than 135 times higher than that of a polymer having no carbamate groups and two hydroxy groups in the monomer unit with maintaining similar oxygen permselectivity. A better performance in membrane-forming ability and oxygen permeability may be caused by a more extended and flexible cis-transoid conformation and lower polarity. On the other hand, the other two new polymers having one carbamate group and two hydroxy groups in the monomer unit showed lower performances in membrane-forming abilities and oxygen permeabilities. It may be caused by a very tight cis-cisoid conformation, which was maintained by intramolecular hydrogen bonds.

    DOI: 10.3390/membranes10090199

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  • Synthesis and Permselectivity of a Soluble Two-Dimensional Macromolecular Sheet by Solid–Solid Interfacial Polycondensation Followed by Chemical Exfoliation Reviewed

    Yanqing Qu, Xiaoyu Du, Kehan Cheng, Yu Zang, Liang Xu, Ken-ichi Shinohara, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    ACS Materials Letters   1121 - 1128   2020.8

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acsmaterialslett.0c00178

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  • Synthesis of Well-Defined Chiral Oligopinanylsiloxane Graft Copoly(phenylacetylene)s Using the Macromonomer Method and Their Enantioselective Permeability Reviewed

    Yu Zang, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Liqun Ma, Hongge Jia, Fengjuan Miao

    ACS Applied Polymer Materials   2 ( 2 )   853 - 861   2020.2

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    DOI: 10.1021/acsapm.9b01111

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  • Synthesis, in-situ membrane preparation, and good gas permselectivity of insoluble poly(substituted acetylene)s loosely cross-linked with short and soft siloxane and silanol linkages Reviewed

    Jianjun Wang, Toshiki Aoki, Takashi Kaneko, Masahiro Teraguchi

    Polymer   187   122081 - 122081   2020.1

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    Publishing type:Research paper (scientific journal)   Publisher:Elsevier BV  

    DOI: 10.1016/j.polymer.2019.122081

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  • Helix-sense-selective Polymerization of 3,5-bis(hydroxymethyl)phenylacetylene Rigidly Bearing Galvinoxyl Residues and Their Chiroptical Properties Reviewed

    Zhichun Shi, Jianjun Wang, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    Polymers   11 ( 11 )   1877   2019.11

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    DOI: 10.3390/polym11111877

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  • Antiparallel Arrangement of 2,7-Substituted 9,10-Bis(phenylethynyl)anthracene Assisted by Hydrogen Bonding of Terminal Units Reviewed

    Takashi Kaneko, Yosuke Araki, Ken-ichi Shinohara, Masahiro Teraguchi, Toshiki Aoki

    Bulletin of the Chemical Society of Japan   92   1672 - 1678   2019.7

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  • Synthesis of a novel AB block copolyaceylene consisting of a dynamic cis-transoidal racemic helical sequence and a static cis-cisoidal one-handed helical sequence Reviewed

    Guanwu Yin, Junpei Suzuki, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    Chemistry Letters   48 ( 6 )   506 - 509   2019.6

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  • New Synthetic Methods of Novel Nanoporous Polycondensates and Excellent Oxygen Permselectivity of Their Composite Membranes Reviewed

    Yu Zang, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Hongge Jia, Liqun Ma, Fengjuan Miao

    Nanomaterials   9   859 - 873   2019.6

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  • Simultaneous improvement of permeability and selectivity in enantioselective permeation through solid chiral membranes from a newly synthesized one-handed helical polyphenylacetylene with aldehyde pendant groups by enantioselective reaction Reviewed

    Yu Zanga, Yanqing Qu, Toshiki Aokib, Masahiro Teraguchi, Takashi Kaneko, Hongge Jia, Liqun Ma, Fengjuan Miao

    Polymer   171   45 - 49   2019.3

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  • Helix-Sense-Selective Polymerization of Phenylacetylenes Having a Porphyrin and a Zinc-Porphyrin Group: One-Handed Helical Arrangement of Porphyrin Pendants Reviewed

    Masahiro Teraguchi, Nobuyuki Nahata, Takahiro Nishimura, Toshiki Aoki, Takashi Kaneko

    Polymers   11 ( 2 )   274 - 284   2019.2

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  • Synthesis and oxygen permeability of novel graft copolymers consisting of a polyphenylacetylene backbone and long oligosiloxane grafts from phenylacetylene-type macromonomers Reviewed

    Yu Zang, Toshiki Aokia, Takashi Kaneko, Masahiro Teraguchi, Liqun Ma, Hongge Jia, Fengjuan Miao

    Polymer   156   66 - 70   2018.11

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  • Enhanced performances of enantioselective permeation through one-handed helical polymer membranes by enantioselective imine exchange reaction with permeants and by partially decomposed reaction of the membrane Reviewed

    Yanqing Qu, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    Polymer   156   39 - 43   2018.11

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  • Chiral teletransmission in the cis-cisoidal sequence of copoly(substituted acetylene)s by multiple stage solvent exchange of the copolymer solution through a membrane Reviewed

    Lijia Liu, Yuanyuan Gu, Yudan Wang, Toshiki Aoki, Guan Wang, Takeshi Kaneko, Masahiro Teraguchi

    Polymer   154   253 - 257   2018.10

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  • Synthesis and ultrahigh oxygen permeability of silicon-containing cis-cisoidal poly (substituted phenylacetylene)s Reviewed

    Chenxi Xu, Toshiki Aoki, Liqun Ma, Hongge Jia, Massahiro Teraguchi, Takashi Kaneko

    Chem. Lett.   47   1314 - 1317   2018.10

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  • Synthesis and oxygen permeation of novel well-defined homopoly(phenylacetylene)s with different sizes and shapes of oligosiloxanyl side groups Reviewed

    Yu Zang, Toshiki Aoki, Kazuki Shoji, Masahiro Teraguchi, Takashi Kaneko, Liqun Ma, Hongge Jia, Fengjuan Miao

    Journal of Membrane Science   561   26 - 38   2018.9

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Elsevier B.V.  

    Six new silicon-containing phenylacetylenes having short oligosiloxane substituents with different sizes and shapes have been synthesized. Homopolymerization of the monomers yielded the corresponding homopoly(substituted phenylacetylene)s with high molecular weights and good solubility. These comb-shaped homopolymers gave self-standing membranes whose PO2 and PO2 /PN2 could be measured. We discuss the effect of the chemical structures on their membrane performances together with the other seven related polymers we synthesized before and commercially available cross-linked polydimethylsiloxane (PDMS). While the homopolymers with linear oligodimethylsiloxanes (ODMS) show very high PO2 values which are higher than PDMS, the homopolymers with branched ODMS show high PO2 /PN2 values which are close to that of poly(phenylacetylene) (poly(PA)) and, in addition, had ten times higher PO2 than poly(PA). Introduction of the branched spherical ODMS substituents increases PO2 without any drop of PO2 /PN2 and introduction of the linear ODMS substituents increases PO2 largely which is higher than that of PDMS. It was found that the chemical structures, i.e., the shapes of the ODMS substituents were more important than that of composition for determining their performance as oxygen permselective membrane materials. In conclusion, oxygen permeation could be tuned by changing sizes and shapes of the ODMS side groups.

    DOI: 10.1016/j.memsci.2018.04.031

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  • Ultrahigh oxygen permeability of chemically-modified membranes of novel (co)polyacetylenes having a photodegradative backbone and crosslinkable side chains Reviewed

    Mingyu Zhang, Toshiki Aoki, Lijia Liu, Jianjun Wang, Masahiro Teraguchi, Takashi Kaneko

    Polymer   149   117 - 123   2018.8

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  • Dimesitylboryl-containing polydiphenylacetylene with a large Stokes shift, high fluorescence efficiency, and fluoride ion sensing ability Reviewed

    Young-Jae Jin, Daichi Araki, Masahiro Teraguchi, Toshiki Aoki, Giseop Kwak

    Polymer (United Kingdom)   148   310 - 315   2018.7

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Elsevier Ltd  

    A diphenylacetylene monomer carrying a dimesitylboryl functional group was newly synthesized and polymerized by heating the toluene solution at 80 °C, using TaCl5–n-Bu4Sn as a catalyst. A polydiphenylacetylene (PDPA) derivative was obtained in high yield despite the presence of the heteroatom
    the polymer had an extremely high weight-average molecular weight of 1.27 × 106 gmol−1 and readily dissolved in organic solvents. This polymer was highly resistant to heat and existed in an amorphous, glassy state at room temperature. Unlike the usual PDPA derivatives, the fluorescence (FL) maximum for this derivative appeared at 526 nm through efficient intramolecular energy transfer from the side dimesitylboryl groups to the polyene backbone upon excitation at a very short wavelength of 320 nm, indicating an extremely large Stokes shift of 206 nm. Moreover, the polymer showed considerably higher FL efficiency of 49.3% in a tetrahydrofuran solution and 19.1% in a film as compared to the usual PDPA derivatives. This polymer reacted with fluoride ions to exhibit critical changes in absorption and FL emission, which were expressed by an exponential and a Gaussian functional equation, respectively.

    DOI: 10.1016/j.polymer.2018.06.044

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  • Synthesis of soluble oligsiloxane-end-capped hyperbranched polyazomethine and their application to CO2/N2 separation membranes Reviewed

    Liang Xu, Tianyang Lei, Boyu Jing, Yu Zang, Fengjuan Miao, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    Des. Monomers Polym.   21(1)   99 - 104   2018.5

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  • Solvent-tuned dual emission of a helical poly[3,5-bis(hydroxymethyl)phenylacetylene] connected with a π-conjugated chromophore Reviewed

    Zhichun Shi, Giseop Kwak, Young-Jae Jin, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    Polym. J.   50(7) ( 7 )   533 - 537   2018.3

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Springer Science and Business Media LLC  

    DOI: 10.1038/s41428-018-0045-7

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    Other Link: http://www.nature.com/articles/s41428-018-0045-7.pdf

  • Solvent-tuned dual emission of a helical poly[3,5-bis(hydroxymethyl)phenylacetylene] connected with a π-conjugated chromophore Reviewed

    Zhichun Shi, Giseop Kwak, Young-Jae Jin, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    Polymer Journal   1 - 5   2018.3

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Nature Publishing Group  

    For THF solutions of an optically active helical poly[3,5-bis(hydroxymethyl)phenylacetylene] derivative bearing a biphenyl group, photoexcitation of the terphenyl moiety at 300 nm led to photoluminescence at 390 nm. On the other hand, the photoluminescence resulting from excitation at 280 nm caused dual emission at 310 and 390 nm, whose intensities were tuned by the polar-solvent stimuli which induced the collapse of the intramolecular stack structure of the side groups, and the change in the emission wavelength accompanied disappearance of the optical activity.

    DOI: 10.1038/s41428-018-0045-7

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  • Fluorescence emission and image patterning from selective photocyclic aromatization of cis–cisoid helical poly(phenylacetylene)s in situ in a film via top-down photodegradation Reviewed

    Young-Jae Jin, Hyosang Park, Chang-Lyoul Lee, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki, Giseop Kwak

    Dyes and Pigments   149   444 - 448   2018.2

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    Selective photocyclic aromatization (SCAT) of cis–cisoid helical poly(phenylacetylene) derivatives was investigated during the in situ photodegradation in a film. An infrared absorption peak appeared at ∼1700 cm−1 owing to the overtone vibration of the 1,3,5-trisubstituted benzene and the peak at 1060 cm−1 due to the cis C=C bending of the main chain decreased, indicating occurrence of SCAT. Simultaneously, the polymer film became emissive in visible region during SCAT. The fluorescence (FL) quantum efficiency was approximately 0.92% in the film and not so much high relative to usual fluorophores. The FL emission disappeared in an instant when the decomposition product dissolved in a solvent. The FL lifetime of the polymer film increased with photodegradation. These all indicated the occurrence of excimer emission. A finely resolved FL image pattern was readily obtained using a photomask.

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  • Synthesis of Two Well-Defined Quadruple-Stranded Copolymers having Two Kinds of Backbones by Postpolymerization of a Helical Template Polymer Reviewed

    Yu Zang, Toshiki Aoki, Hiroyoki Tanagi, Kana Matsui, Masahiro Teraguchi, Takashi Kaneko, Liqun Ma, Hongge Jia, Ken-Ichi Shinohara

    Macromolecular Rapid Communications   39 ( 4 )   1700556 - 1700560   2018.2

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    A brand new, soluble quadruple-stranded copolymer is synthesized by using a self-template polymer from a new monomer. In addition, another very unique quadruple-stranded copolymer having a π−π stacking supramolecular polymer main chain is synthesized by selective photocyclic aromatization of the quadruple-stranded copolymer. The two quadruple-stranded copolymers gave self-standing membranes.

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  • A New Analysis Method for Quantitative Determination of Triads of Copoly(substituted acetylene) Backbones by Highly Selective Photocyclic Aromatization Reviewed

    Guanwu Yin, Nennei Nagaoka, Lijia Liu, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    CHEMISTRY LETTERS   46 ( 11 )   1608 - 1611   2017.11

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    Since highly selective photocyclic aromatization (SCAT) of poly(substituted acetylene) s yields quantitatively the corresponding 1,3,5-trisubstituted benzene derivatives, the SCAT products were applied for quantitative determination of microstructures of copoly(substituted acetylene) s by NMR (nuclear magnetic resonance). By this SCAT-NMR method for two copolymers of two different types of substituted acetylenes, quantitative analysis for microstructures, i. e., triad distributions and compositions, have been achieved successfully under mild conditions, although they could not be obtained from the NMR of the original copolymers because of their broad and overlapped peaks.

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  • Oxygen permselectivities through supramolecular polymer membranes prepared by highly selective photocyclic aromatization of poly(substituted acetylene) Reviewed

    Guanwu Yin, Eri Ohtaka, Toshiki Aoki, Jianjun Wang, Masahiro Teraguchi, Takashi Kaneko

    POLYMER   127   232 - 235   2017.10

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    In order to estimate oxygen permselectivities through a supramolecular polymer membrane for the first time, we prepared three kinds of composite membranes consisting of a supramolecular polymer membrane and a conventional organic polymer membrane. Supramolecular polymer membranes were prepared by using highly selective photocyclic aromatization of poly(substituted acetylene)s. It was found that the supramolecular polymer membrane had oxygen permselectivity (alpha = P-O2/P-N2) around three in spite of its low molecular weight. (C) 2017 Published by Elsevier Ltd.

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  • Transformer of Achiral Amounts to Chirality: Double Reversal of Enantioselectivity Using a Single Cocatalyst in Asymmetric Polymerization Reviewed

    Guanwu Yin, Geng Zhang, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Jesus Rodriguez Castanon, Masashi Shiotsuki, Fumio Sanda

    MACROMOLECULES   50 ( 19 )   7468 - 7474   2017.10

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    Chiral compounds play a vital role in our lives because we are made up of chiral polymers. A strict rule of chirality synthesis is "to obtain one enantiomer of a new chiral product, one enantiomer of a chiral source is needed". If two enantiomers can be synthesized using a single chiral compound, we can both break the above rule and open up a more efficient route to useful chiral materials using a cheaper chiral source. Here we report the first example of double reversals of enantioselectivity in catalytic asymmetric polymerization of achiral monomers using a single isomer of simple chiral compounds as cocatalyst. Furthermore, we achieved this by changing only one achiral condition, that is, the amount of the chiral cocatalyst, without any other changes in the polymerization conditions. As a result, we easily and directly synthesized (+)- or (-)-polymer using a single chiral compound as a cocatalyst.

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  • Subnanoporous Highly Oxygen Permselective Membranes from Poly(conjugated hyperbranched macromonomer)s Synthesized by One-Pot Simultaneous Two-Mode Homopolymerization of 1,3-Bis(silyl)phenylacetylene Using a Single Rh Catalytic System: Control of Their Structures and Permselectivities Reviewed

    Jianjun Wang, Jun Li, Toshiki Aoki, Takashi Kaneko, Masahiro Teraguch, Zhichun Shi, Hongge Jia

    MACROMOLECULES   50 ( 18 )   7121 - 7136   2017.9

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    Novel well-defined complex,polymers, polymers of acetylene type macronionomers having silylene-vinylene-phenylene-ethynylene hyper-branches, investigated as a new class of subnanoporous oxygen permselective membrane materials, were synthesized very easily by one-pot Simultaneous two-mode homopolymerization of a single monomer with a single catalyst. For this "simultaneous polymerization" we synthesized AB(2)-type monomers (1,3-bis(dimethylsilyl)phenylacetylenes) containing one terminal triple bond and two Si-H groups. The resulting poly(hyperbrancIed mactornonomer)s had high molecular weights, low densities, high solubility, and good self-membrane forming ability. They had higher oxygen permselectivities (a = P-O2/P-N2) than any other reported polymers having similar oxygen permeabilities (P-O2). These excellent polymer membranes could be obtained only by the simultaneous polymerization. In the one-pot simultaneous polymerization, the two different modes of polymerizations, i.e., addition polymerization of the triple bond and polyaddition of the triple bond and two SiH groups in the single monomer, occurred simultaneously by using one catalytic system, i.e., [Rh(norbornadiene)Cl](2)/various amines. The ratio of the branches (RB), i.e., the addition polymerization and the polyaddition, could be controlled by changing the amine cocatalysts. Their oxygen permselectivities could be adjusted by controlling the polymer structures including RB.

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  • Annealing-Induced Circular Dichroism Enhancement in Luminescent Conjugated Polymers with an Intramolecular Stack Structure Reviewed

    Young-Jae Jin, Kyo-Un Seo, Young-Ghil Choi, Masahiro Teraguchi, Toshiki Aoki, Giseop Kwak

    MACROMOLECULES   50 ( 17 )   6433 - 6438   2017.9

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    Two poly(diphenylacetylene) derivatives containing identical chiral pinanyl groups on the para- and meta-positions of the side phenyl ring were prepared, and their circular dichroism (CD) and photoluminescence (PL) spectra were compared. The magnitudes of circular polarization (g(CD)) of the para- and meta-polymers were determined to be 3.1 x 10(3) and 1.4 x 10(3), respectively. The PL quantum yield (PLQY) of the para-polymer was much greater (27.8%) than that of the meta-polymer (2.61%). When the two polymers were annealed at 80 C in toluene, their CD spectra were remarkably enhanced and reached equilibrium at g(CD) values of 9.6 x 10(3) and 6.0 x 10(3), respectively. The para-polymer was kinetically more favored for the CD enhancement as known from the fact that the activation energies for the reactions of para- and meta-polymers were determined to be 88 and 187 kJ mol(1), respectively. The PLQYs of both polymers were unaffected by annealing.

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  • Thermodynamically stable, highly emissive poly(diphenylacetylene) derivative containing long alkyl side chain without silylene linkage Reviewed

    Young-Jae Jin, Yuto Kawamura, Masahiro Teraguchi, Toshiki Aoki, Giseop Kwak

    POLYMER   123   81 - 86   2017.8

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    A PDPA derivative with a long alkyl side chain connected directly onto the backbone (1) was synthesized and compared to a corresponding polymer with a silylene linkage between the side chain and the backbone (2). Polymers 1 and 2 showed similar solubilities: both polymers dissolved well in organic solvents such as toluene, THF, and chloroform but not in polar solvents such as DMF and alcohols. When cast from toluene solutions, smooth and transparent films were readily obtained. Thermogravimetric analysis showed that 1 was more thermally stable than 2 owing to the absence of the relatively weak silylene linkage. Differential scanning calorimetry showed that 1 exhibited a local thermodynamic relaxation due to the long alkyl side chains at a higher temperature than 2. In photoluminescence spectroscopy, 1 was found to be more emissive, with quantum yields being as high as 63.1 and 27.4% in solution and films, respectively, while those of 2 were 49.4 and 20.6%. Consequently, 1 was more thermally stable, stiffer, and more emissive than 2. (C) 2017 Elsevier Ltd. All rights reserved.

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  • Oxygen Permselectivities of Novel Multi-bridged Copolymers Synthesized by Imine Metathesis between N-Imines and C-Imines in the Pendant Groups of Two Poly(substituted acetylene)s Reviewed

    Yinghui Lun, Yu Zang, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    CHEMISTRY LETTERS   46 ( 3 )   401 - 404   2017.3

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    New types of multi-bridged copolymers were designed and examined as oxygen permselective membrane materials. The multi-bridged copolymers were synthesized by imine metathesis reactions between N-imine (synthetic equivalent of amine)containing poly(substituted acetylene)s and C-imine (synthetic equivalent of aldehyde)-containing poly(substituted acetylene) s in the membrane state. The resulting copolymers maintained good self-membrane forming ability. The introduction of multibridge structures enhanced both oxygen permselectivities and oxygen permeabilities simultaneously.

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  • Fluorescence emission enhancement of poly(phenylacetylene) via thermal annealing Reviewed

    Young-Jae Jin, Hyojin Kim, Dong-Yeon Hwang, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki, Giseop Kwak

    MOLECULAR CRYSTALS AND LIQUID CRYSTALS   645 ( 1 )   50 - 57   2017

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    Both cis- and trans-rich poly[p-(trimethylsilyl)phenylacetylene]s (PTM-SPAs) were synthesized using [Rh(norbornadiene)Cl](2)-TEA (TEA: triethylamine) and WCl6-Ph4Sn as catalysts, respectively. The Rh-based cis-rich polymer exhibited a remarkable fluorescence (FL) emission enhancement after thermal annealing (heating at 200 degrees C in N-2 atmosphere for 1 min), while the pristine polymer was almost entirely non-emissive. NMR and Raman spectroscopic studies clarified the occurrence of irreversible cis-trans isomerization under thermal annealing and suggested that the FL emission increased with an increase in the trans content of PTMSPA. Computer simulations of 12-mer model compounds clarified that the FL emission is a result of intramolecular excimers formed from side-on -stacking of phenyl groups, which is possible only along the backbone of the trans-based polymer.

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  • Comparative photophysical properties of poly(diphenylacetylene)s with different central atoms in side group Reviewed

    Young-Jae Jin, Toshikazu Sakaguchi, Masahiro Teraguchi, Giseop Kwak

    MOLECULAR CRYSTALS AND LIQUID CRYSTALS   651 ( 1 )   42 - 47   2017

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    Polydiphenylacetylene (PDPA) derivaitves consisting of different central atoms of C, Si, and Ge in the pendent group were comparatively investigated in normal, swollen, and acid-treated states. The Ge-containing PDPA was more emissive than the other two both in solution and in solid states. All the polymers showed emission enhancement in a swollen state: The PL quantum yields increased remarkably when swollen in an appropriate non-solvent. The Si and Ge atoms were easily removed from the polymer chain under acidic condition, as a result, the PL intensity was significantly decreased and the polymers turned to be insoluble in common organic solvents. Although the tert-butyl group of C-containing PDPA remained intact during the acid exposure, similar PL attenuation occurred.

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  • Helix-Sense-Selective Polymerization of Achiral Phenylacetylenes and Unique Properties of the Resulting Cis-cisoidal Polymers Reviewed

    Lijia Liu, Yu Zang, Hongge Jia, Toshiki Aoki, Takashi Kaneko, Shingo Hadano, Masahiro Teraguchi, Mari Miyata, Geng Zhang, Takeshi Namikoshi

    POLYMER REVIEWS   57 ( 1 )   89 - 118   2017

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    One of the authors discovered helix-sense-selective polymerization (HSSP) of an achiral substituted phenylacetylene which has two hydroxymethyl groups and a relatively hydrophobic substituent by using a chiral catalytic system in 2003. The one-handed helicity is stable and static in nonpolar solvents because it is maintained by intramolecular hydrogen bonds. Since the resulting polymer has extremely tight helicity in its main chain, it shows many interesting and unusual properties including highly selective photocyclic aromatization (SCAT). In this review, the discovery and development of the HSSP and SCAT reactions, and the properties and application of the resulting polymers prepared by HSSP and the resulting supramolecular polymers prepared by SCAT will be examined.

    DOI: 10.1080/15583724.2016.1160930

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  • Synthesis of One-Handed Helical Block Copoly(substituted acetylene)s Consisting of Dynamic cis-transoidal and Static cis-cisoidal Block: Chiral Teleinduction in Helix-Sense-Selective Polymerization Using a Chiral Living Polymer as an Initiator Reviewed

    Lijia Liu, Geng Zhang, Toshiki Aoki, Yudan Wang, Takashi Kaneko, Masahiro Teraguchi, Chunhong Zhang, Hongxing Dong

    ACS MACRO LETTERS   5 ( 12 )   1381 - 1385   2016.12

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    By using a living one-handed helical cis-transoidal poly(chiral substituted phenylacetylene) as a polymer initiator (poly(I-n)), helix-sense-selective polymerization (HSSP) of an achiral phenylacetylene 2 having two hydroxy groups successfully afforded a diblock copoly(phenylacetylene) (copoly(I-n/2(m))) consisting of a dynamic one-handed helical cis-transoidal block and a static one-handed helical cis-cisoidal block. The formation of the diblock structure was confirmed by consumption of the chiral initiator, appearance of characteristic CD indicating the one handed helical cis-cisoidal block, and occurrence of the selective photocylic aromatization reaction in the cis-cisoidal block. Therefore, HSSP has been achieved by using the chiral alkenyl groups in the initiator as a chiral source for the first time. In addition, since the HSSP was achieved in spite of the long distance between the chiral initiation site and the propagating site, chiral teleinduction through the rigid and static one-handed helical cis-cisoidal block based on domino effects was confirmed.

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  • Synthesis and oxygen permselectivity of copoly(substituted acetylene)s with bulky fused polycyclic aliphatic groups Reviewed

    Hongge Jia, Jian Luo, Toshiki Aoki, Lijia Liu, Yu Zang, Yinghui Lun, Masahiro Teraguchi, Takashi Kaneko

    POLYMER   99   695 - 703   2016.9

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    We synthesized six phenylacetylenes (RCOPAs, RSOPAs, and RSPAs) having a bulky fused polycyclic aliphatic group, which is adamantyl(Ad), pinanyl(Pi), or cholesteryl(Ch) via oxycarbonyl (CO) or oxydimethylsilyl( SO), and the other two phenylacetylenes having less or non-bulky substituents, i.e., menthyloxycarbonylphenylacetylene (MtCOPA) or ethoxydimethylsilylphenylacetylene (EtSOPA) (Et = Ethyl). The new monomers were polymerized and copolymerized with p-trimethylsilylphenylacetylene (SPA) by using catalyst [ Rh(nbd)Cl](2) (nbd = 2,5-norbornadiene) in trimethylamine to give soluble high molecular-weight polymers in relatively good yields. The resulting copolymers were fabricated to self-supporting membranes which had enough strength for separation membranes by solution casting method. As a result, we can discuss the relationship between bulky chemical structures and permeation behavior systematically for the first time. Oxygen permselectivities (PO2/PN2) of copolyRSOPAs having the bulky fused polycyclic aliphatic groups such as Ad and Pi were higher than those of copolyEtSOPAs. PO2/PN2 values of copolyRCOPAs were higher than those of polyRSOPAs when they had the same content of the identical bulky groups. The rigid spacer was effective for enhancing PO2/PN2. Among copolyRCOPAs with bulky fused polycyclic aliphatic groups, the copolymers with spherical substituents such as Pi and Ad groups showed higher PO2/PN2 values than those with a planer substituent i.e., Ch groups. PO2 values of copolyRSOPAs and copolyRCOPAs were 130-220 and 50-90 barrer, respectively. The flexible silyloxy spacers in RSOPAs were effective in enhancing their PO2 values. (C) 2016 Elsevier Ltd. All rights reserved.

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  • Novel Isolated, L-Amino Acid-Ligated Rhodium Catalysts that Induce Highly Helix-Sense-Selective Polymerization of an Achiral 3,4,5-Trisubstituted Phenylacetylene Reviewed

    Hongge Jia, Yongqiang Shi, Liqun Ma, Xuan Gao, Yazhen Wang, Yu Zang, Jijun Peng, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Toshio Masuda

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   54 ( 15 )   2346 - 2351   2016.8

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    Two novel chiral well-defined rhodium complexes, Rh(cod)(L-Phe) (cod=1,5-cyclooctadiene, Phe=phenylalanine) and Rh(cod)(L-Val) (Val=valine) were synthesized, isolated by recrystallization, and characterized. The helix-senseselective polymerization (HSSP) of an achiral 3,4,5-trisubstituted phenylacetylene, p-dodecyloxy-m, m-dihydroxyphenylacetylene (DoDHPA) was examined by using the two Rh complexes as catalysts. These catalysts provided high molecular weight polymers (M-w 28 x 10(4)-45 x 10(4)) in about 40%-85% yields. The resulting polymers exhibited a bisignated CD signal at about 300 nm and a broad signal around 470 nm, indicating that they have preferential one-handed helical structure. The present catalysts achieved larger molar ellipticity up to [theta](310) = 13.0 x 10(4) deg cm(2)/dmol than those with binary chiral catalytic systems, [Rh(cod)Cl](2)/(L-phenylalaninol), [Rh(cod)Cl](2)/(L-valinol), and [Rh(nbd)Cl](2)/(R)-PEA. All these results manifest that the present, well-defined Rh complexes serve as excellent catalysts for the HSSP of DoDHPA. (C) 2016 Wiley Periodicals, Inc.

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  • Highly Selective Photocyclic Aromatization (SCAT)-GPC Method for Quantitative Determination of Microstructures of Copoly(substituted acetylenes) Backbone Reviewed

    Guanwu Yin, Lijia Liu, Toshiki Aoki, Takeshi Namikoshi, Masahiro Teraguchi, Takashi Kaneko

    CHEMISTRY LETTERS   45 ( 7 )   813 - 815   2016.7

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    Highly selective photocyclic aromatization (SCAT) of poly(substituted acetylene)s, which can quantitatively yield the corresponding 1,3,5-trisubstituted benzene derivative, was applied to quantitative determination of the microstructures of copoly(substituted acetylene)s. By GPC analysis of the SCAT products of the copolymers of two substituted acetylenes having substituents whose molecular weights were greatly different, some clear information regarding the microstructures, such as sequence (triad) distribution and composition, which could not be obtained from NMR because of their broad peaks, could be obtained successfully under a mild condition.

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  • Highly Emissive, Optically Active Poly(diphenylacetylene) Having a Bulky Chiral Side Group Reviewed

    Hyojin Kim, Kyo-Un Seo, Young-Jae Jin, Chang-Lyoul Lee, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki, Giseop Kwak

    ACS MACRO LETTERS   5 ( 5 )   622 - 625   2016.5

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    A highly emissive, optically active poly(diphenylacetylene) derivative, NpSi*-PDPA, was synthesized by introducing a bulky chiral pendant group into the polymer chain. NpSi*-PDPA exists in a glassy state having a highly disordered and amorphous structure. Hence, the fractional free volume is quite high, i.e., 0.29. NpSi*-PDPA emits a green light in solution and a yellow light in film. This polymer is quite emissive, as the photoluminescence (PL) quantum yield is 56.1% in solution and 6.2% in film, and the PL lifetime is relatively long, 1.71 ns in solution and 1.05 ns in film. NpSi*PDPA shows the strongest circular dichroism (CD) signal at 384 nm, with a magnitude of circular polarization (g(CD)) of 0.90 x 10(-3) and an optical rotation of 110 degrees (4.30 X 10(-3) g mL(-1), in CHCl3). The CD intensity is significantly increased by annealing at 80 degrees C, reaching an equilibrium at g(CD) of 7.10 X 10(-3) after 72 h.

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  • Asymmetric Restriction of Intramolecular Rotation in Chiral Solvents Reviewed

    Young-Jae Jin, Hyojin Kim, Jong Jin Kim, Nam Ho Heo, Jong Won Shin, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki, Giseop Kwak

    CRYSTAL GROWTH & DESIGN   16 ( 5 )   2804 - 2809   2016.5

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    Commercially available molecular rotor (MR) compounds were recrystallized using chiral monoterpenes as solvents. The resulting crystals exhibited large circular dichroism signals with opposing signs according to the handedness of the chiral solvent used. X-ray crystallographic analysis showed that the chirality originated from asymmetric restriction of intramolecular rotation in the crystals. The crystals were also highly emissive due to restricted bond rotation, while solutions of the materials were almost nonemissive. The solvent-to-MR chirality transfer approach to. crystallization discussed herein should be a convenient, universal way to obtain highly emissive chiral crystals.

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  • High Oxygen Permselectivity through a Membrane from Novel Soluble Imido-bridged Ladder Polysiloxane Reviewed

    Shuangping Xu, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    CHEMISTRY LETTERS   45 ( 4 )   424 - 426   2016.4

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    A novel soluble well-defined ladder polysiloxane bridged by imido linkages having a high molecular weight was successfully synthesized via the corresponding supramolecular intermediate and was fabricated to a very flexible self-standing membrane. The membrane showed a better oxygen permselectivity than conventional linear polyorganosiloxanes. We directly observed the effect of the regular molecular-sized pores formed by the ladder structure on the oxygen permselectivity for the first time. This is the first report on gas permeability thorough a well-characterized ladder polymer.

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  • Influence of a hydrodynamic environment on chain rigidity, liquid crystallinity, absorptivity, and photoluminescence of hydrogen-bonding-assisted helical poly(phenylacetylene) Reviewed

    Young-Jae Jin, Hyojin Kim, Mari Miyata, Guanwu Yin, Takashi Kaneko, Masahiro Teraguchi, Toshiki Aoki, Giseop Kwak

    RSC ADVANCES   6 ( 43 )   36661 - 36666   2016

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    The chain rigidity, liquid crystallinity, absorptivity, and photoluminescence of a helical poly(phenylacetylene) derivative varied significantly depending on the solvent employed, owing to the conformational changes caused by the formation or destruction of intramolecular hydrogen bonds. The polymer chains were rigid and liquid crystalline when dissolved in such non-solvents as toluene and THF to show lower absorptivity and intramolecular excimer emission while the same polymer chains became flexible in piperidine having a high hydrogen-bonding acceptor strength to exhibit strong absorption in the visible region and the emission was significantly quenched.

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  • Highly Efficient Helix-sense-selective Polymerization of an Achiral Phenylacetylene Having a Bulky Group Reviewed

    Yanqing Qu, Yu Zang, Mingyu Zhang, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Liqun Ma, Hongge Jia

    CHEMISTRY LETTERS   44 ( 12 )   1777 - 1779   2015.12

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    A novel achiral phenylacetylene having a bulky t-butyl group was synthesized and polymerized by a chiral catalytic system containing [Rh(nbd)Cl](2) (nbd: norbomadiene) and chiral amines to yield a one-handed helical polymer having a much higher g value than polymers with no bulky groups. Highly efficient helix-sense-selective polymerization has been achieved using a bulky monomer and a less bulky chiral cocatalyst.

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  • Quantitative Introduction of Perfluoroalkyl Groups to Poly(diphenylacetylene) Membranes via Three-step Membrane Reaction Including Click Reaction and Their Gas Permeability Reviewed

    Takashi Sato, Masahiro Teraguchi, Motohiro Kiuchi, Takashi Kaneko, Toshiki Aoki

    CHEMISTRY LETTERS   44 ( 12 )   1679 - 1681   2015.12

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    Poly(diphenylacetylene) membranes having perfluoroalkyl groups were quantitatively synthesized via a three-step membrane reaction, that is, desilylation (the 1st step), Williamson reaction (the 2nd step), and Click reaction (the 3rd step). The conversions of the all reactions were confirmed by IR. spectra and elemental analysis. Even though the reactions were carried out in membrane state, the conversions were fairly high. These high conversions are attributed to high swelling property of poly(diphenylacetylenes), including the extremely large fractional free volume. The gas permeability and thermal property of the perfluoroalkylated poly(diphenylacetylene) membranes were investigated. Polymer reactions are a very useful and powerful

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  • Helical Conformation Stability of Poly[3,5-bis(hydroxymethyl)phenylacetylene]s Depending on the Length of Their Rigid and Linear pi-Conjugated Side Groups Reviewed

    Zhichun Shi, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    CHEMISTRY LETTERS   44 ( 10 )   1413 - 1415   2015.10

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    We synthesized new 3,5-bis(hydroxymethyl)phenylacetylene (HPA) monomers connected with a rigid and linear pi-conjugated oligomer. The monomers were successfully polymerized with a rhodium catalyst [Rh(nbd)Cl](2) in the presence of chiral PEA to give the corresponding polymers. Helix-sense-selective polymerization proceeded for DBHPA. CD, UV, and WAXS spectroscopic studies revealed that the intramolecular hydrogen bonds of the polymers contributed to the stabilization of their helical conformation but the stability depended on the length of the rigid and linear pi-conjugated side group.

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  • Synthesis of a Fluorine-Containing Cis-Cisoidal One-Handed Helical Polyphenylacetylene and Application of Highly Selective Photocyclic Aromatization Product on Oxygen Permselective Membrane Reviewed

    Yu Zang, Guanwu Yin, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Liqun Ma, Hongge Jia

    CHIRALITY   27 ( 8 )   459 - 463   2015.8

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    A novel phenylacetylene monomer having a perfluorinated alkyl group (M-F) was synthesized and polymerized in a chiral catalytic system to yield a one-handed helical polymer. The ability and efficiency of the chiral induction of the fluorine-containing monomer in the helix-sense-selective polymerization (HSSP) was much higher than those of a monomer having the corresponding alkyl group (M-H) we reported before. The resulting polymer P-F showed cis-cisoidal one-handed helical conformation, and was suitable for highly selective photocyclic aromatization (SCAT) to give a 2D surface modifier (T-F). Oxygen permselectivity through a base polymer membrane was highly enhanced from 1.83 to 2.36 by adding a small amount (1-5wt%) of the 2D surface modifier T-F. The improvement was thought to be caused by improvement of solution selectivity on the membrane surface which the 2D surface modifier effectively covered. Chirality 27:459-463, 2015. (c) 2015 Wiley Periodicals, Inc.

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  • A Helical Polyphenylacetylene Having Amino Alcohol Moieties Without Chiral Side Groups as a Chiral Ligand for the Asymmetric Addition of Diethylzinc to Benzaldehyde Reviewed

    Lijia Liu, Qing Long, Toshiki Aoki, Geng Zhang, Takashi Kaneko, Masahiro Teraguchi, Chunhong Zhang, Yudan Wang

    CHIRALITY   27 ( 8 )   454 - 458   2015.8

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    One-handed helical polyphenylacetylenes having achiral amino alcohol moieties, but no chiral side groups, were synthesized by the helix-sense-selective copolymerization of an achiral phenylacetylene having an amino alcohol side group with a phenylacetylene having two hydroxyl groups. Since the resulting helical copolymers were successfully utilized as chiral ligands for the enantioselective alkylation of benzaldehyde with diethylzinc, we can conclude that the main-chain chirality based on the one-handed helical conformation is useful for the chiral catalysis of an asymmetric reaction for the first time. The enantioselectivities of the reaction were controlled by the optical purities of the helical polymer ligands. In addition, the polymer ligands could be easily recovered by precipitation after the reaction. Chirality 27:454-458, 2015. (c) 2015 Wiley Periodicals, Inc.

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  • A Chiral Supramolecular Polymer Membrane with no Chiral Substituents by Highly Selective Photocyclic Aromatization of a One-Handed Helical Cis-cisoidal Polyphenylacetylene Reviewed

    Lijia Liu, Qing Long, Toshiki Aoki, Takeshi Namikoshi, Yunosuke Abe, Mari Miyata, Masahiro Teraguchi, Takashi Kaneko, Yudan Wang, Chunhong Zhang

    MACROMOLECULAR CHEMISTRY AND PHYSICS   216 ( 5 )   530 - 537   2015.3

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    A one-handed helical cis-cisoidal polyphenylacetylene (P) is successfully synthesized by an asymmetric-induced polymerization of a chiral-substituted phenylacetylene having two hydroxymethyl groups. Quantitative photocyclic aromatization of P in a membrane-state followed by in situ removal of the chiral substituents affords a one-handed helical supramolecular polymer membrane of the corresponding cyclic trimer (T) with no chiral substituents. The original one-handed helicity of the precursor P is successfully transmitted to the resulting supramolecular helicity of de-T. Both the hydrogen bonds and the pi-pi stacking are thought to contribute to the retention of the chirality during the two-step reaction in the membrane state.

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  • Helix-sense-selective Polymerization of Achiral Phenylacetylenes by Using One-handed Helical Poly(phenylacetylene)s as Chiral Cocatalysts Prepared by Helix-sense-selective Polymerization of Achiral Phenylacetylenes Reviewed

    Geng Zhang, Lijia Liu, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    CHEMISTRY LETTERS   44 ( 3 )   318 - 320   2015.3

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    We found that the helix-sense-selective polymerization (HSSP) of achiral phenylacetylenes having two hydroxy groups was realized by using one-handed helical poly(phenylacetylene)s as chiral cocatalysts prepared by HSSP of the same or similar achiral phenylacetylenes having two hydroxy groups. In other words, the chirality caused only by the one-handed helical backbone was found to be able to work as a cocatalyst in the chiral catalytic system. In addition, the efficiency of the chiral induction was high and almost the same as that of the HSSP by using enatiomerically pure phenylethylamine as a cocatalyst.

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  • Selective Polymerization of Dimethylsilylphenylacetylene and the Gas Permselectivity of the Resulting Polymer Membranes Reviewed

    Jun Li, Jianjun Wang, Toshiki Aoki, Takashi Kaneko, Masahiro Teraguchi

    CHEMISTRY LETTERS   44 ( 2 )   182 - 184   2015.2

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    Three types of homopolymerizations of p-(dimethylsilyl)-phenylacetylene (HSPA) having a terminal triple bond and a Si-H group were selectively carried out by using three kinds of polymerization catalysts. Among them poly(HSPA) synthesized by addition polymerization of its triple bond using [Rh(nbd)Cl](2) (nbd: norbornadiene)/phenylethylamine (PEA) showed a good membrane forming ability. The copolymerizations of HSPA with p-(trimethylsilyl)phenylacetylene (SPA) were carried out using [Rh(nbd)Cl](2)/PEA and the resulting copolymers were fabricated to self-supporting membranes. These membranes, including the homopolymer of HSPA, showed higher permselectivities for oxygen and carbon dioxide over nitrogen than those of poly(SPA). Incorporation of HSPA unit to poly(SPA) effectively enhanced its permselectivities with only small decrease in its permeability.

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  • Synthesis and oxygen permeation of novel polymers of phenylacetylenes having two hydroxyl groups via different lengths of spacers Reviewed

    Yu Zang, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Liqun Ma, Hongge Jia

    POLYMER   56   199 - 206   2015.1

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    Three novel phenylacetylenes having two hydroxyl groups via different kinds of spacers between the two hydroxyl groups and benzyl group were synthesized and polymerized. Two of the resulting polymers having oxyalkylene spacers between the hydroxyl group and benzyl group had good membrane forming ability, relatively high oxygen permselectivity and high oxygen permeability. By introducing the oxyalkylene spacers, the membrane forming abilities and oxygen permselectivity were enhanced. Oxygen permselectivity (P-O2/P-N2 = 2.67) of the polymer membrane having the longest spacers was higher than that (2.19) of polymer without any spacers. It may be because the columnar content and then defects decreased when the cis-cisoid conformation was changed to cis-transoid conformation. In addition, by decreasing the columnar content of the membrane from the polymer without any spacers, which could be controlled by conditions in membrane preparation, the membrane forming ability and oxygen permselectivity were effectively enhanced (from 2.19 to 2.61) without any drop of oxygen permeability. (C) 2014 Elsevier Ltd. All rights reserved.

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  • Two-Dimensional and Related Polymers: Concepts, Synthesis, and their Potential Application as Separation Membrane Materials Reviewed

    Yu Zang, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Liqun Ma, Hongge Jia

    POLYMER REVIEWS   55 ( 1 )   57 - 89   2015.1

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    Although two-dimensional polymers (2DPs) and related materials are very attractive subjects for research because they are expected to function as ideal gas separation membrane materials, we need to answer some basic questions about them. For example, "Why are they not a common or popular topic, especially in textbooks?"; "How can they be synthesized?"; and "Whatever are 2DPs? and "How can we define 2DPs?" In this review, we try to answer these questions. First, the significance of 2DP as molecular-sieving membrane materials is explained in Section 1. Second, the definitions and classifications are proposed that take into account their first-order and high-order structures in Section 2. Third, syntheses and function of a few real 2DPs and many related polymers described in the literature are reviewed, including such materials as covalent organic frameworks(COFs), carbonized molecular sieving membranes(CMSMs), polymers of intrinsic porosity(PIM), and our recent results on the synthesis and function of 2DPs and related polymers in Sections 3 and 4. Finally, in Section 5 we evaluate the two-dimensional (2D) characters of 2DPs described in Section 3 using some 2D characteristic values defined in Section 2, and the future of 2DPs is discussed in Section 6.

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  • Catalytic helix-sense-selective polymerisation of achiral substituted acetylenes containing bulky pi-conjugated planar substituents yielding soluble and statically stable one-handed helical polymers Reviewed

    Y. Zang, X. Wang, W. Zhang, T. Aoki, M. Teraguchi, T. Kaneko, L. Ma, H. Jia

    RSC ADVANCES   5 ( 129 )   106819 - 106823   2015

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    Helix-sense-selective polymerisation of three new achiral substituted acetylenes containing two bulky pi-conjugated planar substituents via imino groups by using catalytic amounts of a chiral source yielded soluble and statically stable one-handed helical polymers which were stabilized by intramolecular steric hindrance.

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  • Helix-sense-selective Degradation of Poly[4-dodecyloxy-3,5-bis(hydroxymethyl)phenylacetylene] by Selective Photocyclic Aromatization (SCAT) Using Circularly Polarized Light (CPL) Reviewed

    Mari Miyata, Masahiro Teraguchi, Hiromichi Endo, Takashi Kaneko, Toshiki Aoki

    CHEMISTRY LETTERS   43 ( 9 )   1476 - 1477   2014.9

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    Helix-sense-selective photodegaradation of poly[4-dodecyloxy-3,5-bis(hydroxymethyl)phenylacetylene] (poly(DoDHPA)) in membrane state was achieved by selective photocyclic aromatization (SCAT) using single-handed circularly polarized light (CPL). This is the first example of kinetic optical resolution of helical polymers by using CPL.

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  • Synthesis of Poly(1,2-phenyleneethynylene-1,2-phenylenevinylene) Bearing Phenol Residues and Forming Ability of the Folded Helical Conformation Reviewed

    Takashi Kaneko, Yuta Togashi, Masahiro Teraguchi, Toshiki Aoki

    CHEMISTRY LETTERS   43 ( 8 )   1219 - 1221   2014.8

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    5,4'-Bis(3,5-di-tert-buty1-4-acetoxypheny1)-2-ethynyl-2'-iodo-stilbene was synthesized and polymerized by the Sonogashira reaction to give the corresponding regioregular head-totail poly(1,2-phenyleneethynylene-1,2-phenylenevinylene). The polymer was converted to the corresponding hydroxy polymer after complete elimination of the protecting acetyl group by treatment with an alkaline solution. It was found that the folded helical conformation was preferred for the polymer containing the poly(1,2-phenylenevinylene) structure upon addition of methanol to the chloroform solution owing to the solvophobic interaction.

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  • Facile synthesis of five 2D surface modifiers by highly selective photocyclic aromatization and efficient enhancement of oxygen permselectivities of three polymer membranes by surface modification using a small amount of the 2D surface modifiers Reviewed

    Jianjun Wang, Yu Zang, Guanwu Yin, Toshiki Aoki, Hiroyuki Urita, Ken Taguwa, Lijia Liu, Takeshi Namikoshi, Masahiro Teraguchi, Takashi Kaneko, Liqun Ma, Hongge Jia

    POLYMER   55 ( 6 )   1384 - 1396   2014.3

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    A facile synthesis of novel five 2D (planar) surface modifiers having a triphenylbenzene derivatives as a 2D structure has been achieved by the highly selective photocyclic aromatization reaction. Efficient enhancement of oxygen permselectivities through the three polymer membranes has been achieved by adding a small amount (&lt; 5.0 wt%) of the 20 surface modifiers. Among the five 2D surface modifiers, a modifier compound having oligoethylene oxide groups showed the best performance for the enhancement. These improvements were thought to be caused mainly by improvement of the solution selectivity on the membrane surface where the 2D surface modifiers were accumulated. In some of the surface-modified blend membranes, their plots in the P-O2(-alpha) graph were over or close to the upper boundary line by Robeson in 1991. Since all the membranes containing the 2D surface modifiers showed better permselectivities than the corresponding substrate membranes, it is very promising for the future. (C) 2013 Elsevier Ltd. All rights reserved.

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  • Synthesis of sequential poly(1,3-phenyleneethynylene)-based polyradicals and through-space antiferromagnetic interaction of their solid state Reviewed

    Takashi Kaneko, Kyohei Iwamura, Ryo Nishikawa, Masahiro Teraguchi, Toshiki Aoki

    POLYMER   55 ( 5 )   1097 - 1102   2014.3

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    Some 1,3-PPE-based polyradicals with pendent phenoxy radicals whose repeating unit consisted of four 1,3-phenyleneethynylene units were synthesized via polymerization between monomers and trimeric monomers in the presence of the Pd(PPh3)(4) complex catalysts. The ESR spectra of the polyradicals in dichloromethane showed unimodal broad signals. For the solid samples which were prepared from the dichloromethane solution by evaporating the solvent and by drying in vacuo, the signal intensity decreased with broadening of peak-to-peak line-width (Delta H-pp). However, the ESR spectra almost recover to the initial intensity and shapes due to redissolving in dichloromethane. In particular, the decrease of doubly integrating the ESR signal (I-ESR) was more remarkable for the polyradical bearing galvinoxyl and phenoxyl residues than others. This behavior suggests that strong antiferromagnetic interaction partially arose for the polyradical. (C) 2014 Elsevier Ltd. All rights reserved.

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  • Synthesis and Enantioselective Permeability of One-handed Helical Multihydroxy Poly(phenylacetylene) Membrane by In Situ Removal of the Original Chiral Substituents Reviewed

    Lijia Liu, Kazuomi Mottate, Toshiki Aoki, Takashi Kaneko, Masahiro Teraguchi

    CHEMISTRY LETTERS   43 ( 2 )   237 - 239   2014.2

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    An insoluble chiral membrane of one-handed helical multihydroxy poly(phenylacetylene) without the coexistence of any other chiral moieties has been synthesized by in situ complete removal of a one-handed helical poly(phenylacetylene) having multihydroxymethyl groups and chiral pinanyl groups in each polymeric unit in the membrane state. Although the enantiopermselectivity was decreased, the permeability increased four times by removing the chiral groups. In comparison with the corresponding poly(phenylacetylene) having no hydroxymethyl groups and chiral pinanyl groups, the loss of enantiopermselectivity was much lower. It is believed that the multihydroxy groups could maintain the main-chain chirality or enhanced interaction with permeant.

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  • Helix-sense-selective polymerization of novel substituted acetylenes having a rigid planar imino-linked substituent and quantitative polymer reactions in the optically active polymer membranes Reviewed

    Mari Miyata, Yuya Katsushika, Toshiki Aoki, Masahiro Teracuchi, Takashi Kaneko

    Kobunshi Ronbunshu   71 ( 8 )   372 - 381   2014

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    Novel substituted acetylenes having a rigid planar substituent via a dynamic covalent imino group were synthesized and subsequently polymerized by using a chiral initiator system consisting of an achiral rhodium complex and a chiral N,N-dimethylphenylethylamine to produce one-handed helical polymers having dynamic covalent imino groups. Furthermore, membranes could be produced from these chiral polymers that showed highly selective photocyclic aromatization (SCAT) and quantitative substitution of the side groups (RIM). Supramolecular polymer membranes having a high strength were obtained by SCAT. Chiral polymer membranes having many different kinds of side groups were easily obtained by RIM of the side groups. © 2014, The Society of Polymer Science.

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  • Helix-Sense-Selective Polymerization of Novel Substituted Acetylenes Having a Rigid Planar Imino-Linked Substituent and Quantitative Polymer Reactions in the Optically Active Polymer Membranes Reviewed

    Mari Miyata, Yuya Katsushika, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    KOBUNSHI RONBUNSHU   71 ( 8 )   372 - 381   2014

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    Novel substituted acetylenes having a rigid planar substituent via a dynamic covalent imino group were synthesized and subsequently polymerized by using a chiral initiator system consisting Of an achiral rhodium complex and a chiral N,N-dimethylphenylethylamine to produce one-handed helical polymers having dynamic covalent imino groups. Furthermore, membranes could be produced from these chiral polymers that showed highly selective photocyclic aromatization (SCAT) and quantitative substitution of the side groups (RIM). Supramolecular polymer membranes having a high strength were obtained by SCAT. Chiral polymer membranes having many different kinds of side groups were easily obtained by RIM of the side groups.

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  • Helix-sense-selective Polymerization of 3,5-Bis(hydroxymethyl)phenylacetylene Connected with a Rigid and pi-Conjugated Substituent Reviewed

    Zhichun Shi, Yoshinori Murayama, Takashi Kaneko, Masahiro Teraguchi, Toshiki Aoki

    CHEMISTRY LETTERS   42 ( 9 )   1087 - 1089   2013.9

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    An achiral 3,5-bis(hydroxymethyl)phenylacetylene connected with a rigid and pi-conjugated substituent was polymerized using a rhodium (Rh) complex catalyst in the presence of chiral 1-phenylethylamines. The circular dichroism (CD) spectra of the polymers indicated that an excess of one-handed helical polyacetylene backbone was induced by helix-sense-selective polymerization under the asymmetric conditions despite the achiral monomer. The split-type-induced CD signals at 300 nm were attributed to the chromophore including the conjugated side group since the signal appeared at a longer wavelength than the poly[3,5-bis(hydroxymethyl)phenylacetylene] without conjugated substituent.

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  • Facile Synthesis of an Amphiphilic 1,3,5-Trisubstituted Benzene as a Novel Surface Modifier by Selective Photocyclic Aromatization and Efficient Improvement of Oxygen Permselectivity by the Addition of the Surface Modifier Reviewed

    Jianjun Wang, Toshiki Aoki, Lijia Liu, Takeshi Namikoshi, Masahiro Teraguchi, Takashi Kaneko

    CHEMISTRY LETTERS   42 ( 9 )   1090 - 1092   2013.9

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    An amphiphilic 1,3,5-trisubstituted benzene as a new 2D surface modifier (T-EO) which has six hydroxy groups and three oligoethylene groups was successfully and easily synthesized by selective photocyclic aromatization in high conversion and selectivity for the first time. We prepared four kinds of blend membranes based on PVA or poly(trimethylsilylphenylacetylene) (poly(SPA)) containing the new amphiphilic cyclic trimer (T-EO) or the corresponding polymer (P-EO), that is, T-EO/PVA, P-EO/PVA, and T-EO/poly(SPA) membranes prepared by conventional solvent casting method (Method 1) and T-EO/poly(SPA) membranes prepared by a new solvent casting method (Method 11). T-EO/PVA membranes by Method I and T-EO/poly(SPA) membranes by Method II showed better performance in oxygen permeation than P-EO/PVA membranes by Method I and T-EO/poly(SPA) membranes by Method I, respectively. A PVA-based membrane containing 1.0 wt % T-EO showed the best performance, that is, the alpha became twice that of the original PVA membrane without any decrease in P-O2. The ideal improvement may be caused by effective surface modification by T-EO.

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  • Flexible self-supporting supramolecular polymeric membranes consisting of 1,3,5-trisubstituted benzene derivatives synthesized by highly selective photocyclic aromatization of helical poly(phenylacetylene)s in the membrane state Reviewed

    Mari Miyata, Takeshi Namikoshi, Lijia Liu, Yu Zang, Toshiki Aoki, Yunosuke Abe, Yoshiyuki Oniyama, Toyokazu Tsutsuba, Masahiro Teraguchi, Takashi Kaneko

    Polymer (United Kingdom)   54 ( 17 )   4431 - 4435   2013.8

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    It has been achieved to obtain flexible self-supporting supramolecular polymeric membranes consisting of only 1,3,5-trisubstituted benzene derivatives prepared by highly selective photocyclic aromatization of the corresponding poly (substituted phenylacetylene)s having a columnar structure. The flexibilities of the self-supporting supramolecular polymeric membranes were enhanced by introducing hydroxyl groups or phenylene groups to the starting polymers (monomers). There were two reasons for the enhanced strength: 1) introduction of intercolumnar hydrogen bonds and 2) enhancement of the degree of intracolumnar stackings. This strength depended on the structure of the starting polymers which functioned as a template. © 2013 Elsevier Ltd. All rights reserved.

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  • Chiral Amplification during Asymmetric-Induced Copolymerization of Phenylacetylenes with Tight Cis-Cisoidal Main Chains Reviewed

    Lijia Liu, Kazuomi Mottate, Geng Zhang, Toshiki Aoki, Takashi Kaneko, Masahiro Teraguchi

    MACROMOLECULAR RAPID COMMUNICATIONS   34 ( 14 )   1140 - 1144   2013.7

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    A novel phenylacetylene (1) having two hydroxyl groups and a chiral pinanyl group together with the other three related phenylacetylenes has been synthesized and (co)polymerized by using an achiral catalytic system. Among the four monomers, only 1 is suitable to the asymmetric-induced polymerization (AIP). Chiral amplification phenomenon is only observed in the copolymerization of 1 with an achiral phenylacetylene having two hydroxyl groups (3). The tight helical cis-cisoidal main chain formed by making intramolecular hydrogen bonds between the hydroxyl groups in the copoly(1/3) enhances the efficiency of chiral induction and as a result chiral amplification phenomenon is observed during the copolymerization.

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  • Excellent oxygen permselectivity of fluorine-containing poly(trimethylsilyldiphenylacetylene)s prepared by direct alkylation of perfluorodecyl groups in membrane state Reviewed

    Takashi Sato, Naoki Yoshida, Akihiro Ishida, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    Polymer (United Kingdom)   54 ( 9 )   2231 - 2234   2013.4

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    Two poly(trimethylsilyldiphenylacetylene) membranes containing different contents of fluorine-containing groups were prepared by direct perfluorodecylation of poly(trimethylsilyldiphenylacetylene) (poly 1) in the membrane state using different ratios of (perfluorodecyl)phenyliodonium triflates to the phenyl groups in the polymer. The resulting perfluorodecylated poly(trimethylsilyldiphenylacetylene) (poly 2a and poly 2b) membranes were self-standing and tough. The two membranes showed better performance in oxygen permselectivity compared with all the membranes reported by many researchers. The performance (PO2 &gt
    103 barrer and α = PO 2/PN2 = 2.9) of the poly 2a membrane having a lower content of the fluorine groups located on the upper boundary line reported by Robeson in 2008. The poly 2b membrane having a higher content of the fluorine groups was one of the polymers having the highest PO2 values (PO 2 &gt
    104 barrer) in all the polymers reported.

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  • Folding-Induced Through-Space Magnetic Interaction of Poly(1,3-phenyleneethynylene)-Based Polyradicals Reviewed

    Takashi Kaneko, Hiromasa Abe, Masahiro Teraguchi, Toshiki Aoki

    MACROMOLECULES   46 ( 7 )   2583 - 2589   2013.4

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    We synthesized poly(1,3-phenyleneethynylene)s bearing galvinoxyl moieties. The absorption ratio of the anion form in 1 M KOH methanol solution between 309 and 294 nm (A(309)/A(294)) decreased with increasing degree of polymerization. The wide-angle X-ray scattering of the powder, which was prepared by precipitation in dilute hydrochloric acid solution from the anion form in 1 M KOH methanol solution, showed a crystalline peak at 2 theta = 28 degrees. Polymers in which the chiral diethynyl-1,1'-binaphthyl moiety was inserted into the poly(1,3-phenyleneethynylene) chain were synthesized, and clear Cotton effects were observed in the absorption region of the galvinoxyl anion chromophore in the CD spectra taken in 1 M KOH-MeOH solution, indicating an excess of one-handed folded helical conformation. A relatively strong antiferromagnetic interaction was observed for the polyradicals prepared by precipitating the anionic form from alkaline methanol solution accompanied with oxidation using aqueous K3Fe(CN)(6) solution. These observations suggest that the relatively strong antiferromagnetic interaction of the polyradicals was caused by the close packing between galvinoxyl radicals induced by the formation of the folded helical structure.

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  • Living-like helix-sense-selective polymerization of an achiral substituted acetylene having bulky substituents Reviewed

    Yu Zang, Kazuki Nakao, Hiroki Yotsuyanagi, Toshiki Aoki, Takeshi Namikoshi, Toyokazu Tsutsuba, Masahiro Teraguchi, Takashi Kaneko

    POLYMER   54 ( 7 )   1729 - 1733   2013.3

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    By using a new achiral phenylacetylene having bulky substituents as a monomer, living-like helix-sense-selective polymerization (HSSP) has been achieved. This is the first example of the HSSP of substituted acetylenes where the degree of polymerization was controlled. The resulting one-handed helical living polymer initiated polymerization of a second monomer to successfully yield a block copolymer. (C) 2013 Elsevier Ltd. All rights reserved.

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  • Helix-sense-selective Polymerization of Achiral Acetylene Monomer Catalyzed by Rh Zwitterionic Complexes with Tethered Chiral Amino and Ether Groups Reviewed

    Naoya Onishi, Toshiki Aoki, Takashi Kaneko, Masahiro Teraguchi, Natsuhiro Sano, Toshio Masuda, Masashi Shiotsuki, Fumio Sanda

    CHEMISTRY LETTERS   42 ( 3 )   278 - 280   2013.3

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    Zwitterionic rhodium (Rh) complexes with tethered chiral amino and ether groups were synthesized by the reaction of [(C2H4)(2)RhCl](2) with the 2,5-norbornadiene tether, (CH2)(4)R [2: R = (R)-NHCH(CH3)Ph, 3: (R)-OCH(CH3)Ph], followed by exchange of Cl with BPh4. The resultant Rh complexes, 2 and 3, catalyzed the polymerization of 4-dodecyloxy-3,5-bis(hydroxymethyl)phenylacetylene (1) to afford polymers [poly(1)s] with number-average molecular weights of 16000 and 82000, respectively. The poly(1)s showed clear circular dichroism resulting from their polyacetylene backbones, which indicates the formation of predominantly one-handed helical structures.

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  • Top-down preparation of self-supporting supramolecular polymeric membranes using highly selective photocyclic aromatization of cis-cisoid helical poly(phenylacetylene)s in the membrane state Reviewed

    Lijia Liu, Takeshi Namikoshi, Yu Zang, Toshiki Aoki, Shingo Hadano, Yunosuke Abe, Ikuya Wasuzu, Toyokazu Tsutsuba, Masahiro Teraguchi, Takashi Kaneko

    Journal of the American Chemical Society   135 ( 2 )   602 - 605   2013.1

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    A novel, highly selective photocyclic aromatization (SCAT) of π-conjugated polymers from phenylacetylene having two hydroxyl groups to exclusively yield a 1,3,5-trisubstituted benzene derivative was developed, and its success was confirmed by 1H NMR, GPC, and TOF-MS. The SCAT reaction has many unique characteristics. (1) It is a quantitative reaction: it gave only the corresponding cyclic trimer, i.e., a 1,3,5-trisubstituted benzene derivative, quantitatively (100%). No byproducts were produced under the best conditions. (2) It is an intramolecular reaction: it occurred between three adjacent monomer units in one macromolecule. (3) It is a stereospecific and topochemical or template reaction: the reactivity strongly depended on the configuration and conformation of the starting polymer substrates. (4) It is a photoreaction: high selectivity (100%) was observed only by the use of visible light irradiation, not by heating. (5) It is a solid-state reaction: high selectivity (100%) was observed only in the solid state, not in solution. In addition, (6) the resulting cyclic trimers could form a self-supporting membrane, despite their low molecular weights. This new approach resulted in a new class of supramolecular polymers consisting of a 1,3,5-trisubstituted benzene derivative, numbers of which were linearly linked by hydrogen bonds and stacked benzene derivatives. Since SCAT has such high selectivities and is useful for the preparation of a self-supporting supramolecular polymer membrane, many applications can be expected. © 2012 American Chemical Society.

    DOI: 10.1021/ja3113214

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  • Helix-sense-selective polymerization of substituted acetylenes by using an isolated rh chiral initiator with an amino acid ligand Reviewed

    Yu Zang, Tomoyuki Ohishi, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    Chemistry Letters   42 ( 4 )   430 - 432   2013

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    Helix-sense-selective polymerization (HSSP) of substituted acetylenes by using an isolated chiral Rh initiator with an amino acid ligand has been achieved. The sense of the helix of the main chain of the resulting polymer was controlled by the sign of the chirality of the ligand. The isolated initiator needed less of the chiral ligand and gave polymers having a higher value than the two component chiral initiator systems we reported previously. The resulting polymers had a higher Mw. © 2013 The Chemical Society of Japan.

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  • Two modes of asymmetric polymerization of phenylacetylenes having an L-amino alcohol residue and two hydroxy groups Reviewed

    Hongge Jia, Jun Li, Yu Zang, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   50 ( 24 )   5134 - 5143   2012.12

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    Four novel chiral phenylacetylenes having an L-amino alcohol residue and two hydroxymethyl groups were synthesized and polymerized by an achiral catalyst ((nbd)Rh+[?6-(C6H5)B-(C6H5)3]) or a chiral catalytic system ([Rh(nbd)Cl]2/(S)- or (R)-phenylethylamine ((S)- or (R)-PEA)). The two resulting polymers having an L-valinol or L-phenylalaninol residue showed Cotton effects at wavelengths around 430 nm. This observation indicated that they had an excess of one-handed helical backbones. Positive and negative Cotton effects were observed only for the polymers having an L-valinol residue produced by using (R)- and (S)-PEA as a cocatalyst, respectively, although the monomer had the same chirality. Even when the achiral catalyst was used, the two resulting polymers having an L-valinol or L-phenylalaninol residue showed Cotton effects despite the long distance between the chiral groups and the main chain. We have found the first example of a new type of chiral monomer, that is, a chiral phenylacetylene monomer having an L-amino alcohol residue and two hydroxy groups that was suitable for both modes of asymmetric polymerization, that is, the helix-sense-selective polymerization (HSSP) with the chiral catalytic system and the asymmetric-induced polymerization (AIP) with the achiral catalyst. The other two monomers having L-alaninol and L-tyrosinol were found to be unsuitable to neither HSSP nor AIP because of their polymers' low solubility. (C) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

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  • Helix-Sense-Selective Polymerization of Achiral Phenylacetylenes with Two N-Alkylamide Groups to Generate the One-Handed Helical Polymers Stabilized by Intramolecular Hydrogen Bonds Reviewed

    Masahiro Teraguchi, Daisuke Tanioka, Takashi Kaneko, Toshiki Aoki

    ACS MACRO LETTERS   1 ( 11 )   1258 - 1261   2012.11

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    In this study, we investigated the helix-sense-selective polymerizations of newly synthesized achiral phenylacetylenes having two N-alkylamide groups, such as 3,5-bis(dodecylamide)phenylacetylene (DAPA), 3,5-bis(octylamide)phenylacetylene (OAPA), and 3,5-bis(butylamide)phenylacetylene (BAPA), by using a chiral rhodium catalyst system ([Rh(nbd)Cl](2)-(R)-(+)-1-phenylethylamine [(R)-PEA]). Poly(BAPA) was insoluble in any solvents. On the other hand, poly(DAPA) and poly(OAPA) were soluble in toluene, THF, and CHCl3, and the obtained polymers showed intense circular dichroism signals at the absorption region of the main chain in the UVvis region. This result suggested those polymers were present in helical conformations with an excess of one-handed screw sense. The chiral helix structures of the formed polymers were stable in toluene at room temperature for a long time because of intramolecular hydrogen bonds. This result is the second example about polyacetylenes with one-handed helical conformation stabilized by intramolecular hydrogen bonds.

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  • Enhanced Gas Permselectivity of Copoly(Hyperbranched Macromonomer) Synthesized by One-pot Simultaneous Copolymerization of Dimethylsilyl-containing Phenylacetylenes Reviewed

    Jun Li, Jianjun Wang, Yu Zang, Toshiki Aoki, Takashi Kaneko, Masahiro Teraguchi

    CHEMISTRY LETTERS   41 ( 11 )   1462 - 1464   2012.11

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    Copoly(hyperbranched macromonomer)s, i.e., poly(phenylacetylene)s having many branches were synthesized by one-pot simultaneous copolymerization of two kinds of dimethylsilyl-phenylacetylenes. Membranes from the copoly(hyperbranched macromonomer)s having several kinds of branches showed higher permselectivities for oxygen and carbon dioxide over nitrogen than those of the corresponding copoly(hyperbranched macromonomer)s without any branches. In particular, the copoly(hyperbranched macromonomer)s having long and rigid branches had both the advantages of poly(phenylacetylene)s and poly(dendron)s. In summary, copoly(hyperbranched macromonomer)s showing good performance as gas-separation membranes were synthesized very easily by the one-pot simultaneous polymerization method. To our knowledge, this is the first synthesis of such complex copolymers showing good performance as gas-separation membranes.

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  • Synthesis of stable and soluble one-handed helical poly(substituted acetylene)s without chiral pendant groups via polymer reaction in membrane state Reviewed

    Yunosuke Abe, Toshiki Aoki, Hongge Jia, Shingo Hadano, Takeshi Namikoshi, Yuriko Kakihana, Lijia Liu, Yu Zang, Masahiro Teraguchi, Takashi Kaneko

    POLYMER   53 ( 11 )   2129 - 2133   2012.5

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    A soluble and stable one-handed helical conjugated polymer without the coexistence of any other chiral moieties was successfully synthesized by asymmetric-induced polymerization of a chiral monomer having two hydroxyl groups followed by desubstitution of the chiral groups in a solid membrane state. The reason for the success was the polymer reaction was carried out in the membrane state. This is an alternative method to obtain such a unique chiral polymer which was obtained only by the helix-sense-selective polymerization (HSSP) we reported before. In addition the efficiency of the chiral induction was higher than that of the HSSP. It is interesting that the "Membrane state" acted like as if a protecting group. (C) 2012 Elsevier Ltd. All rights reserved.

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  • Transformation from preformed racemic helical poly(phenylacetylene)s to the enantioenriched helical polymers by chiral solvation, followed by removal of the chiral solvents Reviewed

    Takashi Kaneko, Xiaoyun Liang, Atsuko Kawami, Masayuki Sato, Takeshi Namikoshi, Masahiro Teraguchi, Toshiki Aoki

    POLYMER JOURNAL   44 ( 4 )   327 - 333   2012.4

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    Homochiral or enantioenriched helical polymers are essential for investigating the relationship between chirality of helical structures and their performance in the design of various optically active functional polymers. We have succeeded in obtaining the helical poly(phenylacetylene)s poly(1)-poly(6) possessing no chiral moieties, except for helicity; the enantioenriched helical sense of these polymers was induced by transformation in chiral solvents, followed by removal of the chiral solvents, even if the interaction between the chiral molecule and the polymer was weak such as solvent-solute interaction. In particular, the newly synthesized poly(6) retained the induced helical sense even in an achiral solvent. Polymer Journal (2012) 44, 327-333; doi:10.1038/pj.2011.144; published online 18 January 2012

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  • Asymmetric-induced polymerization and polymer reaction of the resulting one-handed helical polymer membranes Reviewed

    Abe Yunosuke, Namikoshi Takeshi, Zang Yu, Teraguchi Masahiro, Kaneko Takashi, Aoki Toshiki

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   243   2012.3

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  • Helix-sense-selective polymerization of chiral or achiral silicon-containing phenylacetylenes Reviewed

    Liu Lijia, Zang Yu, Jia Hongge, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   243   2012.3

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  • Chiral Teleinduction in Asymmetric Polymerization of 3,5-Bis(hydroxymethyl)phenylacetylene Having a Chiral Group via a Very Long and Rigid Spacer at 4-Position Reviewed

    Yunosuke Abe, Toshiki Aoki, Hongge Jia, Shingo Hadano, Takeshi Namikoshi, Yuriko Kakihana, Lijia Liu, Yu Zang, Masahiro Teraguchi, Takashi Kaneko

    CHEMISTRY LETTERS   41 ( 3 )   244 - 246   2012.3

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    A new polymer prepared by polymerization of 3,5-bis(hydroxymethyl)phenylacetylene having a chiral menthyl group via a very long and rigid spacer by an achiral rhodium complex with triethylamine as an initiator showed strong CD absorptions assigned to the main chain in spite of the long distance (23 angstrom) between the chiral group and the polymerizing group in the monomer. This distance is the longest to the best of our knowledge. In addition, switching between the two chiralities of the resulting polymer was realized in the CD spectrum.

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  • Synthesis of Stable and Soluble One-Handed Helical Homopoly(substituted acetylene)s without the Coexistence of Any Other Chiral Moieties via Two-Step Polymer Reactions in Membrane State: Molecular Design of the Starting Monomer Reviewed

    Yunosuke Abe, Toshiki Aoki, Hongge Jia, Shingo Hadano, Takeshi Namikoshi, Yuriko Kakihana, Lijia Liu, Yu Zang, Masahiro Teraguchi, Takashi Kaneko

    MOLECULES   17 ( 1 )   433 - 451   2012.1

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    A soluble and stable one-handed helical poly(substituted phenylacetylene) without the coexistence of any other chiral moieties was successfully synthesized by asymmetric-induced polymerization of a chiral monomer followed by two-step polymer reactions in membrane state: (1) removing the chiral groups (desubstitution); and (2) introduction of achiral long alkyl groups at the same position as the desubstitution to enhance the solubility of the resulting one-handed helical polymer (resubstitution). The starting chiral monomer should have four characteristic substituents: (i) a chiral group bonded to an easily hydrolyzed spacer group; (ii) two hydroxyl groups; (iii) a long rigid hydrophobic spacer between the chiral group and the polymerizing group; (iv) a long achiral group near the chiral group. As spacer group a carbonate ester was selected. The two hydroxyl groups formed intramolecular hydrogen bonds stabilizing a one-handed helical structure in solution before and after the two-step polymer reactions in membrane state. The rigid long hydrophobic spacer, a phenylethynylphenyl group, enhanced the solubility of the starting polymer, and realized effective chiral induction from the chiral side groups to the main chain in the asymmetric-induced polymerization. The long alkyl group near the chiral group avoided shrinkage of the membrane and kept the reactivity of resubstitution in membrane state after removing the chiral groups. The g value (g = ([theta]/3,300)/epsilon) for the CD signal assigned to the main chain in the obtained final polymer was almost the same as that of the starting polymer in spite of the absence of any other chiral moieties. Moreover, since the one-handed helical structure was maintained by the intramolecular hydrogen bonds in a solution, direct observation of the one-handed helicity of the final homopolymer has been realized in CD for the solution for the first time.

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  • Polymerization of Phenylacetylene-Based Monodendrons with Alkoxy Peripheral Groups and Oxygen/Nitrogen Permeation Behavior of Their Membranes Reviewed

    Takashi Kaneko, Kazuaki Sato, Yoshihiko Uchiya, Masahiro Teraguchi, Toshiki Aoki

    INTERNATIONAL JOURNAL OF POLYMER SCIENCE   doi:10.1155/2012/974204   2012

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    Monodendron monomers with alkoxy peripheral groups were synthesized, and the focal point of monodendrons, terminal acetylene, was polymerized with rhodium catalyst to yield corresponding polydendrons with a high molecular weight. The polydendrons were soluble in common organic solvents and readily formed membranes. Oxygen permselectivity was improved in the polydendrons with a space-persistent dendritic crowd. It was found that the well-defined dendritic and rod-like structure of the polydendrons was useful for permselective membrane.

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  • Pseudo helix-sense-selective polymerisation of achiral substituted acetylenes Reviewed

    Yu Zang, Toshiki Aoki, Lijia Liu, Yunosuke Abe, Yuriko Kakihana, Masahiro Teraguchi, Takashi Kaneko

    CHEMICAL COMMUNICATIONS   48 ( 39 )   4761 - 4763   2012

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    Pseudo helix-sense-selective polymerisation of a wide range of achiral substituted acetylenes having dynamic covalent bonds has been realised to yield static one-handed helical polymers without any other chiral moieties.

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  • Synthesis and Function of Chiral π-Conjugated Polymers from Phenylacetylenes Reviewed

    Toshiki Aoki, Takashi Kaneko, Masahiro Teraguchi

    Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis   423 - 455   2011.6

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    DOI: 10.1002/9781118063965.ch15

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  • Enantioselective Pervaporation through Membranes from Poly(1,3-phenyleneethynylene)-based One-handed Helical Foldamer and Unfoldamer Reviewed

    Makoto Inoue, Masahiro Teraguchi, Toshiki Aoki, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko

    CHEMISTRY LETTERS   40 ( 4 )   384 - 386   2011.4

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    We synthesized two kinds of poly(1,3-phenyleneethynylenes), one has (+)-menthoxycarbonyl groups at all repeating units and the other has (+)-menthoxycarbonyl groups and n-dodecyloxy groups alternately. Self-supporting membranes could be obtained easily by solvent casting. Enantioselective permeations of the polymers were investigated by pervaporation of 2-butanol. Enantioselective permeabilities of the membrane consisting of one-handed helical foldamer and unfoldamer were clarified.

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  • Program for Promoting High-Quality University Education "Breaking Away from Shallow Learning Habits" and Practice of Design Education in Department of Chemistry and Chemical Engineering Reviewed

    SHIMIZU Tadaaki, KODAMA Tatsuya, KIMURA Isao, YOSHIDA Masanori, KANEKO Takashi, TERAGUCHI Masahiro

    Journal of Jsee   59 ( 1 )   74 - 78   2011.3

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    An educational practice entitled "Breaking Away from Shallow Learning Habits" of the Faculty of Engineering, Niigata University is adopted as "Good Practice (GP) of Education" by The Ministry of Education, Culture, Sports, Science and Technology. This practice consists of a new introductory educational program for freshmen entitled "Introduction to Engineering Literacy" , as well as improvement of other lectures/experimentations/exercises for design education. "Introduction to Engineering Literacy" of The Department of Chemistry and Chemical Engineering, is programmed to let the students make "failure" (discrepancy from the knowledge obtained from the textbooks) in experiments, let them propose improvement, and let them conduct the same experiment again after the improvement, so that the freshmen can experience a PDCA (Plan-Do-Check-Action) cycle.

    DOI: 10.4307/jsee.59.2_74

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  • New Achiral Phenylacetylene Monomers Having an Oligosiloxanyl Group Most Suitable for Helix-Sense-Selective Polymerization and for Obtaining Good Optical Resolution Membrane Materials Reviewed

    Lijia Liu, Yu Zang, Shingo Hadano, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Takeshi Namikoshi

    MACROMOLECULES   43 ( 22 )   9268 - 9276   2010.11

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    To develop new phenylacetylene monomers more suitable for helix-sense selective polymerization (HSSP) we reported previously and to improve the efficiency of the HSSP and membrane performance of the resulting polymers, novel phenylacetylenes having a flexible oligosiloxanyl group (SnBDHPA) together with the other related three series of monomers were synthesized and polymerized by using a chiral catalytic system and enantioselectivity in permeation of the membranes from the resulting chiral polymers were examined SnBDHPA was the most suitable for the HSSP and the CD absorptions (G values) of poly (SnBDHPA) were stronger and more stable than those of the corresponding polymers having rigid alkyl groups The polymers could be fabricated to flexible self supporting membranes by using solvent casting method In addition, enantioselectivity in permeation of one of poly(SnBDHPA) membranes was much higher than that of a poly(phenylacetylene) membrane having alkyl groups This was because the polymers having oligosiloxane groups had high regularity of structures, i e, chemical structures of the macromolecules such as one handedness and high order structures such as columnar contents in the membranes, and the membranes were flexible and had almost no defects These good properties as optical resolution membrane materials were caused by flexibility, hydrophobicity, and bulkiness of the oligosiloxane chains S3BDHPA having a trisiloxanyl group was found to be the best monomer for the HSSP and for obtaining good optical resolution membrane materials

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  • Three Mechanisms of Asymmetric Polymerization of Phenylacetylenes Having an L-Amino Ether Residue and Two Hydroxy Groups Reviewed

    Hongge Jia, Masahiro Teraguchi, Toshiki Aoki, Yunosuke Abe, Takashi Kaneko, Shingo Hadano, Takeshi Namikoshi, Tomoyuki Ohishi

    MACROMOLECULES   43 ( 20 )   8353 - 8362   2010.10

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    Three novel chiral phenylacetylenes having in octyloxyethanolamine residue derived from a L-aminoalcohol and two hydroxymethyl groups were synthesized and polymerized by two achiral catalysts ((nbd)Rh(+)[eta(6)-(C(6)H(5))B(-)(C(6)H(5))(3)] and [Rh(nbd)Cl](2)/triethylamine (TEA)) and a chiral catalytic system ([Rh(nbc)Cl](2)/(S)- or (R)-phenylethylamine ((S)- or (R())-PEA)). All of the resulting polymers showed Cotton effects at wavelengths around 430 nm. This observation indicated that they had an excess of one-handed helical backbones. Positive and negative Cotton effects were observed for the polymers having an L-valinol residue produced by using (S)- and (R)-PEA as it cocatalyst, respectively, although the monomers had the same chirality. The two polymers having in L-aliminol or L-phenylalaninol residues obtained by using (S)- and (R)-PEA as a cocatalyst showed CD absorptions with identical signs. Therefore, we found that the chiral monomer having an L-valinol residue was suitable for both modes of asymmetric polymerization, that is, helix-sense-selective polymerization (HSSP) with the chiral catalytic system and asymmetric-induced polymerization (AIP) with the achiral catalysts. However, the other two monomers having an L-alaninol or L-phenylalaninol residue were not suitable for HSSP because the helix sense could not be controlled by the chirality of PEA. To explain the unexpected behaviors in the asymmetric polymerizations of the two chiral monomers having a chiral bidentate ligand, a novel third mechanism of asymmetric polymerization, that is, self-helix-sense-selective polymerization (SHSSP), is proposed in this Article. This Article discusses the contribution of the three mechanisms (AIP, HSSP, and SHSSP) in asymmetric polymerizations of the three monomers.

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  • Synthesis and helix-sense-selective polymerization of a novel phenylacetylene having a trisiloxanyl group and two hydroxyl groups and enantioselective permeability of the resulting chiral polymeric membrane: Effect of the trisiloxanyl group on the polymerization and enantioselective permeability Reviewed

    Lijia Liu, Yoshiyuki Oniyama, Yu Zang, Shingo Hadano, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Takeshi Namikoshi, Edy Marwanta

    POLYMER   51 ( 12 )   2460 - 2464   2010.5

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    To develop a new phenylacetylene monomer suitable for helix-sense-selective polymerization (HSSP) we reported previously and to improve the efficiency of the HSSP and membrane performance of the resulting polymer, a novel phenylacetylene having a trisiloxanyl group (S3BDHPA) was synthesized and polymerized by using a chiral catalytic system and enantioselectivity in permeation of its membrane was examined. S3BDHPA was suitable for the HSSP and the CD absorption of poly(S3BDHPA) was stronger and more stable than that of the corresponding polymer having no siloxanyl groups. In addition, enantioselectivity in permeation of poly(S3BDHPA) was much higher than that of a polymer membrane having no siloxanyl groups. They are thought to be caused by the flexibility and hydrophobicity of the trisiloxane groups. (C) 2010 Elsevier Ltd. All rights reserved.

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  • Helix-Sense-Selective Polymerization of Achiral Phenylacetylenes and Selective Cyclicaromatization of the Resulting Cis-Cisoidal Poly(phenylacetylene)s Invited

    Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    22nd International Symposium on Chirality (ISCD-22), Pre-Symposium, Molecular Chirality 2010   2010

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  • Optically active helical structure and magnetic interaction of poly(phenylacetylene)-based polyradicals Reviewed

    Takashi Kaneko, Hiroo Katagiri, Yasuhiro Umeda, Takeshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Toshiki Aoki

    POLYHEDRON   28 ( 9-10 )   1927 - 1929   2009.6

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    We synthesized optically active polyradicals possessing an excess of one-handed helical backbone by helix-sense-selective polymerization (HSSP) of achiral monomers which was promoted by rhodium complex catalyst in the presence of (R)- or (S)-1-phenylethylamine. The monomer, which had two hydroxy groups and a hydrogalvinoxyl unit, gave the corresponding polymer with an optically active helical conformation stabilized by intramolecular hydrogen bonding. The chemical oxidation of the polymer yielded the corresponding optically active helical polyradical with high spin concentration. The static magnetic susceptibility of the chiral polyradical was measured using a SQUID magnetometer. We have found that the stronger antiferromagnetic interaction was observed for the polyradical synthesized by HSSP in comparison with the polyradical via polymerization in the presence of racemic phenylethylamine. (C) 2008 Elsevier Ltd. All rights reserved

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  • Synthesis of poly(1,3-phenyleneethynylenes) membranes having one-handed helical conformation without any chiral side groups by in-situ desubstitution of D-menthoxy groups Reviewed

    Makoto Inoue, Masahiro Teraguchi, Toshiki Aoki, Shingo Hadano, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko

    SYNTHETIC METALS   159 ( 9-10 )   854 - 858   2009.5

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    In this study, we synthesized four chiral helical poly(phenyleneethynylenes) having optically active menthoxycarbonyl groups and desubstituted the chiral groups in membrane state. Polycondensations of (+)-menthyl 3,5-diethynylbenzoate with (+)-menthyl 3,5-diiodobenzoate, 1,2-diiodobenzenen, 1,3-diiodobenzene, and 1,4-diiodobenzene using PdCl(2)(PPh(3))(2)-PPh(3)-Cul were afforded helical polymers in good yields (named as PMtMt, o-PMtH, m-PMtH, and p-PMtH, respectively). Among them, PMtMt in a mixture of chloroform/benzene showed the largest Cotton effect in absorption region and gave self-supporting membrane by solvent-casting method. PMtMt membrane also showed a Cotton signal similar to that observed in solution. Desubstitution of PMtMt proceeded quantitatively by immersing the membrane into alkaline solution at room temperature for 3 days. The desubstituted PMtMt membrane showed circular dichroism (CD) signals similar shape to that of the original membrane in the UV region in despite of the polymer having no chiral moieties except for helical conformation. This is the first example of synthesis of chiral helical poly(phenyleneethynylenes) without the coexistence of any other chiral moieties. (C) 2009 Elsevier B.V. All rights reserved.

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  • Synthesis of an optically active poly(aryleneethynylene) bearing galvinoxyl residues and its chiroptical and magnetic properties Reviewed

    Takashi Kaneko, Hiromasa Abe, Takeshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Toshiki Aoki

    SYNTHETIC METALS   159 ( 9-10 )   864 - 867   2009.5

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    We synthesized an optically active poly(binaphthyl-6,6&apos;-diylethynylene-1,3-phenyleneethynylene) with pendant galvinoxyl residues. The hydrogalvinoxyl precursor polymer was given by polymerization of (1,3-diiodophenyl)hydrogalvinoxyl and 6,6&apos;-diethynyl-2,2&apos;-dihexyloxybinaphthyl using Pd(PPh(3))(4) catalyst (M(w) = 4.6 x 10(4), M(w)/M(n) = 30). The polymer yielded the corresponding polyradical with high spin concentration by treatment of the polymer solution with PbO(2). In the CD spectra of the polymer and polyradical taken in various solutions, clear Cotton effects were observed in the absorption region of the binaphthyl chromophore, while no Cotton effect was observed in that of the galvinoxyl chromophore. On the other hand, in the MCD, Faraday effects were observed in the absorption region of the backbone and galvinoxyl chromophore. The static magnetic susceptibility of the chiral polyradical was measured using a SQUID magnetometer, and showed weak antiferromagnetic interaction. (C) 2009 Elsevier B.V. All rights reserved.

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  • Helix-Sense-Selective Polymerization of Achiral Bis(hydroxymethyl)phenylacetylenes Bearing Alkyl Groups of Different Lengths Reviewed

    Shingo Hadano, Takuya Kishimoto, Tomonori Hattori, Daisuke Tanioka, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko, Takeshi Namikoshi, Edy Marwanta

    MACROMOLECULAR CHEMISTRY AND PHYSICS   210 ( 9 )   718 - 727   2009.5

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    4-Alkyloxy-3,5-bis(hydroxymethyl)phenylacetylenes with eight types of alkyl groups were synthesized and polymerized with a chiral catalytic system. We found that the length of the alkyl groups played a very important role in achieving helix-sense-selective polymerization. Five helix-sense-selective polymerizations were achieved resulting in polymers with alkyl groups whose chain length was longer than six. We think that the longer-chain alkyl groups prevented the polymers from becoming insoluble by forming intermolecular hydrogen bonds between the hydroxyl groups, and stabilized their one-handed helical structure by promoting the formation of intramolecular hydrogen bonds.

    DOI: 10.1002/macp.200800594

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  • Two Modes of Asymmetric Polymerization of Phenylacetylene Having a L-Valinol Residue and Two Hydroxy Groups Reviewed

    Hongge Jia, Masahiro Teraguchi, Toshiki Aoki, Yunosuke Abe, Takashi Kaneko, Shingo Hadano, Takeshi Namikoshi, Edy Marwanta

    MACROMOLECULES   42 ( 1 )   17 - 19   2009.1

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    DOI: 10.1021/ma802313z

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  • Phenyleneethynylene Macrocycle-Fused Phenylacetylene Monomers: Synthesis and Polymerization Reviewed

    Takashi Kaneko, Takahiro Horie, Shinji Matsumoto, Masahiro Teraguchi, Toshiki Aoki

    MACROMOLECULAR CHEMISTRY AND PHYSICS   210 ( 1 )   22 - 36   2009.1

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    Phenyleneethynylene macrocycle-substituted acetylenes were synthesized by repetition of the Sonogashira coupling reaction, and the elimination reaction of the terminal acetylene protecting group. The monomers were polymerized with a rhodium catalyst, [Rh(nbd)Cl](2), at the terminal acetylene unit, and the polymerization mixtures were purified by precipitating into methanol to yield the corresponding poly(phenylacetylene) derivatives as yellow-red powders, which had a high degree of polymerization ((DP) over bar approximate to 500) in spite of their steric bulkiness. The trimethylsilyl and pentamethyldisiloxanyl groups of polymers improved their solubility, and the polymers were soluble in common organic solvents, such as toluene, chloroform and tetrahydrofuran.

    DOI: 10.1002/macp.200800429

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  • Copper(I) iodide accelerates catalytic activation in rhodium complex-catalyzed helix-sense-selective polymerization of achiral phenylacetylene monomers Reviewed

    Hiroo Katagiri, Takashi Kaneko, Masahiro Teraguchi, Toshiki Aoki

    CHEMISTRY LETTERS   37 ( 4 )   390 - 391   2008.4

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    Achiral phenylacetylene monomers were polymerized using a rhodium (Rh) complex catalyst in the presence of (S)1-phenylethylamine. Addition of copper(I) iodide (CuI) into the catalytic system improved the polymer yield. The monomer, which had two hydroxy groups and a hydrogalvinoxyl unit, gave the corresponding polymer with an optically active helical conformation stabilized by intramolecular hydrogen bonding. The chemical oxidation of the polymer yielded the corresponding optically active helical polyradical with high spin concentration.

    DOI: 10.1246/cl.2008.390

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  • Helix-sense-selective polymerization of trimethylsilyl or siloxanyl group containing monomer

    Liu Lijia, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    2008 Niigata-Inha Joint Symposium on Advanced Polymeric Materials   6   2008

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  • Synthesis of Chiral Helical Poly(phenyleneethynylene) Membranes by Desubstitution of Chiral Group /2008 Niigata-Inha Joint Symposium on Advanced Polymeric Materials

    Makoto Inoue, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    2008 Niigata-Inha Joint Symposium on Advanced Polymeric Materials   3   2008

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  • Function of one-handed helical backbone of polyphenylacetylenes Invited

    Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    The 5th International Symposium on Advanced Materials in Asia-Pacific Rim (5th ISAMAP)   2008

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  • Synthesis and Properties of Chiral Polyphenylacetylenes Having their Chiral Structures Only in the Backbone Invited

    Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    International Symposium on Polymer Chemistry (PC'2008, Hefei)   2008

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  • Helix-sense tunability induced by achiral diene ligands in the chiral catalytic system for the helix-sense-selective polymerization of achiral and bulky phenylacetylene monomers Reviewed

    Takashi Kaneko, Yasuhiro Umeda, Honge Jia, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    MACROMOLECULES   40 ( 20 )   7098 - 7102   2007.10

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    Helix-sense-selective polymerization of {4-[(3,5-di-tert-butyl-4-hydroxyphenyl)(3,5-di-tert-butyl-4-oxo-cyclohexa-2,5-dienylidene)methyl]phenyl}acetylene (abbreviated as (4-ethynylphenyl)hydrogalvinoxyl) was promoted by [Rh(cod)Cl](2) and [Rh(nbd)Cl](2) catalyst in the presence of (R)-(+)-1-phenylethylamine or (S)-(-)-1-phenylethylamine (PEA). The [Rh(cod)C](2) Catalyst system gave red polymers whose CD spectra showed the stronger Cotton effect though the yield (2-3%) and molecular weight (M-n = (1.1 - 1.4) x 10(4)) were lower than those of polymers obtained by [Rh(nbd)Cl](2). Moreover, we investigated the effect of bulkiness of the catalyst, cocatalyst, and monomer on helix-sense-selective polymerization of (4-ethynylphenyl)hydrogalvinoxyl in the presence of (R)-PEA. The CD patterns of polymers obtained by [Rh(nbd)Cl](2) and [Rh(cod)Cl](2) were nearly mirror image of each other, except for the magnitudes of the signals in spite of the same chiral condition, i.e., in the presence of (R)-PEA. That is, [Rh(nbd)Cl](2) and [Rh(cod)Cl](2) catalysts generated P-helix and M-helix, respectively. This is a novel result, since the control of helix sense is usually achieved by enantiomeric moieties of catalysts or initiators for the helix-sense-selective polymerization.

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  • Efficient charge transport through a metal oxide semiconductor in the nanocomposite film with tris(2,2 '-bipyridine)ruthenium(II) Reviewed

    Koji Sone, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki, Masayuki Yagi

    JOURNAL OF PHYSICAL CHEMISTRY C   111 ( 31 )   11636 - 11641   2007.8

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    A nanocomposite film of tungsten trioxide (WO3) and [Ru(bpy)(3)](2+) (bpy = 2,2'-bipyridine) (denoted as Ru-WO3) was prepared from an aqueous colloidal triad solution containing peroxotungstic acid, [Ru(bpy)(3)](2+), and poly(sodium 4-styrenesulfonate) by an electrodeposition technique. The electrochemical features of the Ru-WO3 film were investigated using cyclic voltammetry (CV) and potential-step chronoamperospectrometry (PSCAS) techniques, compared with those in a [Ru(bpy)(3)](2+)/Nafion (Ru-Nf) film. PSCAS data spectrophotometrically showed that Ru-II is completely oxidized for 0.3 s in the Ru-WO3 film, in contrast to the corresponding reaction completed for 30 s in the Ru-Nf film. The apparent diffusion coefficient (D-app = (0.1-1.1) x 10(-7) cm(2) s(-1)) for charge transport (CT) by a Ru-II/Ru-III redox in the Ru-WO3 film was higher than that (2.4 x 10(-10) cm(2) s(-1)) in the Ru-Nf film by 2 or 3 orders of magnitude. Activation energy (E-a) for CT (14.1 kJ mol(-1)) for the Ru-WO3 film was 3.5 times lower than that (E-a = 49.8 kJ mol(-1)) for the Ru-Nf film. The lower E-a could be responsible for the faster CT in the Ru-WO3 film than the Ru-Nf film. D-app in the Ru-WO3 film increased linearly with an increase of the final applied potential (E-f) for PSCAS from 1.2 to 1.5 V vs SCE and saturated above E-f = 1.5 V. The mechanism for CT in the Ru-WO3 film is proposed, in which electrons are injected from [Ru(bpy)(3)](2+) into the conduction band (CB) of WO3 and go through there to a collector electrode.

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  • Electrochemical and photosensitized redox reactions of a Prussian blue film layered on a WO3/[Ru(bpy)(3)](2+)/polymer hybrid film Reviewed

    Koji Sone, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki, Masayuki Yagi

    CHEMPHYSCHEM   8 ( 9 )   1357 - 1362   2007.6

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    A hybrid film of WO3/tris(2,2'-bipyridine)ruthenium(II) ([Ru(bpy)(3])(2+)) /poly(sodium 4-styrenesulfonote) (PSS) (denoted as a WRP hybrid film) was prepared as a base layer on an indium tin oxide electrode substrate by cathodic electrodeposition from a colloidal ternary solution containing peroxotungstic acid, [Ru(bpy)(3)](2+), and PSS. Prussian blue, Fe-4(III)[Fe-II(CN)(6)](3) (Fe-II-Fe-III) was cathodically electrodeposited on the WRP hybrid film from a Berlin brown (Fe-II-Fe-III) colloidal solution to give a WRP/Fe-II-Fe-III biloyer film. Spectrocyclic voltammetry measurement of the WRP/ Fe-II-Fe-III bilayer film reveals that Prussian white (Fe-II-Fe-III) is oxidized to Fe-II-Fe-III by electrogenerated Ru-III, and Fe-II-Fe-III is re-reduced to Fe-II-Fe-III by electrogenerated HxWO3. Visible-light irradiation of the WRP hybrid film generates a small photocurrent (approximate to 8 nA cm(-2)) at 0.4 V of an applied potential, whereas irradiation of the WRP/Fe-II-Fe-III bilayer film (Fe-II-Fe-III is electrochemically reduced to the Fe-II-Fe-III state) significantly generates a steady photoonodic current of 2.0-1.1 mu A cm(-2) under the some conditions, thus demonstrating that the photoanodic current is produced by the layered Fe-II-Fe-III film. The photoaction spectrum of the bilayer film reveals that the photoanodic current is based on the photoexcitation of [Ru(bpy)(3)](2+). The photogeneration of Fe-II-Fe-III from Fe-II-Fe-III is shown by the absorption spectral change of the bilayer film on irradiation. These results corroborate the notion that Fe-II-Fe-III is oxidized by photogenerated Ru-III to generate Fe-II-Fe-III. However, the rote of photogenerotion of Fe-II-Fe-III is slow, which could be ascribed to the fast back electron transfer (ET) from WO3 to Ru-III, comparable with the forward ET from Fe-II-Fe-III to Ru-III. The fast back ET could be a crucial problem for the [Ru(bpy)(3)](2+)-sensitized reaction in the hybrid film.

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  • Synthesis of an optically active helical poly(1,3-phenyleneethynylene) bearing stable radicals and its chiroptical and magnetic properties Reviewed

    Takashi Kaneko, Shota Yoshimoto, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    POLYHEDRON   26 ( 9-11 )   1825 - 1829   2007.6

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    We synthesized an optically active helical poly(1,3-phenyleneethynylene) with pendant galvinoxyl residues and dimethyl(10-(1S)pinanyl)silyl groups. The hydrogalvinoxyl precursor polymer was given by polymerization of (1,3-diiodophenyl)hydrogalvinoxyl and 1,3-diethynyl-5-[dimethyl(10-(1S)-pinanyl)silyl]benzene using Pd(PPh3)(4) catalyst (M-w = 1.7 x 10(5), M-w/M-n = 3.7). In the CD spectrum taken in ethyl acetate solution, clear Cotton effects were observed in the absorption region of the backbone and hydrogalvinoxyl chromophore, indicating an excess of one-handed helical foldamer conformation. The polymer yielded the corresponding polyradical with high spin concentration by treatment of the polymer solution with PbO2. The Cotton effects appeared in CD spectra of the polymer and polyradical by addition of methanol to the chloroform solution, although the Cotton effects were hardly observed in chloroform. On the other hand, in the MCD spectra of the polymer and polyradical taken in chloroform solution, Faraday effects were observed in the absorption region of the backbone and galvinoxyl chromophore. The static magnetic susceptibility of the chiral polyradical was measured using a SQUID magnetometer, and showed the antiferromagnetic interaction. (c) 2006 Elsevier Ltd. All rights reserved.

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  • Enantioselective permeability through membranes from a poly(substituted phenylacetylene) having a chiral helical backbone and achiral bidentate ligands as pendant groups Reviewed

    Shingo Hadano, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    CHEMISTRY LETTERS   36 ( 2 )   220 - 221   2007.2

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    A chiral helical poly(phenylacetylene) bearing N-(2-hydoroxyethyl)aminomethyl groups as ligand sites was synthesized by helix-sense-selective polymerization. In the obtained polymeric membrane, the ligands could complex with Cu2+. In permeation of aqueous solution of racemic phenylalanine, enantioselectivity in permeation through the Cu2+ complexing membrane was about 3 times higher than that of the original membrane.

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  • Helix-Sense-Selective Polymerization of Disiloxane and Trisiloxane Containing Monomer

    Lijia Liu, Shingo Hadano, Yuya Hoshi, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Proceedings of International Symposium on Fusion Technology 2006-2007 at Niigata   2007.1

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  • Helix-sense-selective copolymerization of phenylacetylene having two silanol groups and chemical fixation of ladder chiral double helical structure of the resulting copolymer

    Shingo Hadano, Kazuo Futamata, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    International Symposiumon Fusion Tech 2006-2007   41   2007

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  • Electrochemical and photosensitized redox reactions of a Prussian blue film layered on a WO3 / tris(2,2'-bipyridine)ruthenium(II) / polymer hybrid film

    Koji Sone, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki, Masayuki Yagi

    International Symposiumon Fusion Tech 2006-2007   38   2007

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  • Synthesis of optically active helical polyacetylenes bearing stable radicals via helix-sense-selective polymerization

    Takashi Kaneko, Yasuhiro Umeda, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    International Symposiumon Fusion Tech 2006-2007   40   2007

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  • Synthesis of poly(phenylacetylene)-based polydendrons consisting of a phenyleneethynylene repeating unit, and oxygen/nitrogen permeation behavior of their membranes Reviewed

    T Kaneko, K Yamamoto, M Asano, M Teraguchi, T Aoki

    JOURNAL OF MEMBRANE SCIENCE   278 ( 1-2 )   365 - 372   2006.7

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    Monodendrons consisting of m-linked phenyleneethynylene repeating unit with trimethylsilyl-, pentamethyldisiloxanyl- and nonamethyltetrasiloxanyl-peripheral groups were synthesized using the convergent approach. The focal point of monodendrons, terminal acetylene, was polymerized with rhodium catalyst to yield corresponding polydendrons with a high molecular weight. The polydendrons were solubile in common organic solvents, and readily formed membranes. Oxygen permselectivity was improved in the polydendrons with a space-persistent dendritic crowd. It was found that the well-defined dendritic and rod-like structure of the polydendrons was useful for pemselective membrane. Oxygen permselectivity was increased in polydendrons with a trimethylsilyl group compared to the corresponding zero generation poly(phenylacetylene) derivatives. (c) 2005 Elsevier B.V. All rights reserved.

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  • Synthesis of optically active helical polymers bearing stable radicals via helix-sense-selective polymerization of phenylacetylenes Reviewed

    Kancko Takashi, Umeda Yasuhiro, Hadano Shingo, Teraguchi Masahiro, Aokil Toshiki

    WMSCI 2006: 10TH WORLD MULTI-CONFERENCE ON SYSTEMICS, CYBERNETICS AND INFORMATICS, VOL III, PROCEEDINGS   8   2006

  • Analysis and regulation of unusual adsorption of phthalocyanine zinc(II) into a Nafion film as investigated by UV-vis spectroscopic techniques Reviewed

    T Kuwabara, M Teraguchi, T Kaneko, T Aoki, M Yagi

    JOURNAL OF PHYSICAL CHEMISTRY B   109 ( 44 )   21202 - 21208   2005.11

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    Phthalocyanine zinc(II) (ZnPc) was found to be adsorbed well into a Nafion (Nf) film. The kinetic analysis suggested that the adsorption of ZnPc into the Nf film is controlled by its diffusion in the Nf film with a diffusion coefficient of D = 1.9 x 10(-6) cm(2) s(-1) that is higher than those (10(-9)-10(-12) cm(2) s(-1)) of cationic redox molecules in the Nf film by 3-6 orders of magnitude. The adsorption isothermal was analyzed by a Brunauer-Emmett-Teller (BET) equation suggesting multilayer adsorption of ZnPc into the film. The BET analysis provided the amount of ZnPc for monolayer adsorption (w(m) = 1.50 x 10(-7) mol cm(-2)), from which the effective area for the ZnPc adsorption was estimated to be larger by a factor of 1.7 x 103 than the Nf film area (1.0 cm(2)). The absorption spectra of a Nf film adsorbing ZnPc ((Nf/ZnPc)(ads) film) exhibited two broad absorption bands at 385 and 680-750 nm without any structural features, which is significantly different from the absorption spectra of either ZnPc solution in DMF or a (Nf/ZnPc)(mix) film prepared from a DMF solution containing Nf and ZnPc by solvent evaporation. This is ascribed to the formation of a ZnPc aggregate in the (Nf/ZnPC)(ads) film. Photoluminescence data for the (Nf/ZnPc)(mix) film suggested the presence of a ZnPc monomer and dimer at equilibrium in the film with a concentration of 0.1 M and that energy transfer occurs from the monomer to the dimer in excitation of the monomer (at A x = 609 nm) to yield emission from the dimer. By contrast, photoluminescence data for the (Nf/ZnPc)(ads) film suggested that the excited ZnPc is self-quenched significantly by the formation of the ZnPc aggregate in the film. The lesser electroactivity of ZnPc in the (Nf/ZnPc)(ads) film compared with that in the (Nf/ZnPc)(mix) film could be ascribable to more difficult diffusion of ZnPc in the former film due to the formation of the ZnPc aggregate. The adsorption of ZnPc into the Nf film was significantly regulated by simple pretreatments of the Nf film such as immersion in solvents and storage under solvent vapors. The regulation was explained by controlled physical and chemical properties of a channel for mass and ion transport that is formed by sulfonate groups, countercations, and solvent molecules in the Nf film.

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  • Synthesis and magnetic characterization of monodisoerse oligo(9, 10-anthryleneethynylene)-based polyradicals with two pendant stable phenoxyls in one anthracene skeleton Reviewed

    T Kaneko, A Onuma, H Ito, M Teraguchi, T Aoki

    POLYHEDRON   24 ( 16-17 )   2544 - 2549   2005.11

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    We synthesized monodisperse oligo(9,10-anthryleneethynylene)s with pendant phenol residues at the 2- and 7-positions. The absorption maxima of oligomers shifted to longer wavelength with the degree of polymerization, suggesting a developed pi-conjugation correlated with the chain length. The static magnetic susceptibility of the dimeric radical was measured using a SQUID magnetometer, and the 2J (J: spin coupling constant through the dianthrylacetylene unit) value of the dimeric radical was 34 cm(-1), which agreed with the 2J value of the corresponding 2-substituted dimeric radical (31 cm(-1)). These large 2J values of the dimeric radicals can be explained from less steric hindrance between the side chain radicals and the backbone. (c) 2005 Elsevier Ltd. All rights reserved.

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  • Assignment of helical sense for poly(phenylacetylene) bearing achiral galvinoxyl chromophore synthesized by helix-sense-selective polymerization Reviewed

    T Kaneko, Y Umeda, T Yamamoto, M Teraguchi, T Aoki

    MACROMOLECULES   38 ( 23 )   9420 - 9426   2005.11

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    {4-[(3,5-Di-tert-butyl-4-hydroxyphenyl)(3,5-di-tert-butyl-4-oxocyclohexa-2,5-dienylidene)methyl] phenyl}acetylene (abbreviated as (4-ethynylphenyl)hydrogalvinoxyl) was polymerized using [Rh(norbornadiene)Cl](2) catalyst in the presence of (R)-1-phenylethylamine or (S)-1-phenylethylamine to give red polymers. The circular dichroism (CD) spectra of polymers indicated that an excess of one-handed helical polyacetylene backbone was induced by helix-sense-selective polymerization under the asymmetric condition despite the achiral monomer. Results show that the CD signal intensity depends on temperature and decreases reversibly with increasing temperature, although the energy difference between the right-handed and left-handed conformations of each other is almost zero. The sign of the CD signal in the absorption region (420 nm) of the hydrogalvinoxyl chromophore, which was calculated from the polymer geometry, suggests that the excess of right-handed helix was induced by polymerization in the presence of (R)-1-phenylethylamine.

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  • Synthesis of chiral helical poly(hydroxyl-containing phenylacetylene) membranes by in-situ depinanylsilylation and their enantioselective permeabilities Reviewed

    M Teraguchi, K Mottate, SY Kim, T Aoki, T Kaneko, S Hadano, T Masuda

    MACROMOLECULES   38 ( 15 )   6367 - 6373   2005.7

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    Two new chiral helical poly(hydroxyl-containing phenylacetylene) membranes without the coexistence of any other chiral moieties were prepared in the following manner: (1) synthesis and homo-or copolymerization of two new chiral pinanylsiloxy-containing phenylacetylenes, (2) preparation of self-supporting membranes from the (co)poly(chiral pinanylsiloxy-containing phenylacetylene)s by a solvent-casting technique, and (3) depinanylsilylation of the preformed polymer membranes in situ. Complete depinanylsilylation was successfully achieved by treating with trifluoroacetic acid. The resulting membranes exhibited circular dichroism despite the absence of the chiral substituents, a fact indicating that the main chains of the polymers retained their chiral helicity. This is the first method to synthesizing such chiral poly(phenylacetylene) membranes. Since the membranes maintained their self-supporting properties, we were able to use them as enantioselective separation membranes in the permeation of an aqueous solution of a racemate. As a result, the importance of the contribution of the chiral main chain on enantioselective permeation was directly confirmed for the first time. In addition, since some of the depinanylsilylated membranes were insoluble in organic solvents, we could use them as an separation membrane for a toluene solution of a racemate.

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  • Helix-sense-selective polymerization of a phenylacetylene bearing an achiral and bulky galvinoxyl moiety Reviewed

    Y Umeda, T Kaneko, M Teraguchi, T Aoki

    CHEMISTRY LETTERS   34 ( 6 )   854 - 855   2005.6

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    An achiral and bulky phenylacetylene monomer, (4-ethynyl-phenyl)hydrogalvinoxyl), was polymerized using [Rh(nbd)Cl](2) (nbd = 2,5-norbornadiene) catalyst in chiral phenylethylamine. The circular dichroism (CD) spectra of the obtained polymers indicated that an excess of one-handed helical polyacetylene backbone was induced by helix-sense-selective polymerization despite the achiral monomer.

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  • Preparation of chiral polystyrene monoliths by utilizing W/O emulsion polymerization and their optical resolution ability Reviewed

    M Teraguchi, M Ohtake, H Inoue, A Yoshida, T Aoki, T Kaneko, K Yamanaka

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   43 ( 11 )   2348 - 2357   2005.6

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    We synthesized two kinds of chiral polystyrene-based monoliths, which are macroporous gel with continuous open-celled monolith structure. Thus, two chiral styrene monomers, (-)-p-[dimethyl(10-pinanyl)silyl] styrene ((-)-PSSt) and (-)-p-(menthoxycarbonyl)styrene ((-)-MtSt]), were prepared and subjected to water-in-oil emulsion polymerization in the presence of divinylbenzene and AIBN. The macroporous structure of the obtained monoliths was directly confirmed by SEM observation. The obtained monoliths showed an optical resolution ability. That is, in the enantioselective adsorption using trans-stilbene oxide, poly[(-)-PSSt] monolith and poly[(-)-MtSt] monoliths preferentially adsorbed (SS)-isomer [poly[(-)-PSStl monolith: &alpha;((S,S)) = 1.49 (0.25 wt % acetone solution); poly[(-)-MtSt] monolith: &alpha;((S,S)) = 1.39 (0.25 wt % toluene solution)]. Depinanylsilylation of the poly[(-)-PSStl monolith and removal of menthyl groups from the poly[(-)-MtSt] monolith were achieved by acid-catalyzed. scission of the Si-C bond and base-catalyzed hydrolysis, respectively. In addition, de-poly[(-)-PSSt] and de-poly[(-)-MtSt] showed enantioselectivity ((SS)-isomer preferentially absorbed) in adsorption using trans-stilbene oxide in spite of the absence of chiral substituents in the monoliths. &COPY; 2005 Wiley Periodicals, Inc.

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  • Specific ion exchange properties of a new porous ion exchange resin having an open-celled monolith structure Reviewed

    H Inoue, K Yamanaka, A Yoshida, A Nakamura, T Aoki, M Teraguchi, T Kaneko

    KOBUNSHI RONBUNSHU   62 ( 1 )   7 - 16   2005

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    A new porous ion exchange resin having an open-celled monolith structure was prepared and its ion exchange properties were examined. The new ion exchange resin was found to have the following advantages over the conventional ion exchange resins having bead structures. First, the new ion exchange resin has a high adsorption ability for the ions having low selectivity coefficients, and the ion exchange band length is smaller than that of the conventional resins. Second, in an electric field, the rejection time of the ions adsorbed to the new ion exchange resin was about one twentieth of that of the ions containing the conventional resins. These specific properties of the new ion exchange resin are attributable to the quantitative introduction of ion exchange groups into the resin having a uniform open-celled monolith structure.

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  • Specific ion exchange properties of a new porous ion exchange resin having an open-celled monolith structure Reviewed

    Hiroshi Inoue, Koji Yamanaka, Akiko Yoshida, Akira Nakamura, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    Kobunshi Ronbunshu   62 ( 1 )   7 - 16   2005

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    A new porous ion exchange resin having an open-celled monolith structure was prepared and its ion exchange properties were examined. The new ion exchange resin was found to have the following advantages over the conventional ion exchange resins having bead structures. First, the new ion exchange resin has a high adsorption ability for the ions having low selectivity coefficients, and the ion exchange band length is smaller than that of the conventional resins. Second, in an electric field, the rejection time of the ions adsorbed to the new ion exchange resin was about one twentieth of that of the ions containing the conventional resins. These specific properties of the new ion exchange resin are attributable to the quantitative introduction of ion exchange groups into the resin having a uniform open-celled monolith structure.

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  • Role of chiral amine cocatalysts in the helix-sense-selective polymerization of a phenylacetylene using a catalytic system Reviewed

    T Sato, T Aoki, M Teraguchi, T Kaneko, SY Kim

    POLYMER   45 ( 24 )   8109 - 8114   2004.11

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    We have examined the role of the chiral amine cocatalyst in the recently discovered helix-sense-selective polymerization of a phenylacetylene using a catalytic system consisting of an achiral rhodium complex ([Rh(norbornadiene)Cl](2)) as the catalyst and a chiral amine as the cocatalyst. Several chiral amines were effective for the polymerization reaction and their effectiveness depended on their bulkmess and coordination ability to rhodium. The sense selectivity of the polymerization increased with the concentration of the chiral amines. To discuss the structure of the true active species in the catalytic system, we have synthesized a new chiral rhodium complex having two chiral amines as ligands ([Rh (norbomadiene) (chiral amine)(2)]+BF4-). The isolated chiral complex also catalyzed the helix-senses-elective polymerization. These findings suggest that a chiral rhodium complex having two chiral amines may be the true active species when using the catalytic system consisting of [Rh(norbornadiene)Cl](2) and a chiral amine. (C) 2004 Elsevier Ltd. All rights reserved.

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  • Synthesis of chiral helical poly[p-(oligopinanylsiloxanyl)phenylacetylene]s and enantioselective permeability of their membranes Reviewed

    T Aoki, T Fukuda, KI Shinohara, T Kaneko, M Teraguchi, M Yagi

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   42 ( 18 )   4502 - 4517   2004.9

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    To develop better polymeric materials for optical-resolution membranes, we synthesized nine chiral phenylacetylenes containing pinanyl groups. We used them to investigate the effects of chemical structures, including the number and position of the chiral groups in the monomers, on the induction of chirality in the main chain during polymerization and on the degree of enantioselectivity in the permeation of the polymeric membranes. The monomers included six new chiral p-(oligomethylpinanylsiloxanyl)phenylacetylenes. The homopolymerizations of these nine monomers with a Rh complex produced high-molecular-weight polymers (molecular weight = 10(5)-10(6)). Of the five polymers with a chiral pinanyl group at the 1-position of each oligosiloxanyl group, all except for two polymers showed high molar ellipticity in the main-chain region in the circular dichroism spectra. This finding indicated that these polymers had a chiral helical main chain. The membranes fabricated from all the polymers synthesized in this study were high-quality, except for two polymers. All these membranes showed enantioselective permeabilities for two amino acids and an alcohol. The membranes from the polymers with a chiral helical backbone, a high content of pinanyl groups, no oligodimethylsiloxane moieties, or a combination of these showed good enantioselectivities ( = 1.7-640) in permeation. We propose that the sense of the main-chain helicity determined the selectivity. (C) 2004 Wiley Periodicals, Inc.

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  • Synthesis and cation exchange properties of a new porous cation exchange resin having an open-celled monolith structure Reviewed

    H Inoue, K Yamanaka, A Yoshida, T Aoki, M Teraguchi, T Kaneko

    POLYMER   45 ( 1 )   3 - 7   2004.1

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    We succeeded in introducing cation exchange groups quantitatively into a porous resin having an open-celled monolith structure. The resulting new cation exchange resin had the following advantages compared with conventional ion exchange resins having a bead structure. First, it was easier to pack it in a column. Second, the ion exchange rate of the new cation exchange resin was much higher than that of the conventional ion exchange resins, and the ion exchange band length of the new resin was smaller than that of the conventional ones. In addition, the electric conductivity was about five times higher than that of the conventional ones, although they had similar ion exchange capacities. These unique properties of the new cation exchange resin were caused by the quantitative introduction of ion exchange groups into the resin having the open-celled monolith structure. (C) 2003 Elsevier Ltd. All rights reserved.

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  • Synthesis and ion exchange properties of a new porous ion exchange resin having an open-celled monolith structure Reviewed

    Hiroshi Inoue, Koji Yamanaka, Akiko Yoshida, Toshiki Aoki, Takashi Kaneko, Masahiro Teraguchi

    Kobunshi Ronbunshu   61 ( 5 )   301 - 309   2004

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    We successfully introduced ion exchange groups quantitatively into a porous resin having an open-celled monolith structure. The resulting new ion exchange resin had the following advantages compared with conventional ion exchange resins having a bead structure. First, it was easier to pack it in a column. Second, the ion exchange rate of the new ion exchange resin was much higher than that of the conventional ion exchange resins, and the ion exchange band length of the new resin was smaller than that of the conventional ones. Third, the electric conductivity was about five times higher than that of the conventional ones, although they had similar ion exchange capacities. These unique properties of the new ion exchange resin were attributable to the quantitative introduction of ion exchange groups into the resin having the open-celled monolith structure. In addition, many kinds of ion-excharge resin monoliths from soft ones to hard ones were able to be prepared by changing the ratio of DVB.

    DOI: 10.1295/koron.61.301

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  • Synthesis and ion exchange properties of a new porous ion exchange resin having an open-celled monolith structure Reviewed

    H Inoue, K Yamanaka, A Yoshida, T Aoki, T Kaneko, M Teraguchi

    KOBUNSHI RONBUNSHU   61 ( 5 )   301 - 309   2004

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    We successfully introduced ion exchange groups quantitatively into a porous resin having an open-celled monolith structure. The resulting new ion exchange resin had the following advantages compared with conventional ion exchange resins having a bead structure. First, it was easier to pack it in a column. Second, the ion exchange rate of the new ion exchange resin was much higher than that of the conventional ion exchange resins, and the ion exchange band length of the new resin was smaller than that of the conventional ones. Third, the electric conductivity was about five times higher than that of the conventional ones, although they had similar ion exchange capacities. These unique properties of the new ion exchange resin were attributable to the quantitative introduction of ion exchange groups into the resin having the open-celled monolith structure. In addition, many kinds of ion-exchange resin monoliths from soft ones to hard ones were able to be prepared by changing the ratio of DVB.

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  • Enantioselective permeation through membranes of chiral helical polymers prepared by depinanylsilylation of poly(diphenylacetylene) with a high content of the pinanylsilyl group Reviewed

    M Teraguchi, J Suzuki, T Kaneko, T Aoki, T Masuda

    MACROMOLECULES   36 ( 26 )   9694 - 9697   2003.12

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    DOI: 10.1021/ma035493h

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  • Entropy effect on physical displacement of redox molecules in a naflon film as studied by double potential-step chronoabsorptometry Reviewed

    M Yagi, M Takahashi, M Teraguchi, T Kaneko, T Aoki

    JOURNAL OF PHYSICAL CHEMISTRY B   107 ( 46 )   12662 - 12667   2003.11

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    Charge transport (CT) in a Nafion film incorporating [(NH3)(5)Ru(mu-pz)Ru(NH3)(5)](4+) ([Ru-II-Ru-II](4+); pz = pyrazine) was studied using a double potential-step chronoabsorptometry (DPSCA) technique. The oxidative CT by [Ru-II-Ru-II](4+)/[Ru-II-Ru-III](5+) (in a potential step from -0.2 to 0.3 V; first step) was compared with that by [Ru-II-Ru-III](5+)/[Ru-III-Ru-III](6+) (in a successive potential step from 0.3 to 0.7 V; second step). The predominant CTs by a physical displacement mechanism of the complexes were suggested for both of the steps. However, the rate constant of the CT for the first step was 5.2 time higher than that for the second step at 25 degreesC. The results on CT kinetics and dynamics revealed that the CTs in both of the steps are entropy-controlled in the activation at room temperature. The DeltaH(double dagger) (12 kJ mol(-1)) for the physical displacement in the second step was lower than that (24 kJ mol(-1)) for the first step, showing that the physical displacement for the second step is enthalpically favorable compared with that for the first step. The corresponding DeltaS(double dagger) (-234 J K-1 mol(-1)) for the second step is lower than that (DeltaS(double dagger) = -184 J K-1 mol(-1)) for the first step, making the physical displacement for the second step more entropically difficult than that for the first step. The entropy effect on the physical displacement was discussed on the basis of the interaction of the complexes with Nafion and reorganization of the solvent (water) molecule involved in the process. The DeltaS(double dagger) for the physical displacement of redox complexes in the film decreased with the positive charge of the complexes, suggesting that the highly positive-charged complex is entropically unfavorable for physical displacement, presumably due to higher degree of solvation of the complex and the sulfonate groups in their dissociation.

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  • A poly(9, 10-anthryleneethynylene)-based polyradical designed to be a ladder-like ferromagnetic spin coupling network Reviewed

    T Kaneko, T Makino, H Miyaji, A Onuma, M Teraguchi, T Aoki

    POLYHEDRON   22 ( 14-17 )   1845 - 1850   2003.7

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    We synthesized monomers of poly(9,10-anthryieneethynylene)s which were anthracene derivatives substituted with one or two phenol residues at the P-position. The monomers were polymerized by Pd(0) catalyst to give the corresponding precursor polymer with (M) over bar (n) approximate to 5 X 10(3). The polyradicals were synthesized by oxidation of the hydroxyl group. The magnetization plots of the polyradicals showed that the average ground state spin quantum number of the polyradical with two pendant phenoxyls in one anthracene unit (S = 5/2) became larger than that of the polyradical with one pendant phenoxyl (S = 2/2) at the same spin concentration (spin cone.;approximate to 0.35 spin/phenoxyl unit). The statistical simulation of the ground spin states supported that this behavior was caused by ladder-like spin coupling network of the polyradical with two pendant phenoxyls in one anthracene unit. (C) 2003 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0277-5387(03)00251-1

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  • Helix-sense-selective polymerization of phenylacetylene having two hydroxy groups using a chiral catalytic system Reviewed

    T Aoki, T Kaneko, N Maruyama, A Sumi, M Takahashi, T Sato, M Teraguchi

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   125 ( 21 )   6346 - 6347   2003.5

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    DOI: 10.1021/ja021233o

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  • Ladderlike ferromagnetic spin coupling network on a pi-conjugated pendant polyradical Reviewed

    T Kaneko, T Makino, H Miyaji, M Teraguchi, T Aoki, M Miyasaka, H Nishide

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   125 ( 12 )   3554 - 3557   2003.3

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    A poly(9,10-anthryleneethynylene)-based polyradical with two pendant stable phenoxyls in one anthracene skeleton was newly synthesized via polymerization of the corresponding bromoethynylanthracene monomer using a Pd(0) catalyst. The average molecular weight of the polymer reached (M) over bar (n) = 5 x 103 and was soluble in common organic solvents. The polyradical was prepared from the corresponding hydroxyl precursor polymer and was appropriately stable at room temperature. The ESR spectrum of the corresponding monomeric radical suggested an effectively delocalized spin density distribution on the backbone anthracene. The magnetization and the static magnetic susceptibility of the polyradical were measured using a SQUID magnetometer. The large average spin quantum number ((S) over bar = 5/2) of the polyradical indicated that the ferromagnetic spin coupling network of the polyradical had spread throughout the pi-conjugated chain and that it was considerably insensitive to spin defects.

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  • Polymerization of diphenylacetylenes having a ferrocenyl group and polymer properties Reviewed

    M Teraguchi, T Masuda

    JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY   A40 ( 2 )   115 - 124   2003

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    Polymerization of two dipherylacetylenes having a ferrocenyl group at para or meta position, 1-[p-ferrocenylphenyl]-2-phenylacetylene (p-FcDPA) and 1-[m-ferrocenylphenyl]-2-phenyl-acetylene (m-FcDPA) and properties of the formed polymers were investigated. Both monomers polymerized with TaCl5-n-Bu4Sn catalyst in good yields to give reddish brown polymers. Poly(p-FcDPA) was insoluble in any solvents. On the other hand, poly(m-FcDPA) was soluble in CHCl3, THF, anisole, o-dichlorobenzene, and so on, and its weight-average molecular weight (M-w) was 53 x 10(4) and fairly high. A free-standing film of poly(m-FcDPA) could be easily fabricated by solution casting. The onset temperature of weight loss (T-0) of poly(m-FcDPA) in air was ca. 310degreesC, indicating moderate thermal stability. Poly(m-FcDPA) was electrochemically active, and showed redox cycles based on the ferrocene moiety in cyclic voltammetry.

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  • Synthesis and Properties of Polyacetylenes Having Substituted Azobenzene Pendant Groups Reviewed

    T. Nakai, S. M, Abdul Karim, M. Teraguchi, F. Sanda, T. Masuda

    J. Macromol. Sci., Part A: Pure and Appl. Chem.   39 ( 9 )   901 - 913   2002.12

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  • Gas permeability and n-butane solubility of poly(1-trimethylgermyl-1-propyne) Reviewed

    K Nagai, LG Toy, BD Freeman, M Teraguchi, G Kwak, T Masuda, Pinnau, I

    JOURNAL OF POLYMER SCIENCE PART B-POLYMER PHYSICS   40 ( 19 )   2228 - 2236   2002.10

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    The gas permeability and n-butane solubility in glassy poly(1-trimethyl-germyl-1-propyne) (PTMGP) are reported. As synthesized, the PTMGP product contains two fractions: (1) one that is insoluble in toluene and soluble only in carbon disulfide (the toluene-insoluble polymer) and (2) one that is soluble in both toluene and carbon disulfide (the toluene-soluble polymer). In as-cast films, the gas permeability and n-butane solubility are higher in films prepared from the toluene-soluble polymer (particularly in those films cast from toluene) than in films prepared from the toluene-insoluble polymer and increase to a maximum in both fractions after methanol conditioning. For example, in as-cast films prepared from carbon disulfide, the oxygen permeability at 35 degreesC is 330 x 10(-10) cm(3) (STP) cm/(cm(2) s cmHg) for the toluene-soluble polymer and 73 x 10(-10) cm(3) (STP) cm/(cm(2) s cmHg) for the toluene-insoluble polymer. After these films are conditioned in methanol, the oxygen permeability increases to 5200 x 10(-10) cm(3) (STP) cm/(cm(2) s cmHg) for the toluene-soluble polymer and 6200 x 10(-10) cm(3) (STP) cm/(cm(2) s cmHg) for the toluene-insoluble polymer. The rankings of the fractional free volume and nonequilibrium excess free volume in the various PTMGP films are consistent with the measured gas permeability and n-butane solubility values. Methanol conditioning increases gas permeability and n-butane solubility of as-cast PTMGP films, regardless of the polymer fraction type and casting solvent used, and minimizes the permeability and solubility differences between the various films (i.e., the permeability and solubility values of all conditioned PTMGP films are similar). (C) 2002 Wiley Periodicals, Inc.

    DOI: 10.1002/polb.10276

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  • Poly(diphenylacetylene) membranes with high gas permeability and remarkable chiral memory Reviewed

    M Teraguchi, T Masuda

    MACROMOLECULES   35 ( 4 )   1149 - 1151   2002.2

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    DOI: 10.1021/ma011537f

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  • Synthesis and properties of polyacetylenes having substituted azobenzene pendant groups Reviewed

    T Nakai, SMA Karim, M Teraguchi, F Sanda, T Masuda

    JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY   A39 ( 9 )   935 - 951   2002

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    Azobenzene-containing polyacetylenes, poly[(4-butoxyphenyl)(4-ethynylphenyl)diazene] [poly(BuOEAB)] and poly[4-(4-ethynylphenylazo)benzoic acid hexyl ester] [poly(HexOCOEAB)] with number-average molecular weights ranging from 2,800 to 104,000 were synthesized by the polymerization of the corresponding acetylene monomers by [RhCl(norbornadiene)](2) catalyst in conjunction with Et3N, Ph2C=C(Ph)Li, and PPh3 as cocatalysts in toluene and THF in good yields. The polymers exhibited thermogravimetric curves with inflection points corresponding to cleavage of butyl ether and hexyl ester groups. The trans-azobenzene moiety of poly(BuOEAB) isomerized into cis-form upon UV-irradiation at the wavelength of 300-400 nm both in solution and in the filmy state. Oil the other hand, poly(HexOCOEAB) did not isomerize under the same condition.

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  • 光学分割膜-分子設計と分離機構- Reviewed

    青木俊樹, 金子隆司, 寺口昌宏

    化学工業   52 ( 9 )   683 - 691   2001.12

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  • 光学異性体分離膜 Reviewed

    青木俊樹

    高分子   50 ( 2 )   92 - 98   2001.12

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    DOI: 10.1295/kobunshi.50.92

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  • Novel properties of conducting polymers containing azobenzene moieties in side chain Reviewed

    T. Matsui, T. Nagata, M. Ozaki, A. Fujii, M. Onoda, M. Teraguchi, T. Masuda, K. Yoshino

    Synthetic Metals   119 ( 1-3 )   599 - 600   2001.3

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    Photochromic characteristic and optical molecular reorientation in conducting polymers such as polyacetylene and poly(p-phenylenevinylene) derivatives containing photochromic azobenzene moieties in the side chain have been studied. Upon irradiation of a linearly polarized light on these films, accompanying with trans-cis isomerizasion of azobenzene, optical anisotropy is induced.

    DOI: 10.1016/S0379-6779(00)00692-5

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  • Gas permeability and free volume of highly branched substituted acetylene polymers Reviewed

    YP Yampolskii, AP Korikov, VP Shantarovich, K Nagai, BD Freeman, T Masuda, M Teraguchi, G Kwak

    MACROMOLECULES   34 ( 6 )   1788 - 1796   2001.3

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    Gas permeation, sorption, and structural properties of two highly branched polyacetylenes, poly [1-phenyl-2-[p-(triphenylsilyl)phenyl] acetylene] (PPhSiDPA) and poly [1-phenyl-2-[p-(triisopropylsilyl)phenyl] acetylene] (PPrSiDPA), are reported. Structurally, both polymers have much in common; however, their transport properties are quite different. PPhSiDPA has dramatically lower permeability coefficients than PPrSiDPA. For example, the Oz permeability coefficients of PPhSiDPA and PPrSiDPA are 12 x 10(-10) and 230 x 10(-10) cm(3) (STP) cm/(cm(2) s cmHg), respectively at 22 degreesC. Gas solubility is very high in PPrSiDPA, similar to that observed in poly(1-trimethysilyl-1-propyne) (PTMSP), the most permeable polymer known. Gas solubility coefficients of PPhSiDPA are 2-3 times lower than those of PPrSiDPA. Free volume size and size distribution were characterized using positron annihilation lifetime (PAL) spectroscopy. Results from these studies (i.e., a bimodal size distribution of free volume elements and large free volume element size) are consistent with the observed transport and sorption properties of PPrSiDPA. In contrast, the PAL spectrum of PPhSiDPA is similar to that of conventional low free volume glassy polymers.

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  • Fast Dynamics of Substituted Polyacetylenes in Glassy States and its Relation to Gas Permeability. Reviewed

    KANAYA T, TSUKUSHI I, KAJI K, TERAGUCHI M, KWAK G, MASUDA T

    J Phys Soc Jpn   70 ( Supplement A )   332 - 334   2001.3

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  • Exciton dynamics in disubstituted polyacetylenes Reviewed

    R Hidayat, A Fujii, M Ozaki, M Teraguchi, T Masuda, K Yoshino

    SYNTHETIC METALS   119 ( 1-3 )   597 - 598   2001.3

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    Exciton dynamics in luminescent poly(diphenylacetylene) (PDPA) derivatives with different substituents have been studied by time-resolved photoluminescence (PL) spectroscopy. Although their absorption and PL spectra are almost similar, PL of PDPA-nBu decays single-exponentially, whereas PL of PDPA-SiMe3 decays faster with a suppressed exponential decay function indicating exciton dissociation, In the case of PDPA-nBu mixed with a non-luminescent polyphenylacetylene (PPA) derivative, PL decay of PDPA-nBu is significantly shortened. The experimental results show the influences of side chains on exciton confinement in the backbone/main chain. Efficient PL in PDPA-nBu is a result of effective exciton confinement on the main chain, but excitons migration or energy transfer to another main chain segments may take places.

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  • Optical properties of disubstituted polyacetylene thin films Reviewed

    A. Fujii, R. Hidayat, T. Sonoda, T. Fujisawa, M. Ozaki, Z. V. Vardeny, M. Teraguchi, T. Masuda, K. Yoshino

    Synthetic Metals   116 ( 1-3 )   95 - 99   2001.1

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    We have studied the optical properties of thin films of novel disubstituted acetylene polymers such as poly(1-phenyl-2-p-n-butylphenylacetylene) (PDPA-nBu) and poly(1-n-hexyl-2-phenylacetylene) (PHxPA), that show high photoluminescence (PL) quantum efficiency in comparison with unsubstituted or monosubstituted polyacetylene. The polarization dependence of PL and Raman scattering of PDPA-nBu and PHxPA have been studied in order to clarify the emission mechanism. Assuming the model of short polyene conjugation length in the acetylene polymers, we estimate the average conjugation length from the respective stretching vibration frequency of the carbon double bond carbon double bond. The emission mechanism of PHxPA and PDPA-nBu is discussed in relation with the electronic excited states of these polymers.

    DOI: 10.1016/S0379-6779(00)00523-3

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  • Photoexcitations in disubstituted polyacetylene: solitons and polarons Reviewed

    I. Gontia, S.V. Frolov, M. Liess, Z.V. Vardeny, E. Ehrenfreund, K. Tada, H. Kajii, R. Hidayat, A. Fujii, K. Yoshino, M. Teraguchi, T. Masuda

    Synth. Met.   116(1-3)   91 - 94   2001

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  • Synthesis of poly(p-phenylene)-based photoresponsive conjugated polymers having azobenzene units in the main chain Reviewed

    A Izumi, M Teraguchi, R Nomura, T Masuda

    MACROMOLECULES   33 ( 15 )   5347 - 5352   2000.7

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    Poly(p-phenylene)-based novel conjugated polymers having photoisomerizable azobenzene units in the main chain were prepared by the palladium-catalyzed Suzuki coupling of 1,3-propanediol diesters of 1,4-phenylenediboronic acids with 4,4'-diiodoazobenzenes, and the reversible cis-trans isomerizations of azobenzene units were achieved. Despite their stiff structures, the polymers are soluble in common organic solvents such as chloroform, toluene, and tetrahydrofuran if either or both of the monomers possess n-hexyl side chains on the aromatic rings. The resulting polymers possess high molecular weights (M-n &gt; 7 x 10(3)) and are thermally stable (T-0 &gt; 350 degrees C) and fluorescent. The azobenzene units in the conjugated polymer backbone underwent the photochemical cis-trans reversible isomerizations in both tetrahydrofuran and toluene upon irradiation with UV light of appropriate wavelengths at 20 degrees C. The thermal cis-to-trans isomerization was also readily accomplished in toluene at 80 degrees C. Moreover, the solid-state photochemical trans-to-cis isomerization took place at 20 degrees C. These isomerization processes were accompanied by the change in the three-dimensional hydrodynamic volume of the polymer, which was evidenced by size exclusion chromatography.

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  • Gas permeability and hydrocarbon solubility of poly[1-phenyl-2-[p-(triisopropylsilyl) phenyl]acetylene] Reviewed

    Kazukiyo Nagai, Lora G. Toy, Benny D. Freeman, Masahiro Teraguchi, Toshio Masuda, Ingo Pinnau

    Journal of Polymer Science, Part B: Polymer Physics   38 ( 11 )   1474 - 1484   2000.6

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    The effects of film thickness, physical aging, and methanol conditioning on the solubility and transport properties of glassy poly[1-phenyl-2-[p-(triisopropylsilyl) phenyl]acetylene] are reported at 35 °C. In general, the gas permeability coefficients are very high, and this polymer is more permeable to larger hydrocarbons (e.g., C3H8 and C4H10) than to light gases such as H2. The gas permeability and solubility coefficients are higher in as-cast, unaged films than in as-cast films aged at ambient conditions and increase to a maximum in both unaged and aged as-cast films after methanol conditioning. For example, the oxygen permeability of a 20-μm-thick as-cast film is initially 100 barrer and decreases to 40 barrer after aging for 1 week at ambient conditions. After methanol treatment, the oxygen permeabilities of unaged and aged films increase to 430 and 460 barrer, respectively. Thicker as-cast films have higher gas permeabilities than thinner as-cast films. Propane and n-butane sorption isotherms suggest significant changes in the nonequilibrium excess free volume in these glassy polymer films due to processing history. For example, the nonequilibrium excess free volume estimated from the sorption data is similar for as-cast, unaged samples and methanol-conditioned samples
    it is 100% higher in methanol-conditioned films than in aged, as-cast films. The sensitivity of permeability to processing history may be due in large measure to the influence of processing history on nonequilibrium excess free volume and free volume distribution. The propane and n-butane diffusion coefficients are also sensitive to film processing history, presumably because of the dependence of diffusivity on free volume and free volume distribution.

    DOI: 10.1002/(SICI)1099-0488(20000601)38:11<1474::AID-POLB70>3.0.CO;2-6

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  • Pure-gas and vapor permeation and sorption properties of poly[1-phenyl-2-[p-(trimethylsilyl)phenyl]acetylene] (PTMSDPA) Reviewed

    L. G. Toy, K. Nagai, B. D. Freeman, I. Pinnau, Z. He, T. Masuda, M. Teraguchi, Yu P. Yampolskii

    Macromolecules   33 ( 7 )   2516 - 2524   2000.4

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    The pure-gas permeation and sorption properties of poly[1-phenyl-2-[p-(trimethylsilyl)phenyl]acetylene] [PTMSDPA] are presented and compared to those of poly(1-trimethylsilyl-1-propyne)[PTMSP], poly(4-methyl-2-pentyne) [PMP], and poly(1-phenyl-1-propyne) [PPP]. PTMSDPA is more permeable to large, condensable vapors (e.g., n-butane) than to small, permanent gases (e.g., hydrogen). Such behavior is also observed in PTMSP and PMP but not in PPP. PTMSDPA has lower fractional free volume (0.26) and gas permeabilities than PTMSP and PMP. However, relative to conventional glassy polymers, PTMSDPA is a highly permeable, high free volume, glassy material. For example, the oxygen permeability coefficient of PTMSDPA is 1200×10-10 cm3(STP)·cm/(cm2·s·cmHg) at 25 °C. As temperature increases, the permeability in PTMSDPA increases for light gases (helium, hydrogen, and nitrogen) and decreases for more condensable gases. In contrast, the permeabilities of PTMSP and PMP decrease with increasing temperature for both light gases and more condensable hydrocarbons, n-Butane and propane sorption isotherms for PTMSDPA are concave to the penetrant relative pressure axis, consistent with dual-mode sorption behavior. Hydrocarbon sorption levels decrease in the order PTMSP&gt
    PMP&gt
    PTMSDPA&gt
    PPP, in agreement with the ranking of the fractional free volumes of the materials.

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  • Synthesis of Conjugated Polymers with Azobenzene Moieties in the Main Chain Reviewed

    Atsushi Izumi, Masahiro Teraguchi, Ryoji Nomura, Toshio Masuda

    Journal of Polymer Science, Part A: Polymer Chemistry   38 ( 7 )   1057 - 1063   2000.4

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    Poly(phenylenevinylene)-based conjugated polymers with azobenzene groups in the main chains were prepared by the Pd-catalyzed coupling polymerization of divinylarenes with dihaloarenes. The Pd-catalyzed coupling polymerization of 4,4′-divinylazobenzene with dihaloarenes such as 1,3-dibromobenzene, 1,4-dibromo-2,5-dihexylbenzene, 4,4′-dibromoazobenzene, and 4,4′-diiodoazobenzene resulted in polymers with poor solubility. In contrast, soluble polymers containing azobenzene moieties in the main chains were attainable from divinylbenzenes with 4,4′-dihaloazobenzenes if either or both of the monomers possessed hexyl groups on the aromatic rings. The number-average molecular weight of the polymer exceeded 10,000 under optimized conditions, and the polymer showed a remarkably redshifted absorption in the visible region (456 nm). 1H NMR and IR spectra supported that the polymers having only trans-geometry for the double bonds. © 2000 John Wiley &amp
    Sons, Inc.

    DOI: 10.1002/(SICI)1099-0518(20000401)38:7<1057::AID-POLA2>3.0.CO;2-5

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  • Synthesis and properties of copolymers from 1-[3,5-bis(trimethylsilyl)phenyl]2-phenylacetylene Reviewed

    M Teraguchi, T Masuda, A Hachisuka

    JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY   37 ( 10 )   1173 - 1184   2000

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    Copolymerization of 1-[3,5-bis(trimethylsilyl)phenyl]-2phenyl-acetylene (m,m-(Me3Si)(2)DPA) with other diphenylacetylene derivatives and their copolymer properties were investigated. Homopolymerization of m,m-(Me3Si)(2)DPA by TaCl5-n-Bu4Sn (1:2) did not give the polymer due to steric hindrance. However, m,m-(Me3Si)(2)DPA copolymerized with diphenylacetylene (DPA), 1-phenyl-2-[p-(trimethylsilyl)phenyl] acetylene (p-Me3Si DPA), and 1-phenyl-2-[m-(trimethylsilyl)phenyl]acety-lene (mMe(3)SiDPA) in the presence of TaCl5-n-Bu4Sn at various feed ratios to give copolymers in moderate yields. The formed copolymers were yellow to orange solids, which were soluble in common organic solvents such as toluene and CHCl3. The highest weight-average molecular weights (M-w) of these copolymers reached ca. 6 x 105 and tough films could be obtained by solution casting. Their onset temperatures of weight loss in air were observed around 400 degrees C, indicating high thermal stability. The oxygen permeability coefficients at 25 degrees C of copoly(m,m-(Me3Si)(2) DPA/DPA) (feed ratio 1.1) and copoly(m,m-(Me3Si)(2)DPA/pMe(3)SiDPA) (feed ratio 1:2) were 21 and 100 barrers, respectively, medium in magnitude among polymers from substituted acetylenes.

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  • Time-resolved study of luminescence in highly luminescent disubstituted polyacetylene and its blend with poorly luminescent monosubstituted polyacetylene Reviewed

    Rahmat Hidayat, Satoshi Tatsuhara, Dong Wook Kim, Masanori Ozaki, Katsumi Yoshino, Masahiro Teraguchi, Toshio Masuda

    Physical Review B - Condensed Matter and Materials Physics   61 ( 15 )   10167 - 10173   2000

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    A highly luminescent disubstituted polyacetylene, poly(1-phenyl-2-(Formula presented)-butylphenylacetylene) (Formula presented) and its blend with a poorly luminescent monosubstituted polyacetylene, poly(1-(Formula presented)-trimethylsilylphenylacetylene) (Formula presented), are studied by time-resolved photoluminescence (PL) spectroscopy. In pure (Formula presented) PL intensity at short wavelength decays faster than that at long wavelength, whereas PL spectra exhibit a dynamic Stokes shift to longer wavelengths with time. In blends of PDPA-(Formula presented) only PL originating from (Formula presented) is observed, without contribution from (Formula presented) The PL lifetime drastically decreases upon mixing a small amount of (Formula presented) in (Formula presented) The PL characteristics of pure (Formula presented) and its blend with (Formula presented) are discussed in terms of lattice/vibrational relaxation of the excitonic state and exciton migration. © 2000 The American Physical Society.

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  • Synthesis and properties of copolymers from diphenylacetylene having a hexaphenylbenzene moiety Reviewed

    Masahiro Teraguchi, Toshio Masuda, Andreas Fechtenkötter, Klaus Müllen

    Polymer Bulletin   44 ( 3 )   255 - 260   2000

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    Copolymerization of diphenylacetylene having a hexaphenylbenzene group, 1-[p-(pentaphenyl)phenyl]-2-phenylacetylene (1), with a few other diphenylacetylene derivatives (i.e., diphenylacetylene, 1-phenyl-2-[p-(trimethylsilyl)phenyl]acetylene, 1-phenyl-2-[p-n-octylphenyl]acetylene, (2a-c, respectively) and properties of the formed copolymers were investigated. No polymer was obtained in homopolymerization of 1 with TaCl5-n-Bu4Sn catalyst owing to steric hindrance. On the other hand, copolymerization with 2a-c proceeded at various feed ratios to give copolymers in moderate yields. Copoly(1/2a) (feed ratio 25/75) was soluble in toluene and CHCl3 and its weight-average molecular weight (MW) was ca. 31 x 104 and relatively high. Copoly(1/2b) and copoly(1/2c) (both feed ratios 5/95) were soluble in common organic solvents, and had a large MW up to ca. 1 x 106. These copolymers were yellow to orange solids. Oxidative cyclodehydrogenation of hexaphenylbenzene groups in copoly(1/2a) was attempted in order to convert them into more conjugated groups.

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  • Synthesis and properties of polyacetylenes having azobenzene pendant groups Reviewed

    Masahiro Teraguchi, Toshio Masuda

    Macromolecules   33 ( 2 )   240 - 242   2000

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    Polyacetylenes with azobenzene moieties [poly(3-ethynylazobenzene) and poly(4-ethynylazobenzene)] were obtained by polymerization using [(nbd)RhCl]2-Et3N. The results are the first example of synthesis of polyacetylenes with azobenzene moieties directly connected to the main chain. Though poly(4-ethynylazobenzene) was insoluble in any solvents, poly(3-ethynylazobenzene) was soluble in common solvents, had high molecular weight up to 4.9×105, and provided a free-standing film by solution casting. Trans-to-cis photoisomerization of azobenzene moieties in poly(3-ethynylazobenzene) was observed upon ultraviolet irradiation.

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  • Synthesis and properties of polyacetylenes with adamantyl groups Reviewed

    M Teraguchi, T Masuda

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   37 ( 24 )   4546 - 4553   1999.12

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    Three disubstituted acetylenes with an adamantyl group-1-(p-adamantylphenyl)-2-chloroacetylene (ClpAdPA), 1-(p-adamantylphenyl)-1-propyne (pAdPP), and 1-(p-adamantylphenyl)-2-phenylacetylene (pAdDPA)-polymerized in good yields in the presence of MoCl5- or TaCl5-based catalysts. The highest weight-average molecular weights of poly(ClpAdPA), poly(pAdPP), and poly(pAdDPA) reached 3.6 x 10(5), 1.1 x 10(6), and 6.0 x 106, respectively. The polymers were yellow to white solids and completely soluble in toluene, chloroform, and so forth. These polymers thermally were fairly stable, and the onset temperatures of weight loss in air were over 360 degrees C. Poly(pAdPP) and poly(pAdDPA) provided free-standing films by solution casting, and their oxygen permeability coefficients (P-O2) at 25 degrees C were 8.6 and 55 barrers [1 barrer = 1 x 10(-10) cm(3).(STP).cm/(cm(2).s.cm Hg)], respectively, which are relatively small compared to those of other substituted polyacetylenes. (C) 1999 John Wiley & Sons, Inc.

    DOI: 10.1002/(SICI)1099-0518(19991215)37:24<4546::AID-POLA12>3.0.CO;2-R

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  • Electronic Properties and Electroluminescence of Monosubstituted Polyacetylenes and their Mixtures with Disubstituted Polyacetylene Reviewed

    Hidayat, R, Hirohata, M, Fujii, A, Teraguchi, M, Masuda, T, Yoshino, K

    Jpn. J. Appl. Phys.   38 ( 2 )   931 - 935   1999.12

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    Monosubstituted polyacetylenes (PA), that is, poly(phenylacetylene) (PPA) derivatives with various substituents attached at the ortho-position of the phenyl ring, have been studied. The valence band top and the bandgap energy of these polymers were estimated in the range from -5.5 eV to -5.9 eV (vs vacuum level) and from 1.9 eV to 2.3 eV, respectively, depending on the substituents. Although PL of these PPA derivatives is very weak, we have observed electroluminescence (EL), which is considered to be related to the nature of the self-trapped excitonic states of these polymers. The EL characteristics were found to depend on the substituents of polymers. In the mixture of poly(o-trimethylsilylphenylacetylene) (PPA-oSiMe<SUB>3</SUB>) with the strong luminescent disubstituted PA, poly(1-phenyl-2-p-n-butylphenylacetylene) (PDPA-nBu), the enhancement of PL of PPA-oSiMe<SUB>3</SUB> was not observed. However, EL of PPA-oSiMe<SUB>3</SUB> was enhanced in the mixture with PDPA-nBu, which is explained in terms of excitation energy transfer.

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  • Local mobility of substituted polyacetylenes measured by quasielastic neutron scattering and its relationship with gas permeability Reviewed

    T Kanaya, M Teraguchi, T Masuda, K Kaji

    POLYMER   40 ( 25 )   7157 - 7161   1999.12

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    Local mobility of three substituted polyacetylenes was investigated by means of a quasielastic neutron scattering technique aiming at elucidating the origin of gas permeability of these polymers. It was found that the local flux, which is defined as the product of the relaxation rate Gamma, and the mobile fraction f(m), increases with the gas permeability coefficient. This suggests that the local flux is an important factor controlling gas permeability. (C) 1999 Elsevier Science Ltd. All rights reserved.

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  • Study of high permeability polymers by means of the spin probe technique Reviewed

    Y. P. Yampolskii, M. V. Motyakin, A. M. Wasserman, T. Masuda, M. Teraguchi, V. S. Khotimskii, B. D. Freeman

    Polymer   40 ( 7 )   1745 - 1752   1999.3

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    The spin probe technique was systematically applied to study a family of high permeability and high free volume glassy polymers. Rotation correlation times τ(c) or frequencies v = 1/τ(c) of 2,2,6,6-tetramethylpyperidine-1- oxyl (TEMPO) were measured in amorphous teflons random copolymers of tetrafluoroethylene and 2,2-bistrifluoromethyle-4,5-difluoro-1,3-dioxole, polyacetylenes and polynorbornenes. Polymers distinguished by unusually high, for the glassy state, permeability and free volume exhibit large rotational mobility of TEMPO. The correlation times correspond to fast rotation of the spin probe previously observed only in rubbery polymers. Correlations between the frequency v and gas permeability and diffusion coefficients were observed. However, in some polymers, the spin probe's rotation rate is also sensitive to side-chain local mobility, which does not affect translational diffusion coefficients of gas molecules in polymers.

    DOI: 10.1016/S0032-3861(98)00395-4

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  • Synthesis and properties of polymers from disubstituted acetylenes with chiral pinanyl groups Reviewed

    Toshiki Aoki, Yukie Kobayashi, Takashi Kaneko, Eizo Oikawa, Yasufumi Yamamura, Yoji Fujita, Masahiro Teraguchi, Ryoji Nomura, Toshio Masuda

    Macromolecules   32 ( 1 )   79 - 85   1999.1

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    Disubstituted acetylenes with chiral pinanyl groups, (-)-1-{4-[dimethyl(10-pinanyl)silyl]-phenyl}-2-phenylacetylene (1), (-)-1-{3-[dimethyl(10-pinanyl)silyl]phenyl}-2-phenylacetylene (2), (-)-1-{4-[dimethyl(10-pinanyl)silyl]phenyl}-1-propyne (3), and (-)-1-chloro-2-{4-[dimethyl(10-pinanyl)silyl]-phenyl}acetylene (4), polymerized with NbCl5-, TaCl5-, or MoCl5-based catalysts to give high molecular weight polymers in good yields. Poly(1) and poly(2) showed intense circular dichroism (CD) effects in the UV-vis region and large optical rotations, which suggests that these polymers exist in helical conformations with an excess of one-handed screw sense. No significant decrease in the magnitude of CD effects of poly(1) and poly(2) with increasing temperature indicated the relatively high stability of their helical conformations. On the other hand, the intensities of CDs of poly(3) and poly(4) were approximately 1/10 those of poly(1) and poly(2), which means that introduction of two aromatic side groups into the repeating unit is favorable for the induction of helical conformation to disubstituted acetylene polymers. The free-standing membranes of poly(1), poly(2), and poly(3) exhibited characteristic properties as gas-permeable and optical resolution membranes. © 1999 American Chemical Society.

    DOI: 10.1021/ma9810969

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  • Photoluminescence and electroluminescence in polyacetylene derivatives Reviewed

    K. Yoshino, M. Hirohata, R. Hidayat, D. W. Kim, K. Tada, M. Ozaki, M. Teraguchi, T. Masuda

    Synthetic Metals   102 ( 1-3 )   1159 - 1159   1999

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    Electroluminescence (EL) and photoluminescence (PL) have been studied in polyacetylene derivatives with various substituents. Intense green and blue ELs are observed in poly(diphenylacetylene)s and in poly(1-alkyl-2-phenylacetylene)s, respectively. While, red PL and EL in mono-substituted polyacetylene derivatives are much weaker. Detailed dependence of EL and PL on molecular structure of substituents have been discussed. Spectral narrowing of PL and lasing have also been realized with intense excitation.

    DOI: 10.1016/S0379-6779(98)01471-4

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  • PL and EL characteristics of mixture of polyacetylene derivatives and dynamics of excitons Reviewed

    R. Hidayat, M. Hirohata, S. Tatsuhara, M. Ozaki, M. Teraguchi, T. Masuda, K. Yoshino

    Synthetic Metals   101 ( 1 )   210 - 211   1999

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    Photoluminescence (PL) and electroluminescence (EL) of mixtures of polyacetylene derivatives with different substituents have been studied in detail. Remarkable spectral shift of PL and EL from blue to green by changing the concentration of poly(diphenylacetylene) (PDPA) derivatives in poly(alkylphenylacetylene) (PAPA) derivatives has been observed. Marked quenching of PL and EL intensities has been found out in disubstituted polyacetylene such as PDPA derivatives upon introduction of monosubstituted polyacetylene. Dependence of PL decay time on molar ratio proportion of mixtures have been also studied. These characteristics have been discussed in terms of fast interchain interaction such as excitation energy transfer between polyacetylene derivatives with different molecular structures.

    DOI: 10.1016/S0379-6779(98)01273-9

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  • Excitation Dynamics in Disubstituted Polyacetylene Reviewed

    I. Gontia, S. V. Frolov, M. Liess, E. Ehrenfreund, Z. V. Vardeny, B. Tada, H. Kajii, R. Hidayat, A. Fujii, K. Yoshino, M. Teraguchi, T. Masuda

    Physical Review Letters   82 ( 20 )   4058 - 4061   1999

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    We studied the excitation dynamics in films of disubstituted polyacetylene, a degenerate ground-state conjugated polymer, using psec transient and steady-state spectroscopies. The polymer is found to support charged and neutral topological soliton excitations concurrent with a strong intrinsic photoluminescence band with quantum efficiency, η˜=50%. This leads to stimulated emission in thin films and lasing in cylindrical μ cavities. The seeming contradiction of a degenerate ground-state polymer with high η is explained by the lowest excited-state ordering. © 1999 The American Physical Society.

    DOI: 10.1103/PhysRevLett.82.4058

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  • Polymerization of diphenylacetylenes having very bulky silyl groups and polymer properties Reviewed

    M Teraguchi, T Masuda

    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY   36 ( 15 )   2721 - 2725   1998.11

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    Polymerization and polymer properties of 1-phenyl-2-[4-(triphenylsilyl)phenyl] acetylene (pPh(3)SiDPA) and 1-phenyl-2-[4-(triisopropylsilyl)phenyl] acetylene (piPr(3)SiDPA), which have very bulky silyl groups, were examined. These monomers polymerized in good yields in the presence of TaCl5-based catalysts. The highest weight-average molecular weights of poly(pPh(3)SiDPA) and poly(piPr(3)SiDPA) reached about 1 x 10(6) and 4.8 x 106, respectively. The polymers were yellow to orange-colored solids which were soluble in toluene, chloroform, etc., and provided free-standing films by solution casting. The onset temperatures of weight loss of poly(pPh(3)SiDPA) and poly(piPr(3)SiDPA) in TGA in air were 430 and 270 degrees C, respectively. The oxygen permeability coefficients of poly(pPh(3)SiDPA) and poly(piPr(3)SiDPA) at 25 degrees C were 3.8 and 20 barrers, respectively, and relatively small. (C) 1998 John Wiley & Sons, Inc.

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  • Photoluminescence, Electroluminescence, Lasing and Novel Characteristics in Photonic Crystal, Synthetic Opal, of Conducting Polymers, Polyacetylene Derivatives Reviewed

    K.Yoshino, Hidayat Rahmat, K.Tada, S.Tatsuhara, Y.Kawagishi, A.Fujii, M.Ozaki, Masahiro Teraguchi, Toshio Masuda, Z.V.Vardeny, Anvar A.Zakhidov

    Mol.Cryst.Liq.Cryst., Vol.322, pp.253-262   1998.4

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  • Photoluminescence and electroluminescence in polymer mixture of poly(alkylphenylacetylene) and poly(diphenylacetylene) derivatives Reviewed

    R Hidayat, M Hirohata, K Tada, M Teraguchi, T Masuda, K Yoshino

    JAPANESE JOURNAL OF APPLIED PHYSICS PART 2-LETTERS   37 ( 2A )   L180 - L183   1998.2

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    Photoluminescence (PL) and electroluminescence (EL) in polymer mixture of blue emissive poly(1-hexyl-2-phenylacetylene) (PHxPA) and green emissive paly(1-phenyl-2-p-n-butylphenylacetylene) (PDPA-nBu) were studied. Both PL and EL in the polymer mixture change from blue to green by the addition of a small amount of PDPA-nBu into PHxPA. This fact has been interpreted as a result of energy transfer from the larger band eap PHxPA to the smaller band gap PDPA-nBu. PL and EL in the polymer mixture are found to be deconvoluted into PL1 and PL2 peaks originating from PDPA-nBu and PHxPA, respectively. PL1 of PDPA-nBu shifts to a higher energy upon introduction of PHxPA, while PL2 of PHxPA also shifts to a higher energy by adding a small amount of PDPA-nBu. From this change in luminescence, molecular conformation at the excited state in the mixture is interpreted to be distorted, depending on the molar ratio of PDPA-nBu and PHxPA. A similar change in PL and EL spectra with molar ratio implies that in this mixture the energy relaxation process is nearly the same for both the cases and does not strongly depend on whether the excited state is produced by photoexcitation or charge injection.

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  • Optical properties and electroluminescence characteristics of polyacetylene derivatives dependent on substituent and layer structure Reviewed

    K Yoshino, M Hirohata, R Hidayat, K Tada, T Sada, M Teraguchi, T Masuda, SV Frolov, M Shkunov, ZV Vardeny, M Hamaguchi

    SYNTHETIC METALS   91 ( 1-3 )   283 - 287   1997.12

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    Intense photoluminescence (PL) is observed in di-substituted polyacetylene derivatives even though solitonic mid-gap absorption is observed upon doping, contrary to non-substituted trans-polyacetylene and mono-substituted polyacetylene in which strong PL is not observed. Intense green and blue electroluminescence (EL) is realized utilizing poly(diphenylacetylene) derivatives and poly(1-alkyl-2-phenylacetylene) derivatives, respectively. Greenish-blue emission is also observed in poly(1-chloro-2-phenylacetylene) derivatives. The dependence of wavelength and intensity of PL and EL on the molecular structure of substituents is clarified in detail. The effects of molecular alignment and layer structure on the EL characteristics are also discussed. Upon intense light excitation, remarkable spectral narrowing due to stimulated emission is also observed in these di-substituted polyacetylene derivatives. (C) 1997 Elsevier Science S.A.

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  • Spectral narrowing of emission in di-substituted polyacetylene Reviewed

    SV Frolov, M Shkunov, ZV Vardeny, K Tada, R Hidayat, M Hirohata, M Teraguchi, T Masuda, K Yoshino

    JAPANESE JOURNAL OF APPLIED PHYSICS PART 2-LETTERS & EXPRESS LETTERS   36 ( 9AB )   L1268 - L1271   1997.9

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    We studied spontaneous and stimulated optical emission in films of di-substituted trans-polyacetylene (t-PA). We found that di-substitution of t-PA drastically changes the polymer optical emission properties, so that photo-generation of exciton and photoluminescence (PL) quantum yields become much higher than those measured in unsubstituted and mono-substituted t-PA. The strong PL is accompanied by high optical gain and emission spectral narrowing at high excitation intensities; the emission spectrum changes from a broad PL band of 100 nm at low intensities to a narrow stimulated emission band of similar to 8 nm at high intensities. These properties show that di-substituted t-PA films can be good candidates for laser medium in the green and blue spectral ranges.

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  • Optical Properties of Disubstituted Acetylene Polymers Invited

    Kazuya Tada, Rahmat Hidayat, Masaharu Hirohata, Hirotake Kajii, Satoshi Tatsuhara, Akihiko Fujii, Masanori Ozaki, Masahiro Teraguchi, Kyoto University, Toshio Masuda, yoto Un, Katsumi YoshiNo

    1997.7

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  • Effect of molecular structure of substituents on green electroluminescence in disubstituted acetylene polymers Reviewed

    R Hidayat, M Hirohata, K Tada, M Teraguchi, T Masuda, K Yoshino

    JAPANESE JOURNAL OF APPLIED PHYSICS PART 1-REGULAR PAPERS SHORT NOTES & REVIEW PAPERS   36 ( 6A )   3740 - 3743   1997.6

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    Intense green photoluminescence (PL) in the wavelength range of 520 to 540nm was observed in many poly(diphenylacetylene) (PDPA) derivatives. The band gap energy and the highest occupied molecular orbital (HOMO) energy of these polymers were estimated to range from 2.6 to 2.7 eV and -5.6 to -5.9eV depending on the substituent. Green electroluminescence (EL) was observed from EL devices fabricated utilizing these polymers. Among these PDPA derivatives, poly(1-phenyl-2-m-(trimethylsilyl)phenylacetylene) (PDPA-mSiMe(3)) with the smallest band gap energy exhibited the weakest PL and EL of longest wavelength. Polymers with bulkier and/or longer substituents exhibited stronger PL and EL. The results are interpreted in terms of a steric hindrance effect and the interchain interaction depending on the molecular structure of the substituents. In addition, upon electrochemical doping, these light emissive polyacetylene derivatives exhibited evolution of new single midgap absorption suggesting formation of solitons.

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  • Donor polymer (PAT6) - Acceptor polymer (CNPPV) fractal network photocells Reviewed

    K. Tada, K. Hosoda, M. Hirohata, R. Hidayat, T. Kawai, M. Onoda, M. Teraguchi, T. Masuda, A. A. Zakhidov, K. Yoshino

    Synthetic Metals   85   1305 - 1306   1997.3

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    Unique characteristics such as quenching of photoluminescence and improvement of photovoltaic effect were observed in donor polymeracceptor polymer composites, PAT6-CNPPV system and PDPATPSi-CNPPV system. Electronic energy structures of these polymers were determined and these characteristics are interpreted in terms of photoinduced charge transfer between donor polymer (PAT6 and PDPATPSi) and acceptor polymer (CNPPV) and formation of fractal network.

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  • Studies of Raman Scattering in Novel Disubstituted Acetylene Polymers

    A. Fujii, M. N. Shkunov, Z. V. Vardeny, K. Tada, K. Yoshino, M. Teraguchi, T. Masuda

    SPIE's International Symposium Proceedings   3145   533 - 543   1997

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  • Optical properties and blue and green electroluminescence in soluble disubstituted acetylene polymers Reviewed

    K Tada, R Hidayat, M Hirohata, M Teraguchi, T Masuda, K Yoshino

    JAPANESE JOURNAL OF APPLIED PHYSICS PART 2-LETTERS & EXPRESS LETTERS   35 ( 9A )   L1138 - L1141   1996.9

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    Intense photoluminescence (PL) was observed in soluble disubstituted polyacetylenes such as poly(1-phenyl-2-p-adamantylphenyl acetylene (PDPA-Ad) at 530 nm, poly(1-phenyl-2-p-triphenylsilylphenyl acetylene) (PDPA-TPSi) at 530 nm and poly(1-hexyl-2-phenyl acetylene) (PHxPA) at 455 nm, although they are considered to be derivatives of trans-polyacetylene. In monosubstituted acetylene polymers such as poly(o-trimethylsilylphenyl acetylene) (PTMSiPA), PL was negligible. Green and blue light emissions were observed from an electroluminescent (EL) device having soluble poly(diphenyl acetylene) (PDPA) derivatives (PDPA-Ad and PDPA-TPSi) and PHxPA as emission layers, respectively. EL emission is clearly observable under normal room illumination conditions. The electronic energy structures of the disubstituted PA derivatives are also discussed to interpret PL and EL characteristics.

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Books

  • In "Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis", S. Itsuno, Ed.; Chapter 15(pp423-455); "Synthesis and Function of Chiral π-Conjugated Polymers from Phenylacetylenes"(共著)

    Toshiki Aoki, Takashi Kaneko, Masahiro Teraguchi( Role: Joint author)

    John Wiley & Sons, Inc.  2011.9  ( ISBN:0470568208

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  • In "ACS Symposium series 733 Polymer Membranes for Gas and Vapor Separation -Chemistry and Materials Science-", B. D. Freeman and I. Pinnau, Ed.; Chapter 2(pp28-37); "Synthesis and Gas Permeability of Poly(diphenylacetylenes) with Substituents" (共著)

    Toshio Masuda, Masahiro Teraguchi, Ryoji Nomura( Role: Joint author)

    American Chemical Society, Washington, DC  1999.9  ( ISBN:0841236054

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MISC

  • 進化し続ける高分子酸素分離膜

    青木俊樹, 金子隆司, 寺口昌宏

    化学   74 ( 10 )   66 - 67   2019.10

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  • Helix-Sense-Selective Polymerization of Achiral Phenylacetylenes and Unique Properties of the Resulting Cis-cisoidal Polymers Reviewed

    Lijia Liu, Yu Zang, Hongge Jia, Toshiki Aoki, Takashi Kaneko, Shingo Hadano, Masahiro Teraguchi, Mari Miyata, Geng Zhang, Takeshi Namikoshi

    POLYMER REVIEWS   57 ( 1 )   89 - 118   2017

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    One of the authors discovered helix-sense-selective polymerization (HSSP) of an achiral substituted phenylacetylene which has two hydroxymethyl groups and a relatively hydrophobic substituent by using a chiral catalytic system in 2003. The one-handed helicity is stable and static in nonpolar solvents because it is maintained by intramolecular hydrogen bonds. Since the resulting polymer has extremely tight helicity in its main chain, it shows many interesting and unusual properties including highly selective photocyclic aromatization (SCAT). In this review, the discovery and development of the HSSP and SCAT reactions, and the properties and application of the resulting polymers prepared by HSSP and the resulting supramolecular polymers prepared by SCAT will be examined.

    DOI: 10.1080/15583724.2016.1160930

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  • Two-Dimensional and Related Polymers: Concepts, Synthesis, and their Potential Application as Separation Membrane Materials Reviewed

    Yu Zang, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Liqun Ma, Hongge Jia

    POLYMER REVIEWS   55 ( 1 )   57 - 89   2015.1

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    Although two-dimensional polymers (2DPs) and related materials are very attractive subjects for research because they are expected to function as ideal gas separation membrane materials, we need to answer some basic questions about them. For example, "Why are they not a common or popular topic, especially in textbooks?"; "How can they be synthesized?"; and "Whatever are 2DPs? and "How can we define 2DPs?" In this review, we try to answer these questions. First, the significance of 2DP as molecular-sieving membrane materials is explained in Section 1. Second, the definitions and classifications are proposed that take into account their first-order and high-order structures in Section 2. Third, syntheses and function of a few real 2DPs and many related polymers described in the literature are reviewed, including such materials as covalent organic frameworks(COFs), carbonized molecular sieving membranes(CMSMs), polymers of intrinsic porosity(PIM), and our recent results on the synthesis and function of 2DPs and related polymers in Sections 3 and 4. Finally, in Section 5 we evaluate the two-dimensional (2D) characters of 2DPs described in Section 3 using some 2D characteristic values defined in Section 2, and the future of 2DPs is discussed in Section 6.

    DOI: 10.1080/15583724.2014.963235

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  • Synthesis of Two-dimensional Polymer for Molecular-sieve Membranes

    39 ( 3 )   118 - 131   2014.5

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    DOI: 10.5360/membrane.39.118

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  • 『2Dポリマー』膜の合成―究極の分子分離膜をめざして Reviewed

    青木俊樹, 藏雨, 宮田 真理, 棚木宏幸, 中尾和樹, 王建軍, 寺口昌宏

    未来材料   13 ( 2 )   31 - 38   2013.2

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  • Preparation of self-supporting supramolecular membranes by photo-topochemical reaction of membranes of one-handed helical polymers prepared by helix-sense-selective polymerization

    61 ( 11 )   846 - 854   2010.11

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    Other Link: http://id.nii.ac.jp/1450/00007610/

  • P-17 Program for Promoting High-Quality University Education "Breaking Away from Shallow Learning Habits" : Practice of design education in Department of Chemistry and Chemical Engineering, Niigata University

    Shimizu Tadaaki, Kodama Tatsuya, Kimura Isao, Yoshida Masanori, Kaneko Takashi, Teraguchi Masahiro

    22   690 - 691   2010.8

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  • かさ高いイミノ置換基を持つフェニルアセチレンのらせん選択重合のリビング化とブロックコポリマーの合成

    四柳宏基, 寺口昌宏, 寺口昌宏, 寺口昌宏, 浪越毅, 浪越毅, MARWANTA Edy, MARWANTA Edy, 金子隆司, 金子隆司, 青木俊樹, 青木俊樹, 青木俊樹, 青木俊樹

    高分子学会予稿集(CD-ROM)   59 ( 1 Disk1 )   2010

  • 二つの種々のイミノ置換基を持つフェニルアセチレンのらせん選択重合により得られた片巻きらせんポリマーをキラル共触媒に用いたフェニルアセチレンのらせん選択重合

    松本和樹, 四柳宏基, 浪越毅, 浪越毅, 寺口昌宏, 寺口昌宏, 寺口昌宏, 寺口昌宏, MARWANTA Edy, MARWANTA Edy, 金子隆司, 金子隆司, 金子隆司, 青木俊樹, 青木俊樹, 青木俊樹, 青木俊樹, 青木俊樹

    高分子学会予稿集(CD-ROM)   58 ( 1 Disk1 )   2009

  • Optical Resolution Membranes

    Toshiki Aoki, Masahiro Teraguchi

    Kobunshi   57 ( 11 )   898 - 902   2008

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    Optical resolution membranes can separate mixtures of both enantiomers. The study is very challenging and fundamental and also applicable for production of medicine. © 2008, The Society of Polymer Science, Japan. All rights reserved.

    DOI: 10.1295/kobunshi.57.898

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  • 片巻きらせんポリフェニルアセチレン自立膜の選択的芳香環形成による超分子膜の調製

    浪越毅, 浪越毅, 鬼山祥幸, 波多野慎悟, 寺口昌宏, 寺口昌宏, 金子隆司, 金子隆司, 青木俊樹, 青木俊樹, 青木俊樹, 青木俊樹

    高分子学会予稿集(CD-ROM)   57 ( 1 Disk1 )   2008

  • アキラル配位子を持つフェニルアセチレンのらせん選択重合と生成ポリマー膜を用いた不斉反応

    松本和樹, 四柳宏基, 浪越毅, 浪越毅, 寺口昌宏, 寺口昌宏, 寺口昌宏, MARWANTA Edy, MARWANTA Edy, 金子隆司, 金子隆司, 青木俊樹, 青木俊樹, 青木俊樹, 青木俊樹

    高分子学会予稿集(CD-ROM)   57 ( 2 Disk1 )   2008

  • 高スピンπ共役高分子の設計と磁性(共著)

    金子隆司, 青木俊樹, 寺口昌宏

    Electrochemistry(電気化学および工業物理化学)   75 ( 10 )   834 - 838   2007.10

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    DOI: 10.5796/electrochemistry.75.834

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    Other Link: https://jlc.jst.go.jp/DN/JALC/00300958919?from=CiNii

  • キラルらせんポリフェニルアセチレンを用いた選択吸着沈殿法による光学分割

    波多野慎悟, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, 金子隆司

    高分子学会予稿集(CD-ROM)   56 ( 1 Disk1 )   2007

  • 側鎖にガルビノキシルを有するポリ(ビナフチル-6,6′-ジイルエチニレン-1,3-フェニレンエチニレン)型キラルポリラジカルの合成と光学活性・磁気特性

    阿部寛正, 金子隆司, 波多野慎悟, 寺口昌宏, 青木俊樹

    日本化学会講演予稿集   87th ( 2 )   2007

  • 二つのアルキルアミド基を有するアキラルフェニルアセチレンのキラルロジウム触媒系によるらせん選択重合

    寺口昌宏, 寺口昌宏, LIU Chenchen, 谷岡大輔, 波多野慎悟, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司

    日本化学会講演予稿集   87th ( 2 )   2007

  • ガルビノキシル残基を有する3,5-ビス(ヒドロキシメチル)-4-ベンジルオキシフェニルアセチレンのらせん選択重合とそのキラルポリラジカルの光学活性・磁気特性

    片桐寛夫, 金子隆司, 波多野慎悟, 寺口昌宏, 青木俊樹

    日本化学会講演予稿集   87th ( 2 )   2007

  • 側鎖にガルビノキシルを有するポリ(フェニルアセチレン)型キラルポリラジカルの合成と光学活性・磁気特性

    梅田泰裕, 金子隆司, 波多野慎悟, 寺口昌宏, 青木俊樹

    日本化学会講演予稿集   87th ( 2 )   2007

  • 光学分割膜素材としてのイオン交換基含有キラルポリ置換フェニルアセチレンの合成

    石塚真由美, 波多野慎悟, 波多野慎悟, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, 金子隆司

    日本化学会講演予稿集   87th ( 2 )   2007

  • 光学活性なメンチル基やピナニル基を有するポリ(フェニレンエチニレン)膜の脱置換基によるキラルらせん高分子膜の合成

    井上真, 寺口昌宏, 寺口昌宏, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司

    日本膜学会年会講演要旨集   29th   2007

  • ラダー二重らせん構造を有するポリ(フェニルアセチレン)誘導体の合成と特性

    二俣和夫, 波多野慎悟, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, 金子隆司

    高分子学会予稿集(CD-ROM)   56 ( 1 Disk1 )   2007

  • ガルビノキシル残基を有するポリ(フェニルアセチレン)のらせん方向制御とそのポリラジカルの光・磁気特性

    梅田泰裕, 金子隆司, 金子隆司, 波多野慎吾, 波多野慎吾, 寺口昌宏, 寺口昌宏, 青木俊樹, 青木俊樹

    高分子学会予稿集(CD-ROM)   56 ( 1 Disk1 )   2007

  • Synthesis of functional pi-conjugated polymers from aromatic acetylenes

    Toshiki Aoki, Takashi Kaneko, Masahiro Teraguchi

    POLYMER   47 ( 14 )   4867 - 4892   2006.6

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    Because of their unique structures and properties, pi-conjugated polymers have attracted the attention of scientists and engineers. The authors have studied the synthesis of two kinds of pi-conjugated poly(aromatic acetylene)s, i.e. poly(arylacetylene)s and poly(aryleneethynylene)s with the aim of obtaining new polymers having novel functions or higher performances. This review mainly concerns the authors' results, as follows: first, we describe the synthesis and properties of achiral poly (aryl acetylene) s, containing trimethylsilyl groups, oligodimethylsiloxanyl groups, dendritic groups, and glavinoxyl groups, for application as oxygen permselective, membrane materials. Their self-membrane-forming abilities and high oxygen permeabilities are presented. Second, the synthesis by asymmetric-induced polymerization of chiral poly(arylacetylene)s having both a main-chain chirality and chiral pendant groups and their application as optical resolution membranes are described. Third, two new synthetic methods for preparing chiral helical poly (phenyl acetylene) s without the coexistence of any other chiral moieties are presented. One is helix-sense-selective addition polymerization and the other is in situ removal of chiral pendant groups from membranes of poly(arylacetylene)s that also contain a main-chain chirality. The chiral helical poly(arylacetylene)s were tested as optical resolution membranes. The chiral and achiral poly(arylacetylene)s were synthesized by addition polymerization using metathesis catalysts or rhodium complexes. Finally, the synthesis of regiospecific poly(aryleneethynylene)s bearing stable radicals by the polycondensation of bromoethynylanthracene derivatives using a Pd(0) complex is described. The magnetization and the static magnetic susceptibility of the polyradicals are explained. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.polymer.2006.04.047

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  • 光学活性な置換基を持つポリ(フェニレンエチニレン)膜の合成とそれらポリマーの不斉らせん構造

    井上真, 寺口昌宏, 寺口昌宏, 波多野慎悟, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司

    高分子学会北陸支部研究発表講演会講演要旨集   55th   2006

  • 二つの水素結合可能な官能基を有するポリ(フェニルアセチレン)誘導体のラダー二重らせん構造の固定化

    二俣和夫, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, 金子隆司

    高分子学会予稿集(CD-ROM)   55 ( 2 Disk1 )   2006

  • 光学活性なピナニルシリル基と2つの水酸基を持つポリ(フェニルアセチレン)の合成・構造・特性

    持舘和臣, 寺口昌宏, 寺口昌宏, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆, 金子隆

    高分子学会予稿集(CD-ROM)   55 ( 1 Disk1 )   2006

  • キラルなポリ(フェニレンエチニレン)膜の合成とそれらポリマーの不斉らせん構造

    井上真, 寺口昌宏, 寺口昌宏, 波多野慎悟, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司

    高分子学会予稿集(CD-ROM)   55 ( 2 Disk1 )   2006

  • 二つの水酸基を有するポリ(フェニルアセチレン)誘導体の二重らせん構造の固定化

    二俣和夫, 波多野慎悟, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, 金子隆司

    高分子学会北陸支部研究発表講演会講演要旨集   55th   2006

  • 光学活性なピナニルシリル基と2つの水酸基を持つフェニルアセチレンのらせん選択共重合と生成高分子の主鎖らせん構造の刺激応答性,脱シリル化反応および光学異性体選択透過性

    寺口昌宏, 寺口昌宏, 持舘和臣, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司

    高分子学会予稿集(CD-ROM)   55 ( 2 Disk1 )   2006

  • 側鎖に金属錯体部位を有するキラルらせんポリフェニルアセチレンの合成とキラル認識能への金属錯体の効果

    波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, 金子隆司

    高分子学会予稿集(CD-ROM)   55 ( 1 Disk1 )   2006

  • 光学活性なポリ(フェニレンエチニレン)膜の合成と生成ポリマーの主鎖不斉らせん構造

    寺口昌宏, 寺口昌宏, 井上真, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司

    ポリマー材料フォーラム講演予稿集   15th   2006

  • 安定ラジカル骨格を有するフェニルアセチレン誘導体の合成と重合

    佐藤誠之, 金子隆司, 寺口昌宏, 寺口昌宏, 波多野慎悟, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹

    高分子学会北陸支部研究発表講演会講演要旨集   55th   2006

  • Enatioselective permeability through membranes containing one-handed helical polymer as chiral recognition agent

    波多野慎悟, 千野隆之, 寺口昌宏, 寺口昌宏, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司, 田中孝明

    日本化学会講演予稿集   86th ( 2 )   2006

  • 金属錯体を有する片巻きらせんポリマー光学分割膜

    波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, 金子隆司

    日本膜学会年会講演要旨集   28th   2006

  • らせん選択重合による高分子不斉らせん構造を持つ配位子の合成

    松本和樹, 寺口昌宏, 寺口昌宏, 波多野慎悟, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司

    高分子学会北陸支部研究発表講演会講演要旨集   55th   2006

  • ガルビノキシルを有するポリ(1,3-フェニレンエチニレン)型キラルポリラジカルの合成とその磁性及び磁気光学効果

    吉本翔太, 金子隆司, 寺口昌宏, 寺口昌宏, 波多野慎吾, 波多野慎吾, 青木俊樹, 青木俊樹, 青木俊樹

    高分子学会予稿集(CD-ROM)   55 ( 2 Disk1 )   2006

  • 片巻きらせんポリフェニルアセチレンの異常な分解性-分解機構の考察と分解制御-

    波多野慎悟, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, 金子隆司

    高分子学会予稿集(CD-ROM)   55 ( 2 Disk1 )   2006

  • 主鎖のらせんのみに起因する不斉を持つポリフェニルアセチレンの合成-アキラル フェニルアセチレンのらせん選択重合とキラル置換ポリフェニルアセチレンの脱置換基-

    青木俊樹, 寺口昌宏, 金子隆司

    高分子加工   54 ( 12 )   542 - 550   2005.12

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  • 主鎖のみに不斉構造をもつポリフェニルアセチレンのキラルらせん構造の安定性,刺激応答性,分解性-分子内水素結合の効果

    波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, 金子隆司, 金子隆司

    高分子学会予稿集(CD-ROM)   54 ( 2 Disk1 )   2005

  • 分子内水素結合のみにより安定化されたポリフェニルアセチレンのキラルらせん主鎖構の制御-安定性,刺激応答性と分解性

    波多野慎悟, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, KIM Sun-Young, 金子隆司, 金子隆司

    高分子学会予稿集(CD-ROM)   54 ( 1 Disk1 )   2005

  • 膜状態での脱ピナニルシリル化反応による水酸基含有キラルらせんポリフェニルアセチレン膜の合成と光学異性体選択透過性

    寺口昌宏, 寺口昌宏, 持舘和臣, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司, 金子隆司, 波多野慎悟

    高分子学会予稿集(CD-ROM)   54 ( 2 Disk1 )   2005

  • 水酸基含有キラルらせんポリ(フェニルアセチレン)膜の光学異性体選択透過性

    持舘和臣, 寺口昌宏, 寺口昌宏, KIM Sun-Young, 波多野慎悟, 金子隆司, 金子隆司, 青木俊樹, 青木俊樹

    日本膜学会年会講演要旨集   27th   2005

  • 二つのシラノール基をもつフェニルアセチレンのらせん選択共重合と生成キラルらせん主鎖の固定

    二俣和夫, KIM Sun-Young, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 寺口昌宏, 寺口昌宏, 金子隆司, 金子隆司

    高分子学会予稿集(CD-ROM)   54 ( 2 Disk1 )   2005

  • カルボキシル基またはアミノ酸基含有キラルらせんポリ(フェニルアセチレン)膜の光学異性体選択透過性

    持舘和臣, 寺口昌宏, 寺口昌宏, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司, 金子隆司

    高分子学会予稿集(CD-ROM)   54 ( 2 Disk1 )   2005

  • キラル触媒系を用いた4-アルキルオキシ-3,5-ビス(ヒドロキシメチル)フェニルアセチレンのらせん選択(共)重合

    岸本拓也, 波多野慎悟, 青木俊樹, 青木俊樹, 金子隆司, 金子隆司, 寺口昌宏, 寺口昌宏, KIM Sun-Young

    高分子学会予稿集(CD-ROM)   54 ( 1 Disk1 )   2005

  • 光学活性なピナニルシリル基と2つの水酸基を持つフェニルアセチレンのらせん選択共重合と生成高分子の脱シリル化反応,光学異性体選択透過性

    持舘和臣, 寺口昌宏, 寺口昌宏, 波多野慎悟, 青木俊樹, 青木俊樹, 青木俊樹, 金子隆司, 金子隆司

    高分子学会予稿集(CD-ROM)   54 ( 2 Disk1 )   2005

  • 光学活性なピナニルシリル基と2つの水酸基を持つフェニルアセチレンのらせん選択共重合

    持舘和臣, KIM Sun-Young, 寺口昌宏, 寺口昌宏, 青木俊樹, 青木俊樹, 波多野慎吾, 金子隆司, 金子隆司

    高分子学会予稿集(CD-ROM)   54 ( 1 Disk1 )   2005

  • Helix-sense-selective Polymerization of an Achiral Phenylacetylene

    AOKI Toshiki, TERAGUCHI Masahiro

    Kobunshi   53 ( 12 )   946 - 946   2004.12

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    DOI: 10.1295/kobunshi.53.946

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  • 不斉誘起重合によるキラルヘリカルポリ置換アセチレンの合成

    青木俊樹, 金子隆司, 寺口昌宏

    高分子加工   51 ( 4 )   168 - 176   2002.4

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  • 光学分割膜-分子設計と分離機構-

    青木俊樹, 金子隆司, 寺口昌宏

    化学工業   52 ( 9 )   683 - 691   2001.9

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  • Pure- and mixed-gas permeation properties of poly(p-tert-butyl diphenylacetylene).

    Pinnau, I, ZJ He, A Morisato, T Masuda, M Teraguchi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   222   U353 - U353   2001.8

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  • Exciton dynamics in disubstituted polyacetylenes

    HIDAYAT R, FUJII A, OZAKI M, TERAGUCHI M, MASUDA T, YOSHINO K

    Synthetic Metals   119 ( 1/3 )   597 - 598   2001

  • 二置換体ポリアセチレン薄膜のラマン分光解析と発光機構

    藤井彰彦, 西原雄祐, 尾崎雅則, VARDENY V., 寺口昌宏, 増田俊夫, 吉野勝美

    応用物理学会学術講演会講演予稿集   62nd ( 3 )   2001

  • 二置換体ポリアセチレンのPLとEL及び一置換体ポリアセチレンとの複合効果

    HIDAYAT R, TONG L G, 尾崎雅則, 寺口昌宏, 増田俊夫, 吉野勝美

    応用物理学会学術講演会講演予稿集   60th ( 3 )   1999

  • Synthesis and characterization of polyacetylenes having azobenzene pendant groups.

    T Masuda, M Teraguchi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   216   U16 - U16   1998.8

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  • Photoluminescence and Electroluminescence Dependence on Molecular Structure and Mixture Effect in Substituted Polyacetylene

    HIDAYAT R., HIROHATA M., TADA K., TERAGUCHI M., MASUDA T., YOSHINO K.

    Meeting abstracts of the Physical Society of Japan   53 ( 1 )   263 - 263   1998.3

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  • 5a-D-1 Photoluminescence, Electroluminescence and Their Substituent Effects of Polyacetylene Derivatives

    Hirohata M., Hidayat R., Tada K., Teraguchi M., Masuda T., Yoshino K.

    Meeting abstracts of the Physical Society of Japan   52 ( 2 )   265 - 265   1997.9

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  • 5a-D-6 Electronic and Optical Properties of Poly(diphenylacetylene)Derivatives

    Hidayat R., Hirohata M., Tada K., Teraguchi M., Masuda T., Yoshino K.

    Meeting abstracts of the Physical Society of Japan   52 ( 2 )   266 - 266   1997.9

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  • Synthesis and gas permeability of poly(diphenylacetylenes).

    T Masuda, M Teraguchi

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   214   45 - PMSE   1997.9

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  • 5a-D-2 Electronic, Optical and ESR Property of the Polyacetylene Derivatives

    Kajii H., Tada K., Hidayat R., Hirohata M., Araki H., Teraguti M., Masuda T., Yoshino K.

    Meeting abstracts of the Physical Society of Japan   265 - 265   1997

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  • Electronic, Optical and EL Emission Properties and Their Doping Effects of Di-Substituted Polyacetylene Derivatives

    Tada K., Hidayat R., Hirohata M., Teraguchi M., Masuda T., Yoshino K.

    Abstracts of the meeting of the Physical Society of Japan. Sectional meeting   1996 ( 2 )   446 - 446   1996.9

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Presentations

  • 2,6位に(4-アセトキシ-3,5-ジ- t -ブチルフェニル)エチニル基を有するポリ(1,4-フェニレン)の合成とベンズアヌレーション

    岡崎新, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第103春季年会  2023.3 

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    Event date: 2023.3

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  • チオラクトンの開環反応とチオールーエンマイケル付加反応を含むオルソゴナル反応による鎖生長

    菅原良太, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第103春季年会  2023.3 

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    Event date: 2023.3

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  • フェニレンビニレンおよびオリゴフェニレンビニレン部位を有するポリフェニルアセチレンの合成と生成ポリマーの光学的性

    津村美咲, 金子隆司, 青木俊樹, 寺口昌宏

    日本化学会第103春季年会  2023.3 

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    Event date: 2023.3

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  • フェニルアセチレンおよびフェニルアセチレン誘導体のイリジウム触媒による重合の検討

    寺島佳祐, 金子隆司, 青木俊樹, 寺口昌宏

    日本化学会第103春季年会  2023.3 

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  • エチニレンとフェニレンを主鎖に持つ全共役高分子の酸素選択透過膜としての性能

    八代泰成, 石佳, 寺口昌宏, 金子隆司, 青木俊樹

    日本化学会第103春季年会  2023.3 

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  • Oxygen permselectivity of well-defined multi-stranded copolymers synthesized from monomers having some different polymerizable groups

    Yu Zang, Jianjun Wang, Masahiro Teraguchi, Takashi Kaneko, Toshiki

    2022.9 

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  • 分子内に超ミクロ孔を持つ二次元高分子含有膜の合成と酸素選択透過

    程柯涵, 寺口昌宏, 金子隆司, 青木俊樹

    第71回高分子討論会  2022.9 

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  • 2,6-ビス(4-アセトキシ-3,5-ジ-t-ブチルフェニル)ベンゾ[1,2-b:5,4-b']ジフラン誘導体のクロスカップリング重合および対応するフェノキシラジカルの磁気的性質

    三浦悠, 寺口昌宏, 青木俊樹, 金子隆司, 青木俊樹

    第71回高分子学会年次大会  2022.5 

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  • 分子内超ミクロ孔含有二次元高分子膜の合成と透過(3)官能基含有全共役フェニレンエチニレンオリゴマ―配向膜を鋳型とする方法

    石佳, 高橋基, 寺口昌宏, 金子隆司, 青木俊樹

    第71回高分子学会年次大会  2022.5 

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  • 分子内超ミクロ孔含有二次元高分子膜の合成と透過(2)官能基含有全共役ビフェニレンアセチレンマクロマーよりのグラフトコポリマーを鋳型とする方法

    大川恵輔, 程柯涵, 寺口昌宏, 金子隆司, 青木俊樹

    第71回高分子学会年次大会  2022.5 

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  • 分子内超ミクロ孔含有二次元高分子膜の合成と透過(1)官能基含有全共役アセチレンオリゴマー超薄膜を鋳型とする方法

    木村優香, 前山萌奈, 寺口昌宏, 金子隆司, 青木俊樹

    第71回高分子学会年次大会  2022.5 

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  • 異なるタイプのアセチレンモノマーの共重合体の環化芳香族化光分解による主鎖構造の分析

    桑原薫, 寺口昌宏, 金子隆司, 青木俊樹

    日本化学会第102春季年会  2022.3 

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  • らせん置換アセチレンポリマーの環化芳香族化光分解を利用した各種光学分割膜の調製と光学異性体選択透過

    柴田みちる, 寺口昌宏, 金子隆司, 青木俊樹

    日本化学会第102春季年会  2022.3 

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  • 側鎖にアルキルイミダゾリウム塩部位を有するらせんポリフェニルアセチレンの合成と生成ポリマーの性質

    小澤 諒将, 金子隆司, 青木俊樹, 寺口昌宏

    第70回高分子討論会  2021.9 

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  • 2,6-ビス(4-アセトキシ-3,5-ジ-t-ブチルフェニル)ベンゾ[1,2-b:5,4-b’]ジフラン誘導体の合成と重合および対応するフェノキシラジカルの電子状態

    三浦悠, 寺口昌宏, 青木俊樹, 金子隆司

    第70回高分子討論会  2021.9 

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  • 末端と側鎖に官能基を持つ全共役ジエチニレン/ジフェニレン/フェニレンエチニレン重縮合体の合成、反応と気体透過性

    大川 恵輔, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第70回高分子学会年次大会  2021.5 

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  • 3,5 位にアルキルイミダゾリウム基および 4 位にドデシルオキシ基を有するらせんポリフェニルアセチレンの合成と性質

    小澤 諒将, 金子 隆司, 青木 俊樹, 寺口 昌宏

    第70回高分子学会年次大会  2021.5 

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  • 主鎖と側鎖に官能基を持つフェニレンエチニレン重縮合体の合成、反応と気体透過性

    高橋 基, 寺口 昌 宏, 金子 隆司, 青木 俊樹

    第70回高分子学会年次大会  2021.5 

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  • 膜状態でのポリマー側鎖間の重縮合と主鎖の光環化による二次元ネットワークポリマーの合成と膜性能

    石 佳, 武田 翔平, 木村 優香, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第70回高分子学会年次大会  2021.5 

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  • 側鎖に相補的な官能基を持つ二種ポリマーの重ね合わせ膜間の固固界面重縮合とポリマー主鎖の環化芳香族化分解による二次元ポリマー含有膜の合成と気体透過性

    程 柯涵, 遽延慶, 寺口 昌宏, 金子 隆司, 青木 俊 樹

    第70回高分子学会年次大会  2021.5 

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  • 置換アセチレンポリマーの選択的環化芳香族化分解で得た6つの水酸基を持つ 3 官能性モノマーよりの水素結 合性、イオン性、共有結合性多分岐またはネットワークポリマー膜の合成と透過性

    浅井 陸, 徐 晨曦, 成田 隼也, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第70回高分子学会年次大会  2021.5 

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  • 水酸基とアルキル鎖を持つフェニルアセチレンのコポリマー膜の酸素選択透過性

    山口 湧也, 寺口 昌宏, 金子 隆司, 青木 俊樹

    日本化学会第101春季年会  2021.3 

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  • ターフェニル基を含むシス-シソイダル型ポリ[3,5-ビス(ヒドロキシメチル)フェニルアセチレン]の合成とそれらの光学的特性

    澤 真弘, 金子 隆司, 青木 俊樹, 寺口 昌宏

    日本化学会第101春季年会  2021.3 

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  • 側鎖にガルビノキシル残基を有するポリ(アントリルアセチレン)の合成と磁気的性質

    近 祐希, 寺口 昌宏, 青木 俊樹, 金子 隆司

    日本化学会第101春季年会  2021.3 

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  • 4位にかさ高いトリアルキルシリル基を持つシスシソイダル型ポリ{3,5-ビス(ヒドロキシメチル)フェニルアセチレン}の合成および高選択的環化芳香族化分解(SCAT)

    阿部 幸也, 金子 隆司, 青木 俊樹, 寺口 昌宏

    日本化学会第101春季年会  2021.3 

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  • 3種の重合官能基を持つモノマーの段階的な重合によるトリプルストランドネットワーク2Dポリマー膜の合成と酸素選択透過性の向上

    程 柯涵, 寺口 昌宏, 金子 隆司, 青木 俊樹

    日本化学会第101春季年会  2021.3 

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  • 4,10位に安定フェノキシラジカルを置換したピレンの合成および電子状態・磁気的性質

    青山 潤太, 寺口 昌宏, 青木 俊樹, 金子 隆司

    日本化学会第101春季年会  2021.3 

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  • テトラヘドラルな連結を中心に有するフェニルフェノキシル置換ポリ(p-フェニレン)の合成と磁気的性質

    高野泰地, 寺口昌宏, 青木俊樹, 金子隆司

    第69回高分子討論会  2020.9 

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  • プチトップダウン合成による新規超分子ポリマー自立緻密膜の気体透過性

    細野晋太朗, 成田隼也, 寺口昌宏, 金子隆司, 青木俊樹

    日本膜学会第42年会  2020.6 

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  • 膜界面重縮合による官能基含有ポリアセチレンラミネート膜よりの2D ネットワークポリマー含有膜の合成と優れた酸素選択透過性

    遽延慶, 程科涵, 寺口昌宏, 金子隆司, 青木俊樹

    日本膜学会第42年会  2020.6 

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  • 光分解性ポリアセチレンテンプレートと剛直アキラルポリアセチレンマトリックスを用いたインプリント光学分割膜

    尾田友洋, 柴田みちる, 木村優香, 金子隆司, 寺口昌宏, 青木俊樹

    日本膜学会第42年会  2020.6 

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  • 2Dポリマー含有ポリアセチレン複合膜の合成と気体選択透過性(1)膜界面重縮合による2Dポリマーナノシート含有膜の優れた酸素選択透過

    遽延慶, 程科涵, 寺口昌宏, 金子隆司, 青木俊樹

    第69回高分子学会年次大会  2020.5 

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  • 2Dポリマー含有ポリアセチレン複合膜の合成と気体選択透過性(2)鋳型膜ポリマーの集合構造を利用した高分子膜反応による酸素選択透過性の向上

    武田 翔平, 寺口昌宏, 金子隆司, 青木俊樹

    第69回高分子学会年次大会  2020.5 

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  • 2Dポリマー含有ポリアセチレン複合膜の合成と気体選択透過性(3)鋳型膜高分子の集合構造制御による酸素選択透過性の向上

    庄子和樹, 木村優香, 寺口昌宏, 金子隆司, 青木俊樹

    第69回高分子学会年次大会  2020.5 

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  • 2Dポリマー含有ポリアセチレン複合膜の合成と気体選択透過性(4)鋳型膜高分子のコポリマー化による酸素選択透過性の向上

    下斗米伊吹, 細野晋太朗, 桑原薫, 寺口昌宏, 金子隆司, 青木俊樹

    第69回高分子学会年次大会  2020.5 

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  • 二種の鋳型分子を用いた架橋ポリフェニルアセチレンインプリント膜の光学異性体および酸素選択透過性

    尾田友洋, 柴田みちる, 木村優香, 寺口昌宏, 金子隆司, 青木俊樹

    日本化学会第100春季年会  2020.3 

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  • シスシソイダルポリフェニルアセチレンの高選択光環化芳香族化分解で得た超分子ポリマー純粋膜の酸素選択透過性の最適化

    細野晋太朗, 成田隼也, 寺口昌宏, 金子隆司, 青木俊樹

    日本化学会第100春季年会  2020.3 

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  • ビニル基と2つの水酸基を持つフェニルアセチレンよりの剛直らせんポリマー膜の製膜条件の後重合および酸素選択透過性への効果

    庄子和樹, 木村優香, 寺口昌宏, 金子隆司, 青木俊樹

    日本化学会第100春季年会  2020.3 

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  • 第2の官能基と2つの水酸基を持つフェニルアセチレンと疎水性フェニルアセチレンとの共重合体の酸素選択透過性

    下斗米伊吹, 細野晋太朗, 桑原薫, 寺口昌宏, 金子隆司, 青木俊樹

    日本化学会第100春季年会  2020.3 

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  • ポリ(4-ドデシルオキシ-3,5-ビス(アセトキシメチル)フェニルアセチレン)膜のコンフォメーション変化によるクロミズム

    北山智大, 寺口昌宏, 青木俊樹, 金子隆司

    第68回高分子学会北陸支部研究発表会  2019.12 

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  • ニトロニルニトロキシドを置換した2種類の側鎖が交互に積層されるよう設計されたポリ(1,3-フェニレンエチニレン)型フォルダマーの分子内架橋によるらせん安定化と磁気的性質

    永井芳樹, 寺口昌宏, 青木俊樹, 金子隆司

    第68回高分子討論会  2019.9 

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  • メタ位とパラ位にアキラルなエステル基とエーテル基をそれぞれ有するポリフェニルアセチレンの合成とキラル誘起

    北山智大, 寺口昌宏, 青木俊樹, 金子隆司

    第68回高分子討論会  2019.9 

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  • テトラフェニルエチレン部位を有するらせんフォルダマーの合成と刺激応答性蛍光発光

    番場望, 今井淳, 青木俊樹, 金子隆司, 寺口昌宏

    第68回高分子討論会  2019.9 

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  • Synthesis and fluorescence properties of push-pull type poly(diphenylacetylenes) having boron-containing substituents.

    2019.9 

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  • らせんアセチレンポリマーの高選択光環化芳香族化反応生成物の利用と機能-超分子キラルポリマー調製、ポリマーのミクロ構造分析と超分子膜の分離性能-

    長岡年寧, 遽延慶, 山口湧也, 寺口昌宏, 金子隆司, 青木俊樹

    第68回高分子学会年次大会  2019.5 

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  • アミド基を持つアキラルフェニルアセチレンの種々のらせん選択重合と生成ポリマーの反応、性質と機能

    大友諒平, 寺口昌宏, 金子隆司, 青木俊樹

    第68回高分子学会年次大会  2019.5 

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  • Optical resolution of dl-alcohol by enantiomer-selective helix-sense-selective polymerization followed by helix-sense selective highly selective photocyclic aromatization

    Yanan Tang, Jumpei Suzuki, Masairo Teraguchi, Takashi Kaneko, Toshiki Aoki

    2019.5 

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  • Synthesis and good oxygen permselectivity of novel layered network polymer membranes by intermacromolecular condensation between two kinds of imino pendant groups in two tightly helical cis-cisoidal homopolyphenylacetylenes

    Yanqing Qu, Masairo Teraguchi, Takashi Kaneko, Toshiki Aoki

    2019.5 

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  • 第二,第三の重合官能基を有するフェニルアセチレンよりのスターマルチストランドコポリマーの合成と酸素選択透過性

    大野貴矢, 寺口昌宏, 金子隆司, 青木俊樹

    日本膜学会第41年会  2019.5 

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  • ペンダントに多数のビニルエーテル基を有するタイトなポリフェニルアセチレンの高分子反応と小分子選択透過性-ビニルエーテル基のオリゴメリゼーションとポリアセチレンの高選択光環化芳香族化分解による改質と選択透過性の変化-

    坂田俊, 浪越毅, 寺口昌宏, 金子隆司, 青木俊樹

    日本膜学会第41年会  2019.5 

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  • テトラフェニルエチレン部位を有するポリ(1,3-フェニレンエチニレン)の合成と蛍光特性

    番場望, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第99春季年会  2019.3 

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  • ジメシチルボリル基を側鎖に有するポリジフェニルアセチレンの合成と蛍光特性

    荒木大地, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第99春季年会  2019.3 

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  • エナンチオマー選択らせん選択重合体の円偏光らせん選択SCATによるdl-メントールの光学分割

    鈴木純平, 寺口昌宏, 金子隆司, 青木俊樹

    日本化学会第99春季年会  2019.3 

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  • タイトならせん置換ポリフェニルアセチレンよりのスターマルチストランドコポリマーの合成と酸素選択透過性

    大野貴也, 寺口昌宏, 金子隆司, 青木俊樹

    第67回高分子学会北陸支部研究発表会  2018.11 

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  • Excellent oxygen permeability of novel siliconミcontaining cisミcisoidal poly (substituted phenylacetylene) membranes

    張明宇, 徐晨曦, 寺口昌宏, 金子隆司, 青木俊樹

    膜シンポジウム2018  2018.11 

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  • Enantioselective permeation through oneミhanded helical polymer membranes improved by enantioselective imine exchange reaction with permeants and by partially decomposed reaction of the membrane

    2018.11 

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  • ルースまたはタイトならせん置換ポリフェニルアセチレンのペンダント官能基の後重縮合によるスターマルチストランドコポリマーの合成と酸素透過性

    大野貴矢, 寺口昌宏, 金子隆司, 青木俊樹

    第67回高分子討論会  2018.9 

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  • ジメシチルボリル基を側鎖に有するポリジフェニルアセチレンの合成と蛍光特性

    荒木大地, 寺口昌宏, 金子隆司, 青木俊樹, ジン ヤンジェ, 郭 起燮

    第67回高分子討論会  2018.9 

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  • 側鎖にガルビノキシル残基およびフェノキシル残基を有するポリ(9,10-アントリレンエチニレン)共重合体のシークエンスと磁気的相互作用

    安部稔康, 寺口昌宏, 青木俊樹, 金子隆司

    第67回高分子討論会  2018.9 

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  • 3位にガルビノキシル残基を有するポリ(フェニルアセチレン)の合成と磁気的性質

    山崎悠佑史, 寺口昌宏, 青木俊樹, 金子隆司

    第67回高分子討論会  2018.9 

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  • 側鎖のフェニルニトロニルニトロキシドと(p-エチニルフェニル)ニトロニルニトロキシドが交互に積層するよう設計されたポリ(1,3-フェニレンエチニレン)型フォルダマーの合成およびらせん折り畳み形成

    永井芳樹, 老田一生, 寺口昌宏, 青木俊樹, 金子隆司

    第67回高分子学会年次大会  2018.5 

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  • 多分岐ポリフェニレンエチニレンとポリフェニルアセチレンとの複合膜の酸素選択透過性

    宮沢菜美, 王建軍, 寺口昌宏, 金子隆司, 青木俊樹

    第40回日本膜学会年会  2018.5 

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  • ラセミc-t動的らせんと片巻きc-c静的らせんの連鎖よりなる ポリフェニルアセチレンブロック共重合体の調製

    鈴木純平, Yin Guanwu, 寺口昌宏, 金子隆司, 青木俊樹

    第66回高分子学会北陸支部研究発表講演会  2017.11 

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  • 定量的光環化3量体生成物による置換アセチレン重合体の構造の定量分析 (1) GPCまたはNMRによる共重合体の三連子の決定

    長岡年寧, 尹官武, 寺口昌宏, 金子隆司, 青木俊樹

    第66回高分子学会北陸支部研究発表講演会  2017.11 

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  • 3位にガルビノキシル残基を有する光学活性ポリ(フェニルアセチレン)の合成およびそのらせん構造

    山崎悠佑史, 寺口昌宏, 青木俊樹, 金子隆司

    第66回高分子学会北陸支部研究発表講演会  2017.11 

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  • 側鎖にガルビノキシル残基およびフェノキシル残基を有するポリ(9,10-アントリレンエチニレン)共重合体の合成と分子内磁気的相互作用

    安部稔康, 寺口昌宏, 青木俊樹, 金子隆司

    第66回高分子学会北陸支部研究発表講演会  2017.11 

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  • シリル基含有ポリフェニルアセチレンのペンダント末端修飾による気体選択透過性の改良

    宮沢菜美, 王建軍, 寺口昌宏, 金子隆司, 青木俊樹

    膜シンポジウム2017  2017.11 

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  • 二つのN-アルケニルアミド基を持つ片巻きらせん置換ポリアセチレンのポストADMET重縮合による二重らせんポリマーの合成

    大友 諒平, 寺口 昌宏, 金子 隆司, 青木俊樹

    第66回高分子討論会  2017.9 

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  • タイトならせんポリフェニルアセチレン膜のペンダントビニルエーテル基の分子内カチオン重合および主鎖の高選択光環化芳香族化分解による気体透過性の最適化

    坂田俊, 浪越 毅, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第66回高分子討論会  2017.9 

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  • シリレンスペーサーのない直鎖および分岐アルキル基を有するポリジフェニルアセチレンの合成と蛍光特性

    川村祐斗, 寺口 昌宏, 青木 俊樹, 金子 隆司, カク ギソプ, ジン ユンジェ

    第66回高分子討論会  2017.9 

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  • テトラヘドラルな連結を中心に有するビスフェノキシル置換ポリ(アントリレンエチニレン)の合成と磁気的性質

    佐藤 駿広, 寺口 昌宏, 青木 俊樹, 金子 隆司

    第66回高分子討論会  2017.9 

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  • 6つの水酸基と3つのビニル基を有するC3対称ベンゼン誘導体を基本構造とする異なる経路で得られた種々のADMET重縮合体による酸素選択透過性の改良

    武尾駿, 園佳央理, 森谷まどか, 寺口昌宏, 金子隆司, 青木俊樹

    第66回高分子学会年次大会  2017.5 

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  • 規則性ポリ置換フェニルアセチレンのペンダントビニル基のADMET重縮合の前駆体ポリマー構造による分子内・分子間制御:マルチストランドコポリマーと含環コポリマーの合成と環構造の酸素選択透過性への効果

    園佳央理, 武尾駿, 森谷まどか, 寺口昌宏, 金子隆司, 青木俊樹

    第66回高分子学会年次大会  2017.5 

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  • ペンダントに種々の縮合性官能基を有する規則性ポリ置換フェニルアセチレンよりの種々の含環ポリマー膜の気体選択透過性

    森谷まどか, 園佳央理, 寺口昌宏, 金子隆司, 青木俊樹

    第39回日本膜学会年会  2017.5 

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  • 光学活性ピナニルシリル基を有するフェノキシ置換ポリホスファゼンの合成と分離膜機能

    中俣健太郎, 寺口昌宏, 金子隆司, 青木俊樹

    第39回日本膜学会年会  2017.5 

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  • 6 つの水酸基を有するC3 対称ベンゼン誘導体よりの超分子ポリマー含有高分子膜の酸素選択透過能

    大高絵里, 武尾 駿, 寺口昌宏, 金子隆司, 青木俊樹

    第39回日本膜学会年会  2017.5 

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  • 2Dポリマー(2DP)膜の透過(4):剛直なフェニルアセチレン共重合体膜のペンダント官能基の反応および主鎖の高選択光環化芳香族化分解による酸素選択透過性の向上

    森谷まどか, 武尾駿, 園佳央理, 寺口昌宏, 金子隆司, 青木俊樹

    膜シンポジウム2016  2016.12 

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  • 円偏光を用いたシス-シソイダルラセミらせんポリ置換アセチレンのらせん巻き方向選択的光環化芳香族化分解(SCAT): らせん巻き方向選択分解の機構と選択性の向上

    宮田真理, 寺口昌宏, 金子隆司, 青木 俊樹

    第65回高分子討論会  2016.9 

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  • 動的共有結合性分子内架橋によるポリ(1,3-フェニレンエチニレン)らせん構造の安定化

    若田部悟史, 寺口昌宏, 青木 俊樹, 金子隆司

    第65回高分子討論会  2016.9 

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  • 3,4,5位にアルキルエーテル鎖を有するポリ(フェニルアセチレン)の合成とキラル誘起

    羽田彩香, 寺口昌宏, 青木 俊樹, 金子隆司

    第65回高分子討論会  2016.9 

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  • 不斉源非共存下でのアキラルアセチレンのらせん選択重合

    尹官武, 寺口昌宏, 金子隆司, 青木俊樹

    第65回高分子討論会  2016.9 

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  • 2Dポリマー(2DP)膜の透過(3): シス‐シソイダルポリフェニルアセチレンの高選択光環化芳香族化分解生成物よりの2D構造化合物を含むポリマー膜の酸素選択透過性

    武尾駿, 園佳央理, 森谷まどか, 宮田真理, 寺口昌宏, 金子隆司, 青木 俊樹

    第65回高分子討論会  2016.9 

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  • アキラル条件によるらせん選択重合のキラリティーの制御と機構

    尹官武, 寺口昌宏, 金子隆司, 青木俊樹

    第65回高分子討論会  2016.9 

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  • 自立型2Dポリマー(2DP)膜の合成(11):剛直なシス-シソイダルポリフェニルアセチレンを鋳型とした可溶性2D構造含有グラフトポリマーの合成、キャラクタリゼーションと利用

    園佳央理, 森谷まどか, 宮田真理, 寺口昌宏, 金子隆司, 青木 俊樹

    第65回高分子討論会  2016.9 

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  • シスシソイダルラセミらせんポリフェニルアセチレンの円偏光を用いた高選択光環化芳香族化分解(SCAT): らせん巻き方向選択的SCATの選択性と反応速度の向上

    宮田真理, 寺口昌宏, 金子隆司, 青木俊樹

    第65回高分子学会年次大会  2016.5 

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  • 自立型2Dポリマー(2DP)膜の合成(12): 1~3官能性芳香族モノマーの共重縮合による可溶性全共役含環二次元ポリマー(2DP)の合成

    計良祐紀, 宮沢菜美, 寺口昌宏, 金子隆司, 青木俊樹

    第65回高分子学会年次大会  2016.5 

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  • 自立型2Dポリマー(2DP)膜の合成(11):水素結合可能な官能基をペンダントにもつシスーシソイダルポリフェニルアセチレン膜の合成と膜反応

    山下恭平, 森谷まどか, 寺口昌宏, 金子隆司, 青木俊樹

    第65回高分子学会年次大会  2016.5 

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  • 3,5-ビス(ヒドロキシメチル)フェニル基を末端に有するビスフェノキシル置換ポリ(アントリレンエチニレン)モデル化合物による超分子組織体形成と磁気的性質

    荒木陽介, 佐藤駿広, 寺口昌宏, 青木俊樹, 金子隆司

    第65回高分子学会年次大会  2016.5 

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  • 自立型2Dポリマー(2DP)膜の合成(9):種々の重合官能基をペンダントにもつシスーシソイダルポリフェニルアセチレンの合成と膜反応

    勝然勇也, 武尾 駿, 寺口昌宏, 金子隆司, 青木俊樹

    第65回高分子学会年次大会  2016.5 

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  • 自立型2Dポリマー(2DP)膜の合成(10):ビニル基をペンダントに持つシス-シソイダルポリフェニルアセチレンの2DADMET重縮合体膜の高選択光環化芳香族化分解による2D剥離とシロキサングラフト化による可溶化

    佐藤 栞, 園 佳央理, 寺口昌宏, 金子隆司, 青木俊樹

    第65回高分子学会年次大会  2016.5 

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  • 新規な可溶性イミドブリッジ型ラダーポリシロキサン膜の高酸素選択透過性

    徐 双平, 大高絵里, 寺口昌宏, 金子隆司, 青木俊樹

    第38回日本膜学会年会  2016.5 

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  • 共役平面主鎖を有するポリフェニルアセチレン誘導体膜からの可溶性四重鎖および七重鎖グラフェンナノリボンの合成と気体透過性

    深井拓也, 寺口昌宏, 金子隆司, 青木俊樹

    第38回日本膜学会年会  2016.5 

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  • 多孔性2DPのグラフト化による可溶化と酸素選択透過膜への利用

    計良祐紀, 寺口昌宏, 金子隆司, 青木俊樹

    膜シンポジウム2015  2015.11 

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  • ヒドロキシメチル基を有するポリ(1,3-フェニレンエチニレン)のらせん形成能と分子内架橋により固定化されたらせん構造の構築

    吉澤一平, 寺口昌宏, 青木俊樹, 金子隆司

    第64回高分子学会北陸支部研究発表講演会  2015.11 

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  • ホルミル基を有するポリ(1,3-フェニレンエチニレン)の合成と動的共有結合性分子内架橋によるらせん構造の固定化

    若田部悟史, 寺口昌宏, 青木俊樹, 金子隆司

    第64回高分子学会北陸支部研究発表講演会  2015.11 

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  • 側鎖にガルビノキシルを有するヨウ素ドープしたポリ(アントリレンエチニレン)の磁気的性質

    寺島佑亮, 西村一輝, 寺口昌宏, 青木俊樹, 金子隆司

    第64回高分子学会北陸支部研究発表講演会  2015.11 

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  • 自立型2Dポリマー(2DP)膜の合成(7)~シス-シソイダルポリフェニルアセチレンのペンダント末端官能基の高分子間重縮合体膜の合成と高選択光環化芳香族化分解(SCAT)およびグラフト化による可溶化~

    山下恭平, 森谷まどか, 勝然勇也, 宮田真理, 寺口昌宏, 金子隆司, 青木俊樹

    第64回高分子討論会  2015.9 

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  • 気体透過膜素材としてのラダーシロキサン含有ポリマーの合成

    徐双平, 寺口昌宏, 金子隆司, 青木俊樹

    第64回高分子討論会  2015.9 

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  • ラセミらせんポリ置換フェニルアセチレンの円偏光を用いる高選択光環化芳香族化分解(SCAT)によるキラルポリマー膜の合成

    宮田真理, 寺口昌宏, 金子隆司, 青木俊樹

    第64回高分子討論会  2015.9 

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  • シスシソイダルらせんポリ置換アセチレンの高選択光環化芳香族化分解による超分子ポリマー膜の合成と選択透過性

    王建軍, 大高絵里, 宮田真理, 寺口昌宏, 金子隆司, 青木俊樹

    第64回高分子討論会  2015.9 

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  • ワンポット同時重合法によるポリ(ハイパーブランチアセチレン型マクロモノマー)の合成と構造制御および気体分離性能

    王建軍, 寺口昌宏, 金子隆司, 青木俊樹

    第64回高分子学会年次大会  2015.5 

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  • 2Dポリマー膜の透過(2):膜表面での2D表面修飾剤の官能基のin situ 反応による酸素透過性の改良

    瓜田裕之, 王建軍, 武尾駿, 寺口昌宏, 金子隆司, 青木俊樹

    第64回高分子学会年次大会  2015.5 

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  • シス-トランソイダル型ポリフェニルアセチレン誘導体膜の脱水素環化反応によるグラフェンナノリボンの合成

    深井拓也, 齋藤龍輔, 寺口昌宏, 金子隆司, 青木俊樹

    第64回高分子学会年次大会  2015.5 

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  • 円偏光を用いた高選択光環化芳香族化分解(SCAT)によるラセミらせんポリ置換フェニルアセチレンの速度論的光学分割

    宮田真理, 寺口昌宏, 金子隆司, 青木俊樹

    第64回高分子学会年次大会  2015.5 

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  • 側鎖にフェニルニトロニルニトロキシド残基とニトロニルニトロキシド残基を有するポリ(1,3-フェニレンエチニレン)型キラルポリラジカルの合成とらせん折り畳み形成

    老田一生, 寺口昌宏, 青木俊樹, 金子隆司

    第64回高分子学会年次大会  2015.5 

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  • 二官能性および三官能性の芳香族モノマーの重縮合で得た2D 成分含有多分岐ポリマー膜の酸素選択透過性

    高田恭佑, 計良祐紀, 寺口昌宏, 金子隆司, 青木俊樹

    第37回日本膜学会年会  2015.5 

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  • 主鎖のみに不斉を有する置換ポリジフェニルアセチレンおよびイオン液体含有アセチレンポリマーの合成と光学異性体選択透過

    伊藤達也, 金子隆司, 青木俊樹, 寺口昌宏

    第37回日本膜学会年会  2015.5 

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  • 2,6位にフェノール残基を有するポリ(9,10-アントリレンエチニレン)の合成とそのポリラジカルの磁気的性質

    岡田果純, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第95回春季年会  2015.3 

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  • 折り畳まれたポリ(アントリレンエチニレン)のダイマーモデルの合成と性質

    須賀史哉, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第95回春季年会  2015.3 

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  • 2種の重合官能基を持つモノマーの二段階重合により得られたマルチストランドコポリマー膜の酸素選択透過性

    松井香奈, 寺口昌宏, 金子隆司, 青木俊樹

    膜シンポジウム2014  2014.11 

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  • 円偏光を用いた高選択光環化芳香族化分解(SCAT)によるラセミシス-シソイダルポリフェニルアセチレンのらせん巻き方向選択的分解

    宮田真理, 寺口昌宏, 金子隆司, 青木俊樹

    第63回高分子討論会  2014.9 

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  • 自立型2Dポリマー(2DP)膜の合成(2)~シス-シソイダルポリフェニルアセチレンのカラムナー間2DADMET重合体膜の高選択光環化芳 香族化分解(SCAT)による2D剥離~

    佐藤栞, 勝然勇也, 山下恭平, 宮田真理, 寺口昌宏, 金子隆司, 青木俊樹

    第63回高分子討論会  2014.9 

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  • ドナー・アクセプター構造を末端に有するビスフェノキシル置換ポリ(アントリレンエチニレン)モデル化合物による超分子組織体形成と磁気的性質

    荒木陽介, 寺口昌宏, 青木俊樹, 金子隆司

    第63回高分子討論会  2014.9 

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  • らせん選択重合(HSSP)で得られた堅い平面板状イミノ置換基を有する片巻きらせんポリフェニルアセチレンの定量的高分子膜反応(RIM)

    宮田真理, 寺口昌宏, 金子隆司, 青木俊樹

    第63回高分子討論会  2014.9 

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  • 置換アセチレンのらせん選択重合のキラリティーを用いない制御

    田口紗和, 張耿, 寺口昌宏, 金子隆司, 青木俊樹

    第63回高分子学会年次大会  2014.5 

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  • 自立型2Dポリマー膜の合成~シス-シソイダルポリフェニルアセチレンのカラムナー間2D重縮合体膜の高選択光環化芳香族化分解による2D剥離~

    宮田真理, 勝然勇也, 山下恭平, 寺口昌宏, 金子隆司, 青木俊樹

    第63回高分子学会年次大会  2014.5 

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  • 側鎖にガルビノキシルとアントラセン誘導体を有するポリ(1,3-フェニレンエチニレン)らせんフォルダマーの合成と磁気特性

    西川綾, 寺口昌宏, 青木俊樹, 金子隆司

    第63回高分子学会年次大会  2014.5 

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  • 4位にフェニルガルビノキシル残基を有するポリ[3,5-ビス(ヒドロキシメチル)フェニルアセチレン]の光学活性らせん構造の構築と磁気的性質

    村山善則, 時志春, 寺口昌宏, 青木俊樹, 金子隆司

    第63回高分子学会年次大会  2014.5 

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  • 高選択光環化芳香族化分解を用いた超分子ポリマー膜含有ポリマー膜の調製と透過性

    保坂由香里, 王建軍, 彭継軍, 寺口昌宏, 金子隆司, 青木俊樹

    第36回日本膜学会年会  2014.5 

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  • グラフェンナノリボン化ポリ(p-トリメチルシリルフェニルアセチレン) 膜の合成と気体透過性

    齋藤龍輔, 寺口昌宏, 金子隆司, 青木俊樹

    第36回日本膜学会年会  2014.5 

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  • らせん選択重合により得られたシス-シソイダルポリフェニルアセチレンを鋳型としたADMET後重合によるマルチストランドポリマーの合成

    松井香奈, 棚木宏幸, 寺口昌宏, 金子隆司, 青木俊樹

    第62回高分子討論会  2013.9 

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  • シス-トランソイダル型ポリフェニルアセチレン誘導体膜の酸化反応によるグラフェンナノリボンの合成

    齋藤龍輔, 寺口昌宏, 金子隆司, 青木俊樹

    第62回高分子討論会  2013.9 

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  • 低分子量体を用いた超高分子量シス-シソイダルポリフェニルアセチレン片巻きらせん選択重合体の分子構造の解明

    筒場豊和, 寺口昌宏, 金子隆司, 青木俊樹

    第62回高分子討論会  2013.9 

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  • ポリフェニルアセチレンのらせん選択重合におけるらせん巻き方向のアキラル条件による制御

    張耿, 田口紗和, 寺口昌宏, 金子隆司, 青木俊樹

    第62回高分子討論会  2013.9 

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  • 1つまたは2つのアルキルイミダゾリウムイオン液体構造を側鎖に持つポリフェニルアセチレンの合成と二酸化炭素選択透過性

    寺口昌宏, 金子隆司, 青木俊樹

    第62回高分子討論会  2013.9 

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  • フェニルアセチレンのらせん選択重合体膜の高選択光環化芳香族化分解反応による超分子ポリマー自立膜の合成

    宮田真理, 寺口昌宏, 金子隆司, 青木俊樹

    第62回高分子討論会  2013.9 

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  • ビフェニル基を有する3,5-ビス(ヒドロキシメチル)フェニルアセチレンのらせん選択重合とそのポリマーの蛍光特性

    金子隆司, 時志春, 村山善則, 寺口昌宏, 青木俊樹

    第62回高分子討論会  2013.9 

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  • かさ高い置換基を持つアキラルな置換アセチレンのリビング的らせん選択重合

    中尾和樹, 寺口昌宏, 金子隆司, 青木俊樹

    第62回高分子学会年次大会  2013.5 

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  • ビニル基をペンダントに持つらせん選択重合体を鋳型としたリボン、カラム、あるいはシート状特殊構造高分子の合成

    棚木宏幸, 松井香奈, 寺口昌宏, 金子隆司, 青木俊樹

    第62回高分子学会年次大会  2013.5 

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  • U字構造を含む水素結合ユニットを用いた芳香族超分子組織体の会合体形成挙動

    佐藤辰博, 寺口昌弘, 青木俊樹, 金子隆司

    第62回高分子学会年次大会  2013.5 

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  • ポルフィリンまたは亜鉛ポルフィリン部位と2つの水酸基を有するフェニルアセチレンのらせん選択重合

    西村卓浩, 寺口昌広, 名畑信之, 金子隆司, 青木俊樹

    第62回高分子学会年次大会  2013.5 

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  • 円偏光によるポリ[4-ドデシルオキシ-3,5-ビス(ヒドロキシメチル)フェニルアセチレン]のらせん巻き方向選択的光分解(SCAT)反応

    遠藤大慶, 寺口昌宏, 金子隆司, 青木俊樹

    第62回高分子学会年次大会  2013.5 

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  • 2つのフェノール残基を有する2-エチニル-2'-ヨードスチルベンの重合とそのらせんフォルダマー形成能

    富樫勇太, 寺口昌宏, 青木俊樹, 金子隆司

    第62回高分子学会年次大会  2013.5 

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  • Facile Synthesis of Amphiphilic 1,3,5ミTrisubstituted Benzene Derivatives Having Six Hydroxyl Groups and Three Hydrophilic Groups as Novel 2D Surface Modifiers for Efficient Improvement of Oxygen Permselectivity of Polymer Membranes

    藏雨, 王建軍, 寺口昌宏, 金子隆司, 青木俊樹

    第35回日本膜学会年会  2013.5 

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  • New approach to asymmetric polymerizations of substituted phenylacetylenes to yield static one-handed helical polymers

    Yu Zang, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    日本化学会第93回春季年会  2013.3 

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  • Improvement of Oxygen Permselectivity of Membranes by Surface Modification with Amphiphilic Cyclic Trimers(両親媒性環化三量体を用いた表面修飾による酸素選択透過性の改良)

    Yu Zang, Jianjun Wang, Jun L, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    膜シンポジウム2012  2012.11 

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  • Synthesis of Poly(Hyperbranched Acetylene-type Macromonomer)s with Different Spacers by Simultaneous Polymerization of Two Different Modes and Oxygen Permselectivity of the Resulting Polymer Membranes

    Jun Li, Jianjun Wang, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    膜シンポジウム2012  2012.11 

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  • シス-シソイダルポリフェニルアセチレンを鋳型としたマルチストランドポリマーの合成

    棚木宏幸, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子討論会  2012.9 

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  • Helix-sense-selective polymerization of achiral phenylacetylenes having two bulky imino substituents

    藏雨, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子討論会  2012.9 

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  • 架橋シス-シソイダルポリフェニルアセチレン膜の高選択的環化芳香族化分解反応による2Dポリマー膜合成

    宮田真理, 棚木 宏幸, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子討論会  2012.9 

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  • 異種様式同時重合法によるポリ(ハイパーブランチアセチレン型マクロモノマー)の合成と構造制御および気体分離膜としての性能

    李軍, 王建軍, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子討論会  2012.9 

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  • Optimization of the polymerization conditions of pseudo helix-sense-selective polymerization and helix-sense-selective polymerization for achiral substituted phenylacetylenes

    藏雨, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子討論会  2012.9 

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  • ガルビノキシルおよびフェノキシル誘導体を有するシークエンス制御されたポリ(1,3-フェニレンエチニレン)のらせん形成およびそれらポリラジカルの磁気的性質

    金子隆司, 岩村恭平, 寺口昌宏, 青木俊樹

    第61回高分子討論会  2012.9 

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  • 膜状態での高分子反応によるパーフルオロアルキル化ポリ(ジフェニルアセチレン)膜の合成と酸素選択透過性

    寺口昌宏, 佐藤敬, 金子隆司, 青木俊樹

    第61回高分子討論会  2012.9 

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  • Pseudo helix-sense-selective polymerization of achiral substituted acetylenes - A new concept and its realization -

    藏雨, 劉立佳, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子学会年次大会  2012.5 

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  • 水酸基を2つ有する置換アセチレンのらせん選択重合および生成シス-シソイダルポリマーの選択的環化芳香族分解の分子設計を用いた反応機構の提案

    和須津郁弥, 安部佑之介, 菊地一智, 藏雨, 劉立佳, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子学会年次大会  2012.5 

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  • 超分子前駆体よりの可溶性ポリシルセスキオキサンのラダー構造の完全性と気体選択透過性との関係

    加藤史也, 垣花百合子, 金子匠, 劉立佳, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子学会年次大会  2012.5 

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  • Highly selective cycloaromatization of cross-linked helical polyphenylacetylenes for preparation of novel 2D polymer membranes

    劉立佳, 宮田真理, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子学会年次大会  2012.5 

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  • 置換アセチレンのらせん選択重合(HSSP)の種々の特異な挙動と機構-アキラル制御HSSP、絶対HSSP、自己HSSP、不斉増幅HSSPと機構解明

    菊地一智, 田口紗和, 和須津郁弥, 大石智之, 劉立佳, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子学会年次大会  2012.5 

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  • フェノキシラジカルを有するポリ(1,2-フェニレンエチニレン-1,2-フェニレンビニレン)のらせんフォルダマー形成における溶媒効果

    富樫勇太, 劉立佳, 垣花百合子, 寺口昌宏, 青木俊樹, 金子隆司

    第61回高分子学会年次大会  2012.5 

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  • シス-シソイダル片巻きポリ置換フェニルアセチレン膜の光高選択トポケミカル環化芳香族化分解反応の機構

    安部佑之介, 和須津郁弥, 垣花百合子, 劉立佳, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子学会年次大会  2012.5 

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  • 円偏光によるらせんポリ置換アセチレン膜のらせん巻き方向選択的光分解反応

    遠藤大慶, 寺口昌宏, 安部佑之介, 垣花百合子, 劉立佳, 金子隆司, 青木俊樹

    第61回高分子学会年次大会  2012.5 

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  • ビニル基を有するポリフェニルアセチレンの後重合によるヘテロラダーポリマーの合成とキャラクタリゼーション

    棚木宏幸, 垣花百合子, 劉立佳, 寺口昌宏, 金子隆司, 青木俊樹

    第61回高分子学会年次大会  2012.5 

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  • 超分子前駆体よりのラダー構造を含む可溶性ポリシルセスキオキサン含有膜の気体透過性

    垣花百合子, 加藤史也, 金子匠, 劉立佳, 大石智之, 寺口昌宏, 金子隆司, 青木俊樹

    第34回日本膜学会年会  2012.5 

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  • 二つの-SiH基を持つフェニルアセチレンの合成、重合と気体分子選択透過性

    李軍, 王建軍, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第34回日本膜学会年会  2012.5 

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  • 二酸化炭素分離膜素材としてのイミダゾリウム塩構造を側鎖に2つ有するポリアセチレンの合成と生成ポリマーの性質

    小林右弥, 劉立佳, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第34回日本膜学会年会  2012.5 

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  • フェニルアセチレンのらせん選択重合と生成ポリマーの選択的環化分解の機構

    和須津郁弥, 棚木宏幸, 安部佑之介, 劉立佳, 藏雨, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    日本化学会第92回春季年会  2012.3 

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  • U字型構造で結合したフェノキシ置換ポリ(9,10-アントリレンエチニレン)誘導体のダイマーモデルの合成とその電子状態

    塚本圭太, 劉立佳, 垣花百合子, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第92回春季年会  2012.3 

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  • 側鎖にニトロ基とニトロニルニトロキシド残基を有するポリ(1,3-フェニレンエチニレン)型キラルポリラジカルのらせんフォルダマー形成と磁気的性質

    廣野一也, 大石智之, 垣花百合子, 劉立佳, 寺口昌宏, 青木俊樹, 金子隆司

    第60回高分子学会北陸支部研究発表講演会  2011.11 

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  • Improvement of Gas Permselectivity of Membranes by Surface Modification by Using Cyclic Trimers of Phenylacetylene Having Hydrophobic or Hydrophilic Group

    劉立佳, 王建軍, 大石智之, 垣花百合子, 金子隆司, 寺口昌宏, 青木俊樹

    膜シンポジウム2011  2011.11 

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  • ラダーポリシルセスキオキサン構造含有膜の気体透過性

    垣花百合子, 加藤史也, 金子匠, 大石智之, 劉立佳, 寺口昌宏, 金子隆司, 青木俊樹

    膜シンポジウム2011  2011.11 

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  • Gas Permeselectivity Through the Membranes of Substituted Phenylacetylene Polymers Having Two Hydroxyl Groups

    Yu Zang, Lijia Liu, Yuriko Kakihana, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    膜シンポジウム2011  2011.11 

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  • L-アミノ酸を配位子に有する構造明確な単離 Rh 錯体によるフェニルアセチレンのらせん選択重合の精密化

    大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子討論会  2011.9 

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  • シス-シソイダル片巻きポリ置換フェニルアセチレン膜の光による高選択的トポケミカル環化芳香族化分解反応の制御-生成超分子膜の強度向上と光学活性化、反応機構の解明

    安部佑之介, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子討論会  2011.9 

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  • 気体透過膜素材としてのラダー超分子を前駆体とした可溶性ラダーポリシルセスキオキサンの合成

    加藤史也, 垣花百合子, 大石智之, 劉立佳, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子討論会  2011.9 

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  • 1つまたは2つのイミダゾリウムイオン液体構造を側鎖に持つポリフェニルアセチレンの合成と二酸化炭素選択透過性

    小林右弥, 大石智之, 垣花百合子, 劉立佳, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子討論会  2011.9 

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  • 2つのビニル基を有するフェニルアセチレンのらせん選択重合(HSSP)体のADMET後重合による片巻きらせんヘテロラダーポリマーの合成とHSSP体主鎖の選択分解

    棚木宏幸, 江良康貴, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子討論会  2011.9 

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  • Pseudo helix-sense-selective polymerization of substituted phenylacetylenes having two hydroxyl groups and a dynamic covalent bond of imino group

    藏雨, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子討論会  2011.9 

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  • 異種様式同時重合法によるポリ(ハイパーブランチマクロモノマー)の合成と気体分子選択透過性

    李軍, 王建軍, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子討論会  2011.9 

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  • フェノール残基を置換したアントリレンエチニレンへテロダイマー型モノマーの合成と重合

    今野良平, 金子隆司, 大石智之, 垣花百合子, 劉立佳, 寺口昌宏, 青木俊樹

    第60回高分子討論会  2011.9 

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  • 側鎖にガルビノキシルとフェノキシルを有するポリ(1,3-フェニレンエチニレン)型ポリラジカル:コンフォメーションと磁気的性質の関係

    岩村恭平, 金子隆司, 大石智之, 垣花百合子, 劉立佳, 寺口昌宏, 青木俊樹

    第60回高分子討論会  2011.9 

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  • 2つの水酸基を持つアキラルなフェニルアセチレンモノマーのキラル触媒系を用いたらせん選択重合の高度化

    菊地一智, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子討論会  2011.9 

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  • SYNTHESIS OF ONE-HANDED HELICAL p-CONJUGATED POLYMERS AND THEIR ENANTIOSELECTIVE PERMEABILITY International conference

    Masahiro Teraguchi

    14th Asian Chemical Congress 2011 (14 ACC)  2011.9 

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  • イミンの動的共有結合を利用した置換フェニルアセチレンの偽らせん選択重合

    小野雅貴, 中尾和樹, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子学会年次大会  2011.5 

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  • 有機蒸気によるキラルなメンチル基を有するポリ(m-フェニレンエチニレン)のらせん構造の膜状態での刺激応答性

    井上真, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子学会年次大会  2011.5 

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  • アミノ酸を配位子に有する構造明確な Rh 触媒を用いた置換アセチレンのらせん選択重合

    大石智之, 菊地一智, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子学会年次大会  2011.5 

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  • ガルビノキシル残基を有するポリ(1,3-フェニレンエチニレン)の片 巻優 先らせんフォルダマー形成における置換基効果

    二宮浩彰, 金子隆司, 大石智之, 垣花百合子, 寺口昌宏, 青木俊樹

    第60回高分子学会年次大会  2011.5 

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  • シス-シソイダルポリ置換フェニルアセチレン膜の高選択的環化芳香族化分解によるキラルな超分子自己支持膜の調製

    安部佑之介, 遠藤大慶, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子学会年次大会  2011.5 

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  • Polymerization of achiral phenylacetylenes having two hydroxyl groups with different lengths of the spacers

    藏雨, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子学会年次大会  2011.5 

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  • らせん選択重合によるポルフィリン部位を側鎖に持つ片巻きらせんポリフェニルアセチレンの合成

    名畑信之, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子学会年次大会  2011.5 

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  • らせん選択重合に適する新規光学不活性フェニルアセチレンモノマーの合成と重合

    和須津郁弥, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子学会年次大会  2011.5 

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  • 重合官能基を有するペンダントグループを持つ片巻きらせんポリフェニルアセチレンの分子内後重合による可溶なキラルヘテロラダーポリマーの合成

    江良康貴, 棚木宏幸, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第60回高分子学会年次大会  2011.5 

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  • ラダーポリシルセスキオキサン構造を含むポリフェニルアセチレン誘導体膜

    垣花百合子, 加藤史也, 大石智之, 寺口昌宏, 金子隆司, 青木俊樹

    第33回日本膜学会年会  2011.5 

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  • Enhancement of Oxygen Permselectivity of Membranes by Surface Modification by Using Cyclic Trimers of Phenylacetylene Having an Oligosiloxane or Oligo(ethylene oxide) Group

    劉立佳, 田桑謙, 加藤史也, 大石智之, 垣花百合子, 金子隆司, 寺口昌宏, 青木俊樹

    第33回日本膜学会年会  2011.5 

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  • アルキルイミダゾリウム塩構造を側鎖に持つポリフェニルアセチレンの合成と二酸化炭素選択透過性

    小林右弥, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第33回日本膜学会年会  2011.5 

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  • 側鎖にニトロ基とニトロニルニトロキシド残基を有するポリ(1,3-フェニレンエチニレン)型キラルポリラジカルの合成とらせんフォルダマー形成

    廣野一也, 加藤清亮, 大石智之, 垣花百合子, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第91回春季年会  2011.3 

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  • フェノキシ置換ポリ(1,8-ナフチレンエチニレン-9,10-アントリレンエチニレン)およびそのダイマーモデルの合成

    塚本圭太, 大石智之, 垣花百合子, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第91回春季年会  2011.3 

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  • Synthesis and enantioselective permeation of one-handed helical poly(phenyleneethynylene) membranes with chiral menthyl groups and in-situ desubstitution International conference

    Makoto Inoue, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)  2010.12 

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  • Two modes of asymmetric polymerization of phenylacetylenes having an L-amino alcohol residue International conference

    Hongge Jia, Yunosuke Abe, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko, Tomoyuki Ohishi, Yuriko Kakihana

    The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)  2010.12 

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  • Synthesis of polymers from phenylacetylenes for permselective membranes International conference

    Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    The International Chemical Congress of Pacific Basin Societies (Pacifichem 2010)  2010.12 

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  • 側鎖にガルビノキシルとフェノキシルを有するポリ(1,3-フェニレンエチニレン)型ポリラジカルフォルダマーの合成とその磁気的性質

    岩村恭平, 大石智之, 垣花百合子, 寺口昌宏, 青木俊樹, 金子隆司

    第59回高分子学会北陸支部研究発表会  2010.11 

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  • 水素結合形成可能な官能基を有さない新規アセチレンモノマーを用いた触媒的らせん選択重合

    菊地一智, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第59回高分子学会北陸支部研究発表会  2010.11 

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  • 2 つのN-メチルアミド基とアルコキシ基を持つフェニルアセチレンのらせん選択重合

    加藤史也, 大石智之, 垣花百合子, 寺口昌宏, 金子隆司, 青木俊樹

    第59回高分子学会北陸支部研究発表会  2010.11 

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  • フェノール残基を導入した2,6-置換ポリ(9,10-アントリレンエチニレン)の合成とその電子状態

    今野良平, 大石智之, 垣花百合子, 寺口昌宏, 青木俊樹, 金子隆司

    第59回高分子学会北陸支部研究発表会  2010.11 

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  • ポリ(1,3-フェニレンエチニレン)誘導体自立膜の調製と選択透過性

    井上 真, 大石 智之, 垣花 百合子, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第59回高分子討論会  2010.9 

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  • 動的共有結合を利用した置換アセチレンの偽らせん選択重合の最適化

    小野 雅貴, 中尾 和樹, 大石 智之, 垣花 百合子, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第59回高分子討論会  2010.9 

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  • らせん選択重合体膜の高選択的環化芳香族化分解で得られたオリゴエチレンオキシ ド鎖を有する環化三量体の膜表面修飾能

    田桑 謙, 劉 立佳, 安部 佑之介, 大野 弘嗣, 大石 智之, 垣花 百合子, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第59回高分子討論会  2010.9 

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  • Application of reaction and product of selective cycloaromatization of chiral polymeric membranes prepared by helix-sense-selective polymerization of phenylacetylene having an oligosiloxanyl group

    Lijia Liu, Ken Taguwa, Yunosuke Abe, Yu Zang, Hiroshi Oono, Tomoyuki Ohishi, Yuriko Kakihana, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    第59回高分子討論会  2010.9 

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  • シス-シソイダルポリ置換フェニルアセチレン膜の高選択的環化芳香族化分解による 超分子自己支持膜調製の最適化

    安部 佑之介, 田桑 謙, 劉 立佳, 蔵 雨, 遠藤 大慶, 大野 弘嗣, 大石 智之, 垣花 百合, 子, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第59回高分子討論会  2010.9 

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  • らせん選択重合体の側鎖の分子内重合による可溶なキラルヘテロラダー ポリマーの 合成と性質

    江良 康貴, 和須津 郁弥, 棚木 宏幸, 大石 智之, 垣花 百合子, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第59回高分子討論会  2010.9 

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  • Synthesis and Helix-sense-selective Polymerization of a Novel Phenylacetylene Having an Oligosiloxanyl Group and Two Hydroxy Groups: Effect of the Oligosiloxanyl Group on Polymerization, Helix Stability and Membrane Performances of the Resulting Polymers International conference

    Lijia Liu, Yoshiyuki Oniyama, Yu Zang, Shingo Hadano, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko, Takeshi Namikoshi

    22nd International Symposium on Chirality (ISCD-22)  2010.7 

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  • Helix-Sense-Selective Polymerization of Achiral Phenylacetylenes and Selective Cyclicaromatization of the Resulting Cis-Cisoidal Poly(phenylacetylene)s International conference

    Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    22nd International Symposium on Chirality (ISCD-22), Pre-Symposium, Molecular Chirality 2010  2010.7 

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  • Preparation of Chiral Supramolecular Self-supporting Membrane by Highly Selective Cycloaromatization of Helical Poly(phenylacetylene) Membrane Synthesized by Asymmetric-induced Polymerization International conference

    Yunosuke Abe, Takeshi Namikoshi, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    22nd International Symposium on Chirality (ISCD-22)  2010.7 

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  • Highly Selective Cycloaromatization of Polymers Prepared by Helix-sense-selective Polymerization by Light Irradiation International conference

    Takeshi Namikoshi, Lijia Liu, Yunosuke Abe, Yoshiyuki Oniyama, Nobuyuki Nahata, Edy Marwanta, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    22nd International Symposium on Chirality (ISCD-22)  2010.7 

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  • Preparation of Supramolecular Self-Supporting Membranes by Highly Selective Cycloaromatization of Polyphenylacetylene Membranes International conference

    Takeshi Namikoshi, Lijia Liu, Yunosuke Abe, Yoshiyuki Oniyama, Nobuyuki Nahata, Edy Marwanta, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    Interanational Conference on Science and Technology of Synthetic Metals 2010  2010.7 

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  • Helix-Sense-Selective Polymerization of (3,5-Bis(hydroxymethyl)-4-phenyl)phenylacetylenes International conference

    Manami Osawa, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    Interanational Conference on Science and Technology of Synthetic Metals 2010  2010.7 

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  • Synthesis, In-Situ Desubstitution, and Enantioselective Permeation of One-Handed Helical Poly(phenyleneethynylene) Membranes with Chiral Menthyl Groups International conference

    Makoto Inoue, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    Interanational Conference on Science and Technology of Synthetic Metals 2010  2010.7 

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  • Sequential Poly(aryleneethynylene)-Based Polyradicals: Synthesis and Magnetic Property International conference

    Takashi Kaneko, Kiyoaki Kato, Toshihiro Saito, Masahiro Teraguchi, Toshiki Aoki

    Interanational Conference on Science and Technology of Synthetic Metals 2010  2010.7 

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  • Helix-sense-selective Polymerization of a Novel Phenylacetylene Having a Trisiloxanyl Group and Two Hydroxy Groups and Application of the Resulting Membrane International conference

    Lijia Liu, Yoshiyuki Oniyama, Yu Zang, Shingo Hadano, Masahiro Teraguchi, Takashi Kaneko, Takeshi Namikoshi, Edy Marwanta, Toshiki Aoki

    Interanational Conference on Science and Technology of Synthetic Metals 2010  2010.7 

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  • Synthesis of Poly(1,3-phenyleneethynylene)s with Pendant Galvinoxyl, Chiral and Hydrophilic Moieties, and Their Forming Ability of Helical Foldamer International conference

    Hiroaki Ninomiya, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    Interanational Conference on Science and Technology of Synthetic Metals 2010  2010.7 

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  • Synthesis of Optically Active Poly(Binaphthyl-6,6-diylethynylene-9,10-anthryleneethynylene) Bearing Phenoxyls at 2,7-Positions of Anthracene International conference

    Masahiro Tsuchida, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    Interanational Conference on Science and Technology of Synthetic Metals 2010  2010.7 

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  • Synthesis of One-handed Helical Polyacetylenes without the Coexistance of any Other Chiral Moieties via Polymer Reaction International conference

    Yunosuke Abe, Masahiro Teraguchi, Hongge Jia, Makoto Inoue, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    Interanational Conference on Science and Technology of Synthetic Metals 2010  2010.7 

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  • ヘキサフェニルベンゼン部位と2つの水酸基を有するフェニルアセチレンのらせん選択重合

    名畑信之, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第59回高分子学会年次大会  2010.5 

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  • Characterization of chemical structures of one-handed helical graft copolymers from siloxane macromonomers by using highly selective aromatization reaction of the copolymers

    Lijia Liu, Masahiro Teraguchi, Takeshi Namikoshi, Marwanta Edy, Takashi Kaneko, Toshiki Aoki

    第59回高分子学会年次大会  2010.5 

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  • 種々の触媒を用いたL-アミノエーテル残基と二つの水酸基を持つフェニルアセチレンの不斉重合の三つの機構と得られたポリマーの利用

    賈宏葛, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第59回高分子学会年次大会  2010.5 

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  • シスシソイダルポリ置換フェニルアセチレン膜の高選択的芳香環生成分解反応による自己支持性超分子膜の調製

    鬼山祥幸, 安部佑之介, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第59回高分子学会年次大会  2010.5 

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  • シスシソイダルポリ置換フェニルアセチレン膜の高選択的芳香環生成分解反応とその利用

    浪越 毅, 鬼山祥幸, 劉 立佳, 安部佑之介, 江良康貴, 田桑謙, 名畑信之, エディ マルワンタ, 寺口昌宏, 金子隆司, 青木俊樹

    第59回高分子学会年次大会  2010.5 

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  • 膜状態における脱キラル置換基反応によるTEMPO含有片巻きらせんポリフェニルアセチレン膜の合成と利用

    谷本紗代, 安部佑之介, 浪越 毅, エディ マルワンタ, 寺口昌宏, 金子隆司, 青木俊樹

    第59回高分子学会年次大会  2010.5 

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  • 4位にフェニル基を有する3,5-ビス(ヒドロキシメチル)フェニルアセチレンのらせん選択重合と光学不活性な重合体からの片巻優先らせん誘起

    大澤愛実, 浪越 毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    第59回高分子学会年次大会  2010.5 

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  • 片巻きらせんヘテロラダーコポリ(一置換アセチレン/二置換アセチレン)の合成

    江良康貴, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第59回高分子学会年次大会  2010.5 

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  • イミンの動的共有結合を利用したフェニルアセチレンの偽らせん選択重合

    小野雅貴, 浪越 毅, エディ マルワンタ, 寺口昌宏, 金子隆司, 青木俊樹

    第59回高分子学会年次大会  2010.5 

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  • フェニルアセチレン型マクロモノマーの共重合またはクリック反応によるキラルなオリゴフェニレンエチニレン鎖を枝に持つポリアセチレングラフトコポリマーの合成

    三井知明, 井上真, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第59回高分子学会年次大会  2010.5 

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  • かさ高いイミノ置換基を持つフェニルアセチレンのらせん選択重合のリビング化とブロックコポリマーの合成

    四柳宏基, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第59回高分子学会年次大会  2010.5 

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  • キラルなメンチル基を有するポリ(フェニレンエチニレン)膜の合成と脱置換反応および光学異性体選択透過性

    井上真, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第32回日本膜学会年会  2010.5 

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  • 膜反応によるパーフルオロアルキル化ポリ(ジフェニルアセチレン)膜の合成と酸素選択透過特性

    吉田直樹, 佐藤敬, 寺口昌宏, 金子隆司, 青木俊樹

    日本化学会第90回春季年会  2010.3 

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  • 片巻きらせんポリマーを共触媒に用いたらせん選択重合

    小野雅貴, 寺口昌宏, エディ マルワンタ, 浪越毅, 金子隆司, 青木俊樹

    日本化学会第90回春季年会  2010.3 

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  • クリック反応およびマクロモノマー法によるオリゴフェニレンエチニレン鎖を枝に持つ片巻きらせんポリフェニルアセチレングラフトコポリマーの合成

    三井知明, 寺口昌宏, 浪越毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • らせん選択重合で得られた分子内水素結合で保持された片巻きらせん構造の分子内共有結合による固定

    江良康貴, 寺口昌宏, 浪越毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • 種々のアミノエーテル残基と二つの水酸基を持つフェニルアセチレンモノマーのらせん選択重合と不斉誘起重合

    賈宏葛, 寺口昌宏, 浪越毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • キラル置換基を有するポリ(フェニレンエチニレン)膜の高分子膜反応および光学異性体選択透過性

    井上真, 寺口昌宏, 浪越毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • 主鎖の片巻きらせんコンホメーションのみに起因した可溶性キラルポリマーの効率的合成法(1)-長いアルキル基を有するコモノマーとの不斉誘起共重合と高分子膜反応を経る方法

    安部佑之介, 賈宏葛, 寺口昌宏, 浪越毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • 主鎖の片巻きらせんコンホメーションのみに起因した可溶性キラルポリマーの効率的合成(2)-長いスペーサーを有するモノマーの不斉誘起重合と高分子膜反応を経る方法

    安部佑之介, 賈宏葛, 寺口昌宏, 浪越毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • Synthesis and properties of one-handed helical polyphenylacetylenes having oligosiloxanyl groups of different lengths prepared by helix-sense-selective polymerization

    Lijia Liu, Yu Zang, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    第58回高分子討論会  2009.9 

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  • 鎖長の異なるオリゴエチレンオキシド鎖と2つの水酸基を有するフェニルアセチレンのらせん選択重合-オリゴエチレンオキシド鎖の効果

    田桑謙, 寺口昌宏, 浪越毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • ポリフェニルアセチレン膜の高選択的芳香環生成反応による超分子自己支持膜の調製(1)-ポリマーの一次および高次構造の選択性への効果

    浪越毅, 鬼山祥幸, 劉立佳, 安部佑之助, 江良康貴, 田桑 謙, 名畑信之, 松本和樹, エディ マルワンタ, 寺口昌宏, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • ポリフェニルアセチレン膜の高選択的芳香環生成反応による超分子自己支持膜の調製(2)-反応条件の選択性への効果

    鬼山祥幸, 寺口昌宏, 浪越毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • 主鎖のみに不斉構造を持つキラルポリマーを不斉源とするフェニルアセチレンのらせん選択重合

    松本和樹, 小野雅貴, 寺口昌宏, 浪越毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • アルキルイミダゾリウムイオン液体構造を持つポリフェニルアセチレンの合成と性質

    エディ マルワンタ, 浪越毅, 寺口昌宏, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • かさ高いイミノ置換基を持つフェニルアセチレンのらせん選択重合のリビング性を利用した末端変換

    四柳宏基, 浪越毅, 寺口昌宏, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • N-アルキルアミド基を持つフェニルアセチレンのらせん選択重合とN-アルキルアミド基の片巻きらせん構造への効果

    名畑信之, 寺口昌宏, 浪越毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子討論会  2009.9 

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  • 側鎖にニトロニルニトロキシドを有するポリ(1,3-フェニレンエチニレン)型キラルポリラジカルのらせんフォルダマー構造制御と磁気的性質

    加藤清亮, 浪越毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    第58回高分子討論会  2009.9 

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  • オリゴ(9,10-アントリレンエチニレン)構造を介したフェノキシラジカル類の磁気的相互作用

    高村政克, 浪越毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    第58回高分子討論会  2009.9 

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  • 4位にフェニル基を有する3,5-ビス(ヒドロキシメチル)フェニルアセチレンのらせん選択重合

    大澤愛実, 浪越毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    2009年支部合同新潟地方大会(第58回高分子学会北陸支部研究発表講演会)  2009.8 

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  • アントラセンの2,7位にフェノール残基を有する光学活性なポリ(ビナフチル-6,6'-ジイルエチニレン-9,10-アントリレンエチニレン)の合成

    土田昌弘, 浪越毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    2009年支部合同新潟地方大会(第58回高分子学会北陸支部研究発表講演会)  2009.8 

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  • 2位にヒドロキシエトキシ基、5位にガルビノキシル残基を有するポリ(1,3-フェニレンエチニレン)の合成とらせんフォルダマー形成能

    二宮浩彰, 浪越毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    2009年支部合同新潟地方大会(第58回高分子学会北陸支部研究発表講演会)  2009.8 

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  • クリック反応およびマクロモノマー法によるキラルなポリ(m-フェニレンエチニレン)グラフト鎖を有するポリフェニルアセチレンの合成

    三井知明, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • 2つの水酸基と光応答性基を持つフェニルアセチレンのらせん選択重合と生成ポリマー膜の光応答性

    鈴木一平, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • Helix-sense-selective polymerization of phenylacetylenes having two hydroxy groups and an oligosiloxanyl group and properties of membranes from the resulting polymers

    Lijia Liu, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    第58回高分子学会年次大会  2009.5 

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  • 二つの種々のイミノ基を持つフェニルアセチレンのらせん選択重合により得られた片巻きらせんポリマーをキラル共触媒に用いたフェニルアセチレンのらせん選択重合

    松本和樹, 四柳宏基, 浪越 毅, 寺口昌宏, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • イオン液体構造を有する置換ポリアセチレンの合成と気体透過性

    エディ マルワンタ, 浪越 毅, 寺口昌宏, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • 二つのかさ高いイミノ置換基を持つフェニルアセチレンのリビング的らせん選択重合

    四柳宏基, 浪越 毅, 寺口昌宏, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • らせん選択重合体膜の光照射高選択的芳香環生成反応による超分子自己支持膜の調整-(1)二つの水酸基と脂肪族置換基を持つフェニルアセチレンをモノマーとして用いた場合

    浪越 毅, エディ マルワンタ, 寺口昌宏, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • ガルビノキシル置換オリゴ(9,10-アントリレンエチニレン)の合成及び電子構造と磁気的性質

    高村政克, 浪越 毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    第58回高分子学会年次大会  2009.5 

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  • 二つの水酸基とL-メントール残基を持つフェニルアセチレンの不斉誘起重合で得られた片巻きらせんポリマーの高分子膜脱キラル置換基反応による主鎖のみに不斉構造を有するポリマーの合成

    安部佑之介, 賈 宏葛, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • らせん選択重合体膜の光照射高選択的芳香環生成反応による超分子自己支持膜の調整-(2)二つの水酸基と芳香族置換基を持つフェニルアセチレンをモノマーとして用いた場合

    鬼山祥幸, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • 膜中での脱キラル置換基反応によるTEMPO含有片巻きらせんポリフェニルアセチレン膜の合成

    谷本紗代, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • 膜中での脱キラル置換基反応による末端アセチレン部位を持つ片巻きらせんポリジフェニルアセチレン膜の合成

    吉田直樹, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • 二つの水酸基と種々のアミノ酸残基を持つフェニルアセチレンの二つの様式での不斉重合-らせん選択重合と不斉誘起重合の両方に適するモノマー

    賈 宏葛, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • 膜中でのキラル-アキラルイオン交換反応による主鎖のみに不斉構造を持つキラルポリフェニルアセチレン膜の合成

    西本秀之, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第58回高分子学会年次大会  2009.5 

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  • アミノ基と共役系デンドリティック置換基を有するフェニルアセチレンポリマー膜の二酸化炭素選択透過性

    佐藤勇希, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第31回日本膜学会年会  2009.5 

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  • イオン液体構造を有する置換ポリアセチレン膜の調製と気体透過性

    エディ マルワンタ, 浪越 毅, 寺口昌宏, 金子隆司, 青木俊樹

    第31回日本膜学会年会  2009.5 

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  • 2,6-ビス(3-エチル-3-ペンチル)フェノキシル類似安定ラジカルの合成と電子状態

    斉藤俊博, 浪越 毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第89回春季年会  2009.3 

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  • 膜状態におけるクリック反応によるパーフルオロアルキル鎖含有ポリジフェニルアセチレン膜の合成と気体透過性

    木内基裕, 佐藤敬, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第89回春季年会  2009.3 

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  • Synthesis of Soluble One-Handed Helical Poly(phenylacetylene)s by Removal of the Chiral Groups from Poly(phenylacetylene)s Having Chiral Substitutes in Membrane State International conference

    Yunosuke Abe, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    International Symposium on Fusion Tech 2009 at Incheon  2009.1 

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  • Helix-Sense-Selective Polymerization of Phenylacetylenes Having a Di- or Trisiloxanyl Substituent and Two Hydroxy Groups International conference

    Lijia Liu, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    International Symposium on Fusion Tech 2009 at Incheon  2009.1 

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  • Helix-Sense-Selective Polymerization of Phenylacetylene Having Two N-(O-tert-Butylphenyl)imino Groups International conference

    Hiroki Yotsuyanagi, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    International Symposium on Fusion Tech 2009 at Incheon  2009.1 

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  • Synthesis and Selective Cycloaromatization of One-Handed Helical Polyphenylacetylene Having Two Hydroxy Groups and Aromatic Substituent International conference

    Yoshiyuki Oniyama, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    International Symposium on Fusion Tech 2009 at Incheon  2009.1 

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  • Preparation of Supramolecular Self-Supporting Membrane by Selective Cycloaromatization of One-Handed Helical Poly(Phenylacetylene) Membrane Stabilized by Hydrogenbonds International conference

    Takeshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    International Symposium on Fusion Tech 2009 at Incheon  2009.1 

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  • Two Modes of Asymmetric Polymerization of Phenylacetylene Having a L-Valinol Residue and Two Hydroxy Groups International conference

    Hongge Jia, Masahiro Teraguchi, Toshiki Aoki, Yunosuke Abe, Takashi Kaneko, Shingo Hadano, Takeshi Namikosh, Edy Marwanta

    International Symposium on Fusion Tech 2009 at Incheon  2009.1 

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  • Synthesis of One-Handed Helical Poly(Phenyleneethynylene) Membrane by In-Situ Desubstitution of Chiral Menthyl Groups International conference

    Makoto Inoue, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    International Symposium on Fusion Tech 2009 at Incheon  2009.1 

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  • 安定ラジカル部位を有するアントリレンエチニレンユニットと柔軟なオリゴメチレンユニットからなるモノマーの合成と重合

    落合健祐, 浪越 毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    支部合同福井大会(第57回高分子学会北陸支部研究発表会)  2008.11 

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  • 側鎖にニトロニルニトロキシドを有するポリ(1,3-フェニレンエチニレン)型キラルポリラジカルの合成とらせんフォルダマー構造制御

    加藤清亮, 浪越 毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    支部合同福井大会(第57回高分子学会北陸支部研究発表会)  2008.11 

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  • Synthesis of Chiral Polyphenylacetylenes Having their Chiral Structures Only in the Backbone via Desubstitution of the Chiral Groups in Membrane States International conference

    Yunosuke Abe, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    18th Iketani Conference: Interanational Conference of Super-Hierarchical Structures and Innivative Functions of Next-Generation Conjugated Polymers  2008.10 

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  • Synthesis of Optically Active p-Conjugated Polymers Bearing Stable Radicals and Their Chiroptical and Magnetic Properties International conference

    Takashi Kaneko, Hiromasa Abe, Hiroo Katagiri, Atsuko Kawami, Tsuyoshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Toshiki Aoki

    18th Iketani Conference: Interanational Conference of Super-Hierarchical Structures and Innivative Functions of Next-Generation Conjugated Polymers  2008.10 

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  • キラルポリ(m-フェニレンエチニレン)膜の合成、反応と機能

    井上 真, 寺口 昌宏, 浪越 毅, マルワンタ エディ, 金子 隆司, 青木 俊樹

    第57回高分子討論会  2008.9 

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  • L-メントール残基と2 つの水酸基を有する片巻きらせんポリフェニルアセチレン膜の合成、反応と機能

    安部 佑之介, 賈 宏葛, 寺口 昌宏, 浪越 毅, マルワンタ エディ, 金子 隆司, 青木 俊樹

    第57回高分子討論会  2008.9 

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  • ガルビノキシル残基を有するポリ{3,5-ビス(ヒドロキシメチル)-4-ベンジルオキシフェニルアセチレン}の光学活性らせん主鎖構造と磁気特性

    片桐 寛夫, 浪越 毅, エディ マルワンタ, 寺口 昌宏, 青木 俊樹, 金子 隆司

    第57回高分子討論会  2008.9 

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  • アキラル配位子を持つフェニルアセチレンのらせん選択重合と生成ポリマー膜を用いた不斉反応

    松本 和樹, 四柳 宏基, 浪越 毅, 寺口 昌宏, マルワンタ エディ, 金子 隆司, 青木 俊樹

    第57回高分子討論会  2008.9 

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  • 二酸化炭素分離膜用のイオン液体構造を有する置換ポリアセチレンの合成

    マルワンタ エディ, 浪越 毅, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第57回高分子討論会  2008.9 

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  • 光応答性基を持つフェニルアセチレンのらせん選択重合と生成ポリマー膜の光応答性

    鈴木 一平, 寺口 昌宏, 浪越 毅, マルワンタ エディ, 金子 隆司, 青木俊樹

    第57回高分子討論会  2008.9 

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  • 二酸化炭素分離膜用アミノ基含有ポリフェニルアセチレン型ポリデンドロンの合成

    佐藤 勇希, 寺口 昌宏, 浪越 毅, マルワンタ エディ, 金子 隆司, 青木 俊樹

    第57回高分子討論会  2008.9 

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  • ガルビノキシルを有するポリ(1,3-フェニレンエチニレン)の片巻優先らせんフォルダマー形成能及び磁気的性質

    阿部 寛正, 浪越 毅, マルワンタ エディ, 寺口 昌宏, 青木 俊樹, 金子 隆司

    第57回高分子討論会  2008.9 

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  • 種々のL-アミノアルコール残基と二つの水酸基を持つフェニルアセチレンモノマーのらせん選択重合と不斉誘起重合

    賈 宏葛, 寺口 昌宏, 浪越 毅, マルワンタ エデイ, 金子 隆司, 青木 俊樹

    第57回高分子討論会  2008.9 

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  • TEMPO を有するポリ(フェニルアセチレン)の光学活性らせん形成能と磁気的性質

    川見 敦子, 金子 隆司, 浪越 毅, マルワンタ エディ, 寺口 昌宏, 青木 俊樹

    第57回高分子討論会  2008.9 

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  • 水素結合により安定化された種々の片巻きらせんポリフェニルアセチレン膜の選択的芳香環形成による超分子自立膜の調製

    浪越 毅, 鬼山 祥幸, マルワンタエディ, 寺口 昌宏, 金子 隆司, 青木 俊樹

    第57回高分子討論会  2008.9 

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  • Synthesis of Optically Active Helical Poly(phenylacetylene)-based Polyradicals and Magnetic Interaction Depending on Their Helicity International conference

    Takashi Kaneko, Yasuhiro Umeda, Hiroo Katagiri, Atsuko Kawami, Tsuyoshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Toshiki Aoki

    The 11th International Conference of Molecule-Based Magnets  2008.9 

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  • Function of one-handed helical backbone of polyphenylacetylenes International conference

    Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    The 5th International Symposium on Advanced Materials in Asia-Pacific Rim (5th ISAMAP)  2008.8 

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  • Synthesis and Properties of Chiral Polyphenylacetylenes Having their Chiral Structures Only in the Backbone International conference

    Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    International Symposium on Polymer Chemistry  2008.6 

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  • L-メントール残基と二つの水酸基を持つ片巻きらせんポリフェニルアセチレンの合成、高分子膜反応と機能

    安部佑之介, 賈 宏葛, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第57回高分子学会年次大会  2008.5 

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  • 片巻きらせんポリフェニルアセチレン自立膜の選択的芳香環形成による超分子膜の調製

    浪越 毅, 鬼山祥幸, 波多野 慎悟, エディ マルワンタ, 寺口昌宏, 金子隆司, 青木俊樹

    第57回高分子学会年次大会  2008.5 

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  • イミノ基を持つアキラルフェニルアセチレンのらせん選択重合

    松本和樹, 四柳宏基, 浪越 毅, 寺口昌宏, エディ マルワンタ, 金子隆司, 青木俊樹

    第57回高分子学会年次大会  2008.5 

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  • らせん選択重合により得られたガルビノキシル残基を有するポリ[3,5-ビス(ヒドロキシメチル)-4-ベンジルオキシフェニルアセチレン]の光学活性と磁気特性

    片桐寛夫, 浪越 毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    第57回高分子学会年次大会  2008.5 

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  • 主鎖に光学活性なビナフチル構造を含むガルビノキシル置換ポリ(1,3-フェニレンエチニレン)の合成とそのフォルダマー形成能及び磁気特性

    阿部寛正, 浪越 毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    第57回高分子学会年次大会  2008.5 

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  • 長鎖アルキル基と二つの水素結合可能な置換基を持つフェニルアセチレンのらせん選択重合

    劉シンシン, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第57回高分子学会年次大会  2008.5 

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  • L-アミノ酸由来置換基と二つの水酸基を持つフェニルアセチレンモノマーの合成と重合

    賈 宏葛, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第57回高分子学会年次大会  2008.5 

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  • キラル置換基含有片巻きらせんポリ(フェニレンエチニレン)の合成と高分子膜反応

    井上 真, 三井知明, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第57回高分子学会年次大会  2008.5 

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  • 光応答性基を持つフェニルアセチレンのらせん選択重合

    鈴木一平, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第57回高分子学会年次大会  2008.5 

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  • アミノ基含有ポリデンドロン膜の合成と二酸化炭素選択透過性

    佐藤勇希, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第30回日本膜学会年会  2008.5 

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  • Helix-sense-selective polymerization of trimethylsilyl or siloxanyl group containing monomer International conference

    Liu Lijia, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    2008 Niigata-Inha Joint Symposium on Advanced Polymeric Materials  2008.5 

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  • Synthesis of Chiral Helical Poly(phenyleneethynylene) Membranes by Desubstitution of Chiral Group International conference

    Makoto Inoue, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    2008 Niigata-Inha Joint Symposium on Advanced Polymeric Materials  2008.5 

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  • TEMPOを有するポリ(フェニルアセチレン)の光学活性らせん誘起と磁気的性質

    川見敦子, 浪越 毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第88回春季年会  2008.3 

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  • 側鎖にレゾルシノール誘導体を有するアセチレンモノマーの重合とその光学活性らせん誘起

    梁 暁芸, 浪越 毅, エディ マルワンタ, 寺口昌宏, 青木俊樹, 金子隆司

    日本化学会第88回春季年会  2008.3 

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  • L-アミノアルコール部位と二つの水酸基を有するフェニルアセチレンモノマーの合成と重合

    賈 宏葛, 寺口昌宏, 浪越 毅, エディ マルワンタ, 金子隆司, 青木俊樹

    第56回高分子学会北陸支部研究発表講演会  2007.11 

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  • 2 つのアキラルアミド基を有するフェニルアセチレンのらせん選択重合

    劉 しんしん, 寺口 昌宏, 浪越 毅, マルワンタ エディ, 金子 隆司, 青木 俊樹

    第56回高分子討論会  2007.9 

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  • アミノ基を有するポリフェニルアセチレン膜の気体透過性

    佐藤 勇希, 寺口 昌宏, 浪越 毅, マルワンタ エディ, 金子 隆司, 青木 俊樹

    第56回高分子討論会  2007.9 

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  • 脱キラル置換基による主鎖のみ不斉らせんポリ(フェニレンエチニレン)自己支持膜の合成

    井上 真, 寺口 昌宏, 浪越 毅, マルワンタ エディ, 金子 隆司, 青木 俊樹

    第56回高分子討論会  2007.9 

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  • 膜状態での脱キラル置換基法による溶液中で安定な不斉らせんポリフェニルアセチレンの合成

    安部 佑之介, 寺口 昌宏, 浪越 毅, マルワンタ エディ, 金子 隆司, 青木 俊樹

    第56回高分子討論会  2007.9 

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  • 2 つのアミノアルコール残基を持つフェニルアセチレンのらせん選択重合

    松本 和樹, 寺口 昌宏, 浪越 毅, マルワンタ エディ, 金子 隆司, 青木 俊樹

    第56回高分子討論会  2007.9 

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  • 主鎖に片巻きらせん構造を側鎖に光応答性基を持つポリフェニルアセチレンの合成

    鈴木 一平, 寺口 昌宏, 浪越 毅, マルワンタ エディ, 金子 隆司, 青木 俊樹

    第56回高分子討論会  2007.9 

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  • TEMPO を有するフェニルアセチレン誘導体の重合とらせん構造制御

    川見 敦子, 寺口 昌宏, 青木 俊樹, 金子 隆司

    第56回高分子討論会  2007.9 

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  • 安定ラジカル骨格を有するアントリルアセチレン誘導体の重合

    佐藤 誠之, 寺口 昌宏, 青木 俊樹, 金子 隆司

    第56回高分子討論会  2007.9 

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  • (4-エチニルフェニル)ガルビノキシルの共重合におけるらせん方向制御とそのポリラジカルの光・磁気特性

    梅田 泰裕, 寺口 昌宏, 青木 俊樹, 金子 隆司

    第56回高分子討論会  2007.9 

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  • The Control of the Helix Sense in the Copolymerization of (4-Ethynylphenyl)galvinoxyl by the Composition of Comonomer International conference

    Yasuhiro Umeda, Takashi Kaneko, Takeshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Magnetic Properties of TEMPO Radicals Included in a Supramolecular Anthracene Derivative International conference

    Masayuki Sato, Takashi Kaneko, Takeshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Synthesis of TEMPO-pendant Poly(phenylacetylene)s, and Their Chiroptical and Magnetic Properties International conference

    Atsuko Kawami, Takashi Kaneko, Takeshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Synthesis of Oligo(anthryleneethynylene)-based Foldamers Containing Stable Radicals International conference

    Kensuke Ochiai, Takashi Kaneko, Takeshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Synthesis of Poly(binaphthyl-6,6<sup>'</sup>-diylethynylene-1,3-phenyleneethynylene)-based Chiral Polyradical Bearing Galvinoxyl, and Its Chiroptical and Magnetic Properties International conference

    Hiromasa Abe, Takashi Kaneko, Takeshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Synthesis of Chiral Polyphenylacetylenes Bearing an One-handed Helical Backbone and Photo-responsive Side Chains International conference

    Ippei Suzuki, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Synthesis of One -handed Helical Polyphenylacetylenes Stable in Solution by Removing the Chiral Groups from Poly(phenylacetylene having chiral groups) in Membrane State International conference

    Yunosuke Abe, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Helix-sense-selective Polymerization of 3,5-Bis(hydroxymethyl)-4-benzyloxyphenylacetylene Bearing Galvinoxyl, and Chiroptical and Magnetic Properties International conference

    Hiroo Katagiri, Takashi Kaneko, Takeshi Namikoshi, Edy Marwanta, Masahiro Teraguchi, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Helix-sense-selective Polymerization of Phenylacetylene Having Two Aminoalcohol Residues International conference

    Kazuki Matsumoto, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Asymmetric Induced Copolymerization of Achiral Phenylacetylene with a Chiral Amino Group International conference

    Mohammed Hoda, Masahiro Teraguchi, Masayuki Sato, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Synthesis and Gas Permeability of Polyphenylacetylene Membranes Having Amino Groups International conference

    Yuki Sato, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Synthesis and Attempts of Helix-sense-selective Polymerization of Achiral Phenylacetylenes Having Two Alkylamido Groups International conference

    Chen Chen Liu, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Application of Chiral Helical Poly(phenylacetylene)s for Optical Resolution International conference

    Shingo Hadano, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Asymmetric-induced Polymerization of Phenylacetylene Having Two Hydroxyl Groups and A Chiral Pinanylsilyl Group International conference

    Hongge Jia, Kazuomi Mottate, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Synthesis of Chiral Helical Poly(phenyleneethynylene) Membranes by Desubstitution of Chiral Group International conference

    Makoto Inoue, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • Attempt to Living Helix-sense-selective Polymerization of Achiral Phenylacetylenes by MoOCl<sub>4</sub> or WOCl<sub>4</sub> -alkylating agent-chiral alcohol International conference

    Motohiro Kiuchi, Masahiro Teraguchi, Takeshi Namikoshi, Edy Marwanta, Takashi Kaneko, Toshiki Aoki

    The 4th International Symposium on Advanced Materials in Asia-Pacific Rim  2007.7 

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  • The Control of the Helix Sense for Poly(phenylacetylene)s Bearing Galvinoxyl Residues by the Composition of Co-monomer International conference

    Yasuhiro Umeda, Takashi Kaneko, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    The 7th Int. Conf. on Optical Probes of π-Conjugated Polymers and Functional Self-Assemblies  2007.6 

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  • Helix-sense-selective Polymerization of 3,5-bis(hydroxymethyl)-4-benzyloxyphenylacetylene Bearing Galvinoxyl, and Optical Activity International conference

    Hiroo Katagiri, Takashi Kaneko, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    The 7th International Conference on Optical Probes of π-Conjugated Polymers and Functional Self-Assemblies  2007.6 

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  • Synthesis of Optically Active Poly(aryleneethynylene)s Bearing Stable Radicals and Their Chiroptical and Magnetic Properties International conference

    Takashi Kaneko, Hiromasa Abe, Shouta Yoshimoto, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    The 7th International Conference on Optical Probes of π-Conjugated Polymers and Functional Self-Assemblies  2007.6 

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  • ラダー二重らせん構造を有するポリ(フェニルアセチレン)誘導体の合成と特性

    二俣和夫, 波多野 慎悟, 青木 俊樹, 寺口 昌宏, 金子 隆司

    第56回高分子学会年次大会  2007.5 

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  • ルテニウム錯体をドープした酸化タングステン/高分子電解質ハイブリッド膜の電気化学的イオン拡散スイッチ

    曽根浩司, 八木政行, 寺口昌宏, 金子隆司, 青木俊樹

    第56回高分子学会年次大会  2007.5 

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  • キラルらせんポリフェニルアセチレンを用いた選択吸着沈殿法による光学分割

    波多野 慎悟, 青木 俊樹, 寺口 昌宏, 金子 隆司

    第56回高分子学会年次大会  2007.5 

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  • ガルビノキシル残基を有するポリ(フェニルアセチレン)のらせん方向制御とそのポリラジカルの光・磁気特性

    梅田 泰裕, 金子 隆司, 寺口 昌宏, 波多野 慎悟, 青木 俊樹

    第56回高分子学会年次大会  2007.5 

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  • 光学活性なメンチル基やピナニル基を有するポリ(フェニレンエチニレン)膜の脱置換基によるキラルらせん高分子膜の合成

    井上真, 寺口昌宏, 波多野慎悟, 青木俊樹, 金子隆司

    第29回日本膜学会年会  2007.5 

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  • Ru(II)錯体ドープ酸化タングステン薄膜の電気化学応答に伴う対イオン拡散挙動

    曽根浩司, 寺口昌宏, 金子隆司, 青木俊樹, 八木政行

    電気化学会第74回大会  2007.3 

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  • 側鎖にガルビノキシルを有するポリ(フェニルアセチレン)型キラルポリラジカルの合成と光学活性・磁気特性

    梅田泰裕, 金子隆司, 波多野慎悟, 寺口昌宏, 青木俊樹

    日本化学会第87回春季年会  2007.3 

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  • 二つのアルキルアミド基を有するアキラルフェニルアセチレンのキラルロジウム触媒系によるらせん選択重合

    寺口昌宏, 劉シンシン, 谷岡大輔, 波多野慎悟, 青木俊樹, 金子隆司

    日本化学会第87回春季年会  2007.3 

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  • 光学分割膜素材としてのイオン交換基含有キラルポリ置換フェニルアセチレンの合成

    石塚真由美, 波多野慎悟, 青木俊樹, 寺口昌宏, 金子隆司

    日本化学会第87回春季年会  2007.3 

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  • ガルビノキシル残基を有する3,5-ビス(ヒドロキシメチル)-4-ベンジルオキシフェニルアセチレンのらせん選択重合とそのキラルポリラジカルの光学活性・磁気特性

    片桐寛夫, 金子隆司, 波多野慎悟, 寺口昌宏, 青木俊樹

    日本化学会第87回春季年会  2007.3 

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  • 側鎖にガルビノキシルを有するポリ(ビナフチル-6,6'-ジイルエチニレン-1,3-フェニレンエチニレン)型キラルポリラジカルの合成と光学活性・磁気特性

    阿部寛正, 金子隆司, 波多野慎悟, 寺口昌宏, 青木俊樹

    日本化学会第87回春季年会  2007.3 

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  • Helix-sense-selective polymerization of disiloxane and trisiloxane containing monomer International conference

    Liu Lijia, Shingo Hadano, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    International Symposiumon Fusion Tech 2006-2007  2007.1 

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  • Synthesis of optically active helical polyacetylenes bearing stable radicals via helix-sense-selective polymerization International conference

    Takashi Kaneko, Yasuhiro Umeda, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    International Symposiumon Fusion Tech 2006-2007  2007.1 

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  • Helix-sense-selective copolymerization of phenylacetylene having two silanol groups and chemical fixation of ladder chiral double helical structure of the resulting copolymer International conference

    Shingo Hadano, Kazuo Futamata, Masahiro Teraguchi, Toshiki Aoki, Takashi Kaneko

    International Symposiumon Fusion Tech 2006-2007  2007.1 

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  • Electrochemical and photosensitized redox reactions of a Prussian blue film layered on a WO<sub>3</sub>/tris(2,2<sup>'</sup> -bipyridine)ruthenium(II) polymer hybrid film International conference

    Koji Sone, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki, Masayuki Yagi

    International Symposiumon Fusion Tech 2006-2007  2007.1 

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  • 二つの水酸基を有するポリ(フェニルアセチレン)誘導体の二重らせん構造の固定化

    二俣和夫, 波多野慎悟, 青木俊樹, 寺口昌宏, 金子隆司

    第55回高分子学会北陸支部研究発表講演会  2006.11 

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  • らせん選択重合による高分子不斉らせん構造を持つ配位子の合成

    松本和樹, 寺口昌宏, 波多野慎悟, 青木俊樹, 金子隆司

    第55回高分子学会北陸支部研究発表講演会  2006.11 

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  • 光学活性なピナニルシリル基と2つの水酸基を持つフェニルアセチレンのらせん選択共重合と生成高分子の主鎖らせん構造の刺激応答性、脱シリル化反応および光学異性体選択透過性

    寺口昌宏, 持舘和臣, 波多野慎悟, 青木俊樹, 金子隆司

    第55回高分子討論会  2006.9 

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  • キラルなポリ(フェニレンエチニレン)膜の合成とそれらポリマーの不斉らせん構造

    井上真, 寺口昌宏, 波多野慎悟, 青木俊樹, 金子隆司

    第55回高分子討論会  2006.9 

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  • 片巻きらせんポリフェニルアセチレンの異常な分解性

    波多野慎悟, 青木俊樹, 寺口昌宏, 金子隆司

    第55回高分子討論会  2006.9 

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  • ガルビノキシルを有するポリ(1,3-フェニレンエチニレン)型キラルポリラジカルの合成とその磁性及び磁気光学効果

    吉本翔太, 金子隆司, 寺口昌宏, 波多野慎悟, 青木俊樹

    第55回高分子討論会  2006.9 

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  • 二つの水素結合可能な官能基を有するポリ(フェニルアセチレン)誘導体のラダー二重らせん構造の固定化

    二俣和夫, 波多野慎悟, 青木俊樹, 寺口昌宏, 金子隆司

    第55回高分子討論会  2006.9 

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  • Synthesis of Optically Active Helical Polymers Bearing Stable Radicals and Their Chiroptical and Magnetic Properties International conference

    Takashi Kaneko, Yasuhiro Umeda, Shota Yoshimoto, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    The 10th International Conference Molecule-Based Magnets  2006.8 

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  • Synthesis of optically active helical polymers bearing stable radicals via helix-sense-selective polymerization of phenylacetylenes International conference

    Takashi Kaneko, Yasuhiro Umeda, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    The 10th World Multi-Conference on Systemics, Cybernetics and Informatics (WMSCI2006)  2006.7 

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  • Synthesis of Stable One-handed Helical Poly(phenylacetylene)s without the coexistence of any other chiral moieties by Helix-sense-selective (Co)Polymerization as chiral recognition materials International conference

    Toshiki Aoki, Masahiro Teraguchi, Shingo Hadano, Takashi Kaneko

    12rd International Conference on Polymers and Organic Chemistry 2006  2006.7 

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  • 金属錯体を有する片巻きらせんポリマー光学分割膜

    波多野 慎悟, 青木 俊樹, 寺口 昌宏, 金子 隆司

    第28回日本膜学会年会  2006.6 

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  • Helix-sense-selective copolymerization of achiral and chiral phenylacetylenes having two hydroxyl groups International conference

    Masahiro Teraguchi, Toshiki Aoki, Kazuomi Mottate, Shingo Hadano, Takashi Kaneko

    3rd IUPAC-sponsored International Symposium on Macro- and Supramolecular Architectures and Materials (MAM-06)  2006.5 

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  • Helix-sense-selective polymerization of phenylacetylenes bearing galvinoxyl residues International conference

    Takashi Kaneko, Yasuhiro Umeda, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    3rd IUPAC-sponsored International Symposium on Macro- and Supramolecular Architectures and Materials (MAM-06)  2006.5 

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  • 側鎖に金属錯体部位を有するキラルらせんポリフェニルアセチレンの合成とキラル認識能への金属錯体の効果

    波多野慎悟, 青木俊樹, 寺口昌宏, 金子隆司

    第55回高分子学会年次大会  2006.5 

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  • 2,7位にフェノール残基を有するオリゴ(アントリレンエチニレン)の酸化及びその電子状態と磁気特性

    田中毅, 金子 隆司, 八木政行, 寺口 昌宏, 青木 俊樹

    第55回高分子学会年次大会  2006.5 

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  • 光学活性なピナニルシリル基と二つの水酸基を持つポリ(フェニルアセチレン)の合成・構造・特性

    持舘和臣, 寺口昌宏, 波多野慎悟, 青木俊樹, 金子隆司

    第55回高分子学会年次大会  2006.5 

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  • ナフィオン膜分散亜鉛フタロシアニンの可逆的会合-解離反応の熱力学的および動力学的考察

    桑原貴之, 八木政行, 寺口昌宏, 金子隆司, 青木俊樹

    第55回高分子学会年次大会  2006.5 

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  • ガルビノキシル基を有するポリ(1,3-フェニレンエチニレン)型キラルポリラジカルの合成とその光・磁気特性

    吉本翔太, 金子 隆司, 寺口 昌宏, 青木 俊樹

    第55回高分子学会年次大会  2006.5 

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  • Preparation of Chiral Polystyrene Monoliths by Utilizing W/O Emulsion Polymerization and Their Enantioselective adsorption Ability International conference

    Masahiro Teraguchi, Toshiki Aoki, Miyoko Ohtake, Hirosihi Inoue, Shingo Hadano, Takashi Kaneko

    The 3rd International Symposium on Advanced Materials in Asia-Pacific Rim  2006.5 

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  • Effects of The Length of Alkyl Chain on Structure of Main Chain in The Resulting Chiral Polymers in Helix-Sense-Selective Polymerization of 4-Alkyloxy-3,5-Bis(Hydroxymethyl)Phenylacetylenes International conference

    Shingo Hadano, Toshiki Aoki, Masahiro Teraguchi, Takashi Kaneko

    The 3rd International Symposium on Advanced Materials in Asia-Pacific Rim  2006.5 

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  • Helix-sense-selective polymerization of achiral and bulky phenylacetylenes International conference

    Takashi Kaneko, Yasuhiro Umeda, Shingo Hadano, Masahiro Teraguchi, Toshiki Aoki

    The 3rd International Symposium on Advanced Materials in Asia-Pacific Rim  2006.5 

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  • Helix-sense-selective copolymerization of achiral phenylacetylene International conference

    Toshiki Aoki, Masahiro Teraguchi, Kazuomi Mottate, Sun-Young Kim, Takashi Kaneko, Shingo Hadano

    The 3rd International Symposium on Advanced Materials in Asia-Pacific Rim  2006.5 

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  • 塩基量により分子量制御されたオリゴ(アントリレンエチニレン)誘導体の合成と単離した各オリゴマーの電子特性

    田中毅, 金子隆司, 青木俊樹, 寺口昌宏

    日本化学会第86回春季年会  2006.3 

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  • 片巻きらせんポリマーを不斉認識剤として用いた光学分割膜-キラルチャネル効果とキラルインプリント効果の検討-

    波多野慎悟, 千野隆之, 寺口昌宏, 青木俊樹, 金子隆司, 田中孝明

    日本化学会第86回春季年会  2006.3 

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  • アントラセン超分子に包接された安定ラジカルの磁気特性

    佐藤誠之, 金子隆司, 青木俊樹, 寺口昌宏

    日本化学会第86回春季年会  2006.3 

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  • Synthesis of polymermembranes having molecular-scale voids by desilylation in membrane state International conference

    Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki

    8th International Conference on Frontiers of Polymers and Advanced Materials(ICFPAM)  2005.4 

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Industrial property rights

  • 重合体及び重合体の製造方法

    青木俊樹, 寺口昌宏, 佐藤 敬, 山本武継

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    Application no:特願2010-50924  Date applied:2010.3

    Announcement no:特開2010-235928  Date announced:2010.10

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  • ポリフェニルアセチレン膜の芳香環形成による超分子自立膜の製造方法

    青木俊樹, 浪越 毅, 波多野慎悟, エディ・マルワンタ, 寺口昌宏, 金子隆司, 鬼山祥之

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    Application no:特願2009-38313  Date applied:2009.9

    Announcement no:特開2010-189365  Date announced:2010.9

    Patent/Registration no:特許第5120787  Date issued:2012.11

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  • 重合体、気体分離膜、及び重合体の製造方法

    青木俊樹, 寺口昌宏, 佐藤敬, 山本武継

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    Application no:特願2009-189201  Date applied:2009.8

    Announcement no:特開2011-038051  Date announced:2011.2

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  • ハロゲン基を有する重合体膜の製造方法

    青木俊樹, 寺口昌宏, 佐藤 敬, 山本武継

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    Application no:特願2009-55646  Date applied:2009.3

    Announcement no:特開2010-209187  Date announced:2010.9

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  • 置換ポリアセチレン及びその製造方法、置換ポリアセチレン自立膜及びその製造方法、二酸化炭素分離膜、伸縮により可逆的に色変化を呈する膜

    青木俊樹, マルワンタ・エディ, 寺口昌宏, 金子隆司

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    Application no:特願2009-7964  Date applied:2009.1

    Announcement no:特開2010-163561  Date announced:2010.7

    Patent/Registration no:特許第5131643  Date issued:2012.11

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  • 光学分割法

    青木俊樹, 波多野慎悟, 寺口昌宏, 金子隆司

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    Application no:特願2007-121411  Date applied:2007.5

    Announcement no:特開2008-273898  Date announced:2008.11

    Patent/Registration no:特許第4853834  Date issued:2011.11

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  • 光学分割能を有する非粒子状有機多孔質体及びその製造方法

    寺口昌宏, 金子隆司, 青木俊樹, 井上洋, 山中弘次, 吉田晃子

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    Application no:特願2004-9426  Date applied:2004.1

    Announcement no:特開2005-199203  Date announced:2005.7

    Patent/Registration no:特許第4315337  Date issued:2009.5

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  • ガス透過性ポリイミド膜およびその製造方法

    上西理玄, 青木俊樹, 金子隆司, 清水岳人, 熊田真之, 寺口昌宏

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    Application no:特願2003-013529  Date applied:2003.1

    Announcement no:特開2004-224889  Date announced:2004.8

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Awards

  • 平成15年度高分子研究奨励賞

    2004.5   社団法人 高分子学会  

    寺口昌宏

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    Award type:Award from Japanese society, conference, symposium, etc.  Country:Japan

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Research Projects

  • 円偏光を不斉源とするらせん選択重合および選択的重合および選択的分解反応を経由する絶対不斉合成

    2019.4 - 2022.3

    System name:科学研究費助成事業

    Awarding organization:日本学術振興会

    寺口 昌宏

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  • 環境低負荷型有機エレクトロルミネッセンス材料のための発光性ポリ(ジフェニルアセチレン)膜の合成

    2019.4 - 2020.3

    System name:R1年度佐々木環境技術振興財団 試験研究費助成金

    Awarding organization:民間財団等

    寺口 昌宏

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  • 省エネルギー有機エレクトロルミネッセンス材料のための高蛍光性ポリ(ジフェニルアセチレン)の合成

    2018.4 - 2019.3

    System name:H30年度内田エネルギー科学振興財団

    Awarding organization:民間財団等

    寺口昌宏

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\600000 ( Direct Cost: \600000 )

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  • 円偏光を不斉源とするキラリティ発現とそれらを利用したポリアセチレンのらせん選択重合による不斉転写・増幅

    2018.4 - 2019.3

    System name:H30年度財団法人山口育英奨学会 学術研究助成

    Awarding organization:民間財団等

    寺口昌宏

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\800000 ( Direct Cost: \800000 )

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  • Absolute asymmetric polymer synthesis by chiral amplification helix-sense-selective polymerization using circularly polarized light as a chiral source

    Grant number:17K19153

    2017.6 - 2020.3

    System name:Grants-in-Aid for Scientific Research

    Research category:Grant-in-Aid for Challenging Research (Exploratory)

    Awarding organization:Japan Society for the Promotion of Science

    AOKI TOSHIKI

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    Grant amount:\6500000 ( Direct Cost: \5000000 、 Indirect Cost:\1500000 )

    Polymerization in an achiral polymerization system that does not contain any chiral source giving a one-handed helical polymer(spontaneousHSSP)was investigated.As the number of trials increase,the ratio of the cumulative number of polymerizations giving the right-handed and the left-handed polymers were closer to1.We successfully prepared a chiral microcrystalline monomer which does not contain any chiral compound by following two step method:1)Crystallization of the monomer in the presence of a chiral amine;2)Complete removal of the chiral amine under a high vacuum condition.The obtained microcrystalline monomer gave a one-handed helical polymer by using an achiral catalyst system.Therefore,it was suggested that crystal structure with asymmetric alignment accidentally induced may be the cause of spontaneous HSSP.
    Further,the helix-sense-selective degradation(HSSD)of racemic helical polymer by circularly polarized irradiation,was found for the first time to proceed in a solution state.

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  • Self-supporting gas separation membranes by molecular sieving effects of molecular size pores in 2D macromolecules synthesized by SCAT reaction of helical polymers

    Grant number:16H04153

    2016.4 - 2021.3

    System name:Grants-in-Aid for Scientific Research

    Research category:Grant-in-Aid for Scientific Research (B)

    Awarding organization:Japan Society for the Promotion of Science

    AOKI Toshiki

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    Grant amount:\18200000 ( Direct Cost: \14000000 、 Indirect Cost:\4200000 )

    A thin layer of 2D macromolecules with molecular-sized pores was synthesized by solid-solid interface polycondensation in laminated membranes of two cis-cisoid poly(imino-containing phenylacetylene)s followed by highly selective photocyclic aromatization (SCAT). The precise 2D molecular structure including fraction and size of rings (pores) can be fully estimated. The composite membranes of the 2D macromolecule showed good oxygen permselectivity exceeding the Robeson upper line.

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  • Higher-Order Structure and Magneto-Optical Property of Chiral Polyradicals Programmed by Their Monomer Sequence

    Grant number:16H03815

    2016.4 - 2020.3

    System name:Grants-in-Aid for Scientific Research

    Research category:Grant-in-Aid for Scientific Research (B)

    Awarding organization:Japan Society for the Promotion of Science

    KANEKO TAKASHI

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    Grant amount:\18460000 ( Direct Cost: \14200000 、 Indirect Cost:\4260000 )

    Polyradicals which have stable radicals as magnetic source will be possible candidates for new magnetic materials, because various properties can be programmed by their molecular design. For example, new magnetooptical properties will be expected for the polyradicals in combination with their one-handed helical structure. We have succeeded in synthesizing helical polyradicals whose stable one-handed helical structure and magnetic alignment are programmed by their monomer sequences, and found that their strong antiferromagnetic interaction were derived by their well-packed helical structure which were controlled by their monomer sequences.

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  • 光を不斉源とするSCATおよび不斉増幅反応を利用したキラルらせんポリマーの合成

    2016.4 - 2019.3

    System name:科学研究費助成事業

    Research category:基盤研究(C)

    Awarding organization:日本学術振興会

    寺口昌宏

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\3900000 ( Direct Cost: \2730000 、 Indirect Cost:\1170000 )

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  • Helix-sense-selective polymerization by using homochirality derived from selective cycloaromatization (SCAT) of racemic helical polymers using circularly-polarized light

    Grant number:26620096

    2014.4 - 2017.3

    System name:Grants-in-Aid for Scientific Research

    Research category:Grant-in-Aid for Challenging Exploratory Research

    Awarding organization:Japan Society for the Promotion of Science

    Aoki Toshiki

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    Grant amount:\3900000 ( Direct Cost: \3000000 、 Indirect Cost:\900000 )

    Selective cycloaromatization (SCAT) of a racemic helical poly[3,5-bis(hydroxymethyl)-4-dodecyloxyphenylacetylene] by circularly polarized light (CPL) was investigated. The racemic helical polymer, which was synthesized by polymerization of achiral monomer under achiral conditions, has equal amounts of right- and left-handed sense helical main chains. SCAT using CPL proceeded in helix-sense-selective manner and gave a preferentially one-handed helical polymer (creation of chirality). In addition, using the chirality which was a trace amount created by CPL as chiral source, helix-sense-selective polymerization of another monomer was achieved (asymmetric amplification and asymmetric transfer).

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  • キラルナノ空孔をらせん状に配列した高分子分離膜の創製

    2013.4 - 2016.3

    System name:科学研究費助成事業

    Research category:基盤研究(C)

    Awarding organization:日本学術振興会

    寺口昌宏

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\3900000 ( Direct Cost: \2730000 、 Indirect Cost:\1170000 )

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  • イオン液体構造を含むポリジメチルシロキサンおよびポリフェニルアセチレン膜の合成と膜による温室効果ガスの省エネルギー的分離

    2013.4 - 2014.3

    System name:H25年度内田エネルギー科学振興財団

    Awarding organization:民間財団等

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    Grant type:Competitive

    Grant amount:\460000 ( Direct Cost: \460000 )

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  • Magnetic Alignment and Magneto-Optical Property of Chiral Polyradials Programmed by their Monomer Sequence

    Grant number:24310081

    2012.4 - 2016.3

    System name:Grants-in-Aid for Scientific Research

    Research category:Grant-in-Aid for Scientific Research (B)

    Awarding organization:Japan Society for the Promotion of Science

    KANEKO TAKASHI, AOKI TOSHIKI, TERAGUCHI MASAHIRO

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    Grant amount:\19370000 ( Direct Cost: \14900000 、 Indirect Cost:\4470000 )

    Polyradicals which have stable radicals as magnetic source will be possible candidates for new magnetic materials, because various properties can be programmed by their molecular design. For example, new magnetooptical properties will be expected for the polyradicals in combination with their one-handed helical structure. We have succeeded in synthesizing helical polyradicals whose stable one-handed helical structure and magnetic alignment are programmed by their monomer sequences, and found that their antiferromagnetic properties were controlled by their monomer sequences.

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  • 不斉転写されたナノ空孔を階層的に持つ高分子膜の創製と超分離機能の開発

    2011.4 - 2013.3

    System name:科学研究費助成事業

    Research category:若手研究(B)

    Awarding organization:日本学術振興会

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    Grant type:Competitive

    Grant amount:\3100000 ( Direct Cost: \2170000 、 Indirect Cost:\930000 )

    有機高分子膜の膜状態での反応により、「不斉情報を転写したナノ空孔を階層的に配置した高分子膜」を合成する。また、その機能の1つとして光学異性体の高速かつ完全分離(超分離)について検討する。本研究では、申請者が見出した膜状態での脱光学活性基法を活用した不斉転写を利用し、高分子の不斉コンフォメーションを維持しつつ、不斉源を除去し、不斉転写されたナノオーダーの空孔を生成する。反応前の高分子膜の階層構造が反応後に維持されることで、不斉転写されたナノ空孔を階層的に持つ高分子膜の創製を実現する。従来の多孔性物質(無機元素主体)とは異なる有機元素主体のソフトな多孔性物質の合成とその機能を明らかにする。

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  • デンドロン構造を利用した高密度にイミダゾリウム塩を含む二酸化炭素選択透過膜の合成

    2011.4 - 2012.3

    System name:H22年度 向科学技術振興財団 研究助成

    Awarding organization:民間財団等

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    Grant type:Competitive

    Grant amount:\1000000 ( Direct Cost: \1000000 )

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  • Absolute self-asymmetric polymerization : sponteneous, self catalyzed, and amplificated asymmetric polymerization

    Grant number:23655100

    2011 - 2013

    System name:Grants-in-Aid for Scientific Research

    Research category:Grant-in-Aid for Challenging Exploratory Research

    Awarding organization:Japan Society for the Promotion of Science

    AOKI Toshiki, TERAGUCHI Masahiro

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    Grant amount:\4030000 ( Direct Cost: \3100000 、 Indirect Cost:\930000 )

    We have reconfirmed the three unusual phenomena on the helix-sense-selective polymerization(HSSP) as gollows: 1) Spontaneous HSSP: The HSSP happened without any chiral cocatalyst. The best condition was a melt polymerization. 2) HSSP catalyzed by chiral polymers prepared by HSSP: The HSSP proceeded when the chiral polymers prepared by HSSP of the corresponding monomer. 3) Achiral-condition control HSSP: The helical sense of the chiral polymer prepared by HSSP was controlled by ahiral conditions. The mechanism was discussed by some spectra of the chiral catalytic system.

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  • ボトムアップ法によるグラフェンナノリボンの合成

    2010.9 - 2011.8

    System name:H22年度 三菱化学研究奨励基金 研究助成金

    Awarding organization:民間財団等

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    Grant type:Competitive

    Grant amount:\950000 ( Direct Cost: \950000 )

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  • 防汚ユニホーム素材の開発

    2010.8 - 2010.12

    System name:受託研究(一般受託研究)

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    Grant type:Competitive

    Grant amount:\5433750

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  • イオン液体部位を持つ高分子膜の合成と膜による温室効果ガスの省エネルギー的分離

    2010.4 - 2011.3

    System name:H22年度財団法人 内田エネルギー科学振興財団 試験研究助成

    Awarding organization:民間財団等

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    Grant type:Competitive

    Grant amount:\400000 ( Direct Cost: \400000 )

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  • らせん選択重合による片巻きらせん構造を持つ刺激応答性ポリマーの合成と不斉分子認識能の開発

    2009.4 - 2010.3

    System name:H21財団法人 山口育英奨学会 学術研究助成

    Awarding organization:民間財団等

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    Grant type:Competitive

    Grant amount:\500000 ( Direct Cost: \500000 )

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  • 交互共役型ポリ(m-フェニレンエチニレン)の合成と主鎖の刺激応答による光・電子機能のスイッチング

    2009.4 - 2010.3

    System name:H21年度 財団法人ユニオンツール育英奨学会 研究助成金

    Awarding organization:民間財団等

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    Grant type:Competitive

    Grant amount:\700000 ( Direct Cost: \700000 )

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  • イオン液体構造を含む自己支持膜および超分子ゲル膜の合成および二酸化炭素透過分離能の開発

    2009.4 - 2010.3

    System name:H21年度 財団法人佐々木環境技術振興財団 試験研究助成

    Awarding organization:民間財団等

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    Grant type:Competitive

    Grant amount:\850000 ( Direct Cost: \850000 )

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  • 防汚ユニフォーム用素材の開発

    2008.10 - 2009.7

    System name:共同研究(国内共同研究)

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    Grant type:Competitive

    Grant amount:\2400000

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  • フラクタル構造により高密度にアミノ基を含む二酸化炭素分離膜の開発

    2008.7 - 2009.3

    System name:JST 地域イノベーション創出総合支援事業 重点地域研究開発推進プログラム シーズ発掘試験

    Awarding organization:文部科学省

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    Grant type:Competitive

    Grant amount:\1539000 ( Direct Cost: \1078000 、 Indirect Cost:\461000 )

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  • アミノ基含有デンドロン型ポリフェニルアセチレン膜の合成とそれら膜によるCO<sub>2</sub>選択分離

    2008.4 - 2009.3

    System name:H20年度 財団法人 向科学技術振興財団 研究助成

    Awarding organization:民間財団等

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    Grant type:Competitive

    Grant amount:\1500000 ( Direct Cost: \1500000 )

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  • ユニフォーム対応型防汚システムの開発調査

    2008.1 - 2008.5

    System name:共同研究(国内共同研究)

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    Grant type:Competitive

    Grant amount:\600000

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  • Magnetic Alignment Induced by the Well-Designed Nano-Structure of Chiral Polyradials and their Magneto-Optical Property

    Grant number:20310052

    2008 - 2011

    System name:Grants-in-Aid for Scientific Research

    Research category:Grant-in-Aid for Scientific Research (B)

    Awarding organization:Japan Society for the Promotion of Science

    KANEKO Takashi, AOKI Toshiki, TERAGUCHI Masahiro

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    Grant amount:\18070000 ( Direct Cost: \13900000 、 Indirect Cost:\4170000 )

    Polyradicals which have stable radicals as magnetic source will be possible candidates for new magnetic materials, because various properties can be programmed by their molecular design. For example, new magnetooptical properties will be expected for the polyradicals in combination with their one-handed helical structure. We have succeeded in synthesizing chiral polyradicals with excess of one-handed helical structure, and found that some polyradicals increased their antiferromagnetic properties by forming helical conformation.

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  • 新規大容量二次電池に適した酸素選択透過膜の開発

    2007.4 - 2013.3

    System name:共同研究(国内共同研究)

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    Grant type:Competitive

    Grant amount:\7350000

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  • ポリ(フェニレンエチニレン)誘導体膜からの省エネルギー気体分離膜の開発

    2007.4 - 2008.3

    System name:H19年度財団法人 内田エネルギー科学振興財団 試験研究助成

    Awarding organization:民間財団等

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    Grant type:Competitive

    Grant amount:\500000 ( Direct Cost: \500000 )

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  • 主鎖不斉らせんポリ(フェニレンエチニレン)膜の合成とそれら膜による光学異性体分離

    2007.4 - 2008.3

    System name:H19年度財団法人 向科学技術振興財団 研究助成

    Awarding organization:民間財団等

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    Grant type:Competitive

    Grant amount:\1500000 ( Direct Cost: \1500000 )

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  • Supramolecular self-supporting membrane having chiral nano-channel from supramolecular ladder chiral double helical polymer

    Grant number:19350054

    2007 - 2009

    System name:Grants-in-Aid for Scientific Research

    Research category:Grant-in-Aid for Scientific Research (B)

    Awarding organization:Japan Society for the Promotion of Science

    AOKI Toshiki, KANEKO Takashi, TERAGUCHI Masahiro, NAMIKOSHI Takeshi, HADANO Shingo

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    Grant amount:\17290000 ( Direct Cost: \13300000 、 Indirect Cost:\3990000 )

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  • 主鎖のみに不斉構造を持つキラルらせんフェニルアセチレン高分子の第3の合成法と機能

    Grant number:19022009

    2007 - 2008

    System name:科学研究費助成事業

    Research category:特定領域研究

    Awarding organization:日本学術振興会

    青木 俊樹, 寺口 昌宏

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    Grant amount:\2800000 ( Direct Cost: \2800000 )

    1. 水素結合可能基とバルキーキラル置換基を持つモノマーと水素結合可能基を持つアキラルモノマーの共重合とその後の膜状態でのキラル置換基の定量的な除去による主鎖のみに不斉構造を持つ安定キラルらせんフェニルアセチレン高分子の第3の合成法の確立
    平成19年度(1年目)に見出した主鎖のみに不斉構造を持つ安定キラルらせんフェニルアセチレン高分子の第3の合成法を確立した。
    2. 1で得られた方法(第三の方法)の不斉誘起効率の評価
    1 で確立した方法の不斉誘起効率の評価をらせん選択重合により同一の組成の片巻きらせん高分子を合成し、比較することで行い、この方法の優位性を見出した。
    3.水素結合可能基とバルキーキラル置換基を長くて剛直なスペーサーを介して持つモノマーの単独重合とその後の膜状態でのキラル置換基の定鼻的な除去による主鎖のみに不斉構造を持つ安定キラルらせんフェニルアセチレン高分子の第3の合成法の確立
    主鎖のみに不斉構造を持つ安定キラルらせんフェニルアセチレン高分子の第3の合成法の可能性を見出した。
    1 で確立した方法を単独十号に展開し、第三の方法の汎用性を示すことが出来た。

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  • 高酸素透過性ポリジフェニルアセチレン膜の合成

    2006.4 - 2007.3

    System name:共同研究

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  • 共役ボリラジカル超分子をホスト分子とした有機ラジカル包接と化学磁気メモリー

    Grant number:18651046

    2006 - 2007

    System name:科学研究費助成事業

    Research category:萌芽研究

    Awarding organization:日本学術振興会

    金子 隆司, 青木 俊樹, 寺口 昌宏

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    Grant amount:\3500000 ( Direct Cost: \3500000 )

    本研究では、超分子的に集積した高スピン共役ポリラジカルをホストとして、有機ラジカルゲストの包接のON/OFFによりその磁化を制御することで、化学的に記録できる磁気メモリーの実現を狙っている。この目的を達成するために、以下の手順で実施している。「高スピン共役ポリラジカルホストを設計および合成する。」「有機ラジカルゲスト分子の最適化と包接条件の探索および得られた包接体の磁気的性質を探索する。」本年度は、以下の項目について明らかにした。
    1.共役ポリラジカルホストの探索およびその超分子組織体構造の決定
    安定ラジカル骨格のガルビノキシル骨格を有するポリ(1,3-フェニレンエチニレン)誘導体を合成した。酢酸エチル中で中空のフォルダマー構造を形成することを明らかにした。ガルビノキシル残基を有するフェニルアセチレンモノマーと、これに光学活性基を導入したモノマーとの共重合を経て片巻らせん構造に安定ラジカルが導入されたポリラジカルが合成できた。また、共重合組成により主鎖らせんの巻き方向を制御できることが明らかとなった。
    2.アントラセン超分子の有機ラジカル包接およびその磁気的性質
    ゲストフリーの9,10-ビス(3,5-ジヒドロキシフェニル)アントラセン(BPAnt)結晶を安定ニトロキシラジカル類のジクロロメタン溶液に浸漬させて超分子包接体をそれぞれ調製した。t-ブチルフェニルニトロキシドは濃縮状態では不安定であったが,BPAntに包接することで磁気測定が可能となった。包接比0.80のTANOLでは、一次元ハイゼンベルグモデルに従う弱い反強磁性であったのに対し、包接比1.47のTANOLでは,単純な一次元モデルあるいはキュリー-ワイス則では表せない磁気挙動を示しており、部分的に二量化したスピン結合を含む磁気構造を示唆した。一方、フェニルニトロニルニトロキシドはかさ高いため、効率よく包接されなかった。

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  • Supermolecular Ladder Chiral Double Helical Polymer by Helix-sense-selective Polymerization Controlled by Achiral Values

    Grant number:16350061

    2004 - 2006

    System name:Grants-in-Aid for Scientific Research

    Research category:Grant-in-Aid for Scientific Research (B)

    Awarding organization:Japan Society for the Promotion of Science

    AOKI Toshiki, KANEKO Takashi

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    Grant amount:\14200000 ( Direct Cost: \14200000 )

    The investigators of this research project found an induced chirality in the main chain when a phenylacetylene having a bulky chiral substituent was polymerized. We thought this chiral structure did not contain asymmetric centers and was caused only by one-handed helical conformation. However, this chiral polymer contained two kinds of chiral structures and therefore the recognition ability and the precise structure of the chiral main chain itself could not be confirmed.
    To clarify it we realized synthesis of a chiral helical polyphenylacetylene which does not have any other chiral moieties by helix-sense-selective polymerization of an achiral monomer with a chiral catalytic system. In addition, we found the helix sense can be controlled by changing not only chiral amounts but also achiral amounts. And the chiral main-chain of the resulting polymer was found to be maintained by intramolecular hydrogen bonds, i.e., this polymer has a supermolecular ladder chiral double helical polymer structure. Therefore this main chain chirality disappeared when a polar solvent was added.
    In this study, we studied further the following points on the new synthetic method and the new polymer obtained by the method.
    (1) Generalization of the helix-sense-selective polymerization
    (2) Discussion of the mechanism of the helix-sense-selective polymerization
    (3) Development of new functions of the supermolecular ladder chiral double helical polymer
    (4) Discussion of the molecular structure of the supermolecular ladder chiral double helical polymer

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  • Siインプリンテイング法によるキラル分子孔を持つ光学異性体分離膜の創製

    Grant number:15655039

    2003 - 2004

    System name:科学研究費助成事業

    Research category:萌芽研究

    Awarding organization:日本学術振興会

    青木 俊樹, 金子 隆司, 寺口 昌宏

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    Grant amount:\2200000 ( Direct Cost: \2200000 )

    分子インプリンテイング法(MIP法)は分離対象物質を鋳型分子として、これと主として2次結合を生じるモノマーと架橋剤とともに混合し、重合後鋳型分子を除去し、これを認識する空間を材料内に生じさせる方法である。MIP法で得られた高分子はHPLC固定相として分子混合物に対し分離能を示すが、膜としての例はほとんど無い。特に光学異性体分離は従来のMIP法では困難である。そこで本研究では研究代表者らが最近見出した「Siインプリンテイング法」を光学異性体分離膜の創製に有効に用いることを目的とした。「Siインプリンテイング法」は、従来のMIP法が主に2次結合を用いているのに対し、1次結合であるSiCあるいはSiO共有結合を用いている。したがって、より精密にインプリンテイングされたキラル分子孔の創製の可能性が考えられた。
    本年度は、ポリフェニルアセチレンのパラ位にSiO共有結合を介して光学活性なピナニル基を持つ高分子を合成し、製膜した。この膜は光学異性体選択透過性を有していた。その後、膜状態で光学活性基を脱シリル化反応で取り除いた。除去は定量的に行うことができ、かつ膜強度を保っていた。得られた高分子膜は主鎖に光学活性を維持していることが分かった。そのため、光学活性基除去後も光学異性体選択透過性を有しており、Siインプリンティングによる光学異性体分離膜の創製が達成できた。また、この脱シリル化膜は脱シリル化前に比べて、透過速度の向上が見られた。さらにこの膜は有機溶媒に不溶なため従来使用できなかった疎水性の透過対象も分離対象として用いることが可能となった。この他に、光学活性基を持つ架橋高分子であるモノリスから光学活性基を脱シリル化反応で取り除いたモノリスが光学異性体の分離能を有することを見出し、Siインプリンティングの有効性の幅広さを示すことができた。

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  • キラルポリラジカルの合成と光磁気機能

    Grant number:14655344

    2002 - 2003

    System name:科学研究費助成事業

    Research category:萌芽研究

    Awarding organization:日本学術振興会

    金子 隆司, 寺口 昌宏, 青木 俊樹

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    Grant amount:\3300000 ( Direct Cost: \3300000 )

    本研究では、ポリラジカルとキラルポリマーを組み合わせた、新物質系としてのキラルポリラジカルの合成法、物性および機能について探索することを目的としている。具体的には、以下の手順で実施している。
    (1)置換アセチレンモノマーを中心に、モノマーの合成手順および重合法を検討することで、キラルポリラジカルの合成法を確立する。(2)キラルポリラジカルの磁気的性質、光学的性質および磁気光学効果について知見を得る。
    本年度は、t-ブチルニトロキシドおよびフェニルガルビノキシル残基を有するフェニルアセチレンモノマーについてキラル触媒を用いたらせん選択重合を実施し、キラルポリラジカルの合成法およびその誘導体の諸物性について以下のように基礎的な知見を得た
    (1)t-ブチルニトロキシド残基を有するキラルポリラジカルの合成と性質
    メタ位にt-ブチルヒドロキシアミノ基およびヒドロキシメチル基を有する置換アセチレンモノマーを合成し、これを光学活性なフェニルエチルアミン存在下ロジウム錯体触媒で重合して光学活性ならせん構造を有する置換ポリアセチレンを合成した。このポリマーを二酸化鉛で酸化することで対応するポリラジカルが得られた。ESRから算出したスピン濃度は0.20spin/unit程度であったが、室温下の溶液で1日以上安定であり、CDスペクトルも酸化前後でほぼ変わらぬ強度でコットン効果が認められた。
    (2)キラル触媒を用いたヒドロガルビノキシル置換ポリ(フェニルアセチレン)の合成とらせん安定性
    光学活性なフェニルエチルアミンを溶媒兼助触媒とし、(4-エチニルフェニル)ヒドロガルビノキシルをロジウム錯体触媒で重合した。CDスペクトルからは、配位子のノルボルナジエンをシクロオクタジエンに変えるだけで、得られるポリマーのらせん方向が反転することが明らかとなった。また、得られたポリマーのCDおよび紫外可視吸収はサーモクロミズムおよびソルバトクロミズムを示すことを、左右のらせん構造の生成エネルギーが等しいポリマーで初めて明らかにした。

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  • 新規ポリジフェニルアセチレン類の合成および特性と機能の開発

    2000.4 - 2001.3

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Teaching Experience (researchmap)

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Teaching Experience

  • リメディアル演習

    2022
    Institution name:新潟大学

  • 技術文献リサーチC

    2020
    Institution name:新潟大学

  • 技術文献リサーチA

    2020
    Institution name:新潟大学

  • 技術文献リサーチB

    2020
    Institution name:新潟大学

  • 技術文献リサーチD

    2020
    Institution name:新潟大学

  • 最先端技術を支える化学 I

    2018
    Institution name:新潟大学

  • 工学リテラシー入門(化学材料分野)

    2017
    Institution name:新潟大学

  • リメディアル演習

    2017
    -
    2022
    Institution name:新潟大学

  • 大型機器分析技術

    2017
    Institution name:新潟大学

  • 卒業研修

    2009
    Institution name:新潟大学

  • 工学リテラシー入門(化学システム工学科)

    2009
    -
    2016
    Institution name:新潟大学

  • 化学技術英語

    2008
    Institution name:新潟大学

  • 卒業研究

    2007
    Institution name:新潟大学

  • 高分子化学実験

    2007
    Institution name:新潟大学

  • 応用化学演習V

    2007
    Institution name:新潟大学

  • 論文輪講I

    2007
    -
    2019
    Institution name:新潟大学

  • 論文輪講II

    2007
    -
    2018
    Institution name:新潟大学

  • 卒業基礎研究

    2007
    -
    2008
    Institution name:新潟大学

  • 応用化学実習

    2007
    Institution name:新潟大学

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