Updated on 2026/05/24

写真a

 
MATANO Yoshihiro
 
Organization
Academic Assembly Institute of Science and Technology Fundamental Sciences Professor
Graduate School of Science and Technology Fundamental Sciences Professor
Faculty of Science Department of Science Professor
Title
Professor
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Degree

  • 博士（理学） ( 1994.11   京都大学 )

Research Areas

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

Research History (researchmap)

  • Niigata University   Faculty of Science Department of Science   Professor

    2017.4

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  • Niigata University   Graduate School of Science and Technology Fundamental Sciences   Professor

    2013.4

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  • Niigata University   Faculty of Science Department of Chemistry Organic and Biological Chemistry   Professor

    2013.4 - 2017.3

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  • Kyoto University   Graduate School of Engineering   Associate Professor

    2002.4 - 2013.3

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  • Kyoto University   Graduate School of Science   Research Assistant

    1995.4 - 2002.3

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  • Kyoto University   Faculty of Science   Research Assistant

    1990.11 - 1995.3

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Research History

  • Niigata University   Faculty of Science Department of Science   Professor

    2017.4

  • Niigata University   Graduate School of Science and Technology Fundamental Sciences   Professor

    2013.4

  • Niigata University   Graduate School of Science and Technology Fundamental Sciences   Professor

    2013.4

  • Niigata University   Abolition organization Organic and Biological Chemistry   Professor

    2013.4 - 2017.3

Education

  • Kyoto University   Graduate School, Division of Natural Science   化学専攻

    - 1990.10

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    Country： Japan

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  • Kyoto University   Faculty of Science   化学科

    - 1987.3

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    Country： Japan

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Professional Memberships

Studying abroad experiences

  • 米国ワシントン大学（University of Washington）   文部省在外研究員長期

    1996.9 - 1997.8

 

Papers

  • Synthesis, Structure, and Redox and Optical Properties of 5,10,15,20-Tetraaryl-5-azaporphyrinium Salts. International journal

    Yuta Kudoh, Emi Suzuki, Hikari Ochiai, Kakeru Ise, Yoshifumi Kimura, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    Chemistry (Weinheim an der Bergstrasse, Germany)   e202302148   2023.8

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    Language：English   Publishing type：Research paper (scientific journal)  

    The fundamental properties of azaporphyrins can be modulated over a wide range by changing the number of meso-nitrogen atoms. Reported herein are the first examples of 5,10,15,20-tetraaryl-5-azaporphyrinium (MTAMAP) salts, which were prepared via metal-templated cyclization of the corresponding zinc(II) and copper(II) complexes of 10-aryl-1-chloro-19-benzoyl-5,15-dimesityl-10-azabiladiene-ac. The inclusion of one meso-nitrogen atom in the 5,10,15,20-tetraarylporphyrin skeleton considerably changes the redox and optical properties as well as the degree of aromaticity of the porphyrin ring. The present findings suggest that MTAMAP salts would be promising scaffolds for the development of new azaporphyrin-based ionic fluorophores and photosensitizers.

    DOI： 10.1002/chem.202302148

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  • 9‐(Diphenylphosphoryl)‐10‐(phenylethynyl)anthracene Derivatives: Synthesis and Implications for the Substituent and Solvent Effects on the Light‐Emitting Properties Reviewed

    Nina Murayama, Joel Hao Jorolan, Mao Minoura, Haruyuki Nakano, Tadaaki Ikoma, Yoshihiro Matano

    ChemPhotoChem   6 ( 9 )   e202200100   2022.9

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    Authorship：Last author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

    DOI： 10.1002/cptc.202200100

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    Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/cptc.202200100

  • Synthesis, Electrochemical Behavior, and Catalytic Activity of Cobalt Complexes of 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoids Reviewed

    Yuna Satoh, Yuta Kudoh, Ko Furukawa, Yoshihiro Matano

    Organic Letters   24 ( 21 )   3839 - 3843   2022.6

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    Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

    DOI： 10.1021/acs.orglett.2c01411

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  • Synthesis, Optical Properties, and Electrochemical Behavior of 5,10,15,20-Tetraaryl-5,15-diazaporphyrin-Amine Hybrids Reviewed

    Yuna Satoh, Yutaro Fujita, Naoya Muramatsu, Ko Furukawa, Tadaaki Ikoma, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    ChemPlusChem   86 ( 10 )   1476 - 1486   2021.10

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    Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1002/cplu.202100429

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  • Doubly Strapped Redox-Switchable 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoids: Promising Platforms for the Evaluation of Paratropic and Diatropic Ring-Current Effects Reviewed

    Hikari Ochiai, Ko Furukawa, Haruyuki Nakano, Yoshihiro Matano

    The Journal of Organic Chemistry   86 ( 3 )   2283 - 2296   2021.2

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    Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：American Chemical Society (ACS)  

    DOI： 10.1021/acs.joc.0c02433

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  • Effects of the Peripheral Substituents, Central Metal, and Solvent on the Photochemical and Photophysical Properties of 5,15-Diazaporphyrins Reviewed

    Satoshi Omomo, Ryosuke Fukuda, Tomoaki Miura, Tatsuya Murakami, Tadaaki Ikoma, Yoshihiro Matano

    ChemPlusChem   84 ( 6 )   740 - 745   2019

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    Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

    DOI： 10.1002/cplu.201900087

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    Other Link： https://onlinelibrary.wiley.com/doi/full-xml/10.1002/cplu.201900087

  • Direct and Regioselective Amination of β-Unsubstituted 5,15-Diazaporphyrins with Amines: A Convenient Route to Near-Infrared-Responsive Diazaporphyrin Sensitizers Reviewed

    Satoshi Omomo, Takuma Sugai, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    Angewandte Chemie - International Edition   57 ( 14 )   3797 - 3800   2018.3

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    Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Wiley-VCH Verlag  

    DOI： 10.1002/anie.201800471

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  • Syntheses, Properties, and Catalytic Activities of Metal(II) Complexes and Free Bases of Redox-Switchable 20 pi, 19 pi, and 18 pi 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoids Reviewed

    Keisuke Sudoh, Takaharu Satoh, Toru Amaya, Ko Furukawa, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    CHEMISTRY-A EUROPEAN JOURNAL   23 ( 64 )   16364 - 16373   2017.11

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    Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1002/chem.201703664

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  • Redox-Switchable 20-, 19-, and 18-Electron 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoid Nickel(II) Complexes Reviewed

    Takaharu Satoh, Mao Minoura, Haruyuki Nakano, Ko Furukawa, Yoshihiro Matano

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   55 ( 6 )   2235 - 2238   2016.2

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    Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1002/anie.201510734

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  • Synthesis and Structure-Property Relationships of Phosphole-Based pi Systems and Their Applications in Organic Solar Cells Reviewed

    Yoshihiro Matano

    CHEMICAL RECORD   15 ( 3 )   636 - 650   2015.6

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    Authorship：Lead author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1002/tcr.201402101

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  • Synthesis of Chain Type and Fused π-Conjugated Phosphole Derivatives

    MATANO Yoshihiro, IMAHORI Hiroshi

    Journal of Synthetic Organic Chemistry, Japan   70 ( 6 )   629 - 639   2012.1

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    Authorship：Lead author,　Corresponding author   Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：The Society of Synthetic Organic Chemistry, Japan  

    Phosphole has a low aromaticity and exhibits characteristic optical and electrochemical properties derived from the phosphorus-bridged 1,3-diene π system. In addition, phosphole has an active lone pair at phosphorus. The most remarkable feature of the phosphole-based π-systems is that their fundamental properties are tunable by chemical functionalizations at the phosphorus center. In this regard, phosphole-based π-systems are now regarded as one of the future materials for use in optoelectronics. In this article, we would like to briefly summarize our recent results on the synthesis of novel π-conjugated phosphole derivatives with representative examples, which contain phosphole-vinylene, phosphole-acetylene, phosphole-heterole, phosphole-benzene, phosphole-phosphole, benzo[c]phosphole, acenaphtho[c]phoshole, and diacenaphtho[b,d]phosphole skeletons. The target compounds were successfully prepared by two main approaches, titanacycle method and Stille coupling. Selected structural, optical, and electrochemical data for a few derivatives are also presented. The results described herein would give valuable information and guidelines for designing phosphole-based opto-electrochemical materials.

    DOI： 10.5059/yukigoseikyokaishi.70.629

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  • Synthesis, Aromaticity, and Optical and Redox Properties of Nickel(II), Palladium(II), and Platinum(II) Complexes of <i>meso</i> ‐Substituted 5‐Monoazaporphyrin Derivatives Reviewed

    Yui Murata, Kanta Sasaki, Tomoaki Miura, Yui Wakasa, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    Chemistry – An Asian Journal   21 ( 4 )   e70627   2026.2

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    ABSTRACT

    There has been great interest in the development of azaporphyrin‐based photosensitizers. Herein, we report a series of group 10 metal (Ni, Pd, Pt) complexes of 10,15,20‐triaryl‐5‐monoazaporphyrin (Ar <sub>3</sub> MAP; Ar = 4‐MeC <sub>6</sub> H <sub>4</sub> ) and their meso ‐N‐substituted derivatives (RAr <sub>3</sub> MAP; R = Ph, ethynyl, BF <sub>3</sub> ). The freebase of Ar <sub>3</sub> MAP, prepared by annulative condensation between 5,10,15‐tris(4‐methylphenyl)bilane and ammonium carbamate in the presence of an iron(III) salt, was converted into metal complexes by treatment with the corresponding metal salts. The copper‐catalyzed meso ‐N‐phenylation of Ar <sub>3</sub> MAP with a diphenyliodonium salt afforded PhAr <sub>3</sub> MAP salts. The substantial basicity of the meso ‐N atom of Ar <sub>3</sub> MAP was further demonstrated by meso ‐N‐ethynylation with an ethynyl(phenyl)iodonium salt and Lewis acid–base complexation with BF <sub>3</sub> •OEt <sub>2</sub> . The aromatic character and the optical and redox properties of the new MAP derivatives were assessed using spectroscopic and voltammetric measurements and density functional theory calculations. It was revealed that adding a positive charge to the MAP ring weakened the diatropic ring‐current effect, red‐shifted the Q bands, and anodically shifted the π‐centered redox processes. Transient absorption measurements of the Pd and Pt complexes also provide valuable information regarding the effects of meso ‐N substituents and central metals on the excited‐state dynamics of MAP dyes.

    DOI： 10.1002/asia.70627

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    Other Link： https://aces.onlinelibrary.wiley.com/doi/full-xml/10.1002/asia.70627

  • Effects of Peripheral Substituents on the Optical and Electrochemical Properties of Dibenzo‐5,10,15‐triazaporphyrins Reviewed

    Kaori Kuwabara, Uta Sakamaki, Taiyou Tsutsumi, Yui Wakasa, Soji Shimizu, Mao Minoura, Yoshifumi Kimura, Haruyuki Nakano, Yoshihiro Matano

    Chemistry – A European Journal   31 ( 66 )   e02463   2025.10

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    Abstract

    In contrast to the great advances of phthalocyanine‐based materials, the potential of 5,10,15‐triazaporphyrins has not been realized because of the lack of fundamental information about their structure‐property relationships. Here, we report new derivatives of dibenzo‐5,10,15‐triazaporphyrin (DBTriAP) with aryl or alkyl substituents at the meso and/or β positions. Freebases of DBTriAP were prepared by the condensation of two types of 1,9‐dibromodipyrrins with 1,3‐diiminoisoindoline and subsequent functionalization of the β‐pyrrolic carbons. Zinc(II) complexes of DBTriAP were obtained by complexation of the corresponding freebases with zinc(II) acetate. The optical and electrochemical properties of the DBTriAP derivatives were studied by steady‐state and transient ultraviolet/visible absorption/emission spectroscopy, magnetic circular dichroism spectroscopy, cyclic voltammetry (CV), and density functional theory (DFT) calculations. Replacing the β‐pyrrolic hydrogens of the 5‐mesityl‐DBTriAP derivatives with aryl groups resulted in substantial red shifts of the low‐energy absorption band because of the effective π‐delocalization and/or charge‐transfer interaction with the DBTriAP chromophore. The 2,3,17,18‐tetraethyl‐DBTriAP freebase exhibited split redox processes in its cyclic voltammogram, suggesting the rapid formation of a π‐stacked dimer radical cation facilitated by the highly planar structure. Most of the DBTriAP derivatives emitted red fluorescence with quantum yields of 0.07–0.31, indicating their potential as luminescent materials.

    DOI： 10.1002/chem.202502463

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  • Photoexcitation dynamics of azaphosphole compounds: effects of substituents and solvents Reviewed

    Rio Kitakado, Rika Takegami, Kaori Fujii, Hiroaki Nakagomi, Nina Murayama, Yoshihiro Matano, Haruyuki Nakano, Kanami Sugiyama, Masahiro Higashi, Yoshifumi Kimura

    Bulletin of the Chemical Society of Japan   98 ( 8 )   uoaf076   2025.7

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    Language：English   Publishing type：Research paper (scientific journal)   Publisher：Oxford University Press (OUP)  

    Abstract

    Photoexcitation dynamics of a series of 2-aryl-3H-1,3-benzazaphosphole oxides (ABPO) were studied using ultrafast time-resolved fluorescence spectroscopy and transient absorption spectroscopy. The fluorescence quantum yields and lifetimes strongly depended on the substituents on the phenyl ring at the 2-position, and generally fluorescence lifetimes were very short. Compound (1d) that has a 4-(N,N-diphenylamino)phenyl group at the 2-position showed intense fluorescence in nonpolar solvents, although the fluorescence was quite weak in polar solvents. The time-resolved fluorescence spectrum of 1d showed a large dynamic shift, accompanied by a decrease in fluorescence intensity. The transient absorption spectrum of 1d showed complex spectral dynamics. From the singular value decomposition analysis of the time-resolved spectra, the spectral dynamics were assigned to the charge transfer formation accompanying the rotation of the phenyl ring at 2-position predicted by the theoretical calculations (K. Sugiyama et al., J. Phys. Chem. B, 2025, 129, 2701). A compound with an ortho-hydroxyphenyl at the 2-position (1e-OH) showed intramolecular proton transfer in aprotic solvents, showing dual fluorescence from the normal and tautomer bands. In methanol, a new fluorescence band appeared besides the bands from the normal and tautomer states, which was assigned to the hydrogen-bonding complex with the solvent by the theoretical calculations.

    DOI： 10.1093/bulcsj/uoaf076

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  • 6,21-Diaza-<i>m</i>-benziporphyrins and 6,21-Diaza-<i>m</i>-pyriporphyrins with <i>meso</i>-<i>N</i>-Substituents: Synthesis and Evaluation of Antiaromatic Characters Reviewed

    Emi Suzuki, Momo Kaneko, Haruyuki Nakano, Yoshihiro Matano

    Organic Letters   27 ( 31 )   8712 - 8717   2025.7

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    DOI： 10.1021/acs.orglett.5c02644

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  • Air‐Stable Radical Ion Pairs Formed from 20π‐Electron 5,15‐Diazaporphyrinoids and Tetracyanoquinodimethane Derivatives Reviewed

    Sae Ohtani, Momo Kaneko, Yuki Shimizu, Mao Minoura, Ko Furukawa, Yoshihiro Matano

    Asian Journal of Organic Chemistry   14 ( 6 )   e202500312   2025.4

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    Abstract

    With the aim of exploring 5,15‐diazaporphyrinoids with four meso substituents (R<sub>4</sub>DAP) as a new class of π‐electron donors, the generation of air‐stable π‐radical ion pairs formed from R<sub>4</sub>DAP and 7,7,8,8‐tetracyanoquinodimethane (TCNQ) derivatives has been demonstrated. Nickel(II) and copper(II) complexes of the 20π‐electron antiaromatic R<sub>4</sub>DAP (R<sub>4</sub>DAPM; M = Ni, Cu) were prepared via a metal‐templated cyclization method and used for the reaction with TCNQ. Single electron transfer from R<sub>4</sub>DAPM to TCNQ spontaneously occurred in CH<sub>2</sub>Cl<sub>2</sub> at room temperature to afford the corresponding radical ion pair, [R<sub>4</sub>DAPM<sup>•+</sup>][TCNQ<sup>•−</sup>]. Similarly, R<sub>4</sub>DAPNi reacted with 2,3,5,6‐tetrafluoro‐TCNQ (F<sub>4</sub>TCNQ) to afford [R<sub>4</sub>DAPNi<sup>•+</sup>][F<sub>4</sub>TCNQ<sup>•−</sup>]. The absorption spectra of [R<sub>4</sub>DAPM<sup>•+</sup>][TCNQ<sup>•−</sup>] in the visible–near IR region were almost identical to the superposed spectra of the independently prepared cation‐ and anion‐radical references, indicating negligible π─π orbital interaction between the two radical ions in solution. However, the electron paramagnetic resonance spectrum of [R<sub>4</sub>DAPNi<sup>•+</sup>][F<sub>4</sub>TCNQ<sup>•−</sup>] in CH<sub>2</sub>Cl<sub>2</sub> showed a broad signal attributable to the coupled spin state, suggesting the definite contribution of spin–spin interaction between the two ion‐paired radicals. The results of this study provide valuable information for understanding the fundamental properties of π‐radical ion pairs.

    DOI： 10.1002/ajoc.202500312

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  • Si(IV) complexes of 10,20-diaryl-5,15-diazaporphyrin and 5,10,20-triaryl-5,15-diazaporphyrinoids: Evaluation of charge effect on the optical, redox, and magnetic properties Reviewed

    Kanta Sasaki, Yui Murata, Hiroya Suzuki, Mao Minoura, Rio Kitakado, Yoshifumi Kimura, Ko Furukawa, Haruyuki Nakano, Yoshihiro Matano

    Journal of Porphyrins and Phthalocyanines   29 ( 03n04 )   467 - 477   2025.4

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    Publishing type：Research paper (scientific journal)   Publisher：World Scientific Pub Co Pte Ltd  

    The central metals in group 14 metalloporphyrins significantly influence the optical, redox, and magnetic properties of the porphyrin [Formula: see text]-electron systems. This study reports the first examples of Si(IV) complexes of 10,20-diaryl-5,15-diazaporphyrin (Ar<sub>2</sub>DAP) and 5,10,20-triaryl-5,15-diazaporphyrin (Ar<sub>3</sub>DAP), designed to explore the effects of meso-nitrogen atoms and net charge on these fundamental properties of the porphyrin ring. Reacting the free base of Ar<sub>2</sub>DAP with HSiCl<sub>3</sub>, followed by metathesis of axial ligands, yielded the corresponding Si(IV) complexes (Ar<sub>2</sub>DAPSiX<sub>2</sub>; X [Formula: see text] OH, F). Copper-catalyzed [Formula: see text]-phenylation of Ar<sub>2</sub>DAPSiF<sub>2</sub> and subsequent redox reactions produced 18[Formula: see text]- and 19[Formula: see text]-electron derivatives of Ar<sub>3</sub>DAPSiF<sub>2</sub>. Nuclear magnetic resonance spectroscopy, cyclic voltammetry, and density functional theory calculations revealed that the diatropic ring-current effects derived from the aromatic 18[Formula: see text]-electron systems of Ar<sub>2</sub>DAPSiX<sub>2</sub> and Ar<sub>3</sub>DAPSiF<sub>2</sub> strongly depend on the net charge and dipole moment of the DAP ligand. All Si(IV) complexes exhibited fluorescence, with Stokes shifts of 120–310 cm[Formula: see text]. Measurements of fluorescence quantum yields and lifetimes indicated that [Formula: see text]-phenylation primarily reduced the nonradiative decay rate constant. These findings provided insights into the influence of net charge on the aromatic character, as well as the optical and redox properties, of six-coordinate Si(IV) complexes of DAP derivatives.

    DOI： 10.1142/s1088424625500397

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  • Theoretical Study on the Solvent-Dependent Optical Properties of 2-Aryl-3H–1,3-benzazaphosphole Oxide Reviewed

    Kanami Sugiyama, Hiroaki Nakagomi, Yoshihiro Matano, Yoshifumi Kimura, Hirofumi Sato, Masahiro Higashi

    The Journal of Physical Chemistry B   129 ( 10 )   2701 - 2707   2025.2

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

    DOI： 10.1021/acs.jpcb.4c05872

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  • Two Approaches to the Synthesis of Redox‐Switchable 5,10,20‐Triaryl‐5,15‐diazaporphyrinoids Invited Reviewed

    Yui Murata, Keisuke Sudoh, Ko Furukawa, Haruyuki Nakano, Yoshihiro Matano

    Chemistry – An Asian Journal   20 ( 3 )   e202401370   2025.2

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    DOI： 10.1002/asia.202401370

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  • A Zirconium Complex Bearing an [NPN] Tridentate Ligand Composed of Dibenzophosphole and Pyrrolide Moieties: Synthesis, Structure, and Ethylene-Polymerization Ability Reviewed

    Tomoyuki Toda, Yuzuki Kasahara, Jin Iwasaki, Ayana Wakatsuki, Shun Ohta, Yoshihiro Matano, Katsuhiko Takenaka

    Organometallics   44 ( 1 )   128 - 136   2024.12

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

    DOI： 10.1021/acs.organomet.4c00395

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  • Sn(IV) Complexes of 5,10,15,20‐Tetraaryl‐5,15‐diazaporphyrinoids: A Promising Platform for Evaluating the 20π‐Electron Antiaromaticity Reviewed

    Hiroya Suzuki, Mao Minoura, Ko Furukawa, Haruyuki Nakano, Yoshihiro Matano

    Chemistry – A European Journal   31 ( 9 )   e202404092   2024.12

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    Authorship：Last author,　Corresponding author   Publishing type：Research paper (scientific journal)   Publisher：Wiley  

    Abstract

    Porphyrinoids in the 20π‐electron state have been extensively studied from the fundamental viewpoint of investigating their structure–antiaromaticity relationships. However, most of the 20π porphyrinoids are highly distorted and unstable in air, which hinder the comprehensive analysis of paratropic ring‐current effects derived from planar π‐electron systems. Herein, we present the first examples of antiaromatic Sn(IV) complexes of 5,10,15,20‐tetraaryl‐5,15‐diazaporphyrinoids (SnX<sub>2</sub>TADAPs), prepared by the complexation of the corresponding freebases with Sn(II) chloride under aerobic conditions and subsequent metathesis of the axial ligands, that show paratropic ring‐current effects. Notably, both neutral 20π‐electron derivatives and 19π‐electron radical cations of SnX<sub>2</sub>TADAP are extremely stable in air owing to the intrinsic electronic effects of the central Sn(IV) unit and meso nitrogen atoms. NMR spectroscopy, cyclic voltammetry, and density functional theory calculations were performed to assess the ring‐current effects and orbital energies of a series of the 20π‐electron SnX<sub>2</sub>TADAPs, and the results reveal that the paratropic ring‐current effects arising from the planar 20π‐electron DAP ring increases with a decrease in the HOMO–LUMO energy gap.

    DOI： 10.1002/chem.202404092

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  • Synthesis and Polymerization Activity of Phosphine‐Pyrrolido [PN] Titanium and Zirconium Complexes Reviewed

    Jin Iwasaki, Tomoyuki Toda, Ayana Wakatsuki, Shun Ohta, Kei Nishii, Yoshihiro Matano, Katsuhiko Takenaka

    Applied Organometallic Chemistry   39 ( 1 )   e7928   2024.12

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

    ABSTRACT

    A monoanionic bidentate [PN]‐type ligand based on dibenzophosphole was synthesized, and its coordination properties toward titanium and zirconium were investigated. The complexes [PN]M (NR<sub>2</sub>)<sub>3</sub> (M = Ti, R = Me; M = Zr, R = Et) were synthesized through the reaction of 4‐(1H‐pyrrole‐2‐yl)dibenzophosphole, [PN]H, with three equivalents of Ti (NMe<sub>2</sub>)<sub>4</sub> or Zr (NEt<sub>2</sub>)<sub>4</sub>. Both titanium and zirconium complexes featuring the [PN] ligand were characterized by NMR and elemental analysis. Single‐crystal X‐ray crystallography unveiled the solid‐state structure of [PN]Zr (NEt<sub>2</sub>)<sub>3</sub>, with the pyrrolido group coordinated to the zirconium center in the η<sup>1</sup>‐mode. Ethylene polymerization at 0.4 MPa using these complexes and dried modified methylaluminoxane (dMMAO) as a cocatalyst yielded linear polyethylene (PE) with a melting point of 128°C–136°C; the polymerization activity reached up to 64 kg/mol (Zr)·h·bar at 70°C.

    DOI： 10.1002/aoc.7928

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  • 2-Aryl-3H-1,3-Benzazaphosphole Oxides: Synthesis, Optical Properties, and Excited State Intramolecular Proton Transfer Reviewed

    Hiroaki Nakagomi, Nina Murayama, Rika Takegami, Kaori Fujii, Rio Kitakado, Yoshifumi Kimura, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    Chemistry - A European Journal   30 ( 33 )   e202400807   2024.6

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    Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1002/chem.202400807

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  • Improved Synthesis of Free Bases of 5,10,15,20-Tetraaryl-5,15-diazaporphyrinoid for Conversion to Silicon(IV) Complexes Reviewed

    Hiroya Suzuki, Ko Furukawa, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    Bulletin of the Chemical Society of Japan   97 ( 2 )   uoad022   2023.12

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    Authorship：Last author,　Corresponding author   Language：English   Publishing type：Research paper (scientific journal)  

    <jats:title>Abstract</jats:title>
    <jats:p>We report herein an improved method for the quantitative preparation of free bases of 5,10,15,20-tetraaryl-5,15-diazaporphyrinoid (TADAP) using Me3SiBr–MeOH to treat the corresponding zinc(II) complexes. Metallation of the free base with HSiCl3 followed by Si–X metathesis with SbF3 and redox reactions afforded difluorosilicon(IV) complexes of TADAP.</jats:p>

    DOI： 10.1093/bulcsj/uoad022

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  • Theoretical study on counter anion- and solvent-dependent fluorescence quenching mechanism of 2-phenylbenzo[b]phospholium salts Reviewed

    Sara Suzuki, Kosuke Imamura, Kaori Fujii, Yoshifumi Kimura, Yoshihiro Matano, Masahiro Higashi, Hirofumi Sato

    Journal of Molecular Liquids   382   121934   2023.7

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    DOI： 10.1016/j.molliq.2023.121934

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  • Substituent Effect on the Excited-State Dynamics of Benzo[<i>b</i>]phospholium Salts Investigated Using Picosecond Time-Resolved Spectroscopy

    Kaori Fujii, Atsuro Matsumoto, Takayuki Oka, Yuta Kudoh, Hiroaki Nakagomi, Yoshihiro Matano, Yoshifumi Kimura

    Bulletin of the Chemical Society of Japan   96 ( 7 )   686 - 692   2023.7

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    DOI： 10.1246/bcsj.20230071

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  • Synthesis and optical properties of 3,5-bis(10-phenylanthracen-9-yl)benzene-appended porphyrins Reviewed

    Akane Umemiya, Haruyuki Nakano, Nanami Iwaya, Tadaaki Ikoma, Yoshihiro Matano

    Journal of Porphyrins and Phthalocyanines   27   1241 - 1252   2023.6

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    <jats:p> Singlet–singlet and triplet-triplet energy-transfer processes between anthracenes and porphyrins have received considerable attention in materials chemistry. Herein, we report the first examples of 3,5-bis(10-phenylanthracen-9-yl)benzene-appended porphyrins (BPABPs) designed to study intramolecular energy transfer between two chromophores. The Curtius rearrangement of 3,5-bis(10-phenylanthracen-9-yl)benzoyl azide in the presence of the platinum(II) complex of 5,10,15-tris(3,5-di-tert-butylphenyl)-20-(3-hydroxyphenyl)porphyrin or its free base in toluene afforded the corresponding BPABP. Spectroscopy, cyclic voltammetry, and density functional theory calculations revealed that the anthracene and porphyrin [Formula: see text]-electron systems of the BPABPs are not conjugated and consequently do not affect each other’s absorption properties. In contrast, the BPABPs exhibited considerably different luminescence properties to those of phenyl 3,5-bis(10-phenylanthracen-9-yl)carbamate and 5,10,15-tris(3,5-di-tert-butylphenyl)-20-(3-methoxyphenyl)porphyrins; the anthracene units of the BPABPs show considerably quenched fluorescence compared to that of the reference anthracene, indicative of efficient intramolecular singlet–singlet energy transfer from the anthracene to the porphyrin unit. The phosphorescence quantum yield of the Pt complex of BPABP is comparable to that of the reference Pt-porphyrin, which suggests that intramolecular triplet-triplet energy transfer from the Pt-porphyrin to the anthracene unit is inefficient. The present findings improve our understanding of how structural factors and excited-state energy levels affect energy transfer and triplet-triplet annihilation upconversion processes of covalently linked bisanthracene-appended porphyrins. </jats:p>

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  • Synthesis and Optical Properties of 1,2,5,10-Tetraphenylanthra[2,3-b]phosphole Derivatives. Reviewed International journal

    Yuta Kudoh, Kaori Fujii, Yoshifumi Kimura, Mao Minoura, Yoshihiro Matano

    The Journal of Organic Chemistry   87 ( 15 )   10493 - 10500   2022.8

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    1,2,5,10-Tetraphenylanthra[2,3-b]phosphole oxides and 1-methyl-1,2,5,10-tetraphenylanthra[2,3-b]phospholium salts were prepared, and their optical properties were investigated. The substituent at the para position and the fused anthracene moiety were found to exert significant impacts on the fluorescence properties of the P-bridged 2-styrylanthracene skeleton.

    DOI： 10.1021/acs.joc.2c01107

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  • Copper(II) Complexes of 10,20-Diaryl-5,15-diazaporphyrin: Alternative Synthesis, Excited State Dynamics, and Substituent Effect on the <sup>1</sup>O<inf>2</inf>-Generation Efficiency Reviewed

    Hikari Ochiai, Tomoaki Miura, Tadaaki Ikoma, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    Bulletin of the Chemical Society of Japan   95 ( 3 )   427 - 432   2022

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    DOI： 10.1246/bcsj.20220002

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  • Synthesis of Hydrophilic Copper(II) Complexes of 5,10,15,20-Tetraaryl-5,15-diazaporphyrins Substituted with Carboxy or (2,3-Dihydroxypropyl)carbamoyl Groups Invited Reviewed

    Yuki Shimizu, Yoshihiro Matano

    Journal of Porphyrins and Phthalocyanines   25   1005 - 1014   2021.8

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    Porphyrins containing hydrophilic auxiliaries have received considerable attention. Herein we report the first examples of strongly hydrophilic copper(II) complexes of 5,10,15,20-tetraaryl-5,15-diazaporphyrins (TADAPs) substituted with carboxy or (2,3-dihydroxypropyl)carbamoyl groups. Metal-templated cyclization reactions of a common dipyrrin precursor with nickel(II) or copper(II) acetate afforded the corresponding metal(II) complexes of 5,10,15,20-tetrakis(4-alkoxycarbonylphenyl)-5,15-diazaporphyrin (M-TADAP-COOR; M = Ni, Cu) as air-stable 19[Formula: see text] radical cations, which were reversibly interconvertible with 20[Formula: see text]- and 18[Formula: see text]-electron states by redox reactions. NMR spectroscopy of 20[Formula: see text] and 18[Formula: see text] Ni-TADAP-COORs revealed antiaromatic and aromatic characteristics, respectively. Alkaline hydrolysis of the 19[Formula: see text] Cu-TADAP-COOR afforded a carboxylic acid, Cu-TADAP-COOH, which was freely soluble in water under basic conditions, but poorly soluble under neutral or acidic conditions. Dehydrative condensation of Cu-TADAP-COOH with 2,3-bis((tert-butyldimethylsilyl)oxy)propan-1-amine followed by deprotection of the silyl groups afforded an amide, Cu-TADAP-CONHR, with four (2,3-dihydroxypropyl)carbamoyl groups. Although the 20[Formula: see text] Cu-TADAP-CONHR was poorly soluble in water, oxidation of its DAP ring notably changed the solubility, and the resulting 18[Formula: see text] dication was homogeneously dispersed in neutral water. Cyclic voltammetry of the present TADAP derivatives showed the 21[Formula: see text]/20[Formula: see text], 20[Formula: see text]/19[Formula: see text] and 19[Formula: see text]/18[Formula: see text] redox couples in the range of −1.8 to +0.2 V vs. Fc/Fc[Formula: see text]. Furthermore, Cu-TADAP-CONHR exhibited reversible redox processes in neutral water. This study shows that TADAP could be a potential platform for the development of hydrophilic DAP-based materials.

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  • π-Conjugated Molecules Containing Tetrathiafulvalene and Benzo[b]phosphole Oxide: Synthesis, Structure, and Electrochemical and Optical Properties Reviewed

    Shunki Ikeda, Aya Yoshimura, Takashi Shirahata, Yoshihiro Matano, Yohji Misaki

    Chemistry Letters   50 ( 8 )   1581 - 1585   2021.8

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    DOI： 10.1246/cl.210218

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  • Excited-State Intramolecular Proton Transfer Reaction and Ground-State Hole Dynamics of 4′-N,N-Dialkylamino-3-hydroxyflavone in Ionic Liquids Studied by Transient Absorption Spectroscopy Reviewed

    Hanamichi Miyabayashi, Kaori Fujii, Takumi Watanabe, Yoshihiro Matano, Takatsugu Endo, Yoshifumi Kimura

    The Journal of Physical Chemistry B   125 ( 20 )   5373 - 5386   2021.5

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    DOI： 10.1021/acs.jpcb.1c02360

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  • Synthesis and optical, magnetic, and electrochemical properties of 5,10,15,20-tetraaryl-5,15-diazaporphyrin — tertiary amine conjugates Invited Reviewed

    Keisuke Sudoh, Yuna Satoh, Ko Furukawa, Haruyuki Nakano, Yoshihiro Matano

    Journal of Porphyrins and Phthalocyanines   24 ( 01n03 )   286 - 297   2020.1

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    DOI： 10.1142/s1088424619500822

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  • Synthesis of Redox-switchable 5,15-Dialkyl-10,20-diaryl-5,15-diazaporphyrins and Diversification of their N-Alkyl Groups Reviewed

    Mai Mutoh, Keisuke Sudoh, Ko Furukawa, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    Asian Journal of Organic Chemistry   8 ( 3 )   352 - 355   2019.3

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    DOI： 10.1002/ajoc.201900085

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  • Synthesis and Properties of Redox-Switchable Zinc Complexes of 10,15,20-Triaryl-15-aza-5-oxaporphyrin Reviewed

    Keisuke Sudoh, Ko Furukawa, Haruyuki Nakano, Soji Shimizu, Yoshihiro Matano

    Heteroatom Chemistry   29 ( 5-6 )   e21456   2018.12

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    DOI： 10.1002/hc.21456

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  • Synthesis of 3,5-Disubstituted BODIPYs Bearing N-Containing Five-Membered Heteroaryl Groups via Nucleophilic C-N Bond Formation Reviewed

    Takaharu Satoh, Kaori Fujii, Yoshifumi Kimura, Yoshihiro Matano

    Journal of Organic Chemistry   83 ( 9 )   5274 - 5281   2018.5

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    DOI： 10.1021/acs.joc.8b00087

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  • Phosphole-Thiophene Hybrid: A Dual Role of Dithieno[3,4- b:3′,4′- d] phosphole as Electron Acceptor and Electron Donor Reviewed

    Tomohiro Higashino, Keiichi Ishida, Takaharu Satoh, Yoshihiro Matano, Hiroshi Imahori

    Journal of Organic Chemistry   83 ( 6 )   3397 - 3402   2018.3

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    DOI： 10.1021/acs.joc.8b00030

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  • Phosphole-Thiophene Hybrid: A Dual Role of Dithieno[3,4-b:3 ',4 '-d]phosphole as Electron Acceptor and Electron Donor Reviewed

    Tomohiro Higashino, Keiichi Ishida, Takaharu Satoh, Yoshihiro Matano, Hiroshi Imahori

    JOURNAL OF ORGANIC CHEMISTRY   83 ( 6 )   3397 - 3402   2018.3

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    DOI： 10.1021/acs.joc.8b00030

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  • Direct and Regioselective Amination of β-Unsubstituted 5,15-Diazaporphyrins with Amines: A Convenient Route to Near-Infrared-Responsive Diazaporphyrin Sensitizers Reviewed International journal

    Satoshi Omomo, Takuma Sugai, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    Angewandte Chemie   130 ( 14 )   3859 - 3800   2018.3

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    We have established a convenient method for the base-promoted direct amination of β-unsubstituted 5,15-diazaporphyrins (DAPs) with secondary and primary amines to produce 3,7,13,17-tetraamino- and 3-amino-DAPs, respectively, regioselectively. The amino groups attached at the periphery cause significant red shifts of the absorption bands as a result of their perturbation of the HOMO and/or LUMO in the DAP π-system. The palladium complex of a 3,7,13,17-tetrakis(diphenylamino)-DAP generated singlet oxygen in high yield under irradiation with near-infrared light.

    DOI： 10.1002/ange.201800471

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  • β-functionalization of 5, 15-diazaporphyrins with phosphorus, oxygen, and sulfur-containing substituents Reviewed

    Takuma Sugai, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    Bulletin of the Chemical Society of Japan   91 ( 8 )   1264 - 1266   2018

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    DOI： 10.1246/bcsj.20180123

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  • Redox Switchable 19π and 18π 5,10,20-Triaryl-5,15-diazaporphyrinoid–Nickel(II) Complexes Reviewed

    Keisuke Sudoh, Takuroh Hatakeyama, Ko Furukawa, Haruyuki Nakano, Yoshihiro Matano

    Journal of Porphyrins and Phthalocyanines   22 ( 7 )   542 - 551   2018

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  • Regioselective functionalization at the 7-position of 1,2,3-triphenylbenzo[b] phosphole oxide via P=O-directed lithiation Reviewed

    Ayana Wakatsuki, Mariko Yukimoto, Mao Minoura, Kaori Fujii, Yoshifumi Kimura, Yoshihiro Matano

    Dalton Transactions   47 ( 21 )   7123 - 7127   2018

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    DOI： 10.1039/c8dt01503a

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  • Segregated Donor-Acceptor Columns in Liquid Crystals That Exhibit Highly Efficient Ambipolar Charge Transport (vol 133, pg 10736, 2011) Reviewed

    Hironobu Hayashi, Wataru Nihashi, Tomokazu Umeyama, Yoshihiro Matano, Shu Seki, Yo Shimizu, Hiroshi Imahori

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   139 ( 39 )   13957 - 13957   2017.10

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  • Effects of counter anions, P-substituents, and solvents on optical and photophysical properties of 2-phenylbenzo[b]phospholium salts Reviewed

    Yoshinari Koyanagi, Shogo Kawaguchi, Kaori Fujii, Yoshifumi Kimura, Takahiro Sasamori, Norihiro Tokitoh, Yoshihiro Matano

    DALTON TRANSACTIONS   46 ( 29 )   9517 - 9527   2017.8

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    DOI： 10.1039/c7dt01839h

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  • Correction to: Segregated donor-acceptor columns in liquid crystals that exhibit highly efficient ambipolar charge transport (Journal of the American Chemical Society (2011) 133 (10736-10739) DOI: 10.1021/ja203822q) Reviewed

    Hironobu Hayashi, Wataru Nihashi, Tomokazu Umeyama, Yoshihiro Matano, Shu Seki, Yo Shimizu, Hiroshi Imahori

    Journal of the American Chemical Society   133 ( 28 )   10736 - 10739   2017.7

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    DOI： 10.1021/ja203822q

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  • Excited-State Proton Transfer of Cyanonaphthols in Protic Ionic Liquids: Appearance of a New Fluorescent Species Reviewed

    Kaori Fujii, Yoshiro Yasaka, Masakatsu Ueno, Yoshinari Koyanagi, Sora Kasuga, Yoshihiro Matano, Yoshifumi Kimura

    Journal of Physical Chemistry B   121 ( 24 )   6042 - 6049   2017.6

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    DOI： 10.1021/acs.jpcb.7b03658

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  • Unsymmetrically Substituted Donor--Acceptor-Type 5,15-Diazaporphyrin Sensitizers: Synthesis, Optical and Photovoltaic Properties Reviewed

    Satoshi Omomo, Yukihiro Tsuji, Kenichi Sugiura, Tomohiro Higashino, Haruyuki Nakano, Hiroshi Imahori, Yoshihiro Matano

    CHEMPLUSCHEM   82 ( 5 )   695 - 704   2017.5

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    DOI： 10.1002/cplu.201700051

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  • Nitrogen-Bridged Metallodiazaporphyrin Dimers: Synergistic Effects of Nitrogen Bridges and meso-Nitrogen Atoms on Structure and Properties Reviewed

    Masahiro Kawamata, Takuma Sugai, Mao Minoura, Yasuhisa Maruyama, Ko Furukawa, Cole Holstrom, Victor N. Nemykin, Haruyuki Nakano, Yoshihiro Matano

    CHEMISTRY-AN ASIAN JOURNAL   12 ( 7 )   816 - 821   2017.4

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    DOI： 10.1002/asia.201700204

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  • Synthesis of Dibenzophosphole Oxides from Dibenzothiophene Dioxides and Phenylphosphine by Two Successive SNAr Reactions Reviewed

    Mitsuki Onoda, Yoshinari Koyanagi, Hayate Saito, M. Bhanuchandra, Yoshihiro Matano, Hideki Yorimitsu

    ASIAN JOURNAL OF ORGANIC CHEMISTRY   6 ( 3 )   257 - 261   2017.3

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    DOI： 10.1002/ajoc.201600612

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  • Synthesis of Aza-, Oxa-, and Thiaporphyrins and Related Compounds Invited Reviewed

    Yoshihiro Matano

    Chemical Reviews   117 ( 4 )   3138 - 3191   2017.2

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    DOI： 10.1021/acs.chemrev.6b00460

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  • Ring-Strain Effects in Base-Induced Sommelet-Hauser Rearrangement: Application to Successive Stereocontrolled Transformations Reviewed

    Eiji Tayama, Kazutoshi Watanabe, Yoshihiro Matano

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 21 )   3631 - 3641   2016.7

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    DOI： 10.1002/ejoc.201600611

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  • Effects of boryl, phosphino, and phosphonio substituents on optical, electrochemical, and photophysical properties of 2,5-dithienylphospholes and 2-phenyl-5-thienylphospholes Reviewed

    Yoshinari Koyanagi, Yoshifumi Kimura, Yoshihiro Matano

    Dalton Transactions   45 ( 5 )   2190 - 2200   2016.1

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    DOI： 10.1039/c5dt03362d

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  • Synthesis and Photophysical Properties of Two Diazaporphyrin-Porphyrin Hetero Dimers in Polar and Nonpolar Solutions Reviewed

    Fawzi Abou-Chahine, Daisuke Fujii, Hiroshi Imahori, Haruyuki Nakano, Nikolai V. Tkachenko, Yoshihiro Matano, Helge Lemmetyinen

    Journal of Physical Chemistry B   119 ( 24 )   7328 - 7337   2015.6

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    DOI： 10.1021/jp510903a

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  • Comparison of 2-arylnaphtho[2,3- b ]phospholes and 2-arylbenzo[ b ]phospholes: Effects of 2-Aryl groups and fused arene moieties on their optical and photophysical properties Reviewed

    Yoshihiro Matano, Yuta Motegi, Shinsuke Kawatsu, Yoshifumi Kimura

    Journal of Organic Chemistry   80 ( 11 )   5944 - 5950   2015.6

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    DOI： 10.1021/acs.joc.5b00541

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  • Comparison of electronic effects of beta-aryl substituents on optical and electrochemical properties of 5,15-diazaporphyrin pi-systems Reviewed

    Satoshi Omomo, Ko Furukawa, Haruyuki Nakano, Yoshihiro Matano

    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES   19 ( 6 )   775 - 785   2015.6

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    DOI： 10.1142/S1088424615500509

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  • Optical, electrochemical, and magnetic properties of pyrrole- And thiophene-bridged 5,15-diazaporphyrin dimers Reviewed

    Satoshi Omomo, Yasuhisa Maruyama, Ko Furukawa, Taniyuki Furuyama, Haruyuki Nakano, Nagao Kobayashi, Yoshihiro Matano

    Chemistry - A European Journal   21 ( 5 )   2003 - 2010   2015.1

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    DOI： 10.1002/chem.201405482

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  • N,S,P-hybrid donor-π-acceptor organic dyes for dye-sensitized solar cell: Synthesis, optical properties, and photovoltaic performances Invited Reviewed

    Yoshihiro Matano, Yukiko Hayashi, Haruyuki Nakano, Hiroshi Imahori

    Heteroatom Chemistry   25 ( 6 )   533 - 547   2014.6

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    DOI： 10.1002/hc.21188

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  • Phosphole- and Benzodithiophene- Based Copolymers: Synthesis and Application in Organic Photovoltaics Reviewed

    Yoshihiro Matano, Hiroshi Ohkubo, Tetsushi Miyata, Yusuke Watanabe, Yukiko Hayashi, Tomokazu Umeyama, Hiroshi Imahori

    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY   2014 ( 10 )   1620 - 1624   2014.4

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    DOI： 10.1002/ejic.201301132

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  • Covalently Linked 5,15-Diazaporphyrin Dimers: Promising Scaffolds for a Highly Conjugated Azaporphyrin pi System Reviewed

    Yoshihiro Matano, Daisuke Fujii, Tarou Shibano, Ko Furukawa, Tomohiro Higashino, Haruyuki Nakano, Hiroshi Imahori

    CHEMISTRY-A EUROPEAN JOURNAL   20 ( 12 )   3342 - 3349   2014.3

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    DOI： 10.1002/chem.201304626

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  • Slow charge recombination and enhanced photoelectrochemical properties of diazaporphyrin-fullerene linked dyad Reviewed

    M. Yamamoto, Y. Takano, Y. Matano, K. Stranius, N.V. Tkachenko, H. Lemmetyinen, H. Imahori

    Journal of Physical Chemistry C   118 ( 4 )   1808 - 1820   2014

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    DOI： 10.1021/jp410436f

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  • Synthesis of 2-Alkenyl- and 2-Alkynyl-benzo[b]phospholes by Using Palladium-Catalyzed Cross-Coupling Reactions Reviewed

    Yoshihiro Matano, Yukiko Hayashi, Kayo Suda, Yoshifumi Kimura, Hiroshi Imahori

    ORGANIC LETTERS   15 ( 17 )   4458 - 4461   2013.9

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    DOI： 10.1021/ol401994e

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  • Synthesis and Photovoltaic Properties of Phenylethynyl-substituted Diazaporphyrin Reviewed

    Kei Kurotobi, Kyosuke Kawamoto, Yuuki Toude, Yamato Fujimori, Yuriko Kinjo, Seigo Ito, Yoshihiro Matano, Hiroshi Imahori

    CHEMISTRY LETTERS   42 ( 7 )   725 - 726   2013.7

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    Carboxyphenylethynyl-substituted diazaporphyrin has been synthesized to assess the utility of diazaporphyrins in dye-sensitized solar cells for the first time. The diazaporphyrin-sensitized TiO<sub>2</sub> cell exhibited photocurrent generation in the visible region of 400–700 nm together with a power conversion efficiency of 0.08%.

    DOI： 10.1246/cl.130212

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  • Synthesis and Charge-Carrier Transport Properties of Poly(phosphole P-alkanesulfonylimide)s Reviewed

    Yoshihiro Matano, Hiroshi Ohkubo, Yoshihito Honsho, Arihiro Saito, Shu Seki, Hiroshi Imahori

    ORGANIC LETTERS   15 ( 4 )   932 - 935   2013.2

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    DOI： 10.1021/ol4000982

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  • Synthesis and Structure-Property Relationships of 2,2 '-Bis(benzo[b]phosphole) and 2,2 '-Benzo[b]phosphole-Benzo[b]heterole Hybrid pi Systems Reviewed

    Yukiko Hayashi, Yoshihiro Matano, Kayo Suda, Yoshifumi Kimura, Yoshihide Nakao, Hiroshi Imahori

    CHEMISTRY-A EUROPEAN JOURNAL   18 ( 50 )   15972 - 15983   2012.12

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    DOI： 10.1002/chem.201203047

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  • Free Base and Metal Complexes of 5,15-Diaza-10,20-dimesitylporphyrins: Synthesis, Structures, Optical and Electrochemical Properties, and Aromaticities Reviewed

    Yoshihiro Matano, Tarou Shibano, Haruyuki Nakano, Yoshifumi Kimura, Hiroshi Imahori

    INORGANIC CHEMISTRY   51 ( 23 )   12879 - 12890   2012.12

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    DOI： 10.1021/ic301835c

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  • alpha,alpha '-Diarylacenaphtho[1,2-c]phosphole P-Oxides: Divergent Synthesis and Application to Cathode Buffer Layers in Organic Photovoltaics Reviewed

    Yoshihiro Matano, Arihiro Saito, Yuto Suzuki, Tooru Miyajima, Seiji Akiyama, Saika Otsubo, Emi Nakamoto, Shinji Aramaki, Hiroshi Imahori

    CHEMISTRY-AN ASIAN JOURNAL   7 ( 10 )   2305 - 2312   2012.10

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    DOI： 10.1002/asia.201200492

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  • Synthesis of Chain Type and Fused pi-Conjugated Phosphole Derivatives Invited Reviewed

    Yoshihiro Matano, Hiroshi Imahori

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   70 ( 6 )   629 - 639   2012.6

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    Phosphole has a low aromaticity and exhibits characteristic optical and electrochemical properties derived from the phosphorus-bridged 1,3-diene π system. In addition, phosphole has an active lone pair at phosphorus. The most remarkable feature of the phosphole-based π-systems is that their fundamental properties are tunable by chemical functionalizations at the phosphorus center. In this regard, phosphole-based π-systems are now regarded as one of the future materials for use in optoelectronics. In this article, we would like to briefly summarize our recent results on the synthesis of novel π-conjugated phosphole derivatives with representative examples, which contain phosphole-vinylene, phosphole-acetylene, phosphole-heterole, phosphole-benzene, phosphole-phosphole, benzo[c]phosphole, acenaphtho[c]phoshole, and diacenaphtho[b,d]phosphole skeletons. The target compounds were successfully prepared by two main approaches, titanacycle method and Stille coupling. Selected structural, optical, and electrochemical data for a few derivatives are also presented. The results described herein would give valuable information and guidelines for designing phosphole-based opto-electrochemical materials.

    DOI： 10.5059/yukigoseikyokaishi.70.629

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  • Nickel(II) and Copper(II) Complexes of beta-Unsubstituted 5,15-Diazaporphyrins and Pyridazine-Fused Diazacorrinoids: Metal-Template Syntheses and Peripheral Functionalizations Reviewed

    Yoshihiro Matano, Tarou Shibano, Haruyuki Nakano, Hiroshi Imahori

    CHEMISTRY-A EUROPEAN JOURNAL   18 ( 20 )   6208 - 6216   2012.5

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    DOI： 10.1002/chem.201200463

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  • Preparation and Photophysical and Photoelectrochemical Properties of a Covalently Fixed Porphyrin-Chemically Converted Graphene Composite Reviewed

    Tomokazu Umeyama, Junya Mihara, Noriyasu Tezuka, Yoshihiro Matano, Kati Stranius, Vladimir Chukharev, Nikolai V. Tkachenko, Helge Lemmetyinen, Kei Noda, Kazumi Matsushige, Tetsuya Shishido, Zheng Liu, Kaori Hirose-Takai, Kazu Suenaga, Hiroshi Imahori

    CHEMISTRY-A EUROPEAN JOURNAL   18 ( 14 )   4250 - 4257   2012.4

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    DOI： 10.1002/chem.201103843

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  • Effects of Carbon-Metal-Carbon Linkages on the Optical, Photophysical, and Electrochemical Properties of Phosphametallacycle-Linked Coplanar Porphyrin Dimers Reviewed

    Yoshihiro Matano, Kazuaki Matsumoto, Hironobu Hayashi, Yoshihide Nakao, Tatu Kumpulainen, Vladimir Chukharev, Nikolai V. Tkachenko, Helge Lemmetyinen, Soji Shimizu, Nagao Kobayashi, Daisuke Sakamaki, Akihiro Ito, Kazuyoshi Tanaka, Hiroshi Imahori

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   134 ( 3 )   1825 - 1839   2012.1

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    DOI： 10.1021/ja210205v

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  • Thermal Conversion of Precursor Polymer to Low Bandgap Conjugated Polymer Containing Isothianaphthene Dimer Subunits Reviewed

    Tomokazu Umeyama, Kohei Hirose, Kei Noda, Kazumi Matsushige, Tetsuya Shishido, Hironobu Hayashi, Yoshihiro Matano, Noboru Ono, Hiroshi Imahori

    JOURNAL OF PHYSICAL CHEMISTRY C   116 ( 1 )   1256 - 1264   2012.1

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    DOI： 10.1021/jp208775x

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  • Pentavalent Organobismuth Reagents in Organic Synthesis: Alkylation, Alcohol Oxidation and Cationic Photopolymerization Invited

    Yoshihiro Matano

    BISMUTH-MEDIATED ORGANIC REACTIONS   311   19 - 44   2012

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    DOI： 10.1007/128_2011_167

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  • Porphyrin-appended phosphapalladacycle precatalysts: effects of central metals on the catalytic activity in a high-temperature Heck reaction Reviewed

    Yoshihiro Matano, Kazuaki Matsumoto, Tarou Shibano, Hiroshi Imahori

    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES   15 ( 11-12 )   1172 - 1182   2011.11

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    DOI： 10.1142/S1088424611004087

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  • Divergent Synthesis of 2,5-Diarylphospholes Based on Cross-coupling Reactions: Substituent Effects on the Optical and Redox Properties of Benzene-Phosphole-Benzene pi-Systems Reviewed

    Yoshihiro Matano, Yusuke Kon, Arihiro Saito, Yoshifumi Kimura, Toshihiro Murafuji, Hiroshi Imahori

    CHEMISTRY LETTERS   40 ( 9 )   919 - 921   2011.9

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    DOI： 10.1246/cl.2011.919

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  • Optical, Electrochemical, and Photovoltaic Effects of an Electron-Withdrawing Tetrafluorophenylene Bridge in a Push-Pull Porphyrin Sensitizer Used for Dye-Sensitized Solar Cells Reviewed

    Simon Mathew, Hiroaki Iijima, Yuuki Toude, Tomokazu Umeyama, Yoshihiro Matano, Seigo Ito, Nikolai V. Tkachenko, Helge Lemmetyinen, Hiroshi Imahori

    JOURNAL OF PHYSICAL CHEMISTRY C   115 ( 29 )   14415 - 14424   2011.7

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    DOI： 10.1021/jp2030208

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  • Segregated Donor-Acceptor Columns in Liquid Crystals That Exhibit Highly Efficient Ambipolar Charge Transport Reviewed

    Hironobu Hayashi, Wataru Nihashi, Tomokazu Umeyama, Yoshihiro Matano, Shu Seki, Yo Shimizu, Hiroshi Imahori

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   133 ( 28 )   10736 - 10739   2011.7

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    DOI： 10.1021/ja203822q

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  • Density Functional Theory Studies on Chemical Functionalization of Single-Walled Carbon Nanotubes by Bingel Reaction Reviewed

    Tomokazu Umeyama, Hiroyuki Fueno, Eisuke Kawabata, Yoshikazu Kobayashi, Kazuyoshi Tanaka, Noriyasu Tezuka, Yoshihiro Matano, Hiroshi Imahori

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   84 ( 7 )   748 - 753   2011.7

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    DOI： 10.1246/bcsj.20100326

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  • Bisquinoxaline-Fused Porphyrins for Dye-Sensitized Solar Cells Reviewed

    Hiroshi Imahori, Hiroaki Iijima, Hironobu Hayashi, Yuuki Toude, Tomokazu Umeyama, Yoshihiro Matano, Seigo Ito

    CHEMSUSCHEM   4 ( 6 )   797 - 805   2011.6

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    DOI： 10.1002/cssc.201100029

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  • Carbon Nanotube Wiring of Donor-Acceptor Nanograins by Self-Assembly and Efficient Charge Transport Reviewed

    Tomokazu Umeyama, Noriyasu Tezuka, Fumiaki Kawashima, Shu Seki, Yoshihiro Matano, Yoshihide Nakao, Tetsuya Shishido, Masayuki Nishi, Kazuyuki Hirao, Heli Lehtivuori, Nikolai V. Tkachenko, Helge Lemmetyinen, Hiroshi Imahori

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   50 ( 20 )   4615 - 4619   2011.5

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    DOI： 10.1002/anie.201007065

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  • J-aggregation of a sulfonated amphiphilic porphyrin at the air-water interface as a function of pH Reviewed

    Gustavo de Miguel, Kohei Hosomizu, Tomokazu Umeyama, Yoshihiro Matano, Hiroshi Imahori, Marta Perez-Morales, Maria T. Martin-Romero, Luis Camacho

    JOURNAL OF COLLOID AND INTERFACE SCIENCE   356 ( 2 )   775 - 782   2011.4

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    DOI： 10.1016/j.jcis.2011.01.066

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  • 【2011-3】Local stoichiometry in amorphous supramolecular composites analyzed by solid-state C 13 nuclear magnetic resonance Reviewed

    H. Kaji, H. Hayashi, T. Yamada, M. Fukuchi, S. Fujimura, M. Ueda, S. Kang, T. Umeyama, Y. Matano, H. Imahori

    Appl. Phys. Lett.   98 ( 11 )   [113301-1] - [113301-3]   2011.3

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    DOI： 10.1063/1.3565237

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  • Effects of Heterole Spacers on the Structural, Optical, and Electrochemical Properties of 2,5-Bis(1,5-diphenylphosphol-2-yl)heteroles Reviewed

    Yoshihiro Matano, Arihiro Saito, Masato Fujita, Hiroshi Imahori

    HETEROATOM CHEMISTRY   22 ( 3-4 )   457 - 470   2011

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    DOI： 10.1002/hc.20708

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  • Fusion of Phosphole and 1,1 '-Biacenaphthene: Phosphorus(V)-Containing Extended pi-Systems with High Electron Affinity and Electron Mobility Reviewed

    Yoshihiro Matano, Arihiro Saito, Tatsuya Fukushima, Yasuaki Tokudome, Furitsu Suzuki, Daisuke Sakamaki, Hironori Kaji, Akihiro Ito, Kazuyoshi Tanaka, Hiroshi Imahori

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   50 ( 35 )   8016 - 8020   2011

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    DOI： 10.1002/anie.201102782

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  • Photophysics and photoelectrochemical properties of nanohybrids consisting of fullerene-encapsulated single-walled carbon nanotubes and poly(3-hexylthiophene) Reviewed

    Noriyasu Tezuka, Tomokazu Umeyama, Yoshihiro Matano, Tetsuya Shishido, Kaname Yoshida, Tetsuya Ogawa, Seiji Isoda, Kati Stranius, Vladimir Chukharev, Nikolai V. Tkachenko, Helge Lemmetyinen, Hiroshi Imahori

    Energy & Environmental Science   4 ( 3 )   741 - 850   2011

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    DOI： 10.1039/c0ee00482k

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  • Synthesis and photovoltaic properties of thiophene-imide-fused thiophene alternating copolymers with different alkyl side chains Reviewed

    Tomokazu Umeyama, Masaaki Oodoi, Osamu Yoshikawa, Takashi Sagawa, Susumu Yoshikawa, Douvogianni Evgenia, Noriyasu Tezuka, Yoshihiro Matano, Kati Stranius, Nikolai V. Tkachencko, Helge Lemmetyinen, Hiroshi Imahori

    JOURNAL OF MATERIALS CHEMISTRY   21 ( 33 )   12454 - 12461   2011

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    DOI： 10.1039/c1jm11531f

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  • Good Solvent Effects of C-70 Cluster Formations and Their Electron-Transporting and Photoelectrochemical Properties Reviewed

    Noriyasu Tezuka, Tomokazu Umeyama, Yoshihiro Matano, Tetsuya Shishido, Mitsuo Kawasaki, Masayuki Nishi, Kazuyuki Hirao, Heli Lehtivuori, Nikolai V. Ikachenko, Helge Lemmetyinen, Yoshihito Honsho, Shu Seki, Hiroshi Imahori

    JOURNAL OF PHYSICAL CHEMISTRY B   114 ( 45 )   14287 - 14297   2010.11

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    DOI： 10.1021/jp911141s

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  • Synthesis, structures, optical and electrochemical properties, and complexation of 2,5-bis(pyrrol-2-yl)phospholes Reviewed

    Yoshihiro Matano, Masato Fujita, Arihiro Saito, Hiroshi Imahori

    COMPTES RENDUS CHIMIE   13 ( 8-9 )   1035 - 1047   2010.8

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    DOI： 10.1016/j.crci.2010.03.017

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  • Effects of π-Elongation and the Fused Position of Quinoxaline-Fused Porphyrins as Sensitizers in Dye-Sensitized Solar Cells on Optical, Electrochemical, and Photovoltaic Properties Reviewed

    Aiko Kira, Yusuke Matsubara, Hiroaki Iijima, Tomokazu Umeyama, Yoshihiro Matano, Seigo Ito, Marja Niemi, Nikolai V. Tkachenko, Helge Lemmetyinen, Hiroshi Imahori

    JOURNAL OF PHYSICAL CHEMISTRY C   114 ( 25 )   11293 - 11304   2010.7

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    DOI： 10.1021/jp1004049

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  • Synthesis of alpha,alpha &apos;-Linked Oligophospholes and Polyphospholes by Using Pd-Cul-Promoted Stille-Type Coupling Reviewed

    Arihiro Saito, Yoshihiro Matano, Hiroshi Imahori

    ORGANIC LETTERS   12 ( 11 )   2675 - 2677   2010.6

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    DOI： 10.1021/ol100926q

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  • Effects of meso-Diarylamino Group of Porphyrins as Sensitizers in Dye-Sensitized Solar Cells on Optical, Electrochemical, and Photovoltaic Properties Reviewed

    Hiroshi Imahori, Yusuke Matsubara, Hiroaki Iijima, Tomokazu Umeyama, Yoshihiro Matano, Seigo Ito, Marja Niemi, Nikolai V. Tkachenko, Helge Lemmetyinen

    JOURNAL OF PHYSICAL CHEMISTRY C   114 ( 23 )   10656 - 10665   2010.6

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    DOI： 10.1021/jp102486b

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  • Oligothiophene Bearing 1-Hydroxy-1-oxodithieno[2,3-b:3',2'-d]phosphole as a Novel Anchoring Group for Dye-sensitized Solar Cells Reviewed

    Aiko Kira, Yuki Shibano, Soonchul Kang, Hironobu Hayashi, Tomokazu Umeyama, Yoshihiro Matano, Hiroshi Imahori

    CHEMISTRY LETTERS   39 ( 5 )   448 - 450   2010.5

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    DOI： 10.1246/cl.2010.448

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  • Selective Formation and Efficient Photocurrent Generation of [70]Fullerene-Single-Walled Carbon Nanotube Composites Reviewed

    Tomokazu Umeyama, Noriyasu Tezuka, Shu Seki, Yoshihiro Matano, Masayuki Nishi, Kazuyuki Hirao, Heli Lehtivuori, Nikolai V. Tkachenko, Helge Lemmetyinen, Yoshihide Nakao, Shigeyoshi Sakaki, Hiroshi Imahori

    ADVANCED MATERIALS   22 ( 15 )   1767 - 1770   2010.4

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    DOI： 10.1002/adma.200903056

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  • Remarkable effects of p-perfluorophenyl group on the synthesis of core-modified phosphaporphyrinoids and phosphadithiasapphyrin Reviewed

    Takashi Nakabuchi, Yoshihiro Matano, Hiroshi Imahori

    Organic Letters   12 ( 5 )   1112 - 1115   2010.3

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    DOI： 10.1021/ol100114j

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  • Synthesis, structures, and aromaticity of phosphole-containing porphyrins and their metal complexes Reviewed

    Yoshihiro Matano, Takashi Nakabuchi, Hiroshi Imahori

    PURE AND APPLIED CHEMISTRY   82 ( 3 )   583 - 593   2010.3

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    DOI： 10.1351/PAC-CON-09-08-05

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  • Comparison of Cluster Formation, Film Structure, Microwave Conductivity, and Photoelectrochemical Properties of Composites Consisting of Single-Walled Carbon Nanotubes with C60, C70, and C84 Reviewed

    Noriyasu Tezuka, Tomokazu Umeyama, Shu Seki, Yoshihiro Matano, Masayuki Nishi, Kazuyuki Hirao, Hiroshi Imahori

    JOURNAL OF PHYSICAL CHEMISTRY C   114 ( 7 )   3235 - 3247   2010.2

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    DOI： 10.1021/jp910832a

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  • Synthesis and Reactions of Phosphaporphyrins: Reconstruction of pi-Skeleton Triggered by Oxygenation of a Core Phosphorus Atom Reviewed

    Takashi Nakabuchi, Makoto Nakashima, Shinya Fujishige, Haruyuki Nakano, Yoshihiro Matano, Hiroshi Imahori

    JOURNAL OF ORGANIC CHEMISTRY   75 ( 2 )   375 - 389   2010.1

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    DOI： 10.1021/jo902060b

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  • Zinc-Induced Fluorescence Enhancement of the 5,10-Porphodimethene-Type Thiophene-Containing Calixphyrins Reviewed

    Yoshihiro Matano, Masato Fujita, Tooru Miyajima, Hiroshi Imahori

    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS   185 ( 5-6 )   1098 - 1107   2010

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    DOI： 10.1080/10426501003773431

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  • Oligothiophene bearing 1-hydroxy-1-oxodithieno[2,3-b:3′,2′-d] phosphole as a novel anchoring group for dye-sensitized solar cells Reviewed

    Aiko Kira, Yuki Shibano, Soonchul Kang, Hironobu Hayashi, Tomokazu Umeyama, Yoshihiro Matano, Hiroshi Imahori

    Chemistry Letters   39 ( 5 )   448 - 450   2010

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    DOI： 10.1246/cl.2010.448

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  • Dispersion of Carbon Nanotubes by Photo- and Thermal-Responsive Polymers Containing Azobenzene Unit in the Backbone Reviewed

    Tomokazu Umeyama, Kazuhiro Kawabata, Noriyasu Tezuka, Yoshihiro Matano, Yuji Miyato, Kazumi Matsushige, Masahiko Tsujimoto, Seiji Isoda, Mikio Takano, Hiroshi Imahori

    CHEMICAL COMMUNICATIONS   46 ( 32 )   5969 - 5971   2010

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    DOI： 10.1039/c0cc00709a

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  • Meso-Substituent Effects on Redox Properties of the 5,10-Porphodimethene-Type P,S,N-2-Hybrid Calixphyrins and Their Metal Complexes Reviewed

    Yoshihiro Matano, Masato Fujita, Tooru Miyajima, Hiroshi Imahori

    ORGANOMETALLICS   28 ( 21 )   6213 - 6217   2009.11

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    DOI： 10.1021/om900745t

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  • Effects of Porphyrin Substituents and Adsorption Conditions on Photovoltaic Properties of Porphyrin-Sensitized TiO2 Cells Reviewed

    Hiroshi Imahori, Shinya Hayashi, Hironobu Hayashi, Akane Oguro, Seunghun Eu, Tomokazu Umeyama, Yoshihiro Matano

    JOURNAL OF PHYSICAL CHEMISTRY C   113 ( 42 )   18406 - 18413   2009.10

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    DOI： 10.1021/jp907288h

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  • New Palladium(II) Complex of P,S-Containing Hybrid Calixphyrin. Theoretical Study of Electronic Structure and Reactivity for Oxidative Addition Reviewed

    Noriaki Ochi, Yoshihide Nakao, Hirofumi Sato, Yoshihiro Matano, Hiroshi Imahori, Shigeyoshi Sakaki

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   131 ( 31 )   10955 - 10963   2009.8

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    DOI： 10.1021/ja901166a

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  • Phosphole-Containing Calixpyrroles, Calixphyrins, and Porphyrins: Synthesis and Coordination Chemistry Reviewed

    Yoshihiro Matano, Hiroshi Imahori

    ACCOUNTS OF CHEMICAL RESEARCH   42 ( 8 )   1193 - 1204   2009.8

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    DOI： 10.1021/ar900075e

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  • Phosphole-Triazole Hybrids: A Facile Synthesis and Complexation with Pd(II) and Pt(II) Salts Reviewed

    Yoshihiro Matano, Makoto Nakashima, Arihiro Saito, Hiroshi Imahori

    ORGANIC LETTERS   11 ( 15 )   3338 - 3341   2009.8

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    DOI： 10.1021/ol901194m

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  • Synthesis and Photophysical and Photovoltaic Properties of Porphyrin-Furan and -Thiophene Alternating Copolymers Reviewed

    Umeyama, Tomokazu, Takamatsu, Takeshi, Tezuka, Noriyasu, Matano, Yoshihiro, Araki, Yasuyuki, Wada, Takehiko, Yoshikawa, Osamu, Sagawa, Takashi, Yoshikawa, Susumu, Imahori, Hiroshi

    The Journal of Physical Chemistry C   113 ( 24 )   10798 - 10806   2009.6

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    DOI： 10.1021/jp902001z

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  • Effects of electrode structure on photoelectrochemical properties of ZnO electrodes modified with porphyrin-fullerene composite layers with an intervening fullerene monolayer Reviewed

    H. Hayashi, A. Kira, T. Umeyama, Y. Matano, P. Charoensirithavorn, T. Sagawa, S. Yoshikawa, N.Y. Tkachenko, H. Lemmetyinen, H. Imahori

    Journal of Physical Chemistry C   113 ( 24 )   10819 - 10828   2009.6

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    DOI： 10.1021/jp902623g

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  • Supramolecular Donor-Acceptor Heterojunctions by Vectorial Stepwise Assembly of Porphyrins and Coordination-Bonded Fullerene Arrays for Photocurrent Generation

    Aiko Kira, Tomokazu Umeyama, Yoshihiro Matano, Kaname Yoshida, Seiji Isoda, Jong Kang Park, Dongho Kim, Hiroshi Imahori

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   131 ( 9 )   3198 - +   2009.3

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    DOI： 10.1021/ja8096465

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  • A Convenient Method for the Synthesis of α-Ethynylphospholes and Modulation of Their π-Conjugated Systems Reviewed

    Yoshihiro Matano, Makoto Nakashima, Hiroshi Imahori

    Angewandte Chemie International Edition   48 ( 22 )   4002 - 4005   2009

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    DOI： 10.1002/anie.200900542

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  • Acenaphtho[1,2-c]phosphole P-Oxide: A Phosphole-Naphthalene pi-Conjugated System with High Electron Mobility Reviewed

    Arihiro Saito, Tooru Miyajima, Makoto Nakashima, Tatsuya Fukushima, Hironori Kaji, Yoshihiro Matano, Hiroshi Imahori

    CHEMISTRY-A EUROPEAN JOURNAL   15 ( 39 )   10000 - 10004   2009

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    DOI： 10.1002/chem.200901378

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  • Design and synthesis of phosphole-based pi systems for novel organic materials Reviewed

    Yoshihiro Matano, Hiroshi Imahori

    ORGANIC & BIOMOLECULAR CHEMISTRY   7 ( 7 )   1258 - 1271   2009

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    DOI： 10.1039/b819255n

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  • Remarkable Substituent Effects on the Oxidizing Ability of Tetraarylbismuthonium Tetrafluoroborates in Alcohol Oxidation Reviewed

    Yoshihiro Matano, Takeshi Suzuki, Takaharu Iwata, Tomonori Shinokura, Hiroshi Imahori

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   81 ( 12 )   1621 - 1628   2008.12

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    DOI： 10.1246/bcsj.81.1621

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  • Substituent Effects of Porphyrins on Structures and Photophysical Properties of Amphiphilic Porphyrin Aggregates Reviewed

    Kohei Hosomizu, Masaaki Oodoi, Tomokazu Umeyama, Yoshihiro Matano, Kaname Yoshida, Seiji Isoda, Marja Isosomppi, Nikolai V. Tkachenko, Helge Lemmetyinen, Hiroshi Imahori

    JOURNAL OF PHYSICAL CHEMISTRY B   112 ( 51 )   16517 - 16524   2008.12

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    DOI： 10.1021/jp807991k

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  • Synthesis of sterically hindered phthalocyanines and their applications to dye-sensitized solar cells Reviewed

    Seunghun Eu, Takashi Katoh, Tomokazu Umeyama, Yoshihiro Matano, Hiroshi Imahori

    DALTON TRANSACTIONS   2008 ( 40 )   5476 - 5483   2008.10

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    DOI： 10.1039/b803272f

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  • Fused five-membered porphyrin for dye-sensitized solar cells Reviewed

    Shinya Hayashi, Yusuke Matsubara, Seunghun Eu, Hironobu Hayashi, Tomokazu Umeyama, Yoshihiro Matano, Hiroshi Imahori

    CHEMISTRY LETTERS   37 ( 8 )   846 - 847   2008.8

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    Fused five-membered zinc porphyrin carboxylic acid has been synthesized to improve light-harvesting capability in the visible and near-infrared regions. The fused porphyrin-sensitized TiO<SUB>2</SUB> cell exhibited the photocurrent generation extending over 800 nm, although the power conversion efficiency was found to be moderate (0.30%).

    DOI： 10.1246/cl.2008.846

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  • Tunable soret-band splitting of an amphiphilic porphyrin by surface pressure Reviewed

    Gustavo de Miguel, Kohei Hosomizu, Tomokazu Umeyama, Yoshihiro Matano, Hiroshi Imahori, Maria T. Martin-Romero, Luis Camacho

    CHEMPHYSCHEM   9 ( 11 )   1511 - 1513   2008.8

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    DOI： 10.1002/cphc.200800270

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  • Synthesis of thiophene-containing hybrid calixphyrins of the 5,10-porphodimethene type Reviewed

    Yoshihiro Matano, Tooru Miyajima, Noriaki Ochi, Yoshihide Nakao, Shigeyoshi Sakaki, Hiroshi Imahori

    JOURNAL OF ORGANIC CHEMISTRY   73 ( 13 )   5139 - 5142   2008.7

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    DOI： 10.1021/jo800532n

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  • Synthesis, structures, and coordinating properties of phosphole-containing hybrid calixpyrroles Reviewed

    Takashi Nakabuchi, Yoshihiro Matano, Hiroshi Imahori

    ORGANOMETALLICS   27 ( 13 )   3142 - 3152   2008.7

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    DOI： 10.1021/om800099h

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  • Triaryl(1-pyrenyl)bismuthonium salts: Efficient photoinitiators for cationic polymerization of oxiranes and a vinyl ether Reviewed

    Yoshihiro Matano, Tomonori Shinokura, Osamu Yoshikawa, Hiroshi Imahori

    ORGANIC LETTERS   10 ( 11 )   2167 - 2170   2008.6

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    DOI： 10.1021/ol8005453

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  • Quinoxaline-fused porphyrins for dye-sensitized solar cells Reviewed

    Seunghun Eu, Shinya Hayashi, Tomokazu Umeyama, Yoshihiro Matano, Yasuyuki Araki, Hiroshi Imahori

    Journal of Physical Chemistry C   112 ( 11 )   4396 - 4405   2008.3

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    DOI： 10.1021/jp710400p

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  • Light Harvesting and Energy Transfer in Multiporphyrin-Modified CdSe Nanoparticles Reviewed

    Soonchul Kang, Masakazu Yasuda, Hiroshi Miyasaka, Hironobu Hayashi, Mitsuo Kawasaki, Tomokazu Umeyama, Yoshihiro Matano, Kaname Yoshida, Seiji Isoda, Hiroshi Imahori

    ChemSusChem   1 ( 3 )   254 - 261   2008.3

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    DOI： 10.1002/cssc.200700138

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  • Monophosphaporphyrins: Oxidative pi-extension at the peripherally fused carbocycle of the phosphaporphyrin ring Reviewed

    Yoshihiro Matano, Makoto Nakashima, Takashi Nakabuchi, Hiroshi Imahori, Shinya Fujishige, Haruyuki Nakano

    ORGANIC LETTERS   10 ( 4 )   553 - 556   2008.2

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    DOI： 10.1021/ol7029118

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  • Bithiophene-fused benzo[c]phospholes: Novel P,S-Containing hybrid pi-conjugated systems with small HOMO-LUMO energy gaps Reviewed

    Tooru Miyajima, Yoshihiro Matano, Hiroshi Imahori

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2008 ( 2 )   255 - 259   2008.1

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    DOI： 10.1002/ejoc.200701008

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  • Syntheses, structures, and coordination chemistry of phosphole-containing hybrid calixphyrins: Promising macrocyclic P,N-2,X-mixed donor ligands for designing reactive transition-metal complexes Reviewed

    Yoshihiro Matano, Tooru Miyajima, Noriaki Ochi, Takashi Nakabuchi, Motoo Shiro, Yoshihide Nakao, Shigeyoshi Sakaki, Hiroshi Imahori

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   130 ( 3 )   990 - 1002   2008.1

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    DOI： 10.1021/ja076709o

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  • Redox-Coupled Complexation of 23-Phospha-21-thiaporphyrin with Group 10 Metals: A Convenient Access to Stable Core-Modified Isophlorin Metal Complexes Reviewed

    Yoshihiro Matano, Takashi Nakabuchi, Shinya Fujishige, Haruyuki Nakano, Hiroshi Imahori

    Journal of the American Chemical Society   130 ( 49 )   16446 - 16447   2008

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    DOI： 10.1021/ja807742g

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  • Comparative Study on the Structural, Optical, and Electrochemical Properties of Bithiophene-Fused Benzo[c]phospholes Reviewed

    Yoshihiro Matano, Tooru Miyajima, Tatsuya Fukushima, Hironori Kaji, Yoshifumi Kimura, Hiroshi Imahori

    CHEMISTRY-A EUROPEAN JOURNAL   14 ( 27 )   8102 - 8115   2008

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    DOI： 10.1002/chem.200801017

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  • Regioselective β-Metalation of meso-Phosphanylporphyrins. Structure and Optical Properties of Porphyrin Dimers Linked by Peripherally Fused Phosphametallacycles Reviewed

    Yoshihiro Matano, Kazuaki Matsumoto, Yoshihide Nakao, Hidemitsu Uno, Shigeyoshi Sakaki, Hiroshi Imahori

    Journal of the American Chemical Society   130 ( 14 )   4588 - 4589   2008

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    DOI： 10.1021/ja710542e

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  • meso-3,5-Bis(trifluoromethyl)phenyl-Substituted Expanded Porphyrins: Synthesis, Characterization, and Optical, Electrochemical, and Photophysical Properties Reviewed

    Soonchul Kang, Hironobu Hayashi, Tomokazu Umeyama, Yoshihiro Matano, Nikolai V. Tkachenko, Helge Lemmetyinen, Hiroshi Imahori

    CHEMISTRY-AN ASIAN JOURNAL   3 ( 12 )   2065 - 2074   2008

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    DOI： 10.1002/asia.200800229

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  • Clusterizatiou, electrophoretic deposition, and photoelectrochemical properties of fullerene-functionalized carbon nanotube composites Reviewed

    Tomokazu Umeyama, Noriyasu Tezuka, Mitsuru Fujita, Shinya Hayashi, Naoki Kadota, Yoshihiro Matano, Hiroshi Imahori

    CHEMISTRY-A EUROPEAN JOURNAL   14 ( 16 )   4875 - 4885   2008

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    DOI： 10.1002/chem.200702053

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  • Naphthyl-Fused pi -Elongated Porphyrins for Dye-Sensitized TiO2 Cells Reviewed

    Hayashi Shinya, Tanaka Masanobu, Hayashi Hironobu, Eu Seunghun, Umeyama Tomokazu, Matano Yoshihiro, Araki Yasuyuki, Imahori Hiroshi

    Journal of Physical Chemistry C   112 ( 39 )   15576 - 15585   2008

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  • Effects of Porphyrin Substituents on Film Structure and Photoelectrochemical Properties of Porphyrin/Fullerene Composite Clusters Electrophoretically Deposited on Nanostructured SnO2 Electrodes Reviewed

    Hiroshi Imahori, Masahiro Ueda, Soonchul Kang, Hironobu Hayashi, Shnya Hayashi, Hironori Kaji, Shu Seki, Akinori Saeki, Seiichi Tagawa, Tomokazu Umeyama, Yoshihiro Matano, Kaname Yoshida, Seiji Isoda, Motoo Shiro, Nikolai V. Tkachenko, Helge Lemmetyinen

    Chemistry -A European Journal-   13 ( 36 )   10182 - 10193   2007.12

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    DOI： 10.1002/chem.200700446

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  • Hydrogen-bonding effects on film structure and photoelectrochemical properties of porphyrin and fullerene composites on nanostructured TiO2 electrodes Reviewed

    Aiko Kira, Masanobu Tanaka, Tomokazu Umeyama, Yoshihiro Matano, Naoki Yoshimoto, Yi Zhang, Shen Ye, Heli Lehtivuori, Nikolai V. Tkachenko, Helge Lemmetyinen, Hiroshi Imahori

    JOURNAL OF PHYSICAL CHEMISTRY C   111 ( 36 )   13618 - 13626   2007.9

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    DOI： 10.1021/jp0726079

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  • Synthesis of 2-aryl-5-styrylphospholes: Promising candidates for the phosphole-based NLO chromophores Reviewed

    Yoshihiro Matano, Tooru Miyajima, Hiroshi Imahori, Yoshifumi Kimura

    JOURNAL OF ORGANIC CHEMISTRY   72 ( 16 )   6200 - 6205   2007.8

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    DOI： 10.1021/jo070822f

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  • Photoinduced energy transfer in composites of poly[(p-phenylene-1,2-vinylene)-co-(p-phenylene-1,1-vinylidene)] and single-walled carbon nanotubes Reviewed

    Tomokazu Umeyama, Naoki Kadota, Noriyasu Tezuka, Yoshihiro Matano, Hiroshi Imahori

    CHEMICAL PHYSICS LETTERS   444 ( 4-6 )   263 - 267   2007.8

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    DOI： 10.1016/j.cplett.2007.07.013

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  • Electrophoretic Deposition of Single-Walled Carbon Nanotubes Covalently Modified with Bulky Porphyrins on Nanostructured SnO2 Electrodes for Photoelectrochemical Devices Reviewed

    Tomokazu Umeyama, Mitsuru Fujita, Noriyasu Tezuka, Naoki Kadota, Yoshihiro Matano, Kaname Yoshida, Seiji Isoda, Hiroshi Imahori

    Journal of Physical Chemistry C   111 ( 30 )   11484 - 11493   2007.7

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    DOI： 10.1021/jp072075w

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  • Retention of Intrinsic Electronic Properties of Soluble Single-Walled Carbon Nanotubes after a Significant Degree of Sidewall Functionalization by the Bingel Reaction Reviewed

    Tomokazu Umeyama, Noriyasu Tezuka, Mitsuru Fujita, Yoshihiro Matano, Norihiro Takeda, Kei Murakoshi, Kaname Yoshida, Seiji Isoda, Hiroshi Imahori

    Journal of Physical Chemistry   111 ( 27 )   9734 - 9741   2007.6

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    DOI： 10.1021/jp071604t

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  • Electron-donating perylene tetracarboxylic acids for dye-sensitized solar cells Reviewed

    Yuki Shibano, Tomokazu Umeyama, Yoshihiro Matano, Hiroshi Imahori

    ORGANIC LETTERS   9 ( 10 )   1971 - 1974   2007.5

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  • Mesityltriphenylbismuthonium tetrafluoroborate as an efficient bismuth(V) oxidant: remarkable steric effects on reaction rates and chemoselectivities in alcohol oxidation Reviewed

    Yoshihiro Matano, Takeshi Suzuki, Torrionori Shinokura, Hiroshi Imahori

    TETRAHEDRON LETTERS   48 ( 16 )   2885 - 2888   2007.4

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    DOI： 10.1016/j.tetlet.2007.02.085

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  • Effects of 5-membered heteroaromatic spacers on structures of porphyrin films and photovoltaic properties of porphyrin-sensitized TiO2 cells Reviewed

    Seunghun Eu, Shinya Hayashi, Tomokazu Umeyama, Akane Oguro, Mitsuo Kawasaki, Naoki Kadota, Yoshihiro Matano, Hiroshi Imahori

    Journal of Physical Chemistry C   111 ( 8 )   3528 - 3537   2007.3

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    DOI： 10.1021/jp067290b

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  • Electron-Donating Perylene-Tetracarboxylic Acids for Dye-Sensitized Solar Cells Reviewed

    Yuki Shibano, Tomokazu Umeyama, Yoshihiro Matano, Hiroshi Imahori

    Organic Letters   9 ( 10 )   1971 - 1974   2007

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    DOI： 10.1021/ol070556s

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  • Synthesis, structures, and properties of meso-phosphorylporphyrins: Self-organization through P-oxo-zinc coordination Reviewed

    Yoshihiro Matano, Kazuaki Matsumoto, Yukiko Terasaka, Hiroki Hotta, Yasuyuki Araki, Osamu Ito, Motoo Shiro, Takahiro Sasamori, Norihiro Tokitoh, Hiroshi Imahori

    CHEMISTRY-A EUROPEAN JOURNAL   13 ( 3 )   891 - 901   2007

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    DOI： 10.1002/chem.200600835

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  • Synthesis and aggregation Behavior of meso-sulfinylporphyrins: Evaluation of s-chirality effects on the self-organization to S-oxo-tethered cofacial porphyrin dimers Reviewed

    Yoshihiro Matano, Tomonori Shinokura, Kazuaki Matsumoto, Hiroshi Imahori, Haruyuki Nakano

    CHEMISTRY-AN ASIAN JOURNAL   2 ( 11 )   1417 - 1429   2007

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    DOI： 10.1002/asia.200700191

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  • Novel unsymmetrically pi-elongated porphyrin for dye-sensitized TiO2 cells

    Masanobu Tanaka, Shinya Hayashi, Seunghun Eu, Tomokazu Umeyama, Yoshihiro Matano, Hiroshi Imahori

    CHEMICAL COMMUNICATIONS   ( 20 )   2069 - 2071   2007

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  • Large Reorganization Energy of Pyrrolidine-Substituted Perylenediimide in Electron Transfer Reviewed

    Shibano, Yuki, Umeyama, Tomokazu, Matano, Yoshihiro, Tkachenko, Nikolai V, Lemmetyinen, Helge, Araki, Yasuyuki, Ito, Osamu, Imahori, Hiroshi

    Journal of Physical Chemistry C   111 ( 16 )   6133 - 6142   2007

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    DOI： 10.1021/jp068893q

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  • Synthesis of a phosphorus-containing hybrid porphyrin Reviewed

    Yoshihiro Matano, Takashi Nakabuchi, Tooru Miyajima, Hiroshi Imahori, Haruyuki Nakano

    ORGANIC LETTERS   8 ( 25 )   5713 - 5716   2006.12

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    DOI： 10.1021/ol622763

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  • Comparison of electrode structures and photovoltaic properties of porphyrin-sensitized solar cells with TiO2 and Nb, Ge, Zr-added TiO2 composite electrodes Reviewed

    Hiroshi Imahori, Shinya Hayashi, Tomokazu Umeyama, Seunghun Eu, Akane Oguro, Soonchul Kang, Yoshihiro Matano, Tetsuya Shishido, Supachai Ngamsinlapasathian, Susumu Yoshikawa

    LANGMUIR   22 ( 26 )   11405 - 11411   2006.12

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    DOI： 10.1021/la061527d

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  • Phosphorus-containing hybrid calixphyrins: Promising mixed-donor ligands for visible and efficient palladium catalysts Reviewed

    Yoshihiro Matano, Tooru Miyajima, Takashi Nakabuchi, Hiroshi Imahori, Noriaki Ochi, Shigeyoshi Sakaki

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   128 ( 36 )   11760 - 11761   2006.9

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    DOI： 10.1021/ja0640039

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  • Synthesis and photophysical properties of electron-rich perylenediimide-fullerene dyad Reviewed

    Yuki Shibano, Tomokazu Umeyama, Yoshihiro Matano, Nikolai V. Tkachenko, Helge Lemmetyinen, Hiroshi Imahori

    ORGANIC LETTERS   8 ( 20 )   4425 - 4428   2006.9

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    DOI： 10.1021/ol061506a

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  • Ordered Supramolecular Assembly of Porphyrin-Fullerene Composites on Nanostructured SnO2 Electrodes Reviewed

    S. Kang, T. Umeyama, M. Ueda, Y. Matano, H. Hotta, K. Yoshida, S. Isoda, M. Shiro, H. Imahori

    Advanced Materials   18 ( 19 )   2549 - 2552   2006.9

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    DOI： 10.1002/adma.200600312

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  • A convenient method for the synthesis of 2,5-difunctionalized phospholes bearing ester groups Reviewed

    Yoshihiro Matano, Tooru Miyajima, Takashi Nakabuchi, Yuichiro Matsutani, Hiroshi Imahori

    JOURNAL OF ORGANIC CHEMISTRY   71 ( 15 )   5792 - 5795   2006.7

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    DOI： 10.1021/jo0605748

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  • Structure and photoelectrochemical properties of phthalocyanine and perylene diimide composite clusters deposited electrophoretically on nanostructured SnO(2) electrodes Reviewed

    Aiko Kira, Tomokazu Umeyama, Yoshihiro Matano, Kaname Yoshida, Seiji Isoda, Marja Isosomppi, Nikolai V. Tkachenko, Helge Lemmetyinen, Hiroshi Imahori

    LANGMUIR   22 ( 12 )   5497 - 5503   2006.6

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    DOI： 10.1021/la0533314

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  • Phosphole-containing hybrid calixpyrroles: New multifunctional macrocyclic ligands for platinum(II) ions Reviewed

    Yoshihiro Matano, Takashi Nakabuchi, Tooru Miyajima, Hiroshi Imahori

    ORGANOMETALLICS   25 ( 13 )   3105 - 3107   2006.6

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    DOI： 10.1021/om060300a

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  • A Photoelectrochemical Device with a Nanostructured SnO2 Electrode Modified with Composite Clusters of Porphyrin-Modified Silica Nanoparticle and Fullerene Reviewed

    Hiroshi Imahori, Keigo Mitamura, Yuki Shibano, Tomokazu Umeyama, Yoshihiro Matano, Kaname Yoshida, Seiji Isoda, Yasuyuki Araki, Osamu Ito

    The Journal of Physical Chemistry B   110 ( 23 )   11399 - 11405   2006.5

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    DOI： 10.1021/jp061524+

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  • Structure and photoelectrochemical properties of nanostructured SnO(2) electrodes deposited electrophoretically with the composite clusters of porphyrin-modified gold nanoparticle with a long spacer and fullerene Reviewed

    H Imahori, A Fujimoto, S Kang, H Hotta, K Yoshida, T Umeyama, Y Matano, S Isoda

    TETRAHEDRON   62 ( 9 )   1955 - 1966   2006.2

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    DOI： 10.1016/j.tet.2005.05.109

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  • Efficient photocurrent generation by SnO2 electrode modified electrophoretically with composite clusters of porphyrin-modified silica microparticle and fullerene Reviewed

    H Imahori, K Mitamura, T Umeyama, K Hosomizu, Y Matano, K Yoshida, S Isoda

    CHEMICAL COMMUNICATIONS   ( 4 )   406 - 408   2006.1

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    DOI： 10.1039/b513707a

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  • Structure and Photoelectrochemical Properties of Phthalocyanine and Perylene Diimide Composite Clusters Deposited Electrophoretically on Nanostructured SnO2 Electrodes Reviewed

    Aiko Kira, Tomokazu Umeyama, Yoshihiro Matano, Kaname Yoshida, Seiji Isoda, Marja Isosomppi, Nikolai V. Tkachneko, Helge Lemmetyinen, Hiroshi Imahori

    Langmuir   22 ( 12 )   5497 - 5503   2006

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    DOI： 10.1021/la0533314

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  • Host-guest interactions in the supramolecular incorporation of fullerenes into tailored holes on porphyrin-modified gold nanoparticles in molecular photovoltaics Reviewed

    H Imahori, A Fujimoto, S Kang, H Hotta, K Yoshida, T Umeyama, Y Matano, S Isoda, M Isosomppi, NV Tkachenko, H Lemmetyinen

    CHEMISTRY-A EUROPEAN JOURNAL   11 ( 24 )   7265 - 7275   2005.12

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    DOI： 10.1002/chem.200500610

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  • Effects of fullerene substituents on structure and photoelectrochemical properties of fullerene nanoclusters electrophoretically deposited on nanostructured SnO2 electrodes Reviewed

    H Hotta, S Kang, T Umeyama, Y Matano, K Yoshida, S Isoda, H Imahori

    JOURNAL OF PHYSICAL CHEMISTRY B   109 ( 12 )   5700 - 5706   2005.3

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    DOI： 10.1021/jp044725r

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  • Molecular Photoelectrochemical Devices: Supramolecular Incorporation of C60 Molecules into Tailored Holes on Porphyrin-Modified Gold Nanoclusters Reviewed

    Hiroshi Imahori, Atsushi Fujimoto, Soonchul Kang, Hiroki Hotta, Kaname Yoshida, Tomokazu Umeyama, Yoshihiro Matano, Seiji Isoda

    Advanced Materials   17 ( 14 )   1727 - 1730   2005

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    DOI： 10.1002/adma.200401770

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  • Hydrogen Bonding Effects on the Surface Structure and Photoelectrochemical Properties of Nanostructured SnO2 Electrodes Modified with Porphyrin and Fullerene Composites Reviewed

    Hiroshi Imahori, Jia-Chen Liu, Hiroki Hotta, Aiko Kira, Tomokazu Umeyama, Yoshihiro Matano, Guifeng Li, Shen Ye, Marja Isosomppi, Nikolai V. Tkachenko, Helge Lemmetyinen

    The Journal of Physical Chemistry B   109 ( 39 )   18465 - 18474   2005

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    DOI： 10.1021/jp0537409

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  • Effects of Fullerene Substituents on Structure and Photoelectrochemical Properties of Fullerene Nanoclusters Electrophoretically Deposited on Nanostructured SnO2 Electrodes Reviewed

    Hiroki Hotta, Soonchul Kang, Tomokazu Umeyama, Yoshihiro Matano, Kaname Yoshida, Seiji Isoda, Hiroshi Imahori

    The Journal of Physical Chemistry B   109 ( 12 )   5700 - 5706   2005

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    DOI： 10.1021/jp044725r

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  • Host-Guest Interactions in the Supramolecular Incorporation of Fullerenes into Tailored Holes on Porphyrin-Modified Gold Nanoparticles in Molecular Photovoltaics Reviewed

    Hiroshi Imahori, Atsushi Fujimoto, Soonchul Kang, Hiroki Hotta, Kaname Yoshida, Tomokazu Umeyama, Yoshihiro Matano, Seiji Isoda, Marja Isosomppi, Nikolai V. Tkachenko, Helge Lemmetyinen

    Chemistry-A European Journal   11 ( 24 )   7265 - 7275   2005

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    DOI： 10.1002/chem.200500610

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  • Remarkable substituent effects on the oxidizing ability of triarylbismuth dichlorides in alcohol oxidation Reviewed

    Y Matano, T Hisanaga, H Yamada, S Kusakabe, H Nomura, H Imahori

    JOURNAL OF ORGANIC CHEMISTRY   69 ( 25 )   8676 - 8680   2004.12

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    DOI： 10.1021/jo0485740

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  • Diverse structures and remarkable oxidizing ability of triarylbismuthane oxides. Comparative study on the structure and reactivity of a series of triarylpnictogen oxides Reviewed

    Y Matano, H Nomura, T Hisanaga, H Nakano, M Shiro, H Imahori

    ORGANOMETALLICS   23 ( 23 )   5471 - 5480   2004.11

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    DOI： 10.1021/om0494115

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  • A new, efficient method for direct alpha-alkenylation of beta-dicarbonyl compounds and phenols using alkenyltriarylbismuthonium salts Reviewed

    Y Matano, H Imahori

    JOURNAL OF ORGANIC CHEMISTRY   69 ( 16 )   5505 - 5508   2004.8

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    DOI： 10.1021/jo0492721

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  • Substituent effects of porphyrin monolayers on the structure and photoelectrochemical properties of self-assembled monolayers of porphyrin on indium-tin oxide electrode Reviewed

    H Imahori, K Hosomizu, Y Mori, T Sato, TK Ahn, SK Kim, D Kim, Y Nishimura, Yamazaki, I, H Ishii, H Hotta, Y Matano

    JOURNAL OF PHYSICAL CHEMISTRY B   108 ( 16 )   5018 - 5025   2004.4

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    DOI： 10.1021/jp037625e

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  • Hydrogen bonding effect on photocurrent generation in porphyrin fullerene photoelectrochemical devices Reviewed

    H Imahori, JC Liu, K Hosomizu, T Sato, Y Mori, H Hotta, Y Matano, Y Araki, O Ito, N Maruyama, S Fujita

    CHEMICAL COMMUNICATIONS   ( 18 )   2066 - 2067   2004

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    DOI： 10.1039/b404690k

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  • Nanostructured artificial photosynthesis

    Hiroshi Imahori, Yukie Mori, Yoshihiro Matano

    Journal of Photochemistry and Photobiology C: Photochemistry Reviews   4 ( 1 )   51 - 83   2003.4

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    DOI： 10.1016/S1389-5567(03)00004-2

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  • Synthesis and structural comparison of triaryl(sulfonylimino)pnictoranes Reviewed

    Yoshihiro Matano, Hazumi Nomura, Hitomi Suzuki

    Inorganic Chemistry   41 ( 7 )   1940 - 1948   2002.4

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    DOI： 10.1021/ic0110575

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  • New syntheses of bismuthonium salts, bismuthonium ylides and bismuthane imides using triarylbismuth(V)-oxo and -hydroxo compounds Reviewed

    Y Matano, H Nomura

    SYNTHESIS-STUTTGART   ( 5 )   631 - 634   2002.4

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    DOI： 10.1055/s-2002-23536

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  • Synthesis and Structural Comparison of Triaryl(sulfonylimino)pnictoranes Reviewed

    Yoshihiro Matano, Hazumi Nomura, Hitomi Suzuki

    Inorganic Chemistry   41 ( 7 )   1940 - 1948   2002

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    DOI： 10.1021/ic0110575

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  • Facile Oxidation of Alcohols to Carbonyl Compounds Using a Tris(2-methylphenyl)bismuth Dichloride–DBU Binary System Reviewed

    Yoshihiro Matano, Hazumi Nomura

    Angewandte Chemie International Edition   41 ( 16 )   3028 - 3031   2002

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    DOI： 10.1002/1521-3773(20020816)41:16<3028::AID-ANIE3028>3.0.CO;2-U

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  • Synthesis, structure, and reactions of (acylimino)triaryl-λ5-bismuthanes: First comparative study of the (acylimino)pnictorane series Reviewed

    Y. Matano, H. Nomura, H. Suzuki, M. Shiro, H. Nakano

    Journal of the American Chemical Society   123 ( 44 )   10954 - 10965   2001.11

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    DOI： 10.1021/ja003623l

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  • Organic Chemistry Created by Bismuth : Syntheses and Applications

    MATANO Yoshihiro

    J. Synth. Org. Chem. Jpn.   59 ( 9 )   4 - 14   2001.9

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    The syntheses and reactions of bismuthonium salts and bismuth ylides are reported. Various types of bismuthonium salts bearing a Bi-C<I><SUB>sp</SUB></I><I><SUP>3</SUP></I>, Bi-C<I><SUB>sp</SUB></I><I><SUP>2</SUP></I>, or Bi-C<I><SUB>sp</SUB></I> bond have been prepared by the Lewis-acid promoted reaction of triphenylbismuth difluoride with organometallic reagents. The bismuthonium salts thus obtained behave as alkyl cation equivalents, alkenyl cation equivalents, and carbene precursors. The bismuth ylides bearing a carbonyl group at the ylidic carbon react with carbonyl compounds to undergo epoxidation, transposition, or ring expansion depending on the structure of the substrates employed. These reaction modes are characteristic of bismuth among the group 15 elements. The stabilized bismuth ylides bearing a highly cross-conjugated ylidic carbon decompose, at an elevated temperature or in the presence of a copper catalyst, to give trisubstituted oxazoles. The observed unique reactivities of the bismuthonium salts and the bismuth ylides are ascribed to the good leaving ability of the triarylbismuthonio group.

    DOI： 10.5059/yukigoseikyokaishi.59.834

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  • A new synthesis of triarylbismuthanes via directed ligand coupling of oxazoline-substituted tetraarylbismuthonium salts: Synthesis of polystyrenes bearing the diarylbismuthino group Reviewed

    Y Matano, SA Begum, H Suzuki

    SYNTHESIS-STUTTGART   ( 7 )   1081 - 1085   2001.6

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    DOI： 10.1055/s-2001-14565

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  • Dimeric Triarylbismuthane Oxide: A Novel Efficient Oxidant for the Conversion of Alcohols to Carbonyl Compounds Reviewed

    Yoshihiro Matano, Hazumi Nomura

    Journal of the American Chemical Society   123 ( 26 )   6443 - 6444   2001

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    DOI： 10.1021/ja010584k

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  • Stabilized bismuthonium ylides bearing a highly cross-conjugated ylidic carbon atom: synthesis, structures, and reactions Reviewed

    Y Matano, H Nomura, H Suzuki

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   611 ( 1-2 )   89 - 99   2000.10

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    DOI： 10.1016/S0022-328X(00)00295-3

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  • Tp* rhenium(V) oxo-halide, -hydride, -alkyl, -phenyl, and -alkoxide complexes: Syntheses and oxidations Reviewed

    Y Matano, TO Northcutt, J Brugman, BK Bennett, S Lovell, JM Mayer

    ORGANOMETALLICS   19 ( 14 )   2781 - 2790   2000.7

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    DOI： 10.1021/om000133t

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  • Synthesis, structure, and reactions of triaryl(methyl)bismuthonium salts Reviewed

    Y Matano

    ORGANOMETALLICS   19 ( 12 )   2258 - 2263   2000.6

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    DOI： 10.1021/om000095d

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  • Synthesis and first x-ray structural analysis of monomeric imino-λ5-stibanes Reviewed

    Yoshihiro Matano, Hazumi Nomura, Hitomi Suzuki

    Inorganic Chemistry   39 ( 7 )   1340 - 1341   2000.4

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    DOI： 10.1021/ic991120e

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  • First synthesis of alkynyltriphenylbismuthonium salts and their dual reaction modes in sulfonylation Reviewed

    Y Matano

    CHEMICAL COMMUNICATIONS   ( 22 )   2233 - 2234   2000

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  • Electrochemical and reactivity comparisons among isoelectronic oxo, imido, and nitrido complexes of rhenium and osmium Reviewed

    BK Bennett, TJ Crevier, DD DuMez, Y Matano, WS McNeil, JM Mayer

    JOURNAL OF ORGANOMETALLIC CHEMISTRY   591 ( 1-2 )   96 - 103   1999.12

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    DOI： 10.1016/S0022-328X(99)00506-9

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  • Synthesis and stereochemical behavior of unsymmetrical tetraarylbismuthonium salts Reviewed

    Y Matano, SA Begum, T Miyamatsu, H Suzuki

    ORGANOMETALLICS   18 ( 26 )   5668 - 5681   1999.12

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  • Synthesis and reactivity of aryl- and alkyl-rhenium(V) imido-triflate compounds: An unusual mechanism for triflate substitution Reviewed

    WS McNeil, DD DuMez, Y Matano, S Lovell, JM Mayer

    ORGANOMETALLICS   18 ( 18 )   3715 - 3727   1999.8

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  • First synthesis, structure, and reactivity of (acylimino)triaryl-lambda(5)-bismuthanes stabilized by ortho-substituted aryl ligands Reviewed

    Y Matano, H Nomura, M Shiro, H Suzuki

    ORGANOMETALLICS   18 ( 14 )   2580 - 2582   1999.7

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  • Reactions of triphenylbismuthonium 2-oxoalkylides with 1,2-dicarbonyl compounds

    MM Rahman, Y Matano, H Suzuki

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 11 )   1533 - 1541   1999.6

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    DOI： 10.1039/A900751B

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  • An alternative ring expansion mode of acenaphthenequinone to hydroxyphenalenone Reviewed

    MM Rahman, Y Matano, H Suzuki

    SYNTHESIS-STUTTGART   1999 ( 3 )   395 - 397   1999.3

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    DOI： 10.1055/s-1999-3407

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  • Fluoride Reactions with Hydrotris(pyrazolyl)borate Rhenium Oxo Complexes: Re–F vs. B–F Bond Formation Reviewed

    Darin D. DuMez, Todd, O. Northcutt, Yoshihiro Matano, James M. Mayer

    Inorganic Chemistry   38 ( 14 )   3309 - 3312   1999

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    DOI： 10.1021/ic981334g

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  • Synthesis and Reactivity of Aryl- and Alkyl-Rhenium(V) Imido-Triflate Compounds: An Unusual Mechanism for Triflate Substitution Reviewed

    W. Stephen McNeil, Darin D. DuMez, Yoshihiro Matano, Scott Lovell, James M. Mayer

    Organometallics   18 ( 18 )   3715 - 3727   1999

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    DOI： 10.1021/om980914i

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  • Synthesis and Reactions of Bismuthonium Salts and Ylides Bearing an α-Ester Group Reviewed

    Yoshihiro Matano, M. Mizanur Rahman, Masanori Yoshimune, Hitomi Suzuki

    The Journal of Organic Chemistry   64 ( 18 )   6924 - 6927   1999

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    DOI： 10.1021/jo990690t

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  • First Synthesis, Structure, and Reactivity of (Acylimino)triaryl-λ5-bismuthanes Stabilized by Ortho-Substituted Aryl Ligands Reviewed

    Yoshihiro Matano, Hazumi Nomura, Motoo Shiro, Hitomi Suzuki

    Organometallics   18 ( 14 )   2580 - 2582   1999

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    DOI： 10.1021/om990252c

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  • A new and efficient method for the preparation of bismuthonium and telluronium salts using aryl- and alkenylboronic acids. First observation of the chirality at bismuth in an asymmetrical bismuthonium salt Reviewed

    Y Matano, SA Begum, T Miyamatsu, H Suzuki

    ORGANOMETALLICS   17 ( 20 )   4332 - 4334   1998.9

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  • Water-soluble non-ionic triarylbismuthanes. First synthesis and properties Reviewed

    Y Matano, Y Aratani, T Miyamatsu, H Kurata, K Miyaji, S Sasako, H Suzuki

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 16 )   2511 - 2517   1998.8

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    DOI： 10.1039/A803946A

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  • Reaction of triphenylbismuthonium 2-oxoalkylides with benzils. A novel one-pot conversion of symmetrical 1,2-diketones into O-aroyl enolates of unsymmetrical 1,3-diketones

    M. Mizanur Rahman, Yoshihiro Matano, Hitomi Suzuki

    Chemical Communications   ( 13 )   1359 - 1360   1998.7

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  • Synthesis and reactions of rhenium(V) oxo-hydride complexes Reviewed

    Yoshihiro Matano, Seth N. Brown, Todd O. Northcutt, James M. Mayer

    Organometallics   17 ( 14 )   2939 - 2941   1998.7

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    DOI： 10.1021/om980184e

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  • A New and Efficient Method for the Preparation of Bismuthonium and Telluronium Salts Using Aryl- and Alkenylboronic Acids. First Observation of the Chirality at Bismuth in an Asymmetrical Bismuthonium Salt Reviewed

    Yoshihiro Matano, Shameem A. Begum, Takashi Miyamatsu, Hitomi Suzuki

    Organometallics   17 ( 20 )   4332 - 4334   1998

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    DOI： 10.1021/om9804531

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  • Synthesis and Reaction of Unsymmetrical Tetraarylbismuthonium Salts. First Isolation of Bismuthonium Salts Bearing All Different Aryl Groups Reviewed

    Yoshihiro Matano, Takashi Miyamatsu, Hitomi Suzuki

    Chemistry Letters   27 ( 2 )   127 - 128   1998

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    DOI： 10.1246/cl.1998.127

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  • Reaction of Triphenylbismuthonium 2-Oxoalkylides with Benzils. A Novel One-pot Conversion of Symmetrical α-Diketones into O-Aroyl Enolates of Unsymmetrical β-Diketones Reviewed

    M. Mizanur Rahman, Yoshihiro Matano, Hitomi Suzuki

    Chemical Communications   ( 13 )   1359 - 1360   1998

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    DOI： 10.1039/a801879k

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  • Synthesis and Properties of a Series of Phenylene-Bridged Bin-Bismuthanes Reviewed

    Yoshihiro Matano, Haruto Kurata, Toshihiro Murafuji, Nagao Azuma, Hitomi Suzuki

    Organometallics   17 ( 18 )   4049 - 4059   1998

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    DOI： 10.1021/om980411c

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  • Sodium diarylbismuthide as a reagent for the bismuthanation of reactive arenes. Application to the synthesis of mixed triarylbismuthanes bearing a substituent group incompatible with Grignard and organolithium reagents Reviewed

    Mizanur Rahman, Yoshihiro Matano, Hitomi Suzuki

    Organometallics   16 ( 15 )   3565 - 3568   1997.7

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    DOI： 10.1021/om9701377

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  • First Synthesis and Properties of Dendritic Bin-Bismuthanes Reviewed

    Hitomi Suzuki, Haruto Kurata, Yoshihiro Matano

    Chemical Communications   ( 23 )   2295 - 2296   1997

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    DOI： 10.1039/a706338e

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  • A new general method for the preparation of unsymmetrical telluronium salts Reviewed

    Yoshihiro Matano, Hitomi Suzuki, Nagao Azuma

    Organometallics   15 ( 17 )   3760 - 3765   1996.8

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    DOI： 10.1021/om960320k

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  • First synthesis, X-ray structure analysis and reactions of alkenyltriphenylbismuthonium salts Reviewed

    Y Matano, M Yoshimune, N Azuma, H Suzuki

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 16 )   1971 - 1977   1996.8

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    DOI： 10.1039/P19960001971

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  • A new convenient synthesis of triarylbismuthanes bearing three different aryl groups by the grignard arylation of unsymmetrical diarylbismuth triflate-hexamethylphosphoric triamide (HMPA) complexes Reviewed

    Yoshihiro Matano, Takashi Miyamatsu, Hitomi Suzuki

    Organometallics   15 ( 7 )   1951 - 1953   1996.4

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    DOI： 10.1021/om9509709

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  • Reaction of a moderately stabilized bismuthonium ylide with 1,2-dicarbonyl compounds. A novel ring enlargement of ortho-quinones to 3-hydroxytropones Reviewed

    Yoshihiro Matano, Hitomi Suzuki

    Chemical Communications   ( 24 )   2697 - 2698   1996

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    DOI： 10.1039/cc9960002697

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  • A new aspect of organobismuth chemistry: Synthesis, properties, and reactions of bismuthonium compounds Reviewed

    Yoshihiro Matano, Hitomi Suzuki

    Bulletin of the Chemical Society of Japan   69 ( 10 )   2673 - 2681   1996

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    DOI： 10.1246/bcsj.69.2673

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  • ELECTROPHILIC ALLYLATION OF ARENES WITH IN-SITU GENERATED ALLYLTRIARYLBISMUTHONIUM COMPOUND - THE BISMUTH-MEDIATED POLARITY INVERSION OF ALLYLSILANES Reviewed

    Y MATANO, M YOSHIMUNE, H SUZUKI

    TETRAHEDRON LETTERS   36 ( 41 )   7475 - 7478   1995.10

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    DOI： 10.1016/0040-4039(95)01600-7

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  • SYNTHESIS, X-RAY STRUCTURE, THERMAL-STABILITY AND REACTIONS OF TRIARYL(3-OXOALKYL)BISMUTHONIUM SALTS Reviewed

    Y MATANO, N AZUMA, H SUZUKI

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 20 )   2543 - 2549   1995.10

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    DOI： 10.1039/P19950002543

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  • 3-Substituted 2-Acyl-1-sulfonylaziridines from the Reaction of Triphenylbismuthonium 2-Oxoalkylides and N-Sulfonylaldimines. Reversal of the cis/trans-Isomer Ratios Depending on Base and Additive Reviewed

    Yoshihiro Matano, Masanori Yoshimune, Hitomi Suzuki

    Journal of Organic Chemistry   60 ( 14 )   4663 - 4665   1995.7

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    DOI： 10.1021/jo00119a056

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  • TRIPHENYLBISMUTHONIUM 2-OXOALKYLIDE, A MODERATELY STABILIZED BISMUTHONIUM YLIDE - GENERATION AND REACTIONS WITH SOME ELECTROPHILES Reviewed

    Y MATANO

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 19 )   2703 - 2709   1994.10

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    DOI： 10.1039/P19940002703

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  • ULTRASONIC REACTION OF TRIARYLBISMUTHINES AND TRIARYLSTIBINES WITH IODOSYLBENZENE - MILD OXIDIZING ABILITY OF THE ORGANOBISMUTH OXIDE FUNCTION FOR ORGANIC SUBSTRATES Reviewed

    H SUZUKI, T IKEGAMI, Y MATANO

    TETRAHEDRON LETTERS   35 ( 44 )   8197 - 8200   1994.10

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    DOI： 10.1016/0040-4039(94)88281-9

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  • SYNTHESIS, X-RAY STRUCTURE AND REACTIONS OF (2-OXOALKYL)TRIARYLBISMUTHONIUM SALTS Reviewed

    Y MATANO, N AZUMA, H SUZUKI

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 13 )   1739 - 1747   1994.7

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    DOI： 10.1039/P19940001739

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  • CHIRAL CHLOROBISMUTHINES STABILIZED BY THE INTRAMOLECULAR COORDINATION OF AN N,N-DIMETHYLAMINO GROUP - X-RAY STRUCTURE-ANALYSIS, ASYMMETRIC INDUCTION AT THE BISMUTH CENTER, AND DYNAMIC BEHAVIOR IN SOLUTION Reviewed

    H SUZUKI, T MURAFUJI, Y MATANO, N AZUMA

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 23 )   2969 - 2973   1993.12

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    Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1039/P19930002969

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  • IMPROVED SCHMIDT SYNTHESIS OF 1,5-DISUBSTITUTED 1H-TETRAZOLES FROM KETONES Reviewed

    H SUZUKI, YS HWANG, C NAKAYA, Y MATANO

    SYNTHESIS-STUTTGART   1993 ( 12 )   1218 - 1220   1993.12

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    Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1055/s-1993-26027

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  • A NOVEL SYNTHESIS OF ALKYLBISMUTHONIUM SALTS AND THEIR REACTION WITH SOME NUCLEOPHILES - FIRST X-RAY STRUCTURAL-ANALYSIS OF A STABILIZED ALKYLBISMUTHONIUM TETRAFLUOROBORATE Reviewed

    Y MATANO, N AZUMA, H SUZUKI

    TETRAHEDRON LETTERS   34 ( 52 )   8457 - 8460   1993.12

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    Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1016/S0040-4039(00)61358-8

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  • UNEXPECTED FORMATION OF TRIARYLBISMUTH DIFORMATES IN THE OXIDATION OF TRIARYLBISMUTHINES WITH OZONE AT LOW-TEMPERATURES Reviewed

    H SUZUKI, T IKEGAMI, Y MATANO, N AZUMA

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1   ( 20 )   2411 - 2415   1993.10

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    Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1039/P19930002411

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  • PHOTOCHEMICAL AZIDO LIGAND TRANSFER-REACTION OF A TRIARYLBISMUTH DIAZIDE WITH ALKYNES Reviewed

    H SUZUKI, C NAKAYA, Y MATANO

    TETRAHEDRON LETTERS   34 ( 6 )   1055 - 1056   1993.2

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    Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1016/S0040-4039(00)77490-9

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  • Synthesis and Reactions of Some Crowded Triorganobismuthines Reviewed

    Yoshihiro Matano, Masamichi Kinoshita, Hitomi Suzuki

    Bulletin of the Chemical Society of Japan   65 ( 12 )   3504 - 3506   1992

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    Authorship：Lead author   Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

    Bismuth trichloride reacts smoothly with mesityl- and 2,4,6-triisopropylphenylmagnesium bromides in boiling tetrahydrofuran to form the corresponding triarylbismuthines in good yields, while a similar reaction with 2,4,6-triisopropylphenylmagnesium bromide halts at diarylation stage, giving chlorobis(2,4,6-triisopropylphenyl)bismuthine as the sole product. Several crowded alkyl-, alkenyl-, and alkyn-yldiarylbismuthines have been prepared from the above diarychlorobismuthine through the reaction with an appropriate organolithium reagent.

    DOI： 10.1246/bcsj.65.3504

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  • N-Tosyltriarylbismuthimines. Synthesis and Reactions with Some Electrophiles Reviewed

    Hitomi Suzuki, Chie Nakaya, Yoshihiro Matano, Takuji Ogawa

    Chemistry Letters   20 ( 1 )   105 - 108   1991

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

    DOI： 10.1246/cl.1991.105

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  • Product‐determining factors in the grignard reactions of benzophenones. The role of the structure of alkyl groups in grignard reagents Reviewed

    Kazuhiro Maruyama, Yoshihiro Matano, Toshimasa Katagiri

    Journal of Physical Organic Chemistry   4 ( 8 )   501 - 515   1991

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

    DOI： 10.1002/poc.610040806

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  • Photochemically induced single electron transfer reactions of benzils with allylstannane. Direct observation of reactive intermediates by ESR method Reviewed

    Kazuhiro Maruyama, Yoshihiro Matano

    Bulletin of the Chemical Society of Japan   63 ( 8 )   2218 - 2223   1990.8

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

    DOI： 10.1246/bcsj.63.2218

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  • Non-catalyzed Thermal Reactions of Acylquinones with Allylstannanes Reviewed

    Kazuhiro Maruyama, Yoshihiro Matano

    Bulletin of the Chemical Society of Japan   62 ( 12 )   3877 - 3885   1989

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

    Thermal reactions of acylquinones with allylstannanes in benzene afforded several kinds of product after column chromatography on silica gel; acyl allyl quinones, acyl allyl epoxy quinones, cyclopentanoid compounds including stannyl moiety, allyl hydroxy quinones, acyl hydroquinones, and acyl allyl hydroquinones. The main product comprises cyclopentanoid compounds, which are novel [2+3] cyclo adducts with 1,2-migration of trialkylstannyl moiety. Spectroscopic examinations (<SUP>1</SUP>H NMR and Vis-UV) enabled us to confirm the reaction pathways that four types of precursors were initially generated via polarized tight pair and inverted to isolated products during purification by column chromatography. Similar reactions in acetonitrile showed a remarkable difference in the reactivity, that is, acyl allyl quinones and the corresponding hydroquinones are obtained, but the [2+3] cyclo adducts are not produced at all. From <SUP>1</SUP>H NMR examination, it was confirmed that three types of precursor are generated via solvent separated ion pairs at the initial stage. The rather strong reactivity of acylquinones towards allylstannanes will be due to electron withdrawing ability of acyl group.

    DOI： 10.1246/bcsj.62.3877

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  • Application of Electron Spin Resonance Spectroscopy to Reactions of p-Quinones and 9,10-Phenanthraquinone with Allylstannanes Reviewed

    Kazuhiro Maruyama, Yoshihiro Matano

    NIPPON KAGAKU KAISHI   1989 ( 8 )   1351 - 1357   1989

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    Language：English   Publishing type：Research paper (scientific journal)  

    DOI： 10.1246/nikkashi.1989.1351

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Books

  • Main Group Strategies towards Functional Organic Materials

    Yoshihiro Matano（ Role： Sole author ,  Phosphorus-based Porphyrins）

    Wiley  2018.3  （ ISBN:9781119235972 ）

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    Total pages：560   Responsible for pages：265–294   Language：English Book type：Scholarly book

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  • Organic Redox Systems: Synthesis, Properties, and Applications

    Yoshihiro Matano（ Role： Sole author ,  Phospholes and Related Compounds: Syntheses, Redox Properties, and Applications to Organic Electronic Devices）

    Wiley  2015.12  （ ISBN:9781118858745 ）

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    Total pages：616   Responsible for pages：477–502   Language：English Book type：Scholarly book

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  • Topics in Current Chemistry: Bismuth-Mediated Organic Reactions

    Yoshihiro Matano（ Role： Sole author ,  Pentavalent Organobismuth Reagents in Organic Synthesis: Alkylation, Alcohol Oxidation, and Cationic Photopolymerization）

    Springer  2012.1  （ ISBN:9783642272387 ）

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    Total pages：278   Responsible for pages：19–44   Language：English Book type：Scholarly book

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  • Comprehensive Organometallic Chemistry III

    Yoshihiro Matano（ Role： Sole author ,  Antimony and Bismuth）

    Elsevier  2006.12  （ ISBN:9780080445991 ）

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    Total pages：786   Responsible for pages：425–456   Language：English Book type：Scholarly book

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  • Main Group Metals in Organic Synthesis

    Yoshihiro Matano（ Role： Sole author ,  Antimony and Bismuth in Organic Synthesis）

    Wiley-VCH  2004.4  （ ISBN:9783527305087 ）

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    Total pages：905   Responsible for pages：753–811   Language：English Book type：Scholarly book

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  • Organobismuth Chemistry

    Yoshihiro Matano, Tohru Ikegami（ Role： Joint author）

    Elsevier  2001.2 

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    Total pages：636   Responsible for pages：21–245   Language：English Book type：Scholarly book

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  • Organobismuth Chemistry

    Yoshihiro Matano, Tohru Ikegami（ Role： Joint author）

    Elsevier  2001.2 

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    Total pages：636   Responsible for pages：247–327   Language：English Book type：Scholarly book

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  • 芳香環C–H結合直接アミノ化の最前線-異なるアプローチによる¬C–N結合の形成

    俣野善博（ Role： Sole author ,  pp. 70-71）

    化学同人  2018.9 

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  • Chemical Science of π-Electron Systems

    Yoshihiro Matano（ Role： Sole author ,  Heteroatom-Modified Porphyrinoids）

    Springer  2015.11  （ ISBN:9784431553571 ）

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    Total pages：777   Responsible for pages：223–241   Language：English Book type：Scholarly book

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  • 高次π空間の創発と機能開発

    俣野 善博（ Role： Sole author ,  ヘテロ元素を含む新奇ポルフィリンπ空間の創発と機能化）

    シーエムシー  2013.3  （ ISBN:9784781307589 ）

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    Total pages：245   Responsible for pages：123–127   Language：Japanese Book type：Scholarly book

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  • 有機金属化学の最前線（現代化学増刊44）

    俣野 善博（ Role： Sole author ,  14〜16族高周期典型元素化合物の機能）

    東京化学同人  2011.3  （ ISBN:9784807913442 ）

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    Total pages：238   Responsible for pages：102–114   Language：Japanese Book type：Scholarly book

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  • 実験化学講座第5版

    今堀 博, 俣野 善博（ Role： Joint author ,  人工光合成）

    丸善  2005.7  （ ISBN:9784621073278 ）

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    Total pages：409   Responsible for pages：114–131   Language：Japanese Book type：Scholarly book

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  • 実験化学講座第5版

    俣野 善博（ Role： Sole author ,  銀化合物による酸化）

    丸善  2004.7  （ ISBN:9784621073162 ）

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    Total pages：462   Responsible for pages：120–127   Language：Japanese Book type：Scholarly book

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  • 実験化学講座第5版

    俣野 善博（ Role： Sole author ,  ビスマス化合物による酸化）

    丸善  2004.7  （ ISBN:9784621073162 ）

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    Total pages：462   Responsible for pages：173–176   Language：Japanese Book type：Scholarly book

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  • 実験化学講座第5版

    俣野 善博（ Role： Sole author ,  タリウム化合物による酸化）

    丸善  2004.7  （ ISBN:9784621073162 ）

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    Total pages：462   Responsible for pages：127–135   Language：Japanese Book type：Scholarly book

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  • 実験化学講座第5版

    俣野 善博（ Role： Sole author ,  水銀化合物による酸化）

    丸善  2004.7  （ ISBN:9784621073162 ）

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    Total pages：462   Responsible for pages：113–120   Language：Japanese Book type：Scholarly book

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  • 実験化学講座第5版

    俣野 善博（ Role： Sole author ,  鉛化合物による酸化）

    丸善  2004.7  （ ISBN:9784621073162 ）

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    Total pages：462   Responsible for pages：103–113   Language：Japanese Book type：Scholarly book

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  • 実験化学講座第5版

    俣野 善博（ Role： Sole author ,  ケトン：アシル化、カルボニル化による合成）

    丸善  2003.11  （ ISBN:4621073141 ）

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    Responsible for pages：244–294   Language：Japanese Book type：Scholarly book

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  • 有機金属反応剤ハンドブック

    俣野 善博（ Role： Sole author ,  ビスマス）

    化学同人  2003.6  （ ISBN:9784759809367 ）

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    Total pages：272   Responsible for pages：246–250   Language：Japanese Book type：Scholarly book

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  • 季刊化学総説No. 34「有機超原子価化合物」

    俣野善博, 鈴木仁美（ Role： Joint author）

    学会出版センター  1998.4  （ ISBN:9784762218804 ）

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    Total pages：272   Responsible for pages：149–165   Language：Japanese Book type：Scholarly book

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  • Chemistry of Arsenic, Antimony and Bismuth

    Hitomi Suzuki, Yoshihiro Matano（ Role： Joint author）

    Blackie Academic and Professional  1998 

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    Responsible for pages：283–343   Language：English Book type：Scholarly book

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MISC

  • Bismuth in organic transformations

    H Suzuki, T Ikegami, Y Matano

    SYNTHESIS-STUTTGART   ( 3 )   249 - 267   1997.3

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    Language：English   Publishing type：Book review, literature introduction, etc.  

    DOI： 10.1055/s-1997-1194

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  • ジアザポルフィリン二量体の磁気特性

    丸山裕久, 大桃理志, 川俣昌弘, 古川貢, 俣野善博

    電子スピンサイエンス学会年会講演要旨集   55th   2016

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  • Synthesis and photochemistry of diazaporphyrin derivatives

    46 ( 1 )   29 - 36   2015.4

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  • Synthesis and functionalization of π-conjugated phosphole oligomers and polymers by utilizing characteristic properties of acetylene units

    1 - 5   2011

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  • Synthesis, Structure and Reactivity of Monophosphaporphyrin

    Nakashima Makoto, Nakabuchi Takashi, Matano Yoshihiro, Umeyama Tomokazu, Imahori Hiroshi

    Abstracts of Symposium on Physical Organic Chemistry   37 ( 0 )   61 - 61   2007

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    Language：Japanese   Publisher：The Society of Physical Organic Chemistry, Japan  

    The first 21-phosphaporphyrin (1) and its pi-expanded analog (2) were prepared via [3+1] type acid-promoted condensation of phosphatripyrrane with a pyrrole derivative. When [Rh(CO)&lt;SUB&gt;2&lt;/SUB&gt;Cl]&lt;SUB&gt;2&lt;/SUB&gt; was added after the DDQ oxidation, the rhodium(III)-porphyrin (3) was isolated. &lt;SUP&gt;1&lt;/SUP&gt;H NMR spectra of the 18pi-monophosphaporphyrins 1 and 3 suggested that the phosphaporphyrins possess high aromaticity in terms of magnetic criterion. On the other hand, the 22pi-phosphaporphyrin 2 showed a smaller ring current effect in the &lt;SUP&gt;1&lt;/SUP&gt;H NMR spectrum. In the UV-Vis absorption spectra, the Soret- and Q-type bands of 1 were red-shifted as compared to those of TPP. The observed electrochemical redox potentials of 1 and 2 clearly indicate that the HOMO-LUMO energy gaps are considerably smaller than that of TPP. In the crystal structures of 1, 2, and 3, the porphyrin rings of 1 and 2 are slightly ruffled, whereas that of 3 is significantly distorted.

    DOI： 10.11494/kisoyuki.37.0.61.0

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  • Synthesis and Properties of Phosphaporphyrin

    Nakabuchi Takashi, Nakashima Makoto, Miyajima Tooru, Matano Yoshihiro, Umeyama Tomokazu, Imahori Hiroshi

    Abstracts of Symposium on Physical Organic Chemistry   18 ( 0 )   17 - 17   2006

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    Language：Japanese   Publisher：The Society of Physical Organic Chemistry, Japan  

    Core-modified porphyrins are one of the porphyrin analogues, in which at least one core nitrogen atom is replaced by another atom. Although the chemistry of core-modified porphyrins has attracted much attention, phosphorous-containing porphyrins, namely &quot;phosphaporphyrins&quot;, have not been prepared. Here we report the first synthesis of phosphaporphyrin and its aromaticity as well as optical and electrochemical properties. A phosphaporphyrin was synthesized via acid-promoted condensation of phosphatripyrrane with 2,5-bis[hydroxy(phenyl)methyl]thiophene. The NMR and UV-vis absorption spectra, and CV has revealed that the phosphaporphyrin possesses a considerable aromaticity and a relatively narrow HOMO-LUMO energy gap.

    DOI： 10.11494/kisoyuki.18.0.17.0

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  • 有機太陽電池の分子設計 (環境技術特集 有機太陽電池の変換効率の高度化と固体化技術) -- (色素増感太陽電池の固体化技術)

    今堀 博, 俣野 善博, 森 幸恵

    マテリアルステージ   2 ( 9 )   43 - 48   2002.12

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Presentations

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Research Projects

  • Breakdown of the Quantum Spin Statistical Limit in Triplet Fusion

    Grant number：23K17901

    2023.6 - 2026.3

    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

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    Grant amount：\6370000 （ Direct Cost: \4900000 、 Indirect Cost：\1470000 ）

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  • 含窒素ポルフィリンの基礎学理の構築および機能性色素としての展開

    Grant number：22H02061

    2022.4 - 2026.3

    System name：科学研究費助成事業

    Research category：基盤研究(B)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\17160000 （ Direct Cost: \13200000 、 Indirect Cost：\3960000 ）

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  • 含窒素ポルフィリンの基礎学理の構築および機能性色素としての展開

    Grant number：23K23329

    2022.4 - 2026.3

    System name：科学研究費助成事業

    Research category：基盤研究(B)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\17160000 （ Direct Cost: \13200000 、 Indirect Cost：\3960000 ）

    2023年度は、meso位の窒素上に置換基をもつ5,10,15,20-テトラアリール-5,15-ジアザポルフィリン（TADAP）および5,10,20-トリアリール-5,15-ジアザポルフィリン（TriADAP）を題材として、その合成および構造―物性相関の解明に取り組んだ。TADAPについては、前年度に亜鉛錯体の脱メタル化によるフリーベース体の一般的合成法を確立したので、今年度は主にフリーベース体の錯形成と軸配位子の交換を利用してケイ素錯体とスズ錯体を合成した。いずれの錯体においても、DAP環の20π/19π/18π酸化還元反応は可逆的に進行し、20π電子系を持つ反芳香族性TADAPや19π電子系を持つTADAPラジカルが大気下で安定に存在することを確認した。また、得られた金属錯体のX線結晶構造解析、紫外/可視/近赤外吸収スペクトル測定、NMR測定、密度汎関数理論計算を行い、DAP環が高い平面性をもつことや、軸配位子が吸収特性や環電流効果に及ぼす影響は比較的小さいことなどを明らかにした。TriADAPについては、窒素上に置換基を持たないDAPのN-アリール化による合成法を確立し、ニッケル錯体と白金錯体の合成に成功したほか、19π電子系を持つDAP二量体における不対電子の非局在化の様式が、meso-窒素上の置換基の数に依存して大きく変化することを明らかにした。さらに、1個のピロール環の代わりにベンゼン環を構成要素として含む核置換5,10-ジアザポルフィリンの錯形成を行い、白金錯体や銅錯体の合成に成功した。得られた成果の一部については、8件の学会発表を行ったほか、2報の論文として報告した。

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  • アザポルフィリンラジカルをプラットフォームとする高密度共役系の構築

    Grant number：21H05476

    2021.9 - 2023.3

    System name：科学研究費助成事業

    Research category：学術変革領域研究(A)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\7800000 （ Direct Cost: \6000000 、 Indirect Cost：\1800000 ）

    本研究の目的は、meso窒素上に置換基を持つ5-モノアザポルフィリン（RMAP）と5,15-ジアザポルフィリン（RDAP）のラジカルを合成する簡便な方法を確立し、得られた誘導体の構造―物性相関を明らかにした上で、高密度共役の実現へ向け、これらのラジカルをプラットフォームとして利用することである。2021年度は、主に以下の二つの課題に取り組んだ。
    課題１．RMAP金属錯体の合成：アザテトラピリンの鋳型環化法を用いて、カチオン性RMAP亜鉛錯体を合成することに成功した。得られた錯体について、NMR、紫外/可視/近赤外吸収スペクトル、CV測定を行い、芳香族性、光物性、電気化学特性を調べ、対応するカチオン性RDAP亜鉛錯体と比較した結果、分子の対称性と電荷の影響がアザポルフィリン環の環電流効果や酸化還元特性に顕著に現れることが明らかとなった。また、鋳型環化を経由しないRMAPの新規合成法を開発することに成功した。
    課題２．新規RDAPラジカルの合成：共有結合や配位結合を介してRDAPラジカルを連結することを目的として、RDAPを含むフェニレン架橋型ポルフィリン三量体の合成を行った。具体的には、ポルフィリンを置換基とするジブロモジピリンの鋳型環化反応を利用して目的物を合成し、NMR、ESR、紫外/可視/近赤外吸収スペクトル、CV測定を用いて得られた三量体の物性を調べ、参照系となる単量体の物性と比較した。その結果、両側のポルフィリン環が中心に位置するRDAPラジカルの磁気特性や光物性に与える影響は極めて小さいことが明らかとなった。
    得られた研究成果について、国際会議での依頼講演を含む５つの学会発表を行ったほか、２報の論文として報告した。

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  • Development and functionalization of NIR-light-responsive diazaporphyrin sensitizers

    Grant number：18H01961

    2018.4 - 2022.3

    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

    Matano Yoshihiro

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    Grant amount：\17290000 （ Direct Cost: \13300000 、 Indirect Cost：\3990000 ）

    In this research project, we have investigated several subjects concerning the chemistry of azaporphyrins where meso carbons are partially replaced with nitrogen atoms. First, we established several convenient methods for the synthesis of several types of azaporphyrin derivatives. Second, we revealed the aromaticity, optical and electrochemical properties, and singlet-oxygen-generating ability of a series of novel azaporphyrins obtained. Finally, we constructed near-infrared-light-responsive azaporphyrin-based sensitizers and shed light on their potential as functional dyes used for medical application such as photodynamic therapy.

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  • Development of heteroarene-fused and pi-expanded diazaporphyrins as n-type semiconductors

    Grant number：15K13762

    2015.4 - 2018.3

    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

    MATANO YOSHIHIRO, IMAHORI Hiroshi, NAKANO Haruyuki

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    Grant amount：\4030000 （ Direct Cost: \3100000 、 Indirect Cost：\930000 ）

    In order to develop the chemistry of diazaporphyrins that have high electron-accepting and light-harvesting properties, we have (i) synthesized new diazaporphyrin derivatives bearing various substituents at the periphery, (ii) disclosed their structure-property relationships, and (iii) applied some derivatives in organic solar cells. As a result, we have found that the amino-substituted donor-acceptor-type diazaporphyrins show the intramolecular charge-transfer character derived from the intrinsically electron-withdrawing nature of the diazaporphyrin. Furthermore, we have succeeded in fabricating dye-sensitized solar cells using some diazaporphyrin-based dyes and revealed their potential as the photofunctional materials.

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  • 近赤外光感応性をもつジアザポルフィリンーポルフィリン連結分子の創製と利用

    Grant number：15H00931

    2015.4 - 2017.3

    System name：科学研究費助成事業

    Research category：新学術領域研究(研究領域提案型)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\6240000 （ Direct Cost: \4800000 、 Indirect Cost：\1440000 ）

    本研究の目的は、ジアザポルフィリン-ポルフィリン連結分子およびその関連化合物の合成法を確立し、異なるπ系の連結が生み出す物性面での相乗効果を明らかにした上で、近赤外光感応性を持つ医療用増感剤として利用するための道標をつけることである。本年度は、主に次の三つの課題に取り組んだ。(i)非対称置換されたπ共役ジアザポルフィリン誘導体の合成、(ii) (i)で得られたジアザポルフィリン誘導体の光物性、電気化学特性、および一重項酸素発生効率の解明、(iii) ジアザポルフィリン誘導体を用いた色素増感太陽電池の作製とデバイス特性の評価。まず、ジアザポルフィリン環β位の位置選択的な臭素化により得られるブロモ体を共通の出発原料として、鈴木―宮浦カップリング反応により、電子供与性置換基とカルボキシフェニル基で非対称に置換されたDonor-Acceptor型ジアザポルフィリンを系統的に合成した。また、得られた化合物のNMRスペクトル・吸収スペクトル・酸化還元電位・蛍光量子収率の測定およびDFT計算により、π系全体の構造、吸収特性、発光特性、および電気化学特性を調べた。その結果、ジアザポルフィリン環へのアミノ基の導入により大きな電荷移動特性が発現し、吸収帯の大幅な長波長化を達成できることが明らかとなった。次いで、高い光捕集能をもつジアザポルフィリン誘導体を増感剤とする色素増感太陽電池を作製し、デバイス特性を評価した。その結果、複数の電子供与性置換基の導入により光電変換効率が大幅に向上することが明らかとなった。さらに、医療用色素への展開を念頭に置き、一部の化合物について一重項酸素発生効率を評価し、水溶性を持つジアザポルフィリン誘導体を新たに合成した。

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  • 高い近赤外光感応性をもつ水溶性ジアザポルフィリン増感剤の開発

    Grant number：25109524

    2013.4 - 2016.3

    System name：科学研究費助成事業

    Research category：新学術領域研究(研究領域提案型)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\7280000 （ Direct Cost: \5600000 、 Indirect Cost：\1680000 ）

    本年度は、近赤外光に対して高い感応性を持つジアザポルフィリン増感剤の開発を見据えて、期間内に主に次の三つの課題に取り組んだ。(i) 外周部にπ共役可能な置換基を持つジアザポルフィリンの合成、(ii) 水溶性ジアザポルフィリンの合成、(iii)課題(i)で合成した色素の光物性および電気化学特性に対する外周部置換基効果の解明。まず、β-ブロモジアザポルフィリンニッケル錯体および亜鉛錯体のクロスカップリング反応を利用して、ジアザポルフィリンの外周部にπ共役が可能な置換基を導入した。次いで、得られた化合物のX線結晶構造解析、NMRスペクトル・吸収スペクトル・発光スペクトル・酸化還元電位の測定により、π系の構造、吸収・発光特性、および、電気化学特性を調べた。その結果、分子内電荷移動特性の発現により吸収・発光帯の大幅な長波長化が達成できることや、π共役の拡張により電子スピンの非局在化が効率よく起こることが明らかとなった。一部の誘導体については、電荷移動型の吸収帯が800nmを超える近赤外領域に達することを見出した。さらに、外周部の置換基としてカルボキシフェニル基を持つジアザポルフィリン誘導体を合成し、その水溶性を調べた。その結果、弱塩基性で水溶性を示すことを確認した。得られた知見は、可視光のみならず近赤外光に対して高い感応性を持つ医療用増感剤や太陽電池用増感剤を開発するうえで、ジアザポルフィリンが有力な母核となることを示している。

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  • Construction of Phosphole-Containing Hybrid pi-Conjugated Molecules and Their Application to Organic Devices

    Grant number：25288020

    2013.4 - 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

    Matano Yoshihiro, NAKANO Haruyuki, KIMURA Yoshifumi

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    Grant amount：\18850000 （ Direct Cost: \14500000 、 Indirect Cost：\4350000 ）

    New efficient methods for the synthesis of phosphole/thiophene-containing π-conjugated molecules were established, and their structure-property relationships were unveiled using various spectroscopic techniques and X-ray diffraction analyses. Some derivatives with high visible-light absorbing ability were used for organic solar cells. In addition, a new class of highly fluorescent derivatives was constructed. All the results show that the newly constructed phosphole/thiophene-containing hybrid derivatives would be promising candidates as organic materials.

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  • Creation of core-modified azaporphyrins and their application to organic solar cells

    Grant number：25620149

    2013.4 - 2015.3

    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

    MATANO Yoshihiro, NAKANO Haruyuki

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    Grant amount：\4160000 （ Direct Cost: \3200000 、 Indirect Cost：\960000 ）

    In this research project, we aimed to create new core-modified azaporphyrins that absorb visible-near infrared (NIR) light for application to organic solar cells. First, we established a general method for introducing π-conjugative substituents onto the peripheral carbons of diazaporphyrins. We investigated the optical and electrochemical properties of the newly prepared diazaporphyrins. The introduction of an electron-donating substituent to the peripheral carbon causes a large enhancement of the visible-light harvesting ability of the diazaporphyrin π-system. Second, we synthesized novel dipyrrin-boron and azadipyrrin-boron complexes bearing π-conjugative substituents on the pyrrole rings. We have revealed that the aza-substitution of π-extended dipyrrin-boron complexes is an efficient method for enhancing the NIR light-harvesting ability.

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  • 典型元素を含む新奇ポルフィリンπ空間の機能化と集積化

    Grant number：23108708

    2011.4 - 2013.3

    System name：科学研究費助成事業

    Research category：新学術領域研究(研究領域提案型)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\4550000 （ Direct Cost: \3500000 、 Indirect Cost：\1050000 ）

    本年度では『典型元素の特性が最大限に発揮されるようなπ空間を創発し、その機能を利用する』ことを目的として、期間内に主に次の課題に取り組んだ。(i)メソ位に窒素を含むジアザポルフィリンの合成と、それらの構造・物性・配位挙動の解明。(ii)π系が高度に拡張されたジアザポルフィリン二量体の合成、(iii)ジアザポルフィリンの特性を活かした有機太陽電池の作製と性能評価。まず、アジ化ナトリウムとジブロモジピリンとの反応を利用して、β無置換ジアザポルフィリンフリーベースを20％程度の単離収率で合成する事に成功した。次いで、得られてフリーベースの錯形成により、各種金属錯体を構築し、その吸収特性、発光特性、および電子受容性・電子供与性を調べた。その結果、ジアザポルフィリンπ系の物性が、ポルフィリンの場合と同様、中心金属の種類に大きく依存することが明らかとなった。さらに、β無置換ジアザポルフィリン－ニッケル錯体のβ位を位置選択的に臭素化した後、パラジウム触媒を用いて反応させることにより、ジアザポルフィリン二量体を合成する事に成功した。各種スペクトル測定および理論計算の結果、この二量体は高い平面性を持ち、π系は大きく拡張されていることを見いだしている。また、一部の誘導体についてはその吸収帯が近赤外領域に達することから、色素増感太陽電池への利用も検討している。以上の結果は、アザポルフィリン誘導体の構造―物性相関を理解する上で重要な知見を与えるものである。

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  • Construction and Search for the Function of Novel Phosphole-Based π-Conjugated Molecules

    Grant number：22350016

    2010 - 2012

    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

    MATANO Yoshihiro

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    Grant amount：\20020000 （ Direct Cost: \15400000 、 Indirect Cost：\4620000 ）

    New efficient methodsfor the synthesis of phosphole-containing π-conjugated molecules were established, and their structure-property relationships were unveiled by various spectroscopy and X-ray crystallography. In addition, some derivatives with high electron-transporting and/or visible-light absorbing abilities were utilized for organic photovoltaics. All the results represent high potential of the newly constructed phosphole derivatives as functional organic materials.

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  • 15族元素を含む新奇核置換ポルフィリンπ空間の創発と機能化

    Grant number：21108511

    2009 - 2010

    System name：科学研究費助成事業

    Research category：新学術領域研究(研究領域提案型)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\4680000 （ Direct Cost: \3600000 、 Indirect Cost：\1080000 ）

    リンや硫黄などの典型元素とポルフィリンの融合により新奇なπ空間を構築し、基礎物性の解明および光・電子材料としての利用を目指して研究を進めてきたが、平成22年度は以下の課題に取り組んだ。(1)拡張π平面を持つ金属架橋ポルフィリン二量体の光物性と電気化学特性に対する金属架橋効果の解明、(2)湾曲したπ系を持つメソ置換カリックスフィリンの合成、および(3)ホスホールを含む核置換ポルフィリンの参照化合物(鎖状π系)の合成と物性評価。(1)メソ-ホスフィノポルフィリンと2価のパラジウム塩あるいは白金塩との反応により得られる金属架橋ポルフィリン二量体は、高いπ平面性を持ち、金属-π結合に由来する特異な吸収特性を示すが、架橋金属が二量体の光物性や電気化学特性に与える影響については、十分に解釈できていなかった。そこで、金属架橋ポルフィリン二量体および参照化合物の光ダイナミクス、酸化還元挙動、MCDスペクトルの測定を行い、架橋金属が諸物性に与える影響を明らかにした。(2)歪んだポルフィリン系π空間を集積化する新しい方法論を提案する目的で、メソ位にリン原子を組み込んだメソ置換カリックスフィリン(5-ホスファフロリン)を新たに設計し、ジチエニルホスフィンあるいはジフリルホスフィン誘導体とジピロメタンとの脱水縮合反応を利用して合成した。得られた化合物の一部に関してはX線結晶構造解析に成功し、リン架橋により環状π系が湾曲した構造をとり、リン上の非共有電子対は環外へ配向することを明らかにした。(3)ホスホールのα位にπ共役官能基を導入する効率的な合成法を確立し、ポルフィリンの参照系となる種々の鎖状π共役ホスホールを構築し、その構造-物性相関を明らかにした。

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  • 第三周期典型元素を含む核置換ポルフィリンの構造と物性に関する研究

    Grant number：20038039

    2008 - 2009

    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

    中野 晴之, 俣野 善博

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    Grant amount：\3200000 （ Direct Cost: \3200000 ）

    本研究は、理論家と実験家が協力し、第三周期典型元素を含む核置換ポルフィリンの化学を分子理論という立場から体系化し、新規化学事象の解明を行うことを目的としている。本年度は、コアのリン原子がオキソ化されたポルフィリンおよびホスファポルフィリンから得られた金属錯体の芳香族性に関して実験・理論両面から検討を加え、参照化合物との比較から芳香族性・反芳香族性を定量的に評価した。
    1. コアのリン原子がオキソ化されたホスファポルフィリンの芳香族性については、P, S, N_2型18πホスファポルフィリンと過酸化水素との反応により得られる20πポルフィリン(イソフロリン)の芳香族性を、NMRで観測される環電流効果、および、密度汎関数により計算されるNICS値により評価した。その結果、P, S, N_2型18πホスファポルフィリンは高い芳香族性を有すること、一方、20πポルフィリンは予想に反して弱い反芳香族性を有することがわかった。弱い反芳香族性の原因には、大きく歪んだ、堅固なπ系が考えられる。
    2. ホスファポルフィリン金属錯体の芳香族性については、18πホスファポルフィリンの錯形成により得られる18πロジウムポルフィリンおよび20πパラジウムイソフロリンの芳香族性を、同様の手法により評価した。これらの錯体では金属中心の配位形態に合わせてπ平面が柔軟に歪むため、18πロジウムポルフィリンの芳香族性は対応するフリーベース体の芳香族性に比べてやや小さくなり、20πパラジウムイソフロリンは、20π系を持つにもかかわらず、弱い反芳香族性しか示さなかった。ただし、中心金属としてマグネシウムを導入すると20πポルフィリン錯体の反芳香族性が向上するという結果も得ており、錯体のパラメータ(π系の電子状態、中心金属の酸化数や配位数など)が核置換ポルフィリンの芳香族性に与える影響を系統的に解明するための基礎的知見を得た。

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  • ポルフィリン類縁体のハイブリッド化による多機能型環状配位子の開発

    Grant number：20036028

    2008 - 2009

    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

    俣野 善博

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    Grant amount：\3800000 （ Direct Cost: \3800000 ）

    ポルフィリン、カリックスピロール、およびそれらが融合した化合物であるカリックスフィリンにピロール以外の複素環を組み込むことで、多彩な配位形態の発現が可能な新しいタイプの大環状多座配位子を構築することができる。我々は、R,X,N_2型・S,X,N_2型の大環状配位子(X=N,S)の開発と利用をめざして、ホスホールやチオフェンを含むハイブリッドポルフィリン類縁体の化学に関する研究を行っている。今年度は、まず、5,10-ポルフォジメテン型R,S,N_2カリックスフィリンに焦点を絞り、その配位特性の詳細を明らかにした。具体的には、X線結晶構造解析・各種スペクトル測定により、R,S,N_2カリックスフィリンが中性のP,N二座配位子としてロジウム中心に配位すること、および、得られた錯体においてR,S,N_2カリックスフィリンがhemilabileな配位子として振る舞うことなどを見いだした。次いでホスホールと含窒素複素環からなる新しい鎖状P,N配位子の合成と錯形成について検討し、得られたπ共役化合物の構造-物性相関を明らかにした。具体的には、α-エチニルボスホールのHuisgen反応を利用したホスホール=トリアゾールπ共役分子の簡便かつ系統的な合成法を確立し、パラジウムや白金に対する錯形成能を調べた。その結果、パラジウム錯体において、ボスホール=トリアゾール分子はP,N二座配位子として振る舞い、配位によるπ系の大きな歪みや金属-配位子間のCT相互作用が吸収スペクトルのブロード化を引き起こすことを見いだした。

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  • ホスホール環を含むハイブリッドカリックスフィリン錯体の合成と利用

    Grant number：19027030

    2007

    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

    俣野 善博

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    Grant amount：\2400000 （ Direct Cost: \2400000 ）

    カリックスアレーンとポルフィリンが融合した化合物であるカリックスフィリンは、柔軟な骨格と酸化還元活性なπ共役平面を併せ持つ新しいタイプの大環状多座配位子である。しかしながら、カリックスフィリン金属錯体の触媒活性に関しては全く報告例がなかった。本研究では、ホスホール、ピロール、および他の複素環が組み込まれたさまざまなハイブリッドカリックスフィリン配位子を構築し、複数の典型元素が織りなす協同効果がうまく発現されるような反応性金属触媒を創製することを目標として研究を進めてきた。まず、ホスファトリピランとピロール、フラン、およびチオフェン誘導体との酸触媒縮合環化反応と引き続く酸化反応により、14πおよび16πP,N2,X型カリックスフィリンを合成し、X線結晶構造解析によりその構造を明らかにした。次いで、パラジウム、ロジウム、および金との錯形成反応を行い、得られた錯体の構造とπ系の電子状態を調べた。ここで、0価パラジウムと16πP,N2,Sハイブリッドとの組み合わせでは、金属と配位子の間で酸化還元が起こり、2価のパラジウム錯体(Pd-P, N2, X錯体)が生成するという興味深い知見を得た。さらに、パラジウム錯体とロジウム錯体を用いて、Heck反応とアセチレンのヒドロシリル化反応をそれぞれ検討し、これらの錯体が触媒として振る舞うことや、カリックスフィリン骨格を構成する複素環の組み合わせにより触媒活性ならびに反応の選択性が大きな影響を受けることを明らかにした。

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  • Development of Highly Efficient Oxidation Reaction and Polymerizaztionby Utilizing the Oxidizing Ability of HyPERvalent Bismuth

    Grant number：17350018

    2005 - 2007

    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

    MATANO Yoshihiro

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    Grant amount：\16090000 （ Direct Cost: \15100000 、 Indirect Cost：\990000 ）

    We have investigated three main topics to develop new reactions (oxidations and photo-induced cationic polymerizations) by utilizing the characteristic properties of the pentavalent bismuth. Firstly, various tetraarylbismuthonium salts were prepared and used as oxidants for alcohol oxidation. Primary and secondary alcohols were efficiently converted to the corresponding carbonyl compounds by treatment with the above Bi(V) oxidants in the presence of an organic base. It has been found that the introduction of ortho-substituents and/or electron-withdrawing para-substituents onto the aryl ligands enhances the oxidizing ability of the bismuthonium salts significantly. In particular, mesityltriarylbismuthonium salts exhibit high oxidizing ability and high chemoselectivity in the competitive reactions between primary and secondary alcohols. Secondary, we developed highly efficient Bi(V)-based cationic photoinitiators for the first time. Photoirradiation of triaryl(1-pyrenyl)bismuthonium salts in acetonitrile afforded triarylbismuthanes and pyrene, accompanied by the generation of protic acids. Triaryl(1-pyrenyl)bismuthonium hexafluoroantimonates have proven to behave as efficient photoinitiators for the cationic polymerization of oxiranes and a vinyl ether, affording the corresponding polymers in good yields within a short photoirradiation time. During the search of sensitizers, which were anticipated to photoinitiate the Bi-mediated cationic polymerization, we designed new classes of porphyrins bearing phosphorus and sulfur substituents at the meso position. Finally, we successfully prepared several meso-phosphorylporphyrins and meso-sulfinylporphyrins, and elucidated their structures, optical properties, and electrochemical properties in detail.

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  • Synthesis of Hypervalent Organobismuth-oxo Complexes and Application to Oxidation

    Grant number：14540494

    2002 - 2003

    System name：Grants-in-Aid for Scientific Research

    Research category：Grant-in-Aid for Scientific Research (C)

    Awarding organization：Japan Society for the Promotion of Science

    MATANO Yoshihiro

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    Grant amount：\3500000 （ Direct Cost: \3500000 ）

    A systematic series of triarylbismuthane oxides were prepared by treatment of the corresponding triarylbismuth dichlorides with excess water in the presence of two equivalents of potassium tert-butoxide. We disclosed the structures, thermal stability, and reactivity of this class of compounds. The bismuthane oxides exist as a dimeric, hydrated, or oligomeric form, depending on the structure of the aryl ligands attached to the bismuth center. It was found that the bismuthane oxides are thermally unstable and readily decompose to give triarylbismuthanes as the major products. Among the insoluble bismuth-derived byproducts, we successfully characterized the structure of a diarylbismuthinic anhydride by X-ray crystallography. It also was found that the oxidizing ability of the bismuthane oxides is much higher than those of lighter pnictogen counterparts, and is significantly enhanced by introducing ortho-substituents onto the aryl ligands. Based on this finding, we developed a new efficient method for alcohol oxidation using a triarylbismuth dichloride/DBU system, where primary and secondary alcohols were readily oxidized to the corresponding carbonyl compounds in good yields under mild conditions. In this system, the remarkably high substituent effects on the oxidizing ability were observed. Thus, introduction of an electron-withdrawing substituent at the para position and a methyl group at the ortho position enhances the rate of oxidation.

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  • Design of Fine Acid Base Catalysts and their Utility in Selective Organic Synthesis

    Grant number：13853003

    2001 - 2005

    System name：Grants-in-Aid for Scientific Research

    Research category：Grant-in-Aid for Scientific Research (S)

    Awarding organization：Japan Society for the Promotion of Science

    MARUOKA Keiji, OOI Takashi

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    Grant amount：\123890000 （ Direct Cost: \95300000 、 Indirect Cost：\28590000 ）

    In this research project, we focused our attention on the rational design of truly efficient acid/base catalysts for the development of synthetic processes in order to achieve the high reactivity and selectivity, not observable by ordinary, acid/base catalysts. In the sophisticated Lewis acid chemistry, a new, chiral bidentate Ti(IV) complex was successfully designed and can be utilized for simultaneous coordination to aldehyde carbonyls, thereby allowing the precise enantioface discrimination of such carbonyls for a new catalytic, practical enantioselective allylation of aldehydes with allyltributyltin. This chiral bidentate Ti(IV) complex has been successfully applied to asymmetric 1, 3-dipolar cycloaddition of nitrones or diazoacetates. On the other hand, phase transfer catalysis is a very useful approach that typically involves simple experimental operations, mild reaction conditions, inexpensive and environmentally benign reagents and solvents, and the large-scale reactions. Accordingly, structurally rigid, chiral spiro ammoniurn salts derived from commercially available (S)- or (R)-binaphthol have been designed as new C_2-symmetric chiral phase transfer catalysts and successfully applied to the highly efficient, catalytic enantioselective synthesis under mild phase transfer conditions. Quite recently, we have successfully designed simplified, yet very active chiral phase transfer catalysts for practical asymmetric synthesis of α-alkyl- and α,α-dialkylamino acids. In addition, chiral, helical-type phase transfer catalysts were newly designed for effecting asymmetric Strecker reaction for large-scale production of sterically hindered α-alkylamino acids. A bowl-shaped organometallic host, tris(2, 6-diphenylbenzyl)-silyl, -germyl, and -tin compounds can be prepared, and applied to selective organic transformations.

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  • DEVELOPMENT AND APPLICATIONS OF BISMUTH YLIDES AND BISMUTH IMIDES IN ORGANIC SYNTHESIS

    Grant number：12640516

    2000 - 2001

    System name：Grants-in-Aid for Scientific Research

    Research category：Grant-in-Aid for Scientific Research (C)

    Awarding organization：Japan Society for the Promotion of Science

    MATANO Yoshihiro

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    Grant amount：\3500000 （ Direct Cost: \3500000 ）

    In this research project, I aimed to utilize the characteristics of hypervalent organobismuth compounds in organic synthesis and to develop new synthetic tools based on bismuth ylides (Ar_3Bi=CRR') and bismuth imides (Ar_3Bi=NR). (1) New methods for the synthesis of stabilized bismuth ylides and bismuth imides were established, and their structures and reactivities have been disclosed. Bismuth imides bearing an acyl or a sulfonyl group on the imido nitrogen atom were prepared by the metathesis reaction, and stabilized bismuth ylides were synthesized by the addition reaction of the imides with electron-deficient acetylenes. X-ray crystallographic analyses of these compounds have elucidated that the bismuth(V)-carbon and bismuth(V)-nitrodgen bonds possess a highly polarized, single bond character. Additionally, systematic comparisons of the structures of bismuth imides with those of the lighter 15th group element counterparts were made for the first time. (2) New cyclization methods by use of bismuth ylides and by bismuth imides have been developed. For instance, the reaction of alkynylbismuthonium salts with a suitable nucleophile generates bismuth ylides of the type Ar_3Bi=C=CRR', which subsequently undergo cyclization with elimination of triarylbisrnuthane to give cyclopentenes and 2,5-dihydrofurans. Stabilized bismuth ylides also undergo cyclization by heat or in the presence of a copper catalyst to afford oxazoles. The driving force of these transformations is the high leaving ability of the triarylbismuthonio group. (3) A new method for the selective synthesis of organobismuth compounds bearing a styryl group was established. They underwent radical polymerization to afford soluble polystyrenes bearing bismuth substitutes. (4) During the course of studies on the synthesis of bismuth imides, a new and convenient method for the preparation of bismuth oxides has been developed, and further studies on this class of compounds are now in progress.

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  • ビスマス-窒素、酸素および硫黄二重結合を有する高原子価有機ビスマス化合物の化学

    Grant number：11120224

    1999

    System name：科学研究費助成事業

    Research category：特定領域研究(A)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\1000000 （ Direct Cost: \1000000 ）

    1.本課題平成11年度においては、形式的なビスマス=窒素二重結合を有する高原子価有機ビスマス化合物、ビスマスイミド、およびその軽元素類縁体の化学を中心に検討を進めてきた。
    2.オルト位にメチル基もしくはメトキシ基を有するアリール基(ο-トリル基、ο-アニシル基)を用いてビスマス=窒素二重結合を速度論的に安定化することにより、様々なN-アシルおよびN-スルホニルトリアリールビスマスイミドを合成、単離した。また、同様の手法を用いて合成したN-スルホニルトリアリールアンチモンイミドが単量体として存在することを、X線結晶構造解析により初めて明らかにした。一連の15族元素由来のイミドの構造解析および理論計算の検討により、中心元素の周期が下がるに連れ、イミド結合の単結合性が増加し、ビスマス-窒素結合は極めて分極した単結合とみなせることが明かとなった。
    3.合成したN-アシルビスマスイミドの基本的な反応性を調べた結果、様々な基質との反応においてトリアリールビスムトニオ基が良好な脱離基として作用することを見いだした。これは15族元素の中でもビスマスに特徴的な振る舞いである。さらに、電子欠乏型アルキンであるアセチレンジカルボン酸ジエステルとの反応では、イミド窒素のマイケル付加、ビスムトニオ基の転位を経由してビスマスイリドが生成することを見いだした。本反応で得られたイリドは、高度に官能基化されたアルキリデン部位が負電荷を効率良く非局在化できるため、熱的に極めて安定化であり、本反応は安定型ビスマスイリドの新しい合成法と見なすことができる。

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  • ビスマス-窒素および酸素二重結合を有する高原子価有機ビスマス化合物の化学

    Grant number：10133225

    1998

    System name：科学研究費助成事業

    Research category：特定領域研究(A)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\1000000 （ Direct Cost: \1000000 ）

    1. 本課題平成10年度においては、ビスマス=窒素二重結合を有する高原子価有機ビスマス化合物であるビスマスイミドの化学を中心に検討を進めてきた。
    2. オルト位にメチル基もしくはメトキシ基を有するアリール基(o-トリル基、o-アニシル基、メシチル基)がビスマス=窒素二重結合を速度論的に安定化することを見いだし、これを基にN-アシルおよびN-スルホニルトリアリールビスマスイミドを空気中でも安定に取り扱える化合物として合成、単離した。いくつかの化合物についてX線結晶構造解析を行った結果、ビスマス中心は歪んだ正四面体構造を取り、ビスマスー窒素の結合距離は既知のビスマスー窒素単結合の距離に近いことが明かとなった。また、N-アシル体ではカルボニル酸素が、N-スルホニル体ではスルホニル酸素がそれぞれビスマス中心の近傍に存在することがら、酸素原子のビスマス原子への分子内配位もこの結合の化学的安定化に大きく寄与していると思われる。N-アシル体は対応するN-スルホニル体に比べて熱的に不安定であった。
    3. 合成したN-アシルビスマスイミドの基本的な反応性を調べた結果、これらのイミドがホスフィンに対しN-アシルナイトレン等価体として、アルコールやチオールに対し酸化剤として振るまうことが明かとなった。例えばエタノールやイソプロパノールはN-アシルビスマスイミドにより室温でアセトアルデヒドおよびアセトンにそれぞれ酸化される。このような温和な酸化力は15族元素の中でもビスマスに特異的なものである。

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  • 原子価異性を鍵段階とするオン/オフ型機能性有機ビスマス化合物の構築

    Grant number：09740469

    1997 - 1998

    System name：科学研究費助成事業

    Research category：奨励研究(A)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\2000000 （ Direct Cost: \2000000 ）

    1. 本課題平成10年度においては、複数のビスマス原子を分子内に有する有機ビスマス化合物の機能化をめざし、ひとつの展開として非イオン型水溶性ビスマス化合物を合成した。さらに、ビスマス原子上にキラリティを有するビスムチンおよびビスムトニウム化合物の合成法を確立し、キラルなビスマス化合物の基本的な物性を明らかにした。
    2. 非イオン型水溶性ビスマス化合物は例えば造影剤や抗菌剤としての利用が期待されているが、これまでその合成例はなかった。芳香環にN,N-ビス(ヒドロキシエチル)アミノスルホニル基を有するトリアリールビスムチンを合成してその水溶性を調べた結果、オルトおよびパラ位に同官能基を持つビスムチンが中性条件下で高い水溶性を示すことが明かとなった。さらに、昨年度の本研究課題で確立した手法-スルホニル基のポリオルトリチオ化-を本系に適用して、上記官能基を有するフェニレン架橋型オリゴビスムチン(ビスマス原子;2〜4個)をワンポットで合成し、その水溶性について評価した。
    3. ビスマス原子上のキラリティは学術的にも興味が持たれるが、今回、ビスマス上にキラリティを有する非対称テトラアリールビスムトニウム塩の合成法を確立した。オルト位にオキサゾリン置換基を有するビスムトニウム塩の場合、^1H-NMRではビスマス上のキラリティを反映したジアステレオトピックなシグナルが観測されるが、このシグナルをVT-NMRにより追跡することで、ビスマス上における立体化学的な挙動と対イオンや溶媒の極性との関係を明らかにした。

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  • ビスマス-窒素および-ケイ素結合を有する高原子価有機ビスマス化合物の化学

    Grant number：09239225

    1997

    System name：科学研究費助成事業

    Research category：重点領域研究

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\1000000 （ Direct Cost: \1000000 ）

    1.本課題平成9年度においては、ビスマス=炭素およびビスマス=窒素二重結合を有する高原子価有機ビスマス化合物-ビスマスイリドおよびビスマスイミド-の化学を中心に検討を進めた。
    2.2-オキソアルキリデン型ビスマスイリドは1,2-ジカルボニル化合物と低温で円滑に反応するが、生成物の構造は基質の骨格に大きく依存することが明かとなった。すなわち、鎖状ケトエステルとの反応では2,3-二置換エポキシドが、オルトキノンとの反応では3-ヒドロキシトロポンが、さらにベンジルとの反応では非対称1,3-ジケトン由来のエノラートが生成する。いずれの反応においてもトリフェニルビスマス基は中性の良好な脱離基として作用し、遷移状態における立体的混み合いの違いが各反応経路に大きな差を与えているものと思われる。
    3.オルト位に適当な配位性官能基を導入することによりビスマスイミドを空気中でも安定に取り扱える化合物として単離し、X線結晶構造解析によりその構造を明らかにした。もとめられたビスマス=窒素結合の距離は単結合のそれに近いこと、配位性官能基がビスマス中心と大きく相互作用していることから、超原子価構造がこの結合の化学的安定化に大きく寄与していると思われる。
    4.ビスマス原子上に異なる3つのアリール基を持つ非対称トリアリールビスマスイミドの合成に成功した。近傍にオキサゾリン置換基を有する場合、H-NMRにおいてビスマス上のキラリティに反映すると思われるジアステレオトピックなシグナルを与える。これらのキラリティの評価は構造化学的に大変興味が持たれるところであり、現在その詳細について検討中である。

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  • 共役型官能基を有する新規ビスムトニウム化合物の構築と機能性材料への応用

    Grant number：08740492

    1996

    System name：科学研究費助成事業

    Research category：奨励研究(A)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\1000000 （ Direct Cost: \1000000 ）

    1.本課題においては、非対称アリールビスムトニウム塩と求核種との反応における置換基効果を明らかにした。また、分子内にキラル中心を二つ持つ非対称テトラアリールビスムトニウム塩の化学について基礎的な検討を行った。さらに、共役型多環芳香族官能基を有するトリアリールビスムチンの合成に成功した。
    2.アリールビスムトニウム塩の反応性を知る自的で、アニシル、チオアニシル、トリル基を有する非対称アリールビスムトニウム塩を合成し、チオラート、フェノキシド、スルフィナ-トとの反応における置換基効果を検討した結果、求核種はより電子不足なアリール基と優先的に反応することが明らかとなった。
    3.機能性材料の中で光学活性化合物の果たす役割は重要である。我々は既に全てのアリール基が異なるテトラアリールビスムトニウム塩の一般的な合成方法を確立しているが、今回、キラル中心であるビスマス原子の異性化挙動に関する基礎的な知見を得る目的で、対イオンもしくはリガンドに別のキラル中心を持つジアステレオマ-の合成を行い、いずれも安定な化合物として単離することに成功した。定量化までには至っていないが、現在核磁気共鳴法を用いてその異性化挙動を検討中である。
    4.多環共役置換基を有するビスマス化合物はこれまでほとんど報告例がなかったが、ハロビスムチンとアリールリチウム、もしくはビスムチドとヨードアレーンとのカップリング反応によりアンセトラセン、フェナントレン置換基を持つビスムチンの合成に初めて成功した。吸収スペクトルの測定により、これらの化合物におけるビスマス置換基の置換特性が明らかとなった。今後、対応するジクロリド、オニウム塩も含めて多環共役系置換基を有する一連のビスマス化合物の構造と分子内電荷移動状態の相関をさらに詳細に検討する予定である。

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  • 特異な官能基導入反応の開発とその機構解明をめざした新規ビスムトニウム化合物の構築

    Grant number：07740496

    1995

    System name：科学研究費助成事業

    Research category：奨励研究(A)

    Awarding organization：日本学術振興会

    俣野 善博

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    Grant amount：\1000000 （ Direct Cost: \1000000 ）

    1.ビスマスが高原子価状態において示す特異的な挙動は、構造、理論および合成化学の領域において興味深い研究対称として注目を集めている。本課題においては、最近までその姿が全く知られていなかったアルケルビスムトニウム塩およびビスマス上にキラル中心を持つ非対称テトラアリールビスムトニウム塩の一般的な合成法を初めて確立し、その構造と反応性について詳細に検討した。
    2.トリフェニルビスマスジフルオリドを、塩化メチレン中ルイス酸存在下、シリルシアニド、アルケニル錫と順次反応させると、アルケニルトリフェニルビスムトニウム塩が安定な結晶として得られる。X線結晶構造解析の結果、ビスマス中心は歪んだ正四面体型構造を取り、対イオンとの相互作用は比較的弱いことが明かとなった。アルケニルビスムトニウム塩はスルフィン酸塩およびパラジウム錯体と容易に反応してアルケニル基を優先的にトランスファーする。塩基との反応においては、系中でフリーなアルキリデンカルベンを発生し、スチレンが共存する場合にはトリフェニルビスムタンの脱離を伴って対応するシクロプロパンを与える。
    上の反応系において、アルケニル錫の代わりにアリール錫を炭素求核剤として用いると、非対称アリールトリフェニルビスムトニウム塩が高収率で得られる。この手法を利用して、全てのアリール基が異なる非対称テトラアリールビスムトニウム塩の合成に成功した。この化合物はビスマス原子上にキラル中心を有しており、異性化挙動の解明や機能性材料への応用など、様々な展開が期待できる。

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  • 新しいタイプのビスムトニウム化合物の構築およびそれを利用した合成反応の開発

    Grant number：06740480

    1994

    System name：科学研究費助成事業

    Research category：奨励研究(A)

    Awarding organization：日本学術振興会

    俣野 喜博

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    Grant amount：\1200000 （ Direct Cost: \1200000 ）

    1.ビスマスは安定元素の中で最も重い元素であり、しばしば軽元素の化学からは予測できない興味深い挙動を示す。本課題においては、最近までその姿が全く知られていなかったオキソアルキルビスムトニウム塩および準安定型ビスムトニウムイリドの一般的な合成法を初めて確立し、その構造と反応性について詳細に検討した。
    2.トリアリールビスマスジフルオリドをルイス酸存在下、シリルエノールエーテルもしくはシロキシシクロプロパンと反応させると、2-あるいは3-オキソアルキルトリアリールビスムトニウム塩が安定な結晶として得られる。X線結晶構造解析の結果、これらのオニウム塩の安定化にはアルキル鎖のカルボニル基の空間配置が重要な役割を果たしていることが明かとなった。また、それぞれのオニウム塩は求核種との反応においてアルキル基を選択的にトランスファーする。
    3.2-オキソアルキルビスムトニウム塩は、低温下適当な塩基を作用させると、準安定型のトリアリールビスムトニウムイリドに変換される。得られたイリドはアリデヒド、アジリジンとの反応によりα,β-エポキシケトン、α,β-アジリジノケトンとトリアリールビスムチンを良好な収率で与えるが、このような反応形式は同族のリン、ヒ素、アンチモンの類縁体には見られず、この反応においてビスマスの特異性が顕著に現れていることが明かとなった。
    4.上記の結果は、高原子価有機ビスマス化合物の持つユニークな化学性の一面を明らかにするものであり、今後さらに各種ビスムトニウム化合物の合成、構造および反応性について系統的に研究を進めていく予定である。

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  • 高原子価有機ビスマスオキシド・ビスムトニウム塩の特性を活かした新しい増炭・酸化反応の開発

    Grant number：05740392

    1993

    System name：科学研究費助成事業

    Research category：奨励研究(A)

    Awarding organization：日本学術振興会

    俣野 善博

    　 More details

    Grant amount：\1000000 （ Direct Cost: \1000000 ）

    1.ビスマスは安定元素の中で最も重い元素であり、しばしば軽元素の科学からは予測できない興味深い振舞いを示す。本課題においては、今日まで未開拓の化学種であったビスマスオキシド、ビスムトニウム塩の合成法を確立し、さらにその構造および科学挙動について検討した。
    2.ビスマスオキシドの合成を目的としたトリフェニルビスムチンの直接酸化は極めて多彩な結果をもたらした。中でもオゾン/トルエン系による酸化では、予期せぬ生成物であるリトフェニルビスマスジフォルメートが定量的に得られた。一方、ヨードソベンゼンによる酸化では目的とするトリフェニルビスマスオキシドが溶液状態で定量的に生成する。この化学種は同族のリン、ヒ素、アンチモンのオキシドとは異なり各種アルコーを効率よく酸化した。
    3.ビスムトニウム塩、特にアルキル-ビスマス結合を有するビスムトニウム塩の一般的合成法はこれまで全く知られていなかったが、トリアリールビスマスジフルオリド・ルイス酸・シリルエノ-エウエーテルの組み合わせによる2-オキソアルキルビスムトニウム塩の効率的な合成に成功した。得られたビスムトニウム塩の構造をX線解析により確定し、その化学的挙動を知るために種々の求核種との反応について検討した。その結果、4つのリガンドの中で2-オキソアルキル基がアシルカチオン等価体として選択的に求核試剤にトランスファーされることが明らかとなった。
    4.上記の結果は、高原子価ビスマス化合物のもつユニークな一面を明らかにするものであり、今後さらに各種誘導体の合成・構造・反応性について検討していく予定である。

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Teaching Experience

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    Institution name：新潟大学

  • プロジェクト研究特別概説

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  • Chemistry Today II

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  • Chemistry TodayII

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  • SDGsを支える化学

    2024
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  • 有機化学I

    2023
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  • 科学・技術と社会

    2023
    -
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    Institution name：新潟大学

  • グリーンケミストリー概説

    2023
    Institution name：新潟大学

  • 化学コロキウム

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    Institution name：新潟大学

  • 新素材の物性

    2022
    -
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    Institution name：新潟大学

  • 統合化学入門

    2022
    Institution name：新潟大学

  • 大型機器分析技術

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  • 数理物質科学の最前線

    2022
    Institution name：新潟大学

  • 理学スタディ・スキルズ

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    Institution name：新潟大学

  • 化学英語

    2021
    -
    2022
    Institution name：新潟大学

  • 有機合成方法論II

    2021
    Institution name：新潟大学

  • 有機物質合成論

    2021
    Institution name：新潟大学

  • 課題研究 a

    2020
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  • 課題研究 b

    2020
    Institution name：新潟大学

  • 先端科学技術総論

    2020
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  • 理学スタディ・スキルズ

    2018
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    2022
    Institution name：新潟大学

  • 自然科学総論Ⅰ

    2018
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  • 有機化学Ⅱ

    2017
    Institution name：新潟大学

  • 課題研究

    2017
    -
    2023
    Institution name：新潟大学

  • 化学英語

    2017
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    2022
    Institution name：新潟大学

  • 総合力アクティブ・ラーニング

    2017
    -
    2019
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  • 安全教育

    2016
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  • 日本事情自然系A

    2015
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  • 数理物質科学特定研究ⅡA(化学)

    2015
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  • 有機機器分析

    2014
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  • 有機化学演習

    2014
    Institution name：新潟大学

  • 有機物質合成論

    2014
    -
    2021
    Institution name：新潟大学

  • 化学入門

    2014
    -
    2020
    Institution name：新潟大学

  • 有機化学II

    2014
    -
    2016
    Institution name：新潟大学

  • 化学実験

    2014
    -
    2015
    Institution name：新潟大学

  • 数理物質科学特定研究Ⅰ(化学)

    2014
    Institution name：新潟大学

  • 数理物質科学演習Ⅰ(化学)

    2014
    Institution name：新潟大学

  • 社会を支える有機化学

    2013
    Institution name：新潟大学

  • 有機合成方法論Ⅱ

    2013
    -
    2017
    Institution name：新潟大学

  • 課題研究(化学科)

    2013
    -
    2016
    Institution name：新潟大学

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