2021/05/15 更新

写真a

マタノ ヨシヒロ
俣野 善博
MATANO Yoshihiro
所属
教育研究院 自然科学系 数理物質科学系列 教授
自然科学研究科 数理物質科学専攻 教授
理学部 理学科 教授
職名
教授
外部リンク

学位

  • 博士(理学) ( 1994年11月   京都大学 )

研究分野

  • ナノテク・材料 / 構造有機化学、物理有機化学

  • ライフサイエンス / 生物有機化学

経歴(researchmap)

  • 新潟大学   理学部 理学科   教授

    2017年4月 - 現在

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  • 新潟大学   自然科学研究科 数理物質科学専攻   教授

    2013年4月 - 現在

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  • 新潟大学   理学部 化学科   教授

    2013年4月 - 2017年3月

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  • 京都大学   大学院工学研究科   准教授

    2002年4月 - 2013年3月

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  • 京都大学   大学院理学研究科   助手

    1995年4月 - 2002年3月

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  • 京都大学   理学部   助手

    1990年11月 - 1995年3月

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▶ 全件表示

経歴

  • 新潟大学   理学部 理学科   教授

    2017年4月 - 現在

  • 新潟大学   自然科学研究科 数理物質科学専攻   教授

    2013年4月 - 現在

  • 新潟大学   自然科学研究科 数理物質科学専攻   教授

    2013年4月 - 現在

  • 新潟大学   有機物質化学   教授

    2013年4月 - 2017年3月

学歴

  • 京都大学   Graduate School, Division of Natural Science

    - 1990年10月

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    国名: 日本国

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  • 京都大学   理学部   化学科

    - 1987年3月

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    国名: 日本国

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所属学協会

留学歴

  • 1996年09月 - 1997年08月   米国ワシントン大学(University of Washington)   文部省在外研究員長期

 

論文

  • Synthesis of Redox-Switchable 5,15-Dialkyl-10,20-diaryl-5,15-diazaporphyrins and Diversification of Their N-Alkyl Groups 査読

    俣野 善博

    Asian J. Org. Chem8 ( 3 ) 352 - 355   2019年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1002/ajoc.201900085

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  • Synthesis and Optical, Magnetic, and Electrochemical Properties of 5,10,15,20-Tetraaryl-5,15-diazaporphyrin–Tertiary Amine Conjugates 査読

    J. Porphyrins Phthalocyanines   2019年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

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

    ChemPlusChem84   740 - 745   2019年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1002/cplu.201900087

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

    俣野 善博

    Heteroatom Chemistry29   e21456   2018年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    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 査読

    Takaharu Satoh, Kaori Fujii, Yoshifumi Kimura, Yoshihiro Matano

    The Journal of Organic Chemistry83 ( 9 ) 5274 - 5281   2018年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/acs.joc.8b00087

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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 査読

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

    Angewandte Chemie International Edition57 ( 14 ) 3797 - 3800   2018年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/anie.201800471

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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 査読

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

    The Journal of Organic Chemistry83 ( 6 ) 3397 - 3402   2018年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/acs.joc.8b00030

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  • β-Functionalization of 5,15-Diazaporphyrins with Phosphorus, Oxygen, and Sulfur-Containing Substituents 査読

    Takuma Sugai, Mao Minoura, Haruyuki Nakano, Yoshihiro Matano

    Bulletin of the Chemical Society of Japan91 ( 8 ) 1264 - 1266   2018年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    DOI: 10.1246/bcsj.20180123

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

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

    Journal of Porphyrins and Phthalocyanines22 ( 7 ) 542 - 551   2018年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:World Scientific  

    DOI: 10.1142/S1088424618500529

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

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

    Dalton Transactions47 ( 21 ) 7123 - 7127   2018年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry  

    Various 7-substituted benzo[b]phosphole derivatives were prepared by PO-directed lithiation of 1,2,3-triphenylbenzo[b]phosphole P-oxide and subsequent iodination and cross-coupling reactions. The electron-donating groups introduced at the 7-position produced dramatic solvatofluorochromism owing to the strong charge-transfer character of the excited state of the entire π-system.

    DOI: 10.1039/c8dt01503a

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

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

    Chemistry-A European Journal23 ( 64 ) 16364 - 16373   2017年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/chem.201703664

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

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

    Journal of Physical Chemistry B121 ( 24 ) 6042 - 6049   2017年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    Excited-state proton transfer (ESPT) of 5-cyano-2-naphthol (5CN2) and 5,8-dicyano-2-naphthol (DCN2) in three different protic ionic liquids (PILs), triethylammonium trifluoromethanesulfonate ([N222H][CF3SO3]), triethylammonium methanesulfonate ([N222H][CH3SO3]), and triethylammonium trifluoroacetate ([N222H][CF3COO]), was studied by time-resolved fluorescence. In [N222H][CF3SO3], both 5CN2 and DCN2 showed fluorescence only from ROH∗ (normal form of substituted naphthol in the excited states), indicating that no ESPT occurred in [N222H][CF3SO3]. For 5CN2 in [N222H][CH3SO3], fluorescence bands from ROH∗ and RO-∗ (anionic form of substituted naphthol in the excited states) were observed, indicating that 5CN2 could dissociate proton to surrounding solvents and form RO-∗. More interestingly, 5CN2 in [N222H][CF3COO] and DCN2 in [N222H][CH3SO3] and [N222H][CF3COO] showed an anomalous fluorescence band around 470 nm (5CN2) or around 520 nm (DCN2) which has not been reported previously. The kinetics of each fluorescent component of 5CN2 and DCN2 was analyzed on the basis of the time profile of fluorescence intensity. Plausible ESPT schemes of 5CN2 and DCN2 were discussed on the basis of the kinetics and the basicity of anion in PILs. (Graph Presented).

    DOI: 10.1021/acs.jpcb.7b03658

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  • Unsymmetrically Substituted D–π–A Type 5,15-Diazaporphyrin Sensitizers: Synthesis and Optical and Photovoltaic Properties 査読

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

    ChemPlusChem82 ( 5 ) 695 - 704   2017年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    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 査読

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

    Chemistry - An Asian Journal12 ( 7 ) 816 - 821   2017年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:John Wiley and Sons Ltd  

    NH-bridged and pyrazine-fused metallodiazaporphyrin dimers have been prepared from nickel(II) and copper(II) complexes of 3-amino-5,15-diazaporphyrin by Pd-catalyzed C−N cross-coupling and oxidative dimerization reactions, respectively. The synergistic effects of the nitrogen bridges and meso-nitrogen atoms play major roles in enhancing the light-harvesting properties and delocalization of an electron spin over the entire π-skeletons of the metallodiazaporphyrin dimers.

    DOI: 10.1002/asia.201700204

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  • Synthesis of Aza-, Oxa-, and Thiaporphyrins and Related Compounds 招待 査読

    Yoshihiro Matano

    Chemical Reviews117 ( 4 ) 3138 - 3191   2017年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    Chemical modification at the periphery with nitrogen or chalcogens is a highly promising strategy to diversify the optical, electrochemical, magnetic, and coordination properties of the porphyrin family. Indeed, various kinds of phthalocyanines and related benzo-annelated azaporphyrinoids have been synthesized, and their fundamental properties have been extensively investigated. However, the synthesis of heteroatom-containing porphyrins in which the peripheral methine groups are partially replaced with nitrogen or chalcogens remains a considerable challenge. In this review, we will focus mainly on recent advances in the synthesis of aza-, oxa-, and thiaorphyrins and related compounds, including historically important examples.

    DOI: 10.1021/acs.chemrev.6b00460

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  • Synthesis of Dibenzophosphole Oxides from Dibenzothiophenes and Phenylphosphine by Twofold SNAr Reactions 査読

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

    Asian Journal of Organic Chemistry6 ( 3 ) 257 - 261   2017年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/ajoc.201600612

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

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

    Dalton Transactions46 ( 29 ) 9517 - 9527   2017年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry  

    In this work, we investigated the effects of counter anions, P-substituents, and solvents on the optical and photophysical properties of 2-phenylbenzo[b]phospholium salts in solution. A series of 2-phenylbenzo[b]phospholium salts was prepared by P-alkylation or P-phenylation of 1,2-diphenylbenzo[b]phosphole followed by anion exchange reactions. X-ray crystallographic analyses of six benzo[b]phospholium salts showed that each phosphorus center has an onium nature with an essentially tetrahedral geometry. 1H NMR and steady-state UV-vis absorption and fluorescence spectroscopic measurements of these phospholium salts revealed the pivotal role of counter-anion solvation. The observed results are discussed on the basis of the association-dissociation equilibrium between a contact ion pair (CIP) and a solvent-separated ion pair (SSIP) in solution. The hexafluorophosphates exist as SSIPs and emit intense fluorescence, irrespective of the P-substituents and solvents. In contrast, the iodides are present as SSIPs in methanol but exist as equilibrium mixtures of the two emitting species, SSIP and CIP, in dichloromethane. As a consequence, fluorescence intensities of the iodides varied significantly depending on the solvents, P-substituents, and solution concentrations. These findings were studied in more detail using time-resolved fluorescence spectroscopy and fluorescence titration measurements. The light-emitting properties of the 2-phenylbenzo[b]phospholium halides in the CIPs rely on heavy atom effects derived from the counter halide anions on the S1 state of the adjacent cationic benzo[b]phosphole π-systems. The present study suggests that 2-arylbenzo[b]phospholium salts would be promising scaffolds for developing new phosphole-based ionic fluorophores that are capable of responding to external stimuli such as anionic species and solvents.

    DOI: 10.1039/c7dt01839h

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

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

    Angewandte Chemie International Edition55 ( 6 ) 2235 - 2238   2016年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/anie.201510734

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  • Ring-Strain Effect in Base-Induced Sommelet–Hauser Rearrangement: Application to Successive Stereo-controlled Transformations 査読

    Eiji Tayama, Kazutoshi Watanabe, Yoshihiro Matano

    European Journal of Organic Chemistry2016 ( 21 ) 3631 - 3641   2016年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    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 査読

    Yoshinari Koyanagi, Yoshifumi Kimura, Yoshihiro Matano

    Dalton Transactions45 ( 5 ) 2190 - 2200   2016年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry  

    The optical, electrochemical, and photophysical properties of Mes2B- (Mes = 2,4,6-trimethylphenyl), Ph2P-, or Ph2MeP+-substituted 2,5-dithienylphospholes and 2-phenyl-5-thienylphospholes are reported. The Mes2B- and Ph2P-substituted derivatives were prepared via regioselective lithiation and metathesis at the thiophene rings of the corresponding unsubstituted π-systems. The Ph2MeP+-substituted derivatives (phosphonium salts) were obtained via methylation of the Ph2P-substituted π-systems. The optical and electrochemical data and density functional theory calculations showed that the highest occupied molecular orbital and lowest unoccupied molecular orbital energies of these α,α′-linked thiophene-phosphole π-systems were sensitive to the intrinsic nature of the B and P substituents. The fluorescence quantum yields (Φf) of the Ph2MeP+-substituted derivatives varied considerably depending on the counter anion, concentration, and solvent, but the π-π∗ transition energies were unchanged. The emitting ability of the Ph2MeP+-substituted 2,5-dithienylphosphole π-system changed significantly from Φf = 0.07 to 0.87. These findings were investigated using time-resolved fluorescence spectroscopy and fluorescence titration measurements. The results show that phosphonium iodides were present in the equilibrium mixtures of three or two emitting ion pairs in CH2Cl2. The light-emitting abilities of the Ph2MeP+-substituted derivatives rely on heavy atom effects derived from the counter halide anions.

    DOI: 10.1039/c5dt03362d

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  • Synthesis and Photophysical Properties of Two Diazaporphyrin–Porphyrin Hetero Dimers in Polar and Non-Polar Solutions 査読

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

    The Journal of Physical Chemistry B119 ( 24 ) 7328 - 7337   2015年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    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

    Yoshihiro Matano, Yuta Motegi, Shinsuke Kawatsu, Yoshifumi Kimura

    Journal of Organic Chemistry80 ( 11 ) 5944 - 5950   2015年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    Suzuki-Miyaura cross-coupling reactions were used in the divergent synthesis of a series of 2-arylnaphtho[2,3-b]phosphole P-oxides and their benzo[b]phosphole counterparts. We elucidated the electronic and steric effects of the 2-aryl groups and fused arene moieties on the optical and photophysical properties of these two types of phosphole-based π-systems.

    DOI: 10.1021/acs.joc.5b00541

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  • Comparison of Electronic Effects of β-Aryl Substituents on Optical and Electrochemical Properties of 5,15-Diazaporphyrin π-Systems 査読

    Satoshi Omomo, Ko Furukawa, Haruyuki Nakano, Yoshihiro Matano

    Journal of Porphyrins and Phthalocyanines19 ( 6 ) 775 - 785   2015年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:World Scientific  

    DOI: 10.1142/S1088424615500509

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

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

    Chemistry - A European Journal21 ( 5 ) 2003 - 2010   2015年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley-VCH Verlag  

    The first examples of pyrrole- and thiophenebridged 5,15-diazaporphyrin (DAP) dimers are prepared through Stille coupling reactions of nickel(II) and copper(II) complexes of 3-bromo-10,20-dimesityl-5,15-diazaporphyrin (mesityl = 2,4,6-trimethylphenyl) with the respective 2,5-bis-(tributylstannyl)heteroles. The effects of the heterole spacers and meso nitrogen atoms on the optical, electrochemical, and magnetic properties of the DAP dimers are investigated by UV/Vis absorption spectroscopy, density functional theory calculations, magnetic circular dichroism spectroscopy, cyclic voltammetry, and EPR spectroscopy. The heterole spacers are found to have a significant impact on the electronic transitions over the entire p-system. In particular, the pyrrolebridged DAP dimers exhibit high light-harvesting potential in the low-energy visible/near-infrared region owing to the intrinsic charge-transfer character of the lowest excitation.

    DOI: 10.1002/chem.201405482

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  • Synthesis and Structure–Property Relationships of Phosphole-Based π-Systems and Their Applications in Organic Solar Cells 査読

    Yoshihiro Matano

    The Chemical Record15 ( 3 ) 636 - 650   2015年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/tcr.201402101

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  • N,S,P-Hybrid Donor–π–Acceptor Organic Dyes for Dye-Sensitized Solar Cell: Synthesis, Optical Properties, and Photovoltaic Performances 招待 査読

    Yoshihiro Matano, Yukiko Hayashi, Haruyuki Nakano, Hiroshi Imahori

    Heteroatom Chemistry25 ( 6 ) 533 - 547   2014年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/hc.21188

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  • Covalently Linked 5,15-Diazaporphyrin Dimers: Promising Scaffolds for Highly Conjugated Azaporphyrin π-System 査読

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

    Chemistry, A European Journal20 ( 12 ) 3342 - 3349   2014年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1002/chem.201304626

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  • Phosphole- and benzodithiophene-based copolymers: Synthesis and application in organic photovoltaics 査読

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

    European Journal of Inorganic Chemistry ( 10 ) 1620 - 1624   2014年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley-VCH Verlag  

    Two kinds of phosphole- and benzodithiophene-based copolymers bearing PV=O or PV=NSO2C8H17 functions were prepared by Pd-CuI-promoted Stille coupling reactions, and their optical and electrochemical properties were investigated. Bulk heterojunction organic photovoltaic devices comprised of the new P,S-bridged copolymers and (6,6)-phenyl-C71-butyric acid methyl ester (PC71BM) exhibited power conversion efficiencies of up to 0.65-% under AM1.5 irradiation at 100 mW-cm-2. Copyright © 2014 WILEY-VCH Verlag GmbH &amp
    Co. KGaA, Weinheim.

    DOI: 10.1002/ejic.201301132

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

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

    ORGANIC LETTERS15 ( 17 ) 4458 - 4461   2013年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Heck, Stille, and Sonogashira reactions of 2-bromobenzo[b]phosphole P-oxide afforded a series of 2-alkenyl- and 2-alkynyl-benzo[b]phosphole P-oxides. The charge-transfer character of the new benzo[b]phosphole pi-systems in the excited state is enhanced by the terminal electron-donating substituents. Furthermore, the C-Sn cross-coupling of the bromide was applied to the facile synthesis of a new Stille-coupling precursor, 2-stannylbenzo[b]phosphole.

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

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

    ORGANIC LETTERS15 ( 4 ) 932 - 935   2013年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    A new class of polyphospholes bearing alkanesulfonylimino moieties on the phosphorus(V) centers was prepared by the Pd-Cul-promoted Stille coupling reaction to investigate the charge-carrier transport properties of the pi-networks of polyphospholes. Time-of-flight measurements have revealed that the poly(phosphole P-imide)s possess ambipolar charge-carrier mobilities of up to mu(electron) = 6 x 10(-3) cm(2) V-1 s(-1) and mu(hole) = 4 x 10(-3) cm(2) V-1 s(-1).

    DOI: 10.1021/ol4000982

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  • Synthesis and Structure–Property Relationships of 2,2ʹ-Bis(benzo[b]phosphole) and 2,2ʹ-Benzo[b]phosphole–Benzo[b]heterole Hybrid π-Systems 査読

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

    Chemistry, A European Journal18 ( 50 ) 15972 - 15983   2012年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    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 査読

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

    INORGANIC CHEMISTRY51 ( 23 ) 12879 - 12890   2012年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The synthesis, structures, optical and electrochemical properties, and aromaticity of a series of 5,15-diaza-10,20-dimesitylporphyrins (M-DAP; M = Pb, H-2, Ni, Pd, Pt, Zn; mesityl = 2,4,6-trimethylphenyl) are reported. Treatment of mesityl-substituted bis(5,5'-dibromodipyrrin) with sodium azide in the presence of lead(II) acetylacetonate afforded Pb-DAP, which was quantitatively converted to H-2-DAP by acidolysis. The free base H-2-DAP reacted with palladium(II), platinum(II), and zinc(II) salts to give Pd-DAP, Pt-DAP, and Zn-DAP, respectively. The crystal structures, optical and electrochemical properties, and aromaticities of these beta-unsubstituted M-DAPs were comprehensively investigated by X-ray crystallography, UV-vis absorption/fluorescence spectroscopy, nanosecond flash photolysis, cyclic and differential pulse voltammetry, NMR spectroscopy, and density functional theory calculations. The obtained data show that replacement of the 5- and 15-methine carbons with nitrogen atoms alters the intrinsic properties of the porphyrin 18 pi system as follows: (i) the coordination spheres at the N-4 core become contracted while keeping high planarity; (ii) the Q bands are red shifted and largely intensified; (iii) the electron-accepting ability is enhanced, whereas the electron-donating ability is reduced; (iv) the radiative decay rates from the S-1 state are enhanced; and (v) the aromaticity of the 18 pi circuit is slightly reduced in terms of both geometric and magnetic criteria. These optical and electrochemical properties of M-DAPs stem from their characteristic frontier orbitals; two HOMOs and two LUMOs are nondegenerate as a result of the incorporation of the electronegative nitrogen atoms at the two meso positions. In addition, the group 10 metals incorporated at the core finely tune the fundamental properties of DAP pi systems through inductive effects as well as d pi-p pi antibonding orbital interactions; the HOMO-LUMO gaps of the group 10 metal complexes increase in the order Ni-DAP < Pd-DAP < Pt-DAP.

    DOI: 10.1021/ic301835c

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  • α,α’-Diarylacenaphtho[1,2-c]phosphole P–Oxides: Divergent Synthesis and Application to Cathode Buffer Layers in Organic Photovoltaics 査読

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

    Chemistry, An Asian Journal7 ( 10 ) 2305 - 2312   2012年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1002/asia.201200492

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

    Yoshihiro Matano, Tarou Shibano, Haruyuki Nakano, Hiroshi Imahori

    Chemistry, A European Journal18 ( 20 ) 6208 - 6216   2012年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1002/chem.201200463

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

    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 Society134 ( 3 ) 1825 - 1839   2012年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1021/ja210205v

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

    Yoshihiro Matano, Kazuaki Matsumoto, Tarou Shibano, Hiroshi Imahori

    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES15 ( 11-12 ) 1172 - 1182   2011年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WORLD SCI PUBL CO INC  

    The synthesis and the catalytic activity of bis(mu-chloro)-bridged, phosphapalladacyclefused diporphyrins (M-porphyrin-appended phosphapalladacycles: M = Zn, Ni, free-base), as well as the coordinating ability of their precursors, meso-phosphanylporphyrins are reported. Treatment of meso-phosphanylporphyrinatozinc(II) with an equimolar amount of PdCl(2)(NCPh)(2) caused regioselective beta-C-H activation of the porphyrin ring to produce bis(mu-chloro)-bridged Zn-porphyrin-appended phosphapalladacycle, which was further converted to the free-base-and Ni-porphyrin-appended analogs. The UV-vis absorption spectra of these palladium complexes showed weak exciton coupling between two porphyrin chromophores connected by the mu-chloro bridges. The M-porphyrinappended phosphapalladacycles behaved as precatalysts for a high temperature Heck reaction between p-bromobenzaldehyde and butyl acrylate. In a range of the catalyst-loading of 0.05-0.005 mol.%, the catalytic activity was found to significantly depend on the central metal incorporated at the porphyrin core. The Ni-porphyrin-appended phosphapalladacycle showed considerably higher turnover frequency than did the Zn-porphyrin-and free-base-porphyrin-appended counterparts. This trend in the catalytic activity does not simply correlate with the sigma-donating ability of the phosphorus center and the electron-donating ability of the porphyrin pi-systems. Instead, it is related to the durability of the precatalysts under the reaction conditions employed. The observed results corroborate that the central metal of the meso-phosphanylporphyrin ligands plays a crucial role in the active Pd(0) catalyst-loading from the porphyrin-appended phosphapalladacycles at constant efficiency.

    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 π-Systems 査読

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

    Chemistry Letters40 ( 9 ) 919 - 921   2011年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1246/cl.2011.919

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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 査読

    Yoshihiro Matano, Arihiro Saito, Masato Fujita, Hiroshi Imahori

    HETEROATOM CHEMISTRY22 ( 3-4 ) 457 - 470   2011年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-BLACKWELL  

    2,5-Bis(1,5-diphenylphosphol-2-yl)heterole derivatives were prepared via Pd-catalyzed Stille-type cross-coupling reactions of alpha-(tributylstannyl) phosphole or alpha-iodophosphole with the corresponding 2,5-difunctionalized heteroles (pyrrole, furan, and thiophene). X-ray crystallographic analyses of three sigma(4)-P derivatives have elucidated that the coplanar phosphole-heterole-phosphole pi-networks are constructed in both anti-anti and anti-anti conformations. In the case of the pyrrole-linked (sigma(4)-P derivatives, there is a weak hydrogen-bonding interaction between NH and P=X (X = O, S) groups. The optical and electrochemical properties of the sigma(3)-P and sigma(4)-P=O derivatives were revealed experimentally by means of UV-vis absorption/emission spectroscopy and cyclic/differential pulse voltammetry. In all the heterole-linked derivatives, the P-oxidation lowers LUMO levels more efficiently than HOMO levels and, as a result, narrows HOMO-LUMO gaps. In each series (sigma(3)-P or sigma(4)-P=O), the lowest pi-pi* transition energies of the phosphole-heterole-phosphole pi-systems were found to decrease in the following order: thiophene > furan > pyrrole, and their electrochemical oxidation and reduction potentials shift to the negative side in the same order. These results basically reflect the differences in ionization potential and electron affinity of the central heterole spacers. Density functional theory calculations on the model compounds supported the experimentally observed results. The HOMO of the molecule resides on the conjugated polyene network of the pi-system, whereas the LUMO is strongly located on the phosphole subunits. The present comparative study demonstrates, for the first time, that the intriguing electronic structures and the fundamental properties of the 2,5-bis (1,5-diphenylphosphol-2-yl)heteroles can be finely tuned by simple selection of the appropriate heterole spacer. (C) 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:457-470, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20708

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  • Fusion of Phosphole and 1,1’-Biacenaphthene: Phosphorus(V)-Containing Extended π-Systems with High Electron Affinity and Electron Mobility 査読

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

    Angewandte Chemie International Edition50 ( 35 ) 8016 - 8020   2011年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1002/anie.201102782

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

    Yoshihiro Matano, Masato Fujita, Arihiro Saito, Hiroshi Imahori

    COMPTES RENDUS CHIMIE13 ( 8-9 ) 1035 - 1047   2010年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER  

    2,5-Bis(pyrrol-2-yl)phosphole derivatives were prepared using the reaction of titanacycles, generated in situ from a Ti-II reagent and pyrrole-capped 1,6-heptadiynes, with dichloro(phenyl)phosphine. The 2,5-bis(pyrrol-2-yl)phosphole derivatives were found to possess narrower optical HOMO-LUMO gaps and less positive oxidation potentials than those of previously reported 2,5-diarylphosphole analogs. This demonstrates that the intrinsic nature of the electron excessive pyrrole subunits as well as the effective pi-conjugation over the coplanar heterole rings. The sigma(3)-P type 2,5-bis(5-phenylpyrrol-2-yl)phosphole underwent complexation with AuCl(SMe2) and PtCl2 to yield the respective AuCl-monophosphine and PtCl2-bisphosphine complexes. In the square planar Pt-II complex, the pyrrolic NH protons were found to form intramolecular hydrogen bonds with the chlorine atoms that gave rise to symmetrically split, parallel pi-chromophores linked by two Pt-P bonds. Density functional theory calculations on a Pt-II model complex suggested that this cooperative interaction induces a significant split of the original LUMOs of the symmetrical pi-conjugated ligands. (C) 2010 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.

    DOI: 10.1016/j.crci.2010.03.017

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  • Synthesis of α,α’-Linked Oligophospholes and Polyphospholes by Using Pd–CuI-Promoted Stille-Type Coupling 査読

    Arihiro Saito, Yoshihiro Matano, Hiroshi Imahori

    Organic Letters12 ( 11 ) 2675 - 2677   2010年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1021/ol100926q

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

    Takashi Nakabuchi, Yoshihiro Matano, Hiroshi Imahori

    Organic Letters12 ( 5 ) 1112 - 1115   2010年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    (Figure Presented) P,X,N2-type phosphaporphyrins and phosphacalixphyrins (X = N, S) bearing a perfluorophenyl (C6F 5) group at the core phosphorus atom were prepared In high overall yield from 1-perfluorophenyl-2,5-di(ethoxycarbonyl)phosphole as a common starting material. In addition, P-C6F5 P,S 2,N2-type sapphyrin was successfully prepared as the first example of ring-expanded phosphorus-containing porphyrin. © 2010 American Chemical Society.

    DOI: 10.1021/ol100114j

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

    Yoshihiro Matano, Takashi Nakabuchi, Hiroshi Imahori

    PURE AND APPLIED CHEMISTRY82 ( 3 ) 583 - 593   2010年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WALTER DE GRUYTER GMBH  

    Our recent studies on the synthesis, structures, and aromaticity of phosphole-containing porphyrins and their metal complexes are summarized. Core-modified P,X,N-2-porphyrins (X = S, N) are accessible from a sigma(4)-phosphatripyrrane and the corresponding 2,5-difunctionalized heteroles in a few steps. X-ray structural analysis of the sigma(3)-P,N-3 porphyrin revealed that it possesses a slightly distorted 18 pi plane. The phosphorus atom incorporated at the core plays an important role in producing unprecedented reactivity and coordinating ability for the porphyrin ring. The P,N-3 free base reacts with [RhCl(CO)(2)](2) in dichloromethane, ultimately yielding an 18 pi P,N-3-rhodium(III) complex, whereas the P,S,N-2 free base undergoes redox-coupled complexation with zero valent group 10 metals to afford the corresponding P,S,N-2-isophlorin-metal(II) complexes. The aromaticity of the free-base porphyrins and the metal complexes was uncovered based on both experimental and theoretical results. It is of particular interest that the P,S,N-2-isophlorin-metal complexes exhibit only a weak antiaromaticity in terms of the magnetic criterion.

    DOI: 10.1351/PAC-CON-09-08-05

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

    Yoshihiro Matano, Masato Fujita, Tooru Miyajima, Hiroshi Imahori

    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS185 ( 5-6 ) 1098 - 1107   2010年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:TAYLOR & FRANCIS LTD  

    The synthesis, structure, and electrochemical/optical properties of the zinc complexes of 5,10-porphodimethene-type thiophene-containing (S,N3-) and phosphole-containing (P,N3-) calixphyrins are reported. The S,N3- and P,N3-calixphyrin free bases react with zinc(II) salts to give the corresponding zinc complexes in good yields. The S,N3-calixphyrin-ZnI complex adopts a distorted square pyramidal geometry, with the S and N atoms at the basal positions. The S,N3-calixphyrin-ZnX complexes emit red fluorescence with fluorescent quantum yields up to 23%, whereas the P,N3-calixphyrin-ZnCl complex is weakly fluorescent. Among the first-row transition metals (Fe2+, Cu2+, and Zn2+) examined, the chelation-enhanced fluorescence is observed specifically for the Zn2+ ion. These results indicate that the 5,10-porphodimethene-type S,N3-hybrid calixphyrin is a promising turn-on fluorescent probe for Zn2+ sensing.

    DOI: 10.1080/10426501003773431

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

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

    The Journal of Organic Chemistry75 ( 2 ) 375 - 389   2010年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/jo902060b

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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 査読

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

    Chemistry Letters39 ( 5 ) 448 - 450   2010年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    An oligothiophene bearing l-hydroxy-l-oxodithieno[2,3-b:3′,2′- d]phosphole (TP) as a novel anchoring group has been synthesized for dye-sensitized solar cells (DSSC). Attenuated total reflectance-Fourier transform infrared and X-ray photoelectron spectroscopy measurements disclosed the bidentate binding of the phosphinic acid unit to a TiO2 surface. A TPsensitized TiO2 cell yielded a maximum incident photon-tocurrent efficiency of 66% and a power conversion efficiency of 1.8%, indicating that 1-hydroxy-1-oxodithienophosphole is a potential unit as a new type of anchoring groups for DSSC. © 2010 The Chemical Society of Japan.

    DOI: 10.1246/cl.2010.448

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  • Acenaphtho[1,2-c]phosphole P–Oxide: Phosphole–Naphthalene π-Conjugated System with High Electron Mobility 査読

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

    Chemistry, A European Journal15 ( 39 ) 10000 - 10004   2009年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/chem.200901378

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

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

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY131 ( 31 ) 10955 - 10963   2009年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The palladium complex of P,S-containing hybrid calixphyrin 1 was investigated with the DFT method. There are two kinds of valence tautomer in 1: one is a Pd(II) form in which the calixphyrin moiety possesses -2 charges and the Pd center takes +2 oxidation state, and the other is a Pd(0) form in which the calixphyrin is neutral and the Pd center takes zero oxidation state. Complex 1 takes the Pd(II) form in the ground state. Though the Pd center takes +2 oxidation state, DFT computations clearly show that the oxidative addition of phenyl bromide (PhBr) to 1 occurs with moderate activation enthalpy, as experimentally proposed. The first step of the oxidative addition is the coordination of PhBr with the Pd center to form intermediate 1INTa, in which the Pd center and the calixphyrin moiety are neutral; in other words, the valence tautomerization from the Pd(II) form to the Pd(0) form occurs in the palladium calixphyrin moiety. The activation enthalpy is 22.5 kcal/mol, and the enthalpy change of reaction is 20.3 kcal/mol. The next step is the C-Br sigma-bond cleavage of PhBr, which occurs with activation enthalpy of 2.0 kcal/mol relative to 1INTa. On the other hand, the oxidative additions of PhBr to palladium complex of P,S-containing hybrid porphyrin 2 and that of conventional porphyrin 3 need much larger activation enthalpies of 49.1 and 74.4 kcal/mol, respectively. The differences in the reactivity among 1, 2, and 3 were theoretically investigated; in 1, the valence tautomerization occurs with moderate activation enthalpy to afford the Pd(0) form which is reactive for the oxidative addition. In 2, the tautomerization from the Pd(II) form to the Pd(0) form needs very large activation enthalpy (43.3 kcal/mol). In 3, such valence tautomerization does not occur at all, indicating that the Pd(II) must change to the Pd(IV) in the oxidative addition of PhBr to 3, which is a very difficult process. These differences are interpreted in terms of the pi* orbital energies of P,S-containing hybrid calixphyrin, hybrid porphyrin, and conventional porphyrin and the flexibility of their frameworks.

    DOI: 10.1021/ja901166a

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  • Supramolecular donor-acceptor heterojunctions by vectorial stepwise assembly of porphyrins and coordination-bonded fullerene arrays for photocurrent generation 査読

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

    Journal of the American Chemical Society131 ( 9 ) 3198 - 3200   2009年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    A novel strategy for constructing a vertical arrangement of bicontinuous donor-acceptor arrays on a semiconducting electrode has been developed. The relationship between the film structure and the photoelectrochemical properties has been elucidated as a function of the number of donor layers for the first time. The maximum incident photon-to-current efficiency value (21%) is comparable to the highest value (20%) reported for vertical arrangements of bicontinuous donor-acceptor arrays on electrodes. Copyright © 2009 American Chemical Society.

    DOI: 10.1021/ja8096465

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

    Yoshihiro Matano, Makoto Nakashima, Hiroshi Imahori

    Angewandte Chemie International Edition48 ( 22 ) 4002 - 4005   2009年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/anie.200900542

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  • Meso-Substituent Effects on Redox Properties of the 5,10-Porphodimethene-type P,S,N2-Hybrid Calixphyrins and Their Metal Complexes 査読

    Yoshihiro Matano, Masato Fujita, Tooru Miyajima, Hiroshi Imahori

    Organometallics28 ( 21 ) 6213 - 6217   2009年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om900745t

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  • Phosphole-Containing Calixpyrroles, Calilxphyrins, and Porphyrins: Synthesis and Coordination Chemistry 査読

    Yoshihiro Matano, Hiroshi Imahori

    Accounts of Chemical Research42 ( 8 ) 1193 - 1204   2009年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ar900075e

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

    Yoshihiro Matano, Makoto Nakashima, Arihiro Saito, Hiroshi Imahori

    Organic Letters11 ( 15 ) 3338 - 3341   2009年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ol901194m

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

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

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN81 ( 12 ) 1621 - 1628   2008年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:CHEMICAL SOC JAPAN  

    Substituent effects on the oxidizing ability of tetraarylbismuthonium tetrafluoroborates in alcohol oxidation are reported. Intermolecular and intramolecular competition experiments on geraniol oxidation by the combined use of tetraarylbismuthonium tetrafluoroborates and N,N,N',N'-tetrai-netramethylguanidine (TMG) have revealed that the oxidizing ability of the bismuthonium salt increases by the introduction of methyl groups at the ortho position and an electron-withdrawing group at the para position of the aryl ligands. The intermolecular and intramolecular H/D kinetic isotope effects observed for the competitive oxidation of p-bromobenzyl alcohols have shown that the present oxidation reaction consists of fast pre-equilibrium leading to alkoxytetraarylbismuth(V) intermediates (first step) and alpha-hydrogen abstraction by the aryl ligand attached to the bismuth (second step). The experimental results demonstrate that the electron-deficient aryl ligands enhance the electrophilicity at the bismuth center to put forward the first step and that the bulky ligands destabilize the alkoxybismuth(V) intermediates to accelerate the second step. The newly explored mesityl- and 2,6-xylyltriarylbismuthonium salts have proven to convert primary and secondary alcohols to the corresponding carbonyl compounds with high efficiency under mild conditions. A remark-able steric effect of these oxidants has also been exhibited in the chemoselective oxidation between primary and secondary benzylic alcohols.

    DOI: 10.1246/bcsj.81.1621

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

    Takashi Nakabuchi, Yoshihiro Matano, Hiroshi Imahori

    ORGANOMETALLICS27 ( 13 ) 3142 - 3152   2008年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Symmetric and asymmetric hybrid calixpyrroles containing a sigma(4)-phosphole or sigma(4)-2,3-dihydrophosphole unit (symmetric and asymmetric sigma(4)-P,N(2),X-hybrids: X = S, O) were prepared by using acid-promoted condensation reactions of the corresponding sigma(4)-phosphatripyrranes with 2,5-bis(1-hydroxy-1-methylethyl)heteroles. The X-ray crystallographic analyses of the symmetric and asymmetric sigma(4)-P,N(2),X-hybrids show that the cavity sizes of the sigma-P,N(2),S-hybrids are larger than those of the sigma(4)-P,N(2),O-hybrids, mainly reflecting the difference in edge-to-edge distances of the thiophene and furan rings. The symmetric sigma(4)-P,N(2),X-hybrids and the asymmetric sigma(4)-P,N(2),S-hybrid were successfully converted to the corresponding sigma(3) forms by reductive desulfurization at the phosphorus center. Each of the symmetric sigma(3)-P,N(2),X-hybrids was obtained as a mixture of two conformers, where the lone pair of the phosphorus atom is located inside (in) and outside (out) the cavity. The interconversion between the in and out type conformers of the asymmetric sigma(3)-P,N(2),S-hybrid was sufficiently slow to isolate each of them. The complexation reactions of the symmetric sigma(3)-P,N(2),S-hybrid with Au(I), Pt(II), and Pd(II) ions afforded both of the in and out type complexes, where the in type complexes were the thermodynamically favored products. In the complexation reactions of the asymmetric sigma(3)-P,N(2), S-hybrids, the stereochemistry at the phosphorus center was retained to give the in or out type complex exclusively. In the in-in type trans-M(II)-bis(phosphine) complexes (M = Pt, Pd) derived from the symmetric and asymmetric sigma(3)-P,N(2),S-hybrids, the M-Cl fragment is bound above the cavities of the two macrocycles. The crystal structures and the (1)H NMR spectra of these M(II) complexes reveal that the P,N(2),S-hybrid calixpyrroles bind the M-Cl fragments through P-M coordination and cooperative NH-Cl hydrogen-bonding interactions.

    DOI: 10.1021/om800099h

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

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

    JOURNAL OF ORGANIC CHEMISTRY73 ( 13 ) 5139 - 5142   2008年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    The synthesis, structure, and optical and electrochemical properties of thiophene-containing hybrid calixphyrins are reported. The 5,10-porphodimethene type 14 pi- and 16 pi-S,N(2),X-hybrid calixphyrins (X = NH, O, S) were prepared by acid-promoted dehydrative condensation between a thiatripyrrane and the corresponding 2,5-bis[hydroxy(phenyl)methyl]heteroles followed by DDQ oxidation. Both crystallographic and spectroscopic analyses of the newly prepared hybrid calixphyrins have revealed that the combination of heteroles explicitly influences the electronic structures of the pi-conjugated framework. The 14 pi-S,N(2),X-hybrid calixphyrins have proven to be fluorescent in solution.

    DOI: 10.1021/jo800532n

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

    Yoshihiro Matano, Tomonori Shinokura, Osamu Yoshikawa, Hiroshi Imahori

    ORGANIC LETTERS10 ( 11 ) 2167 - 2170   2008年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    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 cationic polymerization of oxiranes and a vinyl ether, affording the corresponding polymers in good yields within 1 min.

    DOI: 10.1021/ol8005453

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

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

    Journal of Physical Chemistry C112 ( 11 ) 4396 - 4405   2008年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    5,10,15,20-Tetrakis(2,4,6-trimethylphenyl)-6′-carboxyquinoxalino[2, 3-β]porphyrinatozinc (II) (ZnQMA) and 5,10,15,20-tetrakis(2,4,6- trimethylphenyl)-6′,7′-dicarboxyquinoxalino[2,3-β] porphyrinatozinc (II) (ZnQDA) have been synthesized to evaluate the effects of β,β′-carboxyquinoxalino moieties on the structure and optical, electrochemical, and photovoltaic properties of the porphyrins. Both ZnQMA and ZnQDA exhibited broadened and red-shifted light absorption in UV-visible absorption spectra compared with 5,10,15,20-tetrakis(2,4,6-trimethylphenyl) porphyrinatozinc (II) (ZnP). ZnQMA and ZnQDA also showed decrease in the highest occupied molecular orbital-lowest unoccupied molecular orbital (HOMO-LUMO) gap due to the extension of the porphyrin π-system. From the results of 1H NMR spectroscopy and DFT calculations, ZnQMA and ZnQDA were found to adopt saddle and planar structures, respectively. ZnQMA-sensitized TiO 2 solar cell with TiO2 nanoparticles (P25) revealed the power conversion efficiency (η) of 5.2%, whereas ZnQDA-sensitized cell showed η = 4.0%. The superior performance of the ZnQMA-sensitized solar cell to the ZnQDA-sensitized one is originated from both the more favorable electron injection and charge collection efficiency. © 2008 American Chemical Society.

    DOI: 10.1021/jp710400p

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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 査読

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

    Journal of the American Chemical Society130 ( 49 ) 16446 - 16447   2008年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ja807742g

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

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

    The Journal of Physical Chemistry B112   16517 - 16524   2008年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/jp807991k

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

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

    CHEMISTRY-A EUROPEAN JOURNAL14 ( 27 ) 8102 - 8115   2008年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Three types of bithiophene-fused benzo[c]phospholes were successfully prepared by Ti(II)-mediated cyclization of the corresponding dialkynylated bithiophene derivatives as a key step. Each sigma(3)-phosphorus center of the benzo[c]phosphole subunits was readily transformed into sigma(4)-phosphorus center by Au coordination or oxygenation. In addition, the bithiophene subunit was functionalized at the alpha,alpha'-carbon atoms by Pd-catalyzed cross-coupling reactions with heteroarylmetals and by an S(N)Ar reaction with hexafluorobenzene. The experimentally observed results (NMR spectroscopy, X-ray analysis, UV/Vis absorption/fluorescence spectroscopy, and cyclic/differential-pulse voltammetry) have revealed that the structural, optical, and electrochemical properties of the bithiophene-fused benzo[c]phospholes vary considerably depending on the pi-conjugation modes at the bithiophene subunits and the substituents of the heterocyclopentadiene components. The appropriately ring-annulated sigma(3)-P derivatives and sigma(4)-P-AuCl complexes were found to emit fluorescence in the orange-red region, and the sigma(4)-P-oxo derivatives proved to undergo reversible one-electron reduction at -1.4 to -1.8V (vs ferrocene/ferrocenium). These results indicate that the bithiophene-fused benzo[c]phospholes possess narrow HOMO-LUMO gaps and low-lying LUMOs, which was confirmed by density functional theory calculations of their model compounds. The time-of-flight measurement of an ITO/benzo[c]phosphole/Al device showed that the electron mobility in the P-oxo derivative is one-order higher than that in Alq(3) at low electric fields. The present study demonstrates that the arene-fused benzo[c]phosphole skeleton could be a highly promising platform for the construction of a new class of phosphole-based optoelectrochemical materials.

    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 査読

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

    Journal of the American Chemical Society130 ( 14 ) 4588 - 4589   2008年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ja710542e

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  • Monophosohaporphyrins: Oxidative π-Extension at the Peripherally-Fused Carbocycle of the Phosphaporphyrin Ring 査読

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

    Organic Letters10 ( 4 ) 553 - 556   2008年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ol7029118

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  • Syntheses, Structures, and Coordination Chemistry of Phosphole-Containing Hybrid Calixphyrins: Promising Macrocyclic P,N2,X-Mixed Donor Ligands for Designing Reactive Transition Metal Complexes 査読

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

    Journal of the American Chemical Society130 ( 3 ) 990 - 1002   2008年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ja076709o

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  • Bithiophene-Fused Benzo[c]phospholes: Novel P,S-Containing Hybrid π-Conjugated Systems with Small HOMO–LUMO Energy Gaps 査読

    Tooru Miyajima, Yoshihiro Matano, Hiroshi Imahori

    European Journal of Organic Chemistry2008 ( 2 ) 255 - 259   2008年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/ejoc.200701008

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

    Yoshihiro Matano, Takeshi Suzuki, Torrionori Shinokura, Hiroshi Imahori

    TETRAHEDRON LETTERS48 ( 16 ) 2885 - 2888   2007年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    In the presence of N,N,N',N'-tetramethylguanidine, mesityltriphenylbismuthonium tetrafluoroborate oxidizes primary and secondary alcohols to aldehydes and ketones, respectively, under mild conditions. In this reaction, the mesityl ligand exclusively abstracts an alpha-hydrogen to afford mesitylene and triphenylbismuthane as side products. A remarkable steric effect has also been exhibited in the chemoselective oxidation between primary and secondary alcohols. (c) 2007 Elsevier Ltd. All rights reserved.

    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 査読

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

    Journal of Physical Chemistry C111 ( 8 ) 3528 - 3537   2007年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    Novel 5-(5-carboxy-2-thienyl)-10,15,20-tris(2,4,6-trimethylphenyl)- porphyrinatozinc(II) (Zn5S), 5-(5-carboxy-2-furyl)-10,15,20-tris(2,4,6- trimethylphenyl)porphyrinatozinc(II) (Zn5O), and 5-(4-carboxy-2-thieny 1)-10,15,-20-tris(2,4,6-trimethylphenyl)porphyrinatozinc(II) (Zn4S) were synthesized to evaluate the spacer effects on the structures of the porphyrin films and the photovoltaic properties of the porphyrin-sensitized TiO 2 solar cells. Each of the porphyrins showed different adsorption behavior and saturated coverage on the TiO2 surface and photovoltaic properties depending on the identity of heteroatoms in the bridge and the position of carboxylic acid. Specifically, Zn5S-sensitized TiO2 cell displayed larger, maximum incident photon-to-current efficiency of 65% and maximum power conversion efficiency of 3.1% than Zn5O-sensitized TiO2 cell by ∼20% and ∼ 40%, respectively. We interpret that these results are stemmed from ancillary electron-transfer pathway through specific interaction between a sulfur atom in the bridge of Zn5S and the TiO2 surface. Optical spectroscopy, attenuated total reflectance-Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, density functional theory calculations, and photovoltaic measurements under standard AM 1.5 conditions were employed to support our proposal. © 2007 American Chemical Society.

    DOI: 10.1021/jp067290b

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

    Yuki Shibano, Tomokazu Umeyama, Yoshihiro Matano, Hiroshi Imahori

    Organic Letters9 ( 10 ) 1971 - 1974   2007年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ol070556s

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  • Synthesis and Aggregation Behavior of meso-Sulfinylporphyrins: Evaluation of the S-Chirality Effects on the Self-Organization to S–Oxo-Tethered Cofacial Porphyrin Dimers 査読

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

    Chemistry, An Asian Journal2 ( 11 ) 1417 - 1429   2007年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1002/asia.200700191

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  • Synthesis of 2-Aryl-5-styrylphospholes: Promising Candidates for the Phosphole-based NLO Chromophores 査読

    Yoshihiro Matano, Tooru Miyajima, Hiroshi Imahori, Yoshifumi Kimura

    The Journal of Organic Chemistry72 ( 16 ) 6200 - 6205   2007年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/jo070822f

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  • Synthesis, Structures, and Properties of Meso-Phosphorylporphyrins. Self-assembly through P–oxo-to-Zinc Coordination 査読

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

    Chemistry, A European Journal13 ( 3 ) 891 - 901   2007年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1002/chem.200600835

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  • Synthesis of a phosphorus-containing hybrid porphyrin 査読

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

    ORGANIC LETTERS8 ( 25 ) 5713 - 5716   2006年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    A phosphorus-containing hybrid porphyrin was successfully prepared via the BF3-promoted dehydrative condensation between sigma(4)-phosphatripyrrane and 2,5-bis[hydroxy(phenyl)methyl]thiophene. The NMR and UV-vis absorption spectra, electrochemical measurements, and DFT calculations revealed that the sigma(3)-P,N-2,S-hybrid porphyrin exhibits high aromaticity as an 18 pi-electron system in terms of both geometric and magnetic criteria.

    DOI: 10.1021/ol622763

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

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

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY128 ( 36 ) 11760 - 11761   2006年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/ja0640039

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

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

    JOURNAL OF ORGANIC CHEMISTRY71 ( 15 ) 5792 - 5795   2006年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Symmetrically and unsymmetrically 2,5-difunctionalized phospholes bearing ester groups were prepared in a one-pot procedure from the corresponding diynes and dichloro-(phenyl) phosphine via titanacyclopentadienes. The observed optical properties of the functionalized phospholes show that the pi-conjugative push-pull interaction between the 2- and 5-substituents plays an important role in controlling the light-emitting efficiency.

    DOI: 10.1021/jo0605748

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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 査読

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

    TETRAHEDRON62 ( 9 ) 1955 - 1966   2006年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Structure and photoelectrochemical properties of nanostructured SnO(2) electrodes deposited electrophoretically with the composite clusters of porphyrin-modified gold nanoparticle with a long, flexible spacer and C(60) molecules have been examined to obtain basic information on the development of organic solar cells with a high performance. The photoelectrochemical system with the long, flexible spacer between the porphyrin and the gold nanoparticle in the porphyrin-modified gold nanoparticle exhibited comparable external quantum yield in the UV-vis regions relative to porphyrin-modified gold nanoparticle with a relatively short spacer-C(60) Composite reference system. These results demonstrate that a suitable spacer to incorporate C(60) molecules efficiently between the porphyrins in porphyrin-modified gold nanoparticles is a prerequisite for improving the performance of porphyrin and fullerene-based organic solar cells. (c) 2005 Elsevier Ltd. All rights reserved.

    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 査読

    Hiroshi Imahori, Keigo Mitamura, Tomokazu Umeyama, Kohei Hosomizu, Yoshihiro Matano, Kaname Yoshida, Seiji Isoda

    Chemical Communications ( 4 ) 406 - 408   2006年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry  

    DOI: 10.1039/b513707a

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  • Phosphole-Containing Hybrid Calixpyrroles: New Multifunctional Macrocyclic Ligands for Platinum(II) Ions 査読

    Yoshihiro Matano, Takashi Nakabuchi, Tooru Miyajima, Hiroshi Imahori

    Organometallics25 ( 13 ) 3105 - 3107   2006年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om060300a

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  • Synthesis and Photophysical Properties of Electron-Rich Perylenediimide-Fullerene Dyad 査読

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

    Organic Letters8 ( 20 ) 4425 - 4428   2006年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ol061506a

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

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

    Langmuir22 ( 12 ) 5497 - 5503   2006年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/la0533314

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

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

    Advanced Materials17 ( 14 ) 1727 - 1730   2005年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    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 査読

    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 B109 ( 39 ) 18465 - 18474   2005年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    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 査読

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

    The Journal of Physical Chemistry B109 ( 12 ) 5700 - 5706   2005年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    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 査読

    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 Journal11 ( 24 ) 7265 - 7275   2005年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    DOI: 10.1002/chem.200500610

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

    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年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    A hydrogen bonding effect on photocurrent generation has been evaluated successfully in a mixed film of porphyrin and fullerene with hydrogen bonding on an ITO electrode, which exhibits efficient cathodic photocurrent generation as compared to the reference system without hydrogen bonding.

    DOI: 10.1039/b404690k

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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 査読

    Hiroshi Imahori, Kohei Hosomizu, Yukie Mori, Tomoo Sato, Tae Kyu Ahn, Seong Keum Kim, Dongho Kim, Yoshinobu Nishimura, Iwao Yamazaki, Hirotake Ishii, Hiroki Hotta, Yoshihiro Matano

    The Journal of Physical Chemistry B108 ( 16 ) 5018 - 5025   2004年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/jp037625e

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  • Remarkable Substituent Effects on the Oxidizing Ability of Triarylbismuth Dichlorides in Alcohol Oxidation 査読

    Yoshihiro Matano, Teppei Hisanaga, Hisatsugu Yamada, Shingo Kusakabe, Hazumi Nomura, Hiroshi Imahori

    The Journal of Organic Chemistry69 ( 25 ) 8676 - 8680   2004年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/jo0485740

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  • Diverse Structures and Remarkable Oxidizing Ability of Triarylbismuthane Oxides. A Comparative Study on the Structure and Reactivity of a Series of Triarylpnictogen Oxides 査読

    Yoshihiro Matano, Hazumi Nomura, Teppei Hisanaga, Haruyuki Nakano, Motoo Shiro, Hiroshi Imahori

    Organometallics23 ( 23 ) 5471 - 5480   2004年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om0494115

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  • A New Efficient Method for Direct α-Alkenylation of β-Dicarbonyl Compounds and Phenols Using Alkenyltriarylbismuthonium Salts 査読

    Yoshihiro Matano, Hiroshi Imahori

    The Journal of Organic Chemistry69 ( 16 ) 5505 - 5508   2004年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/jo0492721

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

    Yoshihiro Matano, Hazumi Nomura, Hitomi Suzuki

    Inorganic Chemistry41 ( 7 ) 1940 - 1948   2002年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    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 査読

    Yoshihiro Matano, Hazumi Nomura

    Angewandte Chemie International Edition41 ( 16 ) 3028 - 3031   2002年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

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

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  • New Syntheses of Bismuthonium Salts, Bismuthonium Ylides and Bismuthane Imides Using Triarylbismuth(V)–Oxo and –Hydroxo Compounds 査読

    Yoshihiro Matano, Hazumi Nomura

    Synthesis ( 5 ) 631 - 634   2002年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Thieme  

    DOI: 10.1055/s-2002-23536

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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 査読

    Yoshihiro Matano, Shameem A. Begum, Hitomi Suzuki

    Synthesis ( 7 ) 1081 - 1083   2001年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Thieme  

    DOI: 10.1055/s-2001-14565

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  • Synthesis, Structure, and Reactions of (Acylimino)triaryl-λ5-bismuthanes: The First Comparative Study of the Acyliminopnictorane Series 査読

    Yoshihiro Matano, Hazumi Nomura, Hitomi Suzuki, Motoo Shiro, Haruyuki Nakano

    Journal of the American Chemical Society123 ( 44 ) 10954 - 10965   2001年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ja003623l

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

    Yoshihiro Matano, Hazumi Nomura

    Journal of the American Chemical Society123 ( 26 ) 6443 - 6444   2001年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ja010584k

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

    Y Matano, H Nomura, H Suzuki

    JOURNAL OF ORGANOMETALLIC CHEMISTRY611 ( 1-2 ) 89 - 99   2000年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE SA  

    The reaction of iminotriaryl-lambda(5)-bismuthanes (2; Ar3Bi=NR; R = COR " or SO2R ") with dialkyl acetylenedicarboxylates (3; R'O2CC=CCO2R') has been found to afford highly stabilized bismuthortium ylides (4; Ar3Bi=C(CO2R')-C(CO2R')=NR) in 50-92% yield. The X-ray crystallographic analyses of two of these ylides demonstrated that their bismuth center possesses a distorted tetrahedral geometry with the highly cross-conjugated ylidic carbon atom. The observed Bi-C-ylide bond lengths of 2.178(7)-2.199(7) Angstrom are close to ordinary Bi-C-Ar bond lengths, suggesting an appreciable single bond character of the Bi-C-ylide bond. The action of two equivalents of acetic acid, hydrogen chloride, or 4-nitrophenol on 4 cleaved the Bi-C-ylide bond to give the corresponding triarylbismuth(V) compounds of the type Ar3BiX2 and olefins (5; R'O2CCH=C(CO2R')NHR). 4-Nitrobenzenethiol was oxidized by 0.5 equivalents of 4 to give bis(4-nitrophenyl) disulfide with a good recovery of triarylbismuthane 6 and olefin 5. On thermolysis at 200 degrees C, or when decomposed in the presence of a copper catalyst at room temperature, the ylides 4 bearing an N-aroyl group gave 2,4,5-trisubstituted oxazoles 7 and triarylbismuthanes 6 in moderate to excellent yields. (C) 2000 Elsevier Science S.A. All rights reserved.

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

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  • Synthesis and First X-ray Structural Analysis of Monomeric Imino-λ5-stibanes 査読

    Yoshihiro Matano, Hazumi Nomura, Hitomi Suzuki

    Inorganic Chemistry39 ( 7 ) 1340 - 1341   2000年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/ic991120e

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  • First Synthesis of Alkynyltriphenylbismuthonium Salts and their Dual Reaction Modes in Sulfonylation 査読

    Yoshihiro Matano

    Chemical Communications   2233 - 2234   2000年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry  

    DOI: 10.1039/b006881k

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  • Tp* Rhenium(V) Oxo–Halide, –Hydride, –Alkyl, –Phenyl, and –Alkoxide Complexes: Syntheses and Oxidations 査読

    Yoshihiro Matano, Todd, O. Northcutt, Johanna Brugman, Brian K. Bennett, Scott Lovell, James M. Mayer

    Organometallics19 ( 14 ) 2781 - 2790   2000年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om000133t

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  • Synthesis, Structure, and Reactions of Triaryl(methyl)bismuthonium Salts 査読

    Yoshihiro Matano

    Organometallics19   2258 - 2263   2000年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om000095d

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

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

    JOURNAL OF ORGANOMETALLIC CHEMISTRY591 ( 1-2 ) 96 - 103   1999年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ELSEVIER SCIENCE SA  

    Cyclic voltammetry has been used to study the electrochemical properties of 29 isoelectronic and isostructural osmium(VI)-nitrido, rhenium(lr)-oxo, and rhenium(V)-imido complexes of the form Tp(()*M-)(E)(X)(Y) [Tp(()*()) = Tp, HB(pz)(3); or Tp*, HB(3,5-Me(2)pz)(3)]. Oxidations from d(2) to d(1) species are typically reversible or quasi-reversible, while reductions to d(3) species are usually irreversible. The E-1/2 values for oxidation vary from &gt; + 2 V for TpOs(N)(Cl)(2) to - 0.11 V for TpRe(Ntolyl)(Ph)(Me) (vs. Cp2Fe+ , 0 in MeCN/(Bu4NPF6)-Bu-n). The potentials follow simple trends, Os(N) &gt; Re(O) &gt; Re(Ntolyl) and Tp &gt; Tp*. Potentials for TpM(E)(X)(Y) are also affected by the X and Y ligands, with OTf &gt; Cl congruent to I &gt; Ph &gt; alkyl, correlating with the Hammett a values for X and Y. In contrast, peak potentials for reduction of the compounds (ca. - 1.0 to - 1.5 V) do not follow simple patterns. The reactivity of these complexes as inner-sphere oxidants does not correlate with their peak reduction potentials. Rather. the ease of oxidation of the compounds better parallels their reactivity as oxidants. (C) 1999 Elsevier Science S.A. All rights reserved.

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

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  • An Alternative Ring Expansion Mode of Acenaphthenequinone to Hydroxyphenalenone 査読

    M. Mizanur Rahman, Yoshihiro Matano, Hitomi Suzuki

    Synthesis1999 ( 3 ) 395 - 397   1999年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Thieme  

    DOI: 10.1055/s-1999-3407

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

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

    The Journal of Organic Chemistry64 ( 18 ) 6924 - 6927   1999年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/jo990690t

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

    Yoshihiro Matano, Hazumi Nomura, Motoo Shiro, Hitomi Suzuki

    Organometallics18 ( 14 ) 2580 - 2582   1999年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om990252c

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  • Reactions of Triphenylbismuthonium 2-Oxoalkylides with 1,2-Dicarbonyl Compounds

    M. Mizanur Rahman, Yoshihiro Matano, Hitomi Suzuki

    Journal of the Chemical Society, Perkin Transactions 1 ( 24 ) 1533 - 1542   1999年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry  

    DOI: 10.1039/A900751B

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

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

    Inorganic Chemistry38 ( 14 ) 3309 - 3312   1999年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    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 査読

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

    Organometallics18 ( 18 ) 3715 - 3727   1999年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om980914i

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  • Synthesis and Stereochemical Behaviors of Unsymmetrical Tetraarylbismuthonium Salts 査読

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

    Organometallics18   5668 - 5681   1999年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om990597v

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

    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年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    The synthesis and properties of some new water-soluble non-ionic triarylbismuthanes are described. o-, m- and p-Tris(methoxymethoxyphenyl)bismuthanes 1a-c are prepared from BiCl3 and the corresponding organolithium or Grignard reagents. Oxidative chlorination of 1a-c with SO2Cl2 affords tris(methoxymethoxyphenyl)bismuth dichlorides 2a-c, which are deprotected by aqueous HCl to give tris(hydroxyphenyl)bismuth dichlorides 3a-c. Treatment of tris(3-hydroxyphenyl)bismuth dichloride 3b with NH2NH2 yields tris(3-hydroxyphenyl)bismuthane 5, which dissolves in dilute aqueous NaOH. N,N-Bis(2-tert-butyl-dimethylsiloxyethyl)benzenesulfonainide, prepared from benzenesulfonyl chloride and silyl-protected diethanolamine, is ortho-lithiated and reacted with 1/3 equiv. of BiCl3 to give Ar3Bi 9a {Ar = 2-[N,N-bis-(2-tert-butyldimethylsiloxyethyl)sulfamoyl]phenyl}. m-Phenylene-bridged Bi-2- and Bi-3-polybismuthanes 12 and 13 are prepared by the reaction between ortho-lithiated 9a and Ar2BiI 10, Desilylation of 9a, 12 and 13 by Bu4NF or p-TsOH . H2O in EtOH leads to the corresponding bismuthanepolyols 11, 14 and 15, The reaction between benzene-1,3-disulfonamide 16 bearing the silyl-protected bis(2-hydroxyethyl)amino side chains and 1/3 equiv. of BiCl3 affords tris{2,4-bis[N,N-bis(2-tert-butyldimethylsiloxyethyl)sulfamoyl]phenyl}bismuthane 17, which is deprotected by p-TsOH . H2O to yield tris{2,4-bis[N,N-bis(2-hydroxyethyl)sulfamoyl]phenyl}bismuthane 18, Compounds 11, 14 and 15 are only slightly soluble in water, but compound 18 is fairly soluble.

    DOI: 10.1039/A803946A

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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 査読

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

    Organometallics17 ( 20 ) 4332 - 4334   1998年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    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 査読

    Yoshihiro Matano, Takashi Miyamatsu, Hitomi Suzuki

    Chemistry Letters27 ( 2 ) 127 - 128   1998年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    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 査読

    M. Mizanur Rahman, Yoshihiro Matano, Hitomi Suzuki

    Chemical Communications ( 13 ) 1359 - 1360   1998年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry  

    DOI: 10.1039/a801879k

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  • Synthesis and Reactions of Rhenium(V) Oxo-Hydride Complexes 査読

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

    Organometallics17 ( 14 ) 2939 - 2941   1998年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om980184e

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

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

    Organometallics17 ( 18 ) 4049 - 4059   1998年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    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 査読

    M. Mizanur Rahman, Yoshihiro Matano, Hitomi Suzuki

    Organometallics16 ( 15 ) 3565 - 3568   1997年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om9701377

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  • First Synthesis and Properties of Dendritic Bin-Bismuthanes 査読

    Hitomi Suzuki, Haruto Kurata, Yoshihiro Matano

    Chemical Communications ( 23 ) 2295 - 2296   1997年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry  

    DOI: 10.1039/a706338e

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

    Y Matano, M Yoshimune, N Azuma, H Suzuki

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ( 16 ) 1971 - 1977   1996年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Treatment of triphenylbismuth difluoride with alkenyltrimethylsilanes 1 or trimethylsilyl cyanide-alkenyltrialkylstannanes 3 in the presence of boron trifluoride-diethyl ether gave the corresponding alkenyltriphenylbismuthonium tetrafluoroborates 2 in moderate to good yields, An X-ray crystallographic analysis of the salt 2e confirmed the distorted tetrahedral geometry of the central bismuth atom, When treated with a sulfinate 5 or the thiolate 11, the salts 2 readily transferred both the vinyl and phenyl moieties to these nucleophiles to afford the sulfones 7-10 or the sulfides 12, 13, respectively, In the presence of a palladium catalyst, the salt 2e underwent the Heck-type reaction with ethyl acrylate 17 to afford the dienoate 18 and cinnamate 19 in moderate yields, Action of KOBu(t) on the salt 2b yielded p-tolylacetylene 22, while a similar reaction with the salt 2e in the presence of the styrenes 23 gave the cyclopropanes 24, A Hammett study of the latter reaction has suggested a possible involvement of an alkylidenecarbene as the intermediate in these base-promoted reactions.

    DOI: 10.1039/P19960001971

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  • A New General Method for the Preparation of Unsymmetrical Telluronium Salts 査読

    Yoshihiro Matano, Hitomi Suzuki, Nagao Azuma

    Organometallics15 ( 17 ) 3760 - 3765   1996年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/om960320k

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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 査読

    Yoshihiro Matano, Takashi Miyamatsu, Hitomi Suzuki

    Organometallics15 ( 7 ) 1951 - 1953   1996年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    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 査読

    Yoshihiro Matano, Hitomi Suzuki

    Chemical Communications ( 24 ) 2697 - 2698   1996年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Royal Society of Chemistry  

    DOI: 10.1039/cc9960002697

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  • A New Aspect of Organobismuth Chemistry: Synthesis, Properties, and Reactions of Bismuthonium Compounds 査読

    Yoshihiro Matano, Hitomi Suzuki

    Bulletin of the Chemical Society of Japan69 ( 10 ) 2673 - 2681   1996年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    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 査読

    Y MATANO, M YOSHIMUNE, H SUZUKI

    TETRAHEDRON LETTERS36 ( 41 ) 7475 - 7478   1995年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Reaction of triarylbismuth difluorides 1 with allyltrimethylsilane 2 in CH2Cl2 in the presence of BF3 . OEt(2) at low temperature generates allyltriarylbismuthonium compound 3 as a pale yellow solution, in which aromatic hydrocarbons and ethers, triphenylphosphine, dimethyl sulfide, p-toluenesulfinate, and thiophenol are all readily allylated to afford the corresponding allyl derivatives in moderate to good yields.

    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 査読

    Y MATANO, N AZUMA, H SUZUKI

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ( 20 ) 2543 - 2549   1995年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Treatment of triarylbismuth difluorides 2 with siloxycyclopropanes 3 in the presence of trimethylsilyl trifluoromethanesulfonate (triflate) or boron trifluoride-diethyl ether gave the corresponding triaryl(3-oxoalkyl)bismuthonium salts 4 as crystals, X-Ray crystallographic;analysis of the triflate 4a showed that the central bismuth atom has a distorted tetrahedral geometry with weak intramolecular coordination by the oxygen atoms of the carbonyl group and triflate anion, Whilst all onium salts 4 are thermally stable in a solid state, the triflate 4a slowly decomposed in chloroform to give triphenylbismuthane 6 and an ester 7 quantitatively, In nucleophilic solvents such as MeOH, DMSO and DMF, both triflate 4a and tetrafluoroborate 4d underwent decomposition in a complicated way to afford the bismuthane 6, 3-methoxypropanoyl compounds 8a,b, alpha,beta-unsaturated carbonyl compounds 9a,b, diphenylbismuth triflate 10a or tetrafluoroborate 10b and alkoxysulfonium salts 11a,b, The formate 12 was an additional product from 4d in DMF. The bismuthonium salt 4d reacted with dimethyl sulfide 13 and sodium benzenesulfinate 15 to afford the sulfonium salt 14 and the sulfonyl ketone 16, respectively, Reaction of the salt 4d with potassium halides 17 in DMF gave the enone 9b, formate 12 and halogeno ketone 18 in varying yields depending on the nucleophilic nature of the halogen anions employed. When treated with KOBu(t), the salt 4d underwent facile beta-elimination to yield the enone 9b. In all of these reactions, the triphenylbismuthane moiety behaved as a good leaving group.

    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 査読

    Yoshihiro Matano, Masanori Yoshimune, Hitomi Suzuki

    Journal of Organic Chemistry60 ( 14 ) 4663 - 4665   1995年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:American Chemical Society  

    DOI: 10.1021/jo00119a056

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

    Y MATANO

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ( 19 ) 2703 - 2709   1994年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Treatment of (2-oxoalkyl)triphenylbismuthonium tetrafluoroborates 3 with potassium tert-butoxide in tetrahydrofuran at -78 degrees C produced triphenylbismuthonium 2-oxoalkylides 4, which readily underwent epoxidation with the aldehydes 5 to give the alpha,beta-epoxy ketones 7 with high trans selectivity. The ylide 4a reacted with dimedone 11, the sulfonic acid 13, the thiol 15 and the isocyanate 17 to afford the corresponding ketones 12, 14, 16 and 19 in moderate to good yields. Reaction of the ylide 4c with the alpha,beta-unsaturated ketones 10 and 21 afforded the 1,2-dibenzoyl- and the 1,2,3-tribenzoyl- cyclopropanes 20 and 22, respectively, although the yields were low. In the presence of a catalytic amount of-nitrosobenzene 23, the ylide 4a suffered a unique decomposition to give the 2,2,7,7-tetramethyloct-4-ene,3,6-dione 24 in quantitative yield, while the reaction with the nitrile oxide 25 yielded the isoxazoline 26. In all of these reactions, triphenylbismuthane 6 was the additional major product.

    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 査読

    H SUZUKI, T IKEGAMI, Y MATANO

    TETRAHEDRON LETTERS35 ( 44 ) 8197 - 8200   1994年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Reaction of triarylbismuthines 1 with iodosylbenzene in dichloromethane under ultrasonic irradiation leads to the generation of triarylbismuthine oxides 2 as a bright yellow solution, in which activated alcohols are easily oxidized to carbonyl compounds, triphenylphosphine is converted into oxide and hydrazobenzene is rapidly dehydrogenated to azobenzene. Triphenylstibine 8 is similarly oxidized to give stibine oxide 9, which lacks the corresponding oxidizing ability.

    DOI: 10.1016/0040-4039(94)88281-9

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

    Y MATANO, N AZUMA, H SUZUKI

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ( 13 ) 1739 - 1747   1994年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Treatment of triarylbismuth difluorides 1 with silyl enol ethers 2 in the presence of boron trifluoride-diethyl ether or trimethylsilyl trifluoromethanesulfonate (triflate) gave (2-oxoalkyl)triarylbismuthonium tetrafluoroborates. 3 and triflates 4 in good yields. A similar reaction of the difluorides 1 with hexamethyldisiloxane in the presence of the latter acid reagent led to the formation of oxybis(triarylbismuth) ditriflates 5. X-Ray cyrstallographic analyses of compounds 3a, 4a and 5a showed that the first two onium salts have a distorted tetrahedral geometry and the last. a mu-oxo type compound, has a distorted trigonal bipyramidal geometry around the bismuth centre. The stability of these bismuthonium salts may reasonably be attributed to the intramolecular coordinative interaction between the bismuth and oxygen atoms and also low nucleophilicity of the counter ions employed. The bismuthonium salt 3f readily underwent onium exchange with the phosphine 6 and the sulfide 9 to afford the corresponding phosphonium and sulfonium salts 7 and 10. The salts 3 and 4 also underwent coupling with a variety of nucleophiles such as the enolate 11, piperidine 13, the phenoxides 15, the thiolates 17, the sulfinate 19 and the halides 21 to afford the corresponding alpha-substituted ketones 12, 14, 16, 18, 20 and 22 in moderate to good yields, together with a good recovery of triphenylbismuthine 8.

    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 査読

    H SUZUKI, T MURAFUJI, Y MATANO, N AZUMA

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ( 23 ) 2969 - 2973   1993年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Chiral chlorobismuthines 3 stabilized by intramolecular coordination of an NN-dimethylamino group have been synthesized by the selective fluorodearylation of the bismuthines 1 with boron trifluoride-diethyl ether, followed by halogen exchange of the resulting fluorobismuthines 2 with brine. An X-ray crystallographic structure analysis of 3b revealed that the bismuth centre has a distorted pseudotrigonal bipyramidal structure through the formation of a hypervalent 3-centre 4-electron bond with the chlorine and nitrogen atoms at apical positions. H-1 NMR spectra of compounds 3 in CDCl3 at room temperature reflected their fixed conformation in the solid state. Chiral chlorobismuthines 7a and 7b were obtained in a similar manner starting from optically pure (R)-N,N-dimethyl-1-phenylethylamine as a mixture of two diastereoisomers (77:23 and 78:22, respectively), the isomeric ratios of which were not influenced by the equatorial aryl groups present. Variable-temperature dynamic H-1 NMR spectra of the diastereoisomeric mixture of 7a provided important information about its behaviour in solution; in [H-2(8)]toluene dynamic but reversible dissociation of intramolecular Bi-N coordination was observed only at elevated temperatures, while in [H-2(6)]-DMSO it occurred quite easily below room temperature, leading to the inversion of configuration at the chiral bismuth centre.

    DOI: 10.1039/P19930002969

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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 査読

    Y MATANO, N AZUMA, H SUZUKI

    TETRAHEDRON LETTERS34 ( 52 ) 8457 - 8460   1993年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Treatment of triarylbismuth difluorides 1 with silyl enol ethers 2 in the presence of BF3.OEt(2) gives (2-oxoalkyl)triarylbismuthonium tetrafluoroborates 3 as a stable crystalline solid, the bismuth centre of which has been found by X-ray analysis to possess a tetragonal geometry. The 2-oxoalkyl moiety of compound 3 couples with enolates and thiolates to afford the corresponding triketones 4 and alpha-thioketones 6, respectively.

    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 査読

    H SUZUKI, T IKEGAMI, Y MATANO, N AZUMA

    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ( 20 ) 2411 - 2415   1993年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    Oxidation of triphenylbismuthine 1 with ozone in toluene at -78-degrees-C gave, unexpectedly, a high yield of triphenylbismuth diformate 3, which was also obtainable as a minor product by a similar oxidation in ethyl acetate and acetone. An X-ray crystallographic study revealed that compound 3 has C2 symmetry, the geometry around the bismuth atom being best described as a distorted trigonal bipyramid as a result of strong intramolecular interaction between the bismuth and carbonyl oxygen atoms. Treatment of compound 3 with aqueous sodium acetate or halides readily converted it into the corresponding triphenylbismuth diacetate 5 or dihalides 7-9.

    DOI: 10.1039/P19930002411

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

    H SUZUKI, C NAKAYA, Y MATANO

    TETRAHEDRON LETTERS34 ( 6 ) 1055 - 1056   1993年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Irradiation of a triarylbismuth diazide in benzene in the presence of alkynes results in the transfer of one of the azido ligands to the triple bond, leading to N-unsubstituted 1,2,3-triazoles in fair to moderate yields.

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

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  • Improved Schmidt Synthesis of 1,5-Disubstituted 1H-Tetrazoles from Ketones 査読

    Hitomi Suzuki, Y. S. Hwang, Chie Nakaya, Yoshihiro Matano

    Synthesis1993 ( 12 ) 1218 - 1220   1993年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Thieme  

    DOI: 10.1055/s-1993-26027

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  • Synthesis and Reactions of Some Crowded Triorganobismuthines 査読

    Yoshihiro Matano, Masamichi Kinoshita, Hitomi Suzuki

    Bulletin of the Chemical Society of Japan65 ( 12 ) 3504 - 3506   1992年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    DOI: 10.1246/bcsj.65.3504

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

    Hitomi Suzuki, Chie Nakaya, Yoshihiro Matano, Takuji Ogawa

    Chemistry Letters20 ( 1 ) 105 - 108   1991年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元: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 査読

    Kazuhiro Maruyama, Yoshihiro Matano, Toshimasa Katagiri

    Journal of Physical Organic Chemistry4 ( 8 ) 501 - 515   1991年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Wiley  

    The mechanism of the Grignard reactions of substituted benzophenones with two kinds of alkyl Grignard reagent, n‐C3H7MgBr, and i‐C3H7MgBr, was investigated. In these reactions, both addition and reduction products were also generated. Based on the results of product analysis and stopped‐flow, ESR and association measurements, it was confirmed that the product distribution was governed by several factors: the oxidizing ability of benzophenones, the association ability of Grignard reagents and the structure of alkyl groups of Grignard reagents. In particular, the strength of CMg and β‐CH bonds of Grignard reagents could strongly affect the product distribution. Copyright © 1991 John Wiley &amp
    Sons Ltd.

    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 査読

    Kazuhiro Maruyama, Yoshihiro Matano

    Bulletin of the Chemical Society of Japan63 ( 8 ) 2218 - 2223   1990年8月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    Although the photochemically induced reaction of benzil with allyltrimethylstannane in benzene afforded α-allylbenzoin as a major product, benzil did not react thermally with the same reagent. An ESR observation disclosed that the benzil anion radical ion-paired upon contact with trimethylstannyl cation (BSnMe3) was generated during irradiation. Its structure was confirmed by the detection of satellite signals arising from tin isotopes. Moreover, a triplet radical pair was also observed during the photolysis of a solid solution containing benzil and allylstannane at 77 K. This reaction proceeded via a single electron transfer from allylstannane to photoexcited benzil, followed by a cleavage of the C-Sn bond of the allyltin cation radical. Ultimately, a radical pair composed of BSnMe3 and the allyl radical was formed and their coupling gave α-allylbenzoin as an isolated product.

    DOI: 10.1246/bcsj.63.2218

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  • Non-catalyzed Thermal Reactions of Acylquinones with Allylstannanes 査読

    Kazuhiro Maruyama, Yoshihiro Matano

    Bulletin of the Chemical Society of Japan62 ( 12 ) 3877 - 3885   1989年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Chemical Society of Japan  

    DOI: 10.1246/bcsj.62.3877

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▶ 全件表示

書籍等出版物

  • Main Group Strategies towards Functional Organic Materials

    Yoshihiro Matano( 担当: 単著 ,  範囲: Phosphorus-based Porphyrins)

    Wiley  2018年3月  ( ISBN:9781119235972

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    総ページ数:560   担当ページ:265–294   記述言語:英語 著書種別:学術書

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  • Organic Redox Systems: Synthesis, Properties, and Applications

    Yoshihiro Matano( 担当: 単著 ,  範囲: Phospholes and Related Compounds: Syntheses, Redox Properties, and Applications to Organic Electronic Devices)

    Wiley  2015年12月  ( ISBN:9781118858745

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    総ページ数:616   担当ページ:477–502   記述言語:英語 著書種別:学術書

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  • Chemical Science of π-Electron Systems

    Yoshihiro Matano( 担当: 単著 ,  範囲: Heteroatom-Modified Porphyrinoids)

    Springer  2015年11月  ( ISBN:9784431553571

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    総ページ数:777   担当ページ:223–241   記述言語:英語 著書種別:学術書

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  • 高次π空間の創発と機能開発

    俣野 善博( 担当: 単著 ,  範囲: 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年3月  ( ISBN:9784781307589

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    総ページ数:245   担当ページ:123–127   記述言語:日本語 著書種別:学術書

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  • Topics in Current Chemistry: Bismuth-Mediated Organic Reactions

    Yoshihiro Matano( 担当: 単著 ,  範囲: Pentavalent Organobismuth Reagents in Organic Synthesis: Alkylation, Alcohol Oxidation, and Cationic Photopolymerization)

    Springer  2012年1月  ( ISBN:9783642272387

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    総ページ数:278   担当ページ:19–44   記述言語:英語 著書種別:学術書

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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( 担当: 単著 ,  範囲: 14〜16族高周期典型元素化合物の機能)

    東京化学同人  2011年3月  ( ISBN:9784807913442

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    総ページ数:238   担当ページ:102–114   記述言語:日本語 著書種別:学術書

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  • Comprehensive Organometallic Chemistry III

    Yoshihiro Matano( 担当: 単著 ,  範囲: Antimony and Bismuth)

    Elsevier  2006年12月  ( ISBN:9780080445991

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    総ページ数:786   担当ページ:425–456   記述言語:英語 著書種別:学術書

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  • 実験化学講座第5版

    今堀 博, 俣野 善博( 担当: 共著 ,  範囲: 人工光合成)

    丸善  2005年7月  ( ISBN:9784621073278

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    総ページ数:409   担当ページ:114–131   記述言語:日本語 著書種別:学術書

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  • 実験化学講座第5版

    俣野 善博( 担当: 単著 ,  範囲: 銀化合物による酸化)

    丸善  2004年7月  ( ISBN:9784621073162

     詳細を見る

    総ページ数:462   担当ページ:120–127   記述言語:日本語 著書種別:学術書

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  • 実験化学講座第5版

    俣野 善博( 担当: 単著 ,  範囲: ビスマス化合物による酸化)

    丸善  2004年7月  ( ISBN:9784621073162

     詳細を見る

    総ページ数:462   担当ページ:173–176   記述言語:日本語 著書種別:学術書

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  • 実験化学講座第5版

    俣野 善博( 担当: 単著 ,  範囲: タリウム化合物による酸化)

    丸善  2004年7月  ( ISBN:9784621073162

     詳細を見る

    総ページ数:462   担当ページ:127–135   記述言語:日本語 著書種別:学術書

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  • 実験化学講座第5版

    俣野 善博( 担当: 単著 ,  範囲: 水銀化合物による酸化)

    丸善  2004年7月  ( ISBN:9784621073162

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    総ページ数:462   担当ページ:113–120   記述言語:日本語 著書種別:学術書

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  • 実験化学講座第5版

    俣野 善博( 担当: 単著 ,  範囲: 鉛化合物による酸化)

    丸善  2004年7月  ( ISBN:9784621073162

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    総ページ数:462   担当ページ:103–113   記述言語:日本語 著書種別:学術書

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  • Main Group Metals in Organic Synthesis

    Yoshihiro Matano( 担当: 単著 ,  範囲: Antimony and Bismuth in Organic Synthesis)

    Wiley-VCH  2004年4月  ( ISBN:9783527305087

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    総ページ数:905   担当ページ:753–811   記述言語:英語 著書種別:学術書

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  • 実験化学講座第5版

    俣野 善博( 担当: 単著 ,  範囲: ケトン:アシル化、カルボニル化による合成)

    丸善  2003年11月  ( ISBN:4621073141

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    担当ページ:244–294   記述言語:日本語 著書種別:学術書

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  • 有機金属反応剤ハンドブック

    俣野 善博( 担当: 単著 ,  範囲: ビスマス)

    化学同人  2003年6月  ( ISBN:9784759809367

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    総ページ数:272   担当ページ:246–250   記述言語:日本語 著書種別:学術書

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  • Organobismuth Chemistry

    Yoshihiro Matano, Tohru Ikegami( 担当: 共著)

    Elsevier  2001年2月 

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    総ページ数:636   担当ページ:21–245   記述言語:英語 著書種別:学術書

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  • Organobismuth Chemistry

    Yoshihiro Matano, Tohru Ikegami( 担当: 共著)

    Elsevier  2001年2月 

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    総ページ数:636   担当ページ:247–327   記述言語:英語 著書種別:学術書

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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( 担当: 共著)

    学会出版センター  1998年4月  ( ISBN:9784762218804

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    総ページ数:272   担当ページ:149–165   記述言語:日本語 著書種別:学術書

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  • Chemistry of Arsenic, Antimony and Bismuth

    Hitomi Suzuki, Yoshihiro Matano( 担当: 共著)

    Blackie Academic and Professional  1998年 

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    担当ページ:283–343   記述言語:英語 著書種別:学術書

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