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

• Project/Area Number: 22350016
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kyoto University
• Principal Investigator: MATANO Yoshihiro 京都大学, 大学院・工学研究科, 准教授 (40231592)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥20,020,000 (Direct Cost: ¥15,400,000、Indirect Cost: ¥4,620,000); Fiscal Year 2012: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2011: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2010: ¥11,440,000 (Direct Cost: ¥8,800,000、Indirect Cost: ¥2,640,000)
• Keywords: ホスホール / チタナサイクル / クロスカップリング / 多量体 / キャリヤ移動度 / 有機太陽電池 / 光活性層 / 光電変換特性 / 有機薄膜太陽電池 / バッファ層 / キャリア移動度 / Time-Of-Flight法 / 酸化還元 / 電荷移動特性 / 縮環 / X線結晶構造解析 / 電子受容能 / 電子輸送能

Research Abstract

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

Research Products

• [Journal Article] Synthesis and Charge-Carrier Transport Properties of Poly(phosphole P-alkanesulfonylimide)s (2013)
  • Author(s): Yoshihiro Matano, Hiroshi Ohkubo, Yoshihito Honsho, Arihiro Saito, Shu Seki, Hiroshi Imahori
  • Journal Title: Org. Lett Volume: 15 Issue: 4 Pages: 932-935
  • DOI: 10.1021/ol4000982
  • Peer Reviewed
• [Journal Article] Synthesis and Charge-Carrier Transport Properties of Poly(phosphole P-alkanesulfonylimide)s (2013)
  • Author(s): Yoshihiro Matano
  • Journal Title: Org. Lett. Volume: 15 Issue: 4 Pages: 932-935
  • DOI: 10.1021/ol303549c
  • Peer Reviewed
• [Journal Article] Synthesis and Structure-Property Relationships of 2,2`-Bis(benzo[b]-phosphole) and 2,2`-Benzo[b]phosphole-Benzo[b]heterole Hybrid π-Systems (2012)
  • Author(s): Yu k iko Hay ashi, Yo shih iro Matano, Kayo Suda, Yoshifumi Kimura,Yo shih ide Nakao , Hiroshi Imahori
  • Journal Title: Chem. Eur. J Volume: 18 Issue: 50 Pages: 15972-15983
  • DOI: 10.1002/chem.201203047
  • Peer Reviewed
• [Journal Article] alpha,alpha'-Diarylacenaphtho[1,2-c]phosphole P-Oxides: Divergent Synthesis and Application to Cathode Buffer Layers in Organic Photovoltaics (2012)
  • Author(s): Yoshihiro Matano
  • Journal Title: Chem. Asian J. Volume: 7 Issue: 10 Pages: 2305-2312
  • DOI: 10.1002/asia.201290039
  • Peer Reviewed
• [Journal Article] Effects of Carbon-Metal-Carbon Linkages on the Optical, Photophysical, and Electrochemical Properties of Phosphametallacycle-Linked Coplanar Porphyrin Dimers (2012)
  • Author(s): 俣野善博、松本和明、林宏暢、中尾嘉秀、Tatu Kumpulainen、Vladimir Chukharev、Nikolai V.Tkachenko、Helge Lemmetyinen、清水宗治、小林長夫、酒巻大輔、伊藤彰浩、田中一義、今堀博
  • Journal Title: Journal of the American Chemical Society Volume: 134 Issue: 3 Pages: 1825-1839
  • DOI: 10.1021/ja210205v
  • Peer Reviewed
• [Journal Article] 1,4-Diaryl-7,10-dimethoxyquinoxalino[2,3-b]quinoxalines and Their Dihydro Derivatives : Redox Switching of NIR Absorption and Fluorescence (2011)
  • Author(s): Youhei Miura, et al
  • Journal Title: Chemistry Letters Volume: 40 Issue: 9 Pages: 975-977
  • DOI: 10.1246/cl.2011.975
  • NAID: 10029522204
  • Peer Reviewed
• [Journal Article] Fusion of Phosphole and 1,1'-Biacenaphthene : Phosphorus(V)-Containing Extended p-Systems with High Electron Affinity and Electron Mobility (2011)
  • Author(s): Y.Matano, A.Saito, T.Fukushima, Y.Tokudome, F.Suzuki, D.Sakamaki, H.Kaji, A.Ito, K.Tanaka, H.Imahori
  • Journal Title: Angew.Chem.Int.Ed. Volume: 50 Issue: 35 Pages: 8016-8020
  • DOI: 10.1002/anie.201102782
  • Peer Reviewed
• [Journal Article] 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 (2011)
  • Author(s): Yoshihiro Matano
  • Journal Title: Chem.Lett. Volume: 40 Pages: 919-921
  • NAID: 10029521509
  • Peer Reviewed
• [Journal Article] 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- (2011)
  • Author(s): Yoshihiro Matano
  • Journal Title: Chemistry Letters Volume: (印刷中)
  • NAID: 10029521509
  • Peer Reviewed
• [Journal Article] Effects of Heterole Spacers on the Structural, Optical, and Electrochemical Properties of 2,5-Bis(1,5-diphenylphosphol-2-yl)heteroles (2011)
  • Author(s): Yoshihiro Matano
  • Journal Title: Heteroatom Chemistry Volume: (印刷中)
  • Peer Reviewed
• [Journal Article] Synthesis of α,α'-Linked Oligophospholes and Polyphospholes by Using Pd-CuI-Promoted Stille-Type Coupling (2010)
  • Author(s): Arihiro Saito, Yo shih iro Matano, Hiroshi Imahori
  • Journal Title: Org. Lett. Volume: 12 Issue: 11 Pages: 2675-2677
  • DOI: 10.1021/ol100926q
  • Peer Reviewed
• [Journal Article] Synthesis, Structures, Optical and Electrochemical Properties, and Complexation of 2, 5-Bis(pyrrol-2-yl)phospholes (2010)
  • Author(s): Yoshihiro Matano
  • Journal Title: C.R.Chimie Volume: 13 Pages: 1035-1047
  • Peer Reviewed
• [Presentation] Phosphole-Containing Macrocycles, Fused π-Systems, and Polymers (2012)
  • Author(s): Yoshihiro Matano
  • Organizer: 9th European Workshop of Phosphorus Chemistry
  • Place of Presentation: Rennes (France)(招待講演)
  • Year and Date: 2012-03-22
• [Presentation] Polymerization of Phospholes by Using Stille Coupling: Optical, Electrochemical, and Semiconducting Properties of α,α'-Linked Polyphospholes (2012)
  • Author(s): Yoshihiro Matano, Hiroshi Ohkubo, Arihiro Saito, Hiroshi Imahori
  • Organizer: 19th International Conference on Phosphorus Chemistry
  • Place of Presentation: Rotterdam(Netherland)
• [Presentation] Phosphole-Containing Macrocycles, Fused π-Systems, and Polymers (2012)
  • Author(s): Yoshihiro Matano
  • Organizer: European Workshop of Phosphorus Chemistry2012
  • Place of Presentation: Rennes(France)
• [Presentation] Synthesis and Properties of Phosphole-Containing π-Conjugated Oligomers and Polymers (2012)
  • Author(s): Yoshihiro Matano
  • Organizer: 10th International Conference on Heteroatom Chemistry
  • Place of Presentation: Kyoto (Japan)
• [Presentation] Synthesis and Peripheral Functionalizations of β-Unsubstituted 5,15-Diazaporphyrin-Metal Complexes (2012)
  • Author(s): Yoshihiro Matano
  • Organizer: Satellite Symposium of 7th International Conference on Porphyrins and Phthalocyaninces
  • Place of Presentation: Kyoto (Japan)
  • Invited
• [Presentation] Metal Complexes of meso-Phosphanylporphyrins: Fundamental Properties and Reactivities (2012)
  • Author(s): Yoshihiro Matano
  • Organizer: 7th International Conference on Porphyrins and Phthalocyaninces
  • Place of Presentation: Jeju (Korea)
  • Invited
• [Presentation] Polymerization of Phospholes by Using Stille Coupling: Optical, Electrochemical, and Semiconducting Properties of α,α’-Linked Polyphospholes (2012)
  • Author(s): Yoshihiro Matano
  • Organizer: 19th International Conference on Phosphorus Chemistry
  • Place of Presentation: Rotterdam (Netherland)
• [Presentation] Synthesis and Optoelectrochemical Properties of Conjugated Oligophospholes and Polyphospholes (2011)
  • Author(s): Yoshihiro Matano
  • Organizer: International Conference on Heterocyclic Chemistry 2011
  • Place of Presentation: Glasgow (United Kingdom)
  • Year and Date: 2011-08-02
• [Presentation] 高い電子受容性と電子輸送特性を持つ縮環ホスホール誘導体の構造と物性 (2011)
  • Author(s): 俣野善博, 齋藤有弘, 今堀博
  • Organizer: 基礎有機化学討論会
  • Place of Presentation: つくば市
• [Presentation] Synthesis and Coordination Chemistry of PhospholeContaining Hybrid Ligands (2010)
  • Author(s): Yoshihiro Matano
  • Organizer: Zhengzhou Chemistry Workshop 2010
  • Place of Presentation: Zhengzhou(China)
  • Year and Date: 2010-09-27
• [Presentation] Synthesis and Optoelectrochemical Properties of Conjugated Oligophospholes and Polyphospholes (2010)
  • Author(s): Yoshihiro Matano, Arihiro Saito, Hiroshi Imahori
  • Organizer: International Conference on Heterocyclic Chemistry 2011
  • Place of Presentation: Glasgow(United Kingdom).
• [Presentation] Synthesis and Aromaticity of Metal Complexes of Phosphorus-Containing Core-Modified Porphyrins (2010)
  • Author(s): Yoshihiro Matano
  • Organizer: 6th International Conference on Porphyrins and Phthalocyanines
  • Place of Presentation: アメリカ合衆国 New Mexico
• [Book] 有機金属化学の最前線(現代化学増刊44) (2011)
  • Author(s): 俣野善博
  • Publisher: 東京化学同人
• [Remarks]
  • URL: http://www.moleng.kyoto-u.ac.jp/~moleng_05/index.html
• [Patent(Industrial Property Rights)] 光電変換材料、光電変換素子、及び太陽電池モジュール (2012)
  • Inventor(s): 俣野善博
  • Industrial Property Rights Holder: 野善博、今堀博、大坪才華、秋山誠治
  • Acquisition Date: 2012-07-05
• [Patent(Industrial Property Rights)] 光電変換材料、光電変換素子、及び太陽電池モジュール (2012)
  • Inventor(s): 俣野善博
  • Industrial Property Rights Holder: 俣野善博、今堀博、大坪才華、秋山誠治
  • Acquisition Date: 2012-07-12