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Invention of Conjugated Electronic Structures and Novel Functions

Research Project

Project/Area Number 16GS0209
Research Category

Grant-in-Aid for Creative Scientific Research

Allocation TypeSingle-year Grants
Research InstitutionKyoto University

Principal Investigator

HIYAMA Tamejiro  Kyoto University, 大学院・工学研究科, 教授 (90026295)

Co-Investigator(Kenkyū-buntansha) CHUJO Yoshiki  京都大学, 大学院・工学研究科, 教授 (70144128)
HAYASHI Tamio  京都大学, 大学院・理学研究科, 教授 (00093295)
SHIMIZU Masaki  京都大学, 大学院・工学研究科, 准教授 (10272709)
IKEDA Tomiki  東京工業大学, 資源化学研究所, 教授 (40143656)
KATO Takashi  東京大学, 大学院・工学系研究科, 教授 (70214377)
YOKOYAMA Masaaki  大阪大学, 先端科学イノベーションセンター, 客員教授 (90029281)
YAMAGUCHI Yoshihiro  近畿大学, 理工学部, 准教授 (30200637)
Project Period (FY) 2004 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥622,960,000 (Direct Cost: ¥479,200,000、Indirect Cost: ¥143,760,000)
Fiscal Year 2008: ¥128,960,000 (Direct Cost: ¥99,200,000、Indirect Cost: ¥29,760,000)
Fiscal Year 2007: ¥128,960,000 (Direct Cost: ¥99,200,000、Indirect Cost: ¥29,760,000)
Fiscal Year 2006: ¥121,680,000 (Direct Cost: ¥93,600,000、Indirect Cost: ¥28,080,000)
Fiscal Year 2005: ¥121,680,000 (Direct Cost: ¥93,600,000、Indirect Cost: ¥28,080,000)
Fiscal Year 2004: ¥121,680,000 (Direct Cost: ¥93,600,000、Indirect Cost: ¥28,080,000)
Keywords選択的合成・反応 / 有機電子材料・素子 / 液晶材料・素子 / 電子共役系 / 交差カップリング反応 / カルボメタル化反応 / カルボシアノ化反応 / σ-π共役 / 液晶 / 発光分子 / 集積化 / パイ共役 / シグマ共役 / 光・電子機能 / δ-π共役 / ホモカップリング反応
Research Abstract

電子共役系有機分子の効率的合成のための革新的合成戦略・方法を創出し,π電子共役系を随意構築する方法論を確立した.これによって新規π共役系モジュールを構築するとともに,その一部を典型金属元素で代用してハイブリッド効果を活用する共役系,すなわちσ-π共役やp-π共役の材料を創製した.これらの新規電子共役系を液晶配向法,オリゴマー形成法あるいは精密重合法を活用して高次構造化させ,電荷輸送能,発光能,非線形光学機能あるいは導電性を示す新規材料を創製した.

Report

(6 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • 2006 Annual Research Report
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • Research Products

    (43 results)

All 2009 2008 2007 2006 2005 2004 Other

All Journal Article (29 results) (of which Peer Reviewed: 6 results) Presentation (7 results) Book (2 results) Patent(Industrial Property Rights) (5 results)

  • [Journal Article] Palladium-catalyzed Intramolecular Coupling of 2-[(2-Pyrrolyl)silyl]aryl Triflates through 1, 2-Silicon Migration2009

    • Author(s)
      K. Mochida, M. Shimizu, T. Hiyama
    • Journal Title

      J. Am. Chem. Soc. 131

      Pages: 8350-8351

    • Related Report
      2008 Final Research Report
  • [Journal Article] Direct Alkenylation and Alkylation of Pyridone Derivatives by Ni/AlMe_3 Catalysis2009

    • Author(s)
      Y.Nakao, H.Idei, K.S.Kanyiva, T.Hiyama
    • Journal Title

      Journal of the American Chemical Society 131

      Pages: 15996-15997

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed Intramolecular Coupling of 2-[(2-Pyrrolyl)silyl]aryl Triflates through 1,2-Silicon Migration2009

    • Author(s)
      K.Mochida, M.Shimizu, T.Hiyama
    • Journal Title

      Journal of the American Chemical Society 131

      Pages: 8350-8351

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stimuli-responsive Luminescent Liquid Crystals: Change of Photoluminescent Colors Triggered by a Shear-induced Phase Transition2008

    • Author(s)
      Y. Sagara, T. Kato
    • Journal Title

      Angew. Chem. Int. Ed. 47

      Pages: 5175-5178

    • Related Report
      2008 Final Research Report
  • [Journal Article] Stimuli-Responsive Luminescent Liquid Crystals : Change of Photoluminescent Colors Triggered by a Shear-Induced Phase Transition2008

    • Author(s)
      Y.Sagara, T.Kato
    • Journal Title

      Angewandte Chemie International Edition 47

      Pages: 5175-5178

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Dramatic Effect of Lewis Acid Catalyst on Nickel-catalyzed Carbocyanation of Alkynes2007

    • Author(s)
      Y. Nakao, A. Yada, S. Ebata, T. Hiyama
    • Journal Title

      J. Am. Chem. Soc. 129

      Pages: 2428-2429

    • Related Report
      2008 Final Research Report
  • [Journal Article] A Silicon-Based Approach to Oligoarenes by Iterative Cross-Coupling Reactions of Organo [(2-hydroxymethyl) phenyl] dimethylsilanes2007

    • Author(s)
      Y. Nakao, J. Chen, M. Tanaka, T. Hiyama
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 11694-11695

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organo [2-(hydroxymethyl) phenyl] dimethylsilanes as Mild and Reproducible Agents for Rhodium-Catalyzed 1, 4-Addition Reactions2007

    • Author(s)
      Y. Nakao, J. Chen, H. Imanaka T. Hiyama, Y. Ichikawa, W.-L. Duan, R. Shintani, T. Hayashi
    • Journal Title

      Journal of the American Chemical Society 129

      Pages: 9137-9143

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 1-Alkyl-2,3,5,6,7,8-hexasilabicyclo [2.2.2] octanes: Unconventional Class of Mesomorphic Columnar Compounds2007

    • Author(s)
      M. Shimizu, M. Nata, K. Mochida, T. Hiyama, S. Ujiie, M. Yoshio, T. Kato
    • Journal Title

      Angewandte Chemie International Edition 46

      Pages: 3055-3058

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Arylmagnesiation of Aryl(alkyl)acetylenes in the Presence of an N-Heterocyclic Carbene Ligand2007

    • Author(s)
      T.Yamagami, R.Shintani, E.Shirakawa, T.Hayashi
    • Journal Title

      Org.Lett. 9

      Pages: 1045-1048

    • Related Report
      2006 Annual Research Report
  • [Journal Article] A Dramatic Effect of Lewis Acid Catalyst on Nickel-catalyzed Carbocyanation of Alkynes2007

    • Author(s)
      Y.Nakao, A.Yada, S.Ebata, T.Hiyama
    • Journal Title

      J.Am.Chem.Soc. 129

      Pages: 2428-2429

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Rigid Molecular Architectures That Comprise a 1, 3, 5-Tri-substituted Benzene Core and Three Oligoaryleneethynylene Arms: Light-emitting Characteristics and p-Conjugation between The Arms2006

    • Author(s)
      Y. Yamaguchi, T. Ochi, S. Miyamura, T. Tanaka, S. Kobayashi, T. Wakamiya, Y. Matsubara, Z. Yoshida
    • Journal Title

      J. Am. Chem. Soc. 128

      Pages: 4504-4505

    • Related Report
      2008 Final Research Report
  • [Journal Article] White Emission from Liquid-Crystalline Copolymers Containing Oxadiazole Moieties in the Side Chain2006

    • Author(s)
      M.Kawamoto, T.Tsukamoto, M.Kinoshita, T.Ikeda
    • Journal Title

      Appl.Phys.Lett. 89

    • Related Report
      2006 Annual Research Report
  • [Journal Article] One-Dimensional Ion-Conductive Polymer Films : Alignment and Fixation of Ionic Channels Formed by Self-Organization of Polymerizable Columnar Liquid Crystals2006

    • Author(s)
      M.Yoshio, T.Kagata, K.Hoshino, T.Mukai, H.Ohno, T.Kato
    • Journal Title

      J.Am.Chem.Soc. 128

      Pages: 5570-5577

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Oxidation of Dithia[3.3]metacyclophane-Containing Through-Space π-Conjugated Polymer2006

    • Author(s)
      Y.Morisaki, T.Ishida, Y.Chujo
    • Journal Title

      Polym.Bull. 57

      Pages: 623-630

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Preparation, Structure, and Properties of Tris(trimethylsilyl)silyl-substituted Anthracenes : Realization of Ideal Conformation for σ-π Conjugation Involving Eclipse of Si-Si σ-Bond with π-Orbital of Aromatic Ring2006

    • Author(s)
      M.Shimizu, K.Oda, T.Bando, T.Hiyama
    • Journal Title

      Chem.Lett. 35

      Pages: 1022-1023

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis and Characterization of Dithia[3.3](2,6)pyridinophane-Containing Polymers : Application to the Palladium-Catalyzed Heck Reaction2006

    • Author(s)
      Y.Morisaki, T.Ishida, Y.Chujo
    • Journal Title

      Org. Lett. 8

      Pages: 1029-1032

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Arylmagnesiation of Alkynes Catalyzed Cooperatively by Iron and Copper Complexes2005

    • Author(s)
      E. Shirakawa, T. Yamagami, T. Kimura, S. Yamaguchi, T. Hayashi
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 17164-17165

    • Related Report
      2008 Final Research Report
  • [Journal Article] Alkenyl- and Aryl[2-(hydroxymethyl)phenyl] dimethylsilanes : An Entry to Tetraorganosilicon Reagents for the Silicon-Based Cross-Coupling Reaction2005

    • Author(s)
      Y.Nakao, H.Imanaka, A.K.Sahoo, A.Yada, T.Hiyama
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 6952-6953

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Stereoselective Cross-Coupling Reaction of 1,1-Diboryl-1-alkenes with Electrophiles : A Highly Stereocontrolled Approach to l,1,2-Triaryl-1-alkenes2005

    • Author(s)
      M.Shimizu, C.Nakamaki, K.Shimono, M.Schelper, T.Kurahashi, T.Hiyama
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 12506-12507

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Arylmagnesiation of Alkynes Catalyzed Cooperatively by Iron and Copper Complexes2005

    • Author(s)
      E.Shirakawa, T.Yamagami, T.Kimura, S.Yamaguchi, T.Hayashi
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 17164-17165

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Effect of Ester Moieties in Dye Structures on Photoinduced Reorientation of Dye-Doped Liquid Crystals2005

    • Author(s)
      M.Yaegashi, A.Shishido, T.Shiono, T.Ikeda
    • Journal Title

      Chem. Mater. 17

      Pages: 4304-4309

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A Nano-Segregated Polymeric Film Exhibiting High lonic Conductivities2005

    • Author(s)
      K.Kishimoto, T.Suzawa, T.Yokota, T.Mukai, H.Ohno, T.Kato
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 15618-15623

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Nickel-Catalyzed Arylcyanation of Alkynes2004

    • Author(s)
      Y.Nakao, S.Oda, T.Hiyama
    • Journal Title

      J.Am.Chem.Soc. 126

      Pages: 13904-13905

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Stannylative Cycloaddition of Enynes Catalyzed by Palladium-Iminophosphine2004

    • Author(s)
      Y.Nakao, Y.Hirata, S.Ishihara, S.Oda, T.Yukawa, E.Shirakawa
    • Journal Title

      J.Am.Chem.Soc. 126

      Pages: 15650-15651

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Facile Synthesis of Dendralenes Based on the Cross-coupling Reaction of 2,3-Bis(pinacolato)boryl-1,3-butadiene2004

    • Author(s)
      M.Shimizu, K.Tanaka, T.Kurahashi, K.Shimono, T.Hiyama
    • Journal Title

      Chem.Lett. 33

      Pages: 1066-1067

    • NAID

      10013448195

    • Related Report
      2004 Annual Research Report
  • [Journal Article] 1) Novel [2.2]Paracyclophane-Fluorene-Based Conjugated Copolymers : Synthesis, Optical and Electrochemical Properties2004

    • Author(s)
      Y.Morisaki, Y.Chujo
    • Journal Title

      Macromolecules 37

      Pages: 4099-4103

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Self-Assembly of an Ionic Liquid and a Hydroxyl-Terminated Liquid Crystal : Anisotropic Ion Conduction in Layered Nanostructures2004

    • Author(s)
      M.Yoshio, T.Mukai, M.Yoshizawa, H.Ohno, T.Kato
    • Journal Title

      Mol.Cryst.Liq.Cryst. 413

      Pages: 99-108

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Novel Liquid-Crystalline Phenylene-Thienylene Co-Oligomers for Photoinduced Reorientation of Liquid Crystals

    • Author(s)
      M.Yaegashi, A.Shishido, T.Shiono, T.Ikeda
    • Journal Title

      Mol.Cryst.Liq.Cryst. (印刷中)

    • Related Report
      2004 Annual Research Report
  • [Presentation] Invention of Transition Metal-Catalyzed Carbon-Carbon Bond Forming Reactions for Organic Synthesis2009

    • Author(s)
      Tamejiro Hiyama
    • Organizer
      CRC Symposium on Cross-Coupling and Organometallics
    • Place of Presentation
      Moscow
    • Year and Date
      2009-09-18
    • Related Report
      2008 Annual Research Report
  • [Presentation] Invention of Transition Metal-Catalyzed Carbon-Carbon Bond Forming Reactions for Organic Synthesis2009

    • Author(s)
      T. Hiyama
    • Organizer
      The 4th ACP Symposium for Cutting-edge Organic Chemistry
    • Place of Presentation
      Bangkok
    • Related Report
      2008 Final Research Report
  • [Presentation] Invention of Transition Metal-Catalyzed Carbon-Carbon Bond Forming Reactions for Organic Synthesis2008

    • Author(s)
      T. Hiyama
    • Organizer
      CRC Symposium on Cross-Coupling and Organometallics
    • Place of Presentation
      Stockholm, Sweden
    • Year and Date
      2008-11-03
    • Related Report
      2008 Final Research Report
  • [Presentation] Invention of Transition Metal-Catalyzed Carbon-Carbon Bond Forming Reactions2008

    • Author(s)
      T. Hiyam
    • Organizer
      5th Asian-Europe Symposium
    • Place of Presentation
      Obernai, France
    • Year and Date
      2008-05-26
    • Related Report
      2008 Final Research Report
  • [Presentation] 高配位金属種の生成と反応制御による精密有機合成2008

    • Author(s)
      檜山 爲次郎
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学池袋キャンパス
    • Year and Date
      2008-03-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] Carbocyanation of Unsaturated Carbon-Carbon Bonds2006

    • Author(s)
      T. Hiyama
    • Organizer
      International Symposium on Organic Chemistry
    • Place of Presentation
      Singapore
    • Year and Date
      2006-12-18
    • Related Report
      2008 Final Research Report
  • [Presentation] Synthetic Reactions of Electron-Conjugated Systems2006

    • Author(s)
      T. Hiyama
    • Organizer
      5th International Forum on Functional Organic Chemicals
    • Place of Presentation
      Tokyo, Japan
    • Year and Date
      2006-11-19
    • Related Report
      2008 Final Research Report
  • [Book] 電子共役系有機構造体の創製と機能開発2008

    • Author(s)
      檜山爲次郎
    • Total Pages
      324
    • Publisher
      CMC
    • Related Report
      2008 Final Research Report
  • [Book] 電子共役系有機構造体の創製と機能開発:現状と展望2008

    • Author(s)
      檜山 爲次郎(監修)
    • Total Pages
      324
    • Publisher
      シーエムシー出版
    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] ベンゼン化合物2009

    • Inventor(s)
      清水正毅, 檜山爲次郎
    • Industrial Property Rights Holder
      国立大学法人京都大学
    • Industrial Property Number
      2009-046049
    • Filing Date
      2009-02-27
    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] ベンゼン化合物2008

    • Inventor(s)
      清水正毅, 檜山爲次郎
    • Industrial Property Rights Holder
      国立大学法人京都大学
    • Industrial Property Number
      2009-046049
    • Filing Date
      2008-02-27
    • Related Report
      2008 Final Research Report
  • [Patent(Industrial Property Rights)] 分子末端に電子供与基を導入したポリシアノオリゴフェニレンエチニレン化合物2008

    • Inventor(s)
      山口仁宏, 若宮建昭, 吉田善一
    • Industrial Property Rights Holder
      近畿大学
    • Patent Publication Number
      2009-209073
    • Filing Date
      2008-09-17
    • Related Report
      2008 Final Research Report
  • [Patent(Industrial Property Rights)] α位アルケニル置換含窒素芳香族複素環化合物の製造方法2007

    • Inventor(s)
      中尾佳亮, 檜山爲次郎
    • Industrial Property Rights Holder
      京都大学
    • Industrial Property Number
      2007-265962
    • Filing Date
      2007-10-11
    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] 含ケイ素クロスカップリング反応剤およびこれを用いる有機化合物の製造方法2005

    • Inventor(s)
      中尾佳亮, 桧山為次郎
    • Industrial Property Rights Holder
      京都大学
    • Industrial Property Number
      2005-117452
    • Filing Date
      2005-04-14
    • Related Report
      2005 Annual Research Report

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Published: 2004-04-01   Modified: 2016-04-21  

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