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Synthesis of belt-shaped fused conjugated molecule "pi belt": actualization as a key material in novel non-planar nano-carbon

Research Project

Project/Area Number 22685006
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

AMAYA Toru  大阪大学, 工学(系)研究科(研究院), 助教 (20397615)

Project Period (FY) 2010-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥24,310,000 (Direct Cost: ¥18,700,000、Indirect Cost: ¥5,610,000)
Fiscal Year 2013: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2011: ¥8,970,000 (Direct Cost: ¥6,900,000、Indirect Cost: ¥2,070,000)
Fiscal Year 2010: ¥7,540,000 (Direct Cost: ¥5,800,000、Indirect Cost: ¥1,740,000)
Keywordsスマネン / πベルト / πボウル / カーボンナノチューブ / ビスマネニリデン / ボウル型π共役系分子 / ナノカーボン / 酸化的環化 / π共役
Research Abstract

This study was conducted toward the synthesis of a belt-shaped fused conjugated molecule (pi belt). The strategy for the synthesis of pi belt was designed based on the use of bowl-shaped molecule sumanene with curved and fused benzene rings as a building block. The methods for linking the sumanene units were investigated. Sumanenes were coupled via three routes based on cross-coupling, oxidative coupling, and reductive coupling. The method to construct the curved and fused structure by intramolecular dehydrogenative oxidation was developed.

Report

(5 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (36 results)

All 2014 2013 2012 2011 2010 Other

All Journal Article (14 results) (of which Peer Reviewed: 14 results) Presentation (17 results) (of which Invited: 3 results) Book (5 results)

  • [Journal Article] Synthesis and Characterization of Bisumanenylidene2014

    • Author(s)
      Toru Amaya, Takanori Ito, Toshikazu Hirao
    • Journal Title

      Eur. J. Org. Chem

      Pages: 3531-3535

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Bisumanenylidene2014

    • Author(s)
      Toru Amaya, Takanori Ito, and Toshikazu Hirao
    • Journal Title

      Europian Journal of Organic Chemistry

      Volume: 2014

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nitrogen-doped Graphitic Carbon Synthesized by Laser Annealing of Sumanenemonoone Imine as a Bowl-shaped π-Conjugated Molecule2013

    • Author(s)
      Yuhi Inada, Toru Amaya, Yasutomo Shimizu, Akinori Saeki, Takeo Otsuka, Ryotaro Tsuji, Toshikazu Hirao
    • Journal Title

      Chem. Asian J

      Volume: 8 Pages: 2569-2574

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Bisumanenyl2013

    • Author(s)
      Toru Amaya, Kenji Kobayashi, Toshikazu Hirao
    • Journal Title

      Asian J. Org. Chem

      Volume: 2 Pages: 642-645

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Bisumanenyl2013

    • Author(s)
      Toru Amaya, Kenji Kobayashi, and Toshikazu Hirao
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 2 Issue: 8 Pages: 642-645

    • DOI

      10.1002/ajoc.201300091

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nitrogen-doped Graphitic Carbon Synthesized by Laser Annealing of Sumanenemonoone Imine as a Bowl-shaped p-Conjugated Molecule2013

    • Author(s)
      Yuhi Inada, Toru Amaya, Yasutomo Shimizu, Akinori Saeki, Takeo Otsuka, Ryotaro Tsuji, Shu Seki, and Toshikazu Hirao
    • Journal Title

      Chemistry An Asian Journal

      Volume: 8 Issue: 11 Pages: 2569-2574

    • DOI

      10.1002/asia.201300500

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bowl-to-bowl Inversion of Sumanene Derivatives2012

    • Author(s)
      Toru Amaya, Toshikazu Hirao
    • Journal Title

      Pure and App. Chem

      Volume: 84 Pages: 1089-1100

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Bowl-to-bowl inversion of sumanene derivatives2012

    • Author(s)
      Toru Amaya
    • Journal Title

      Pure and Applied Chemistry

      Volume: 84 Issue: 4 Pages: 1089-1100

    • DOI

      10.1351/pac-con-11-09-09

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Molecular Bowl Sumanene2011

    • Author(s)
      Toru Amaya, Toshikazu Hirao
    • Journal Title

      Chem. Commun

      Volume: 47 Pages: 10524-10535

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Oxo-sumanenes through Benzylic Oxidation2011

    • Author(s)
      Toru Amaya, Maiko Hifumi, Michiaki Okada, Yasutomo Shimizu, Toshiyuki Moriuchi, Koji Segawa, Yoichi Ando, Toshikazu Hirao
    • Journal Title

      J. Org. Chem

      Volume: 76 Pages: 8049-8052

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] A molecular bowl sumanene2011

    • Author(s)
      Tom Amaya
    • Journal Title

      Chemical Communications

      Volume: 47 Issue: 38 Pages: 10524-10535

    • DOI

      10.1039/c1cc12532j

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Oxosumanenes through Benzylic Oxidation2011

    • Author(s)
      Toru Amaya
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 76 Issue: 19 Pages: 8049-8052

    • DOI

      10.1021/jo2012412

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Theoretical Study of the Bowl-to-bowl Inversion of Sumanene Derivatives2010

    • Author(s)
      Toru Amaya, Toshikazu Hirao
    • Journal Title

      Pure and Applied Chemistry

      Volume: 82 Pages: 969-978

    • Related Report
      2013 Final Research Report 2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sumanenemonoone Imines Bridged by Redox-active π-Conjugated Unit : Synthesis, Stepwise Coordination to Pd(II), and Laser-induced Formation of Nitrogen-doped Graphitic Carbon

    • Author(s)
      Toru Amaya, Yuhi Inada, Yasutomo Shimizu, Akinori Saeki, Takeo Otsuka, Ryotaro Tsuji, Toshikazu Hirao
    • Journal Title

      Chem. Asian J

      Volume: (in press)

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Presentation] ビスマネニリデンの合成2013

    • Author(s)
      伊藤隆宣・雨夜 徹・平尾俊一
    • Organizer
      第3回CSJ フェスタ
    • Place of Presentation
      東京都 タワーホール船堀
    • Year and Date
      2013-10-23
    • Related Report
      2013 Final Research Report
  • [Presentation] A Molecular Bowl Sumanene2013

    • Author(s)
      Toru Amaya
    • Organizer
      International Kick-Off Symposium for ISMCBC
    • Place of Presentation
      Kumamoto University
    • Year and Date
      2013-08-01
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] スマネンの位置選択的誘導化2013

    • Author(s)
      雨夜 徹・○伊藤隆宣・平尾俊一
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀県 立命館大学
    • Year and Date
      2013-03-25
    • Related Report
      2013 Final Research Report
  • [Presentation] ビスマネニリデンの合成2013

    • Author(s)
      伊藤隆宣、雨夜 徹、平尾俊一
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2013 Annual Research Report
  • [Presentation] A Molecular Bowl Sumanene2013

    • Author(s)
      雨夜 徹
    • Organizer
      International Kick-Off Symposium for ISMCBC
    • Place of Presentation
      熊本大学
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] スマネンの位置選択的誘導化2013

    • Author(s)
      伊藤隆宣
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] トリオキソスマネンへの求核付加とボウル反転挙動2013

    • Author(s)
      沖本竜太
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] 分子内酸化的環化反応を用いる高湾曲πボウルの合成2012

    • Author(s)
      雨夜 徹・平尾俊一
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川県慶應義塾大学
    • Year and Date
      2012-03-28
    • Related Report
      2013 Final Research Report
  • [Presentation] ボウル型π共役系分子スマネンの動的挙動・機能化・錯形成2012

    • Author(s)
      雨夜 徹
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      神奈川 県慶應義塾大学
    • Year and Date
      2012-03-28
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] 分子内酸化的環化反応を用いる 高湾曲πボウルの合成2012

    • Author(s)
      雨夜 徹
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2011 Annual Research Report
  • [Presentation] スマネン二量体の合成と特性2011

    • Author(s)
      雨夜 徹・○小林賢司・平尾俊一
    • Organizer
      第5回有機π電子系シンポジウム
    • Place of Presentation
      大阪府 ホテルアウィーナ大阪
    • Year and Date
      2011-11-25
    • Related Report
      2013 Final Research Report
  • [Presentation] スマネンから誘導される非平面π共役系分子の合成と特性2011

    • Author(s)
      雨夜 徹・小林賢司・岡田倫明・平尾俊一
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      茨城県 つくば国際会議場
    • Year and Date
      2011-09-21
    • Related Report
      2013 Final Research Report
  • [Presentation] π共役系拡張スマネン : 合成とフォトエレクトロニクス特性2011

    • Author(s)
      雨夜 徹・清水康智・関 修平・平尾俊一
    • Organizer
      第21回基礎有機化学討論会
    • Place of Presentation
      愛知県 名古屋大学
    • Year and Date
      2011-09-10
    • Related Report
      2013 Final Research Report
  • [Presentation] ボウル型π共役系分子スマネンの動的特性・機能化・錯形成2011

    • Author(s)
      雨夜徹
    • Organizer
      日本化学会第91回春季年会
    • Place of Presentation
      神奈川大学(横浜市)
    • Year and Date
      2011-03-28
    • Related Report
      2010 Annual Research Report
  • [Presentation] スマネンから誘導される非平面π共役系分子の合成と特性2011

    • Author(s)
      雨夜 徹
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      つくば国際会議場
    • Related Report
      2011 Annual Research Report
  • [Presentation] スマネン二量体の合成と特性2011

    • Author(s)
      小林賢司
    • Organizer
      第5回有機π電子系シンポジウム
    • Place of Presentation
      ホテルアウィーナ大阪
    • Related Report
      2011 Annual Research Report
  • [Presentation] π共役系拡張スマネン:合成とフォトエレクトロニクス特性2010

    • Author(s)
      雨夜徹
    • Organizer
      第21回基礎有機化学討論会
    • Place of Presentation
      名古屋大学(名古屋市)
    • Year and Date
      2010-09-10
    • Related Report
      2010 Annual Research Report
  • [Book] Advances in Organometallic Chemistry2014

    • Author(s)
      Toru Amaya, Toshikazu Hirao
    • Total Pages
      736
    • Publisher
      John Wiley & Sons. Inc
    • Related Report
      2013 Final Research Report
  • [Book] Advances in Organometallic Chemistry and Catalysis2014

    • Author(s)
      雨夜 徹、平尾俊一
    • Total Pages
      736
    • Publisher
      John Wiley & Sons, Inc.
    • Related Report
      2013 Annual Research Report
  • [Book] Fragments of Fullerenes and Carbon Nanotubes: Designed Synthesis, Unusual Reactions, and Coordination Chemistry2011

    • Author(s)
      Toshikazu Hirao, Toru Amaya
    • Total Pages
      413
    • Publisher
      John Wiley & Sons. Inc
    • Related Report
      2013 Final Research Report
  • [Book] Carbon Nanotubes: Designed Synthesis, Unusual Reactions, and Coordination Chemistry2011

    • Author(s)
      Toshikazu Hirao
    • Total Pages
      413
    • Publisher
      WILEY
    • Related Report
      2011 Annual Research Report
  • [Book] Fragments of Fullerenes and Carbon Nanotubes : Designed Synthesis, Unusual Reactions, and Coordination Chemistry2011

    • Author(s)
      Toshikazu Hirao, Toru Amaya
    • Publisher
      JOHN WILEY & SONS, INC.(印刷中)
    • Related Report
      2010 Annual Research Report

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Published: 2010-08-23   Modified: 2019-07-29  

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