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Development of functional pi-conjugated molecules and their assemblies by novel catalyst-free click reactions

Research Project

Project/Area Number 19K05640
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 35030:Organic functional materials-related
Research InstitutionNational Institute for Materials Science

Principal Investigator

TAKAI Atsuro  国立研究開発法人物質・材料研究機構, 機能性材料研究拠点, 主任研究員 (90746728)

Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2021: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2019: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Keywordsπ電子系材料 / クリック反応 / 超分子集積体 / 有機-無機ハイブリッド / π電子系化合物 / 超分子 / 近接効果 / π電子材料 / 分子集積体 / 自己組織化単分子膜 / 有機薄膜デバイス
Outline of Research at the Start

π共役分子は、有機薄膜デバイスの主役級の材料であるが、所望の光学および電子物性を引き出すためには、合成上の煩雑さや薄膜上での集積構造制御における困難が伴う。本研究では、研究代表者が見出した電子受容性π共役分子とアミンの無触媒クリック反応を基軸として、新奇π電子材料の物性探索と薄膜上での集積構造の自在制御に取り組む。本クリック反応を独自の切り口として、従来の化学反応では達成し得ないπ電子材料と薄膜科学の融合を図り、有機薄膜デバイス分野におけるパラダイムシフトを目指す。

Outline of Final Research Achievements

In this study, we have extensively studied novel pi-conjugated molecules and their assemblies synthesized by a unique catalyst-free click reaction between electron-accepting pi-conjugated molecules and amines. Concretely, we have successfully achieved the following points: (1) quantitative elucidation of the applicability of the catalyst-free click reaction, (2) development of novel functional pi-conjugated molecules and polymers by the catalyst-free click reaction between vinyl-substituted naphthalenediimides and amines, (3) development of novel organic-inorganic hybrids based on the click reaction at a solid-liquid interface, (4) elucidation of the spatiotemporal dynamics of catalyst-free click reactions using supramolecular assemblies, and (5) precise control over the supramolecular assembling process induced by the catalyst-free click reaction.

Academic Significance and Societal Importance of the Research Achievements

本研究は、無触媒クリック反応が機能性π電子系分子を簡便に合成するためのアトムエコノミカルな新たな手法となることを実証しており、その社会的な意義は大きい。また、ヘテロ界面におけるπ共役分子の修飾法や動的特性を示す超分子集積体のトリガーとしても有用であることを示しており、今後さらなる有機電子デバイスへの応用や有機-無機ハイブリッド材料およびソフトマテリアルへの展開も期待できる。従って、本研究で得られた成果は、π電子系化合物に基づく有機材料研究において有益な知見を与えるものであり、その学術的な意義は大きい。

Report

(4 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • Research Products

    (17 results)

All 2022 2021 2020 2019 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Open Access: 1 results) Presentation (11 results) (of which Int'l Joint Research: 1 results,  Invited: 3 results) Remarks (2 results)

  • [Journal Article] Spatiotemporal dynamics of supramolecular polymers by <i>in situ</i> quantitative catalyst-free hydroamination2022

    • Author(s)
      Tan Minghan、Takeuchi Masayuki、Takai Atsuro
    • Journal Title

      Chemical Science

      Volume: 13 Issue: 15 Pages: 4413-4423

    • DOI

      10.1039/d2sc00035k

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Catalyst‐Free π‐Extended Conjugate Addition of Amines to Various Electron‐Deficient π‐Systems2021

    • Author(s)
      Tan Minghan、Chrostowski Robert、Sanematsu Haruki、Takeuchi Masayuki、Takai Atsuro
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 10 Issue: 4 Pages: 918-925

    • DOI

      10.1002/ajoc.202100046

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Immobilization of Ethynyl‐π‐Extended Electron Acceptors with Amino‐Terminated SAMs by Catalyst‐Free Click Reaction2020

    • Author(s)
      Nakano Kyohei、Sanematsu Haruki、Kaji Yumiko、Takai Atsuro、Tajima Keisuke
    • Journal Title

      Chemistry - A European Journal

      Volume: 26 Issue: 68 Pages: 15931-15937

    • DOI

      10.1002/chem.202001750

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Amino‐Functionalization of Vinyl‐Substituted Aromatic Diimides by Quantitative and Catalyst‐Free Hydroamination2020

    • Author(s)
      Sanematsu Haruki、Matsushita Yoshitaka、Takeuchi Masayuki、Takai Atsuro
    • Journal Title

      Chemistry - A European Journal

      Volume: 27 Issue: 3 Pages: 934-938

    • DOI

      10.1002/chem.202003628

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Presentation] Observation of Negative Activation Enthalpy in Amine Conjugate Addition to π-Conjugated Molecules2022

    • Author(s)
      Haruki Sanematsu, Masayuki Takeuchi, Atsuro Takai
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Surface Modification of Polyethylenimine Films with π-Conjugated Molecules via a Catalyst-Free Click Reaction2022

    • Author(s)
      Lara Rae Holstein, Masayuki Takeuchi, Atsuro Takai
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 新しい無触媒クリック反応に基づくπ電子系材料の構築と機能開拓2022

    • Author(s)
      高井 淳朗
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] 不均一な反応場でのその場修飾によるπ共役分子集積材料の開発2022

    • Author(s)
      高井 淳朗
    • Organizer
      第9回慶應有機化学若手シンポジウム
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] 負の活性化エンタルピーを有するπ共役分子のヒドロアミノ化反応2021

    • Author(s)
      実松 春樹、高井 淳朗、竹内 正之
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Divergent Synthesis of Amino-Functionalized Aromatic Diimides by Quantitative and Catalyst-Free Hydroamination2021

    • Author(s)
      Haruki Sanematsu, Atsuro Takai, Masayuki Takeuchi
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] 新奇無触媒クリック反応によるπ電子系分子集積薄膜の創成2020

    • Author(s)
      高井 淳朗
    • Organizer
      MRM Forum 2020
    • Related Report
      2020 Research-status Report
  • [Presentation] Facile Decoration of Electron-Deficient π-Systems by Novel Catalyst-Free Click Reaction2019

    • Author(s)
      Atsuro Takai
    • Organizer
      18th International Symposium on Novel Aromatic COmpounds
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] π共役分子の新奇な反応性と構造を生かしたπ電子材料の探索2019

    • Author(s)
      高井 淳朗
    • Organizer
      有機合成化学協会関東支部2019年度若手研究者のためのセミナー
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] 2つの反応点を有する電子受容性π共役分子の無触媒クリック反応2019

    • Author(s)
      実松 春樹・高井 淳朗・竹内 正之
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] 電子受容性π共役系分子の新奇無触媒ヒドロアミノ化反応と高分子重合2019

    • Author(s)
      実松 春樹・高井 淳朗・竹内 正之
    • Organizer
      第34回高分子学会茨城地区「若手の会」交流会
    • Related Report
      2019 Research-status Report
  • [Remarks] SAMURAI

    • URL

      https://samurai.nims.go.jp/profiles/takai_atsuro?locale=ja

    • Related Report
      2021 Annual Research Report
  • [Remarks] NIMS Researchers Directory Service

    • URL

      https://samurai.nims.go.jp/profiles/takai_atsuro?locale=en

    • Related Report
      2019 Research-status Report

URL: 

Published: 2019-04-18   Modified: 2023-01-30  

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