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Development of environmental stimuli-responsive functional molecules based on intramolecular electron transfer

Research Project

Project/Area Number 18K05079
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionOsaka University

Principal Investigator

HIRAO Yasukazu  大阪大学, 理学研究科, 講師 (50506392)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywords電子移動 / 有機ラジカル / 刺激応答性分子 / 化学結合論 / クロミズム / 光物性 / 磁気物性 / 構造・機能材料 / 複合材料・物性 / 物性実験
Outline of Final Research Achievements

We synthesized a number of organic compounds coupling strong electron-donating and/or electron-accepting units, and analyzed them under various conditions using various physical techniques to evaluate their environmental stimulus responsiveness. The compounds connecting electron-donating and electron-accepting units became zwitterionic substances. With decreasing solvent polarity, the equilibrium shifted to the neutral biradical species corresponding to the product with intramolecular electron transfer. On the other hand, the compounds with dimerized bulky electron-donating units provided two conformational isomers. Their isomerization equilibrium constants depended on solvent viscosity. The stimuli-responsive properties and response mechanisms of the molecules developed in this project have not been reported before and are promising novel stimuli responsive material.

Academic Significance and Societal Importance of the Research Achievements

本研究課題で合成した有機化合物群は全て新規分子であり、その刺激応答性と応答機構は従来報告されていないものである。特に分子内の電子分布を変化可能な分子を開発したことにより、溶媒の極性や温度の変化に対して磁気的物性の変化で応答する分子を生み出すことができた。また、構造・物性が“ゆらぎやすい”分子を開発したことにより、従来とは全く異なる機構で溶媒粘度を感応する材料を創出することができた。これらの成果は刺激応答性材料の開発に新たな道を拓くものである。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (20 results)

All 2021 2020 2019 2018

All Journal Article (6 results) (of which Peer Reviewed: 5 results) Presentation (14 results) (of which Int'l Joint Research: 2 results,  Invited: 1 results)

  • [Journal Article] Biradicaloid Behavior of a Twisted Double Bond2021

    • Author(s)
      Hamamoto Yosuke, Hirao Yasukazu, Kubo Takashi
    • Journal Title

      The Journal of Physical Chemistry Letters

      Volume: 12 Issue: 19 Pages: 4729-4734

    • DOI

      10.1021/acs.jpclett.1c00664

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] ねじれた二重結合の化学2021

    • Author(s)
      平尾泰一
    • Journal Title

      生産と技術

      Volume: 73

    • NAID

      40022645645

    • Related Report
      2020 Annual Research Report
  • [Journal Article] Synthesis and Electronic Properties of the 1-Naphthoxyl Radical2020

    • Author(s)
      Hirao Yasukazu、Marutani Miki、Tachibana Naoki、Kubo Takashi
    • Journal Title

      Chemistry Letters

      Volume: 49 Issue: 2 Pages: 153-155

    • DOI

      10.1246/cl.190821

    • NAID

      130007795214

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Interaction of the Dihydropyridine/Pyridinium Redox Pair Fixed into a V-Shaped Conformation2019

    • Author(s)
      Hirao Yasukazu、Kubo Takashi、Teraoka Mitsuru
    • Journal Title

      HETEROCYCLES

      Volume: 98 Issue: 10 Pages: 1345-1345

    • DOI

      10.3987/com-19-14163

    • NAID

      40022091318

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Solvent viscosity-dependent isomerization equilibrium of tetramethoxy-substituted bianthrone2019

    • Author(s)
      Hirao Yasukazu、Hamamoto Yosuke、Nagamachi Nobuhiro、Kubo Takashi
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 21 Issue: 23 Pages: 12209-12216

    • DOI

      10.1039/c9cp01836k

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Redox/pH Dual Stimuli‐Responsive Acridine Spiropyran2019

    • Author(s)
      Hirao Yasukazu、Taniguchi Toshiaki、Teraoka Mitsuru、Kubo Takashi
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 8 Issue: 6 Pages: 863-866

    • DOI

      10.1002/ajoc.201900263

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Presentation] プロトン・電子供与および受容部位を併せ持つ新規芳香族化合物の合成と物性2021

    • Author(s)
      平尾泰一、伊延穂波
    • Organizer
      日本化学会、第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ラジカルーイオン性転移を目指したトリメチレンメタン誘導体の合成2021

    • Author(s)
      平尾泰一、内田真人
    • Organizer
      日本化学会、第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Synthesis and Electronic Properties of Donor-Acceptor Type Molecules to Realize a Solvent Polarity Induced Singlet-Triplet Transition2020

    • Author(s)
      平尾泰一
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] The Solvent Viscosity Response of Bianthrone Derivatives2020

    • Author(s)
      平尾泰一、濱本洋輔
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] ビアントロン誘導体のサーモおよびエレクトロクロミック挙動2020

    • Author(s)
      平尾泰一、濱本洋輔
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] プロトン電子ドナーおよびアクセプター骨格からなる水素結合ネットワークの構築2020

    • Author(s)
      平尾泰一、伊延穂波
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] 溶媒粘度に対するビアントロンの異性化応答2020

    • Author(s)
      平尾泰一
    • Organizer
      第13回分子化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] ビアントロン誘導体の固体状態におけるサーモクロミック挙動2020

    • Author(s)
      平尾泰一、濱本洋輔
    • Organizer
      日本化学会 第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] プロトン・電子ドナーおよびアクセプター骨格からなる新規芳香族化合物の合成と物性2020

    • Author(s)
      平尾泰一、伊延穂波
    • Organizer
      日本化学会 第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 熱による電子移動励起を指向したドナーアクセプター型分子の合成と電子物性2019

    • Author(s)
      平尾泰一
    • Organizer
      日本化学会 第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] プロトン-電子の状態を精密に制御設計した分子の開発と機能発現2018

    • Author(s)
      平尾泰一
    • Organizer
      ITbM/IGER Chemistry Workshop 2018
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] 分子内電子移動を鍵とするドナーアクセプター連結分子の電子状態変化と溶媒効果2018

    • Author(s)
      平尾泰一
    • Organizer
      第12回分子化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] 溶媒粘度応答性を示す新規ビアントロン誘導体の合成2018

    • Author(s)
      平尾泰一・濱本洋輔
    • Organizer
      日本化学会 第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ねじれ構造をもつビアントロンの安定化と電子物性2018

    • Author(s)
      平尾泰一・濱本洋輔
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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