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Development of new mechanofluorochromic materials based on borepin structure

Research Project

Project/Area Number 19K15543
Research Category

Grant-in-Aid for Early-Career Scientists

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

Principal Investigator

Adachi Yohei  広島大学, 先進理工系科学研究科(工), 助教 (50805215)

Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2021: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2019: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsホウ素 / ボレピン / 固体発光 / クロミズム / TADF / メカノクロミック / メカノフルオロクロミズム
Outline of Research at the Start

外部からの応力に対し発光色が変化する現象はメカノフルオロクロミズム(MFC)と呼ばれ、センサーやデバイスなどの機能性材料への応用が期待されている。研究代表者が過去に合成したボレピンと呼ばれる骨格を含む有機化合物では、2つの異なる固体状態で、それぞれ赤色と青色の発光色を示した。本研究は、この骨格を基にした新しい化合物の合成と物性の評価を行い、発光特性を詳細に調査することで、革新的な発光性を示す分子材料の、新しい分子設計のコンセプトを得ることが目的である。

Outline of Final Research Achievements

Organic fluorescent molecules with property of changing emission properties in response to external stimuli (mechanofluorochromism, MFC) are expected to be applied to functional materials such as sensors. In this study, we attempted to synthesize new MFC materials based on a structure called benzo[d]dithieno[b,f]bolepin, which exhibits unique solid-state emission properties. By introducing various substituents on the boron, we succeeded to synthesize borepins that exhibit not only MFC but also thermally activated delayed fluorescence and phosphorescence.

Academic Significance and Societal Importance of the Research Achievements

MFC特性を有する分子は、センサー材料やイメージングデバイスなどへの応用が期待されている。しかし純粋な有機分子の場合、MFC特性を示す場合でも発光色の変化が小さいことが多い。本研究ではホウ素を含む分子を用いることで、ドラスティックな発光色の変化を示すMFC材料を得ることができた。今後、その機構をより詳細に解析することで、さらに優れた特性を示す革新的MFC材料の創出へつながると期待できる。

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 Other

All Int'l Joint Research (2 results) Journal Article (7 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 7 results) Presentation (7 results) (of which Int'l Joint Research: 1 results) Remarks (1 results)

  • [Int'l Joint Research] Rutgers University(米国)

    • Related Report
      2020 Research-status Report
  • [Int'l Joint Research] Rutgers University Newark(米国)

    • Related Report
      2019 Research-status Report
  • [Journal Article] m-Phenylene linked macrocycle composed of electron-rich dithienogermole and electron-deficient tricoordinate boron units2022

    • Author(s)
      Adachi Yohei、Kondo Keisuke、Yin Xiaodong、Jaekle Frieder、Ohshita Joji
    • Journal Title

      Polymer

      Volume: 239 Pages: 124404-124404

    • DOI

      10.1016/j.polymer.2021.124404

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and Optical Properties of Anthryl-Substituted Tetracyclic Borepins2022

    • Author(s)
      Adachi Yohei、Yamada Kohei、Ohshita Joji
    • Journal Title

      Chemistry Letters

      Volume: - Issue: 6 Pages: 654-657

    • DOI

      10.1246/cl.220139

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Optical Properties of Boron-Incorporated Analogues of Tetrathienoanthracene2022

    • Author(s)
      Yohei Adachi、Fuka Arai、Kohei Yamada、Maho Kurihara、Joji Ohshita
    • Journal Title

      Organometallics

      Volume: -

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effect of the conjugation pathway on the electronic structures of p-π* conjugated polymers with fused borepin units2021

    • Author(s)
      Adachi Yohei、Arai Fuka、Sakabe Mitsuru、Ohshita Joji
    • Journal Title

      Polymer Chemistry

      Volume: 12 Issue: 23 Pages: 3471-3477

    • DOI

      10.1039/d1py00528f

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Thiophene-based twisted bistricyclic aromatic ene with tricoordinate boron: a new n-type semiconductor2021

    • Author(s)
      Adachi Yohei、Nomura Takanori、Tazuhara Shion、Naito Hiroyoshi、Ohshita Joji
    • Journal Title

      Chemical Communications

      Volume: 57 Issue: 11 Pages: 1316-1319

    • DOI

      10.1039/d0cc07952a

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Optical Characteristics of Hybrid Macrocycles with Dithienogermole and Tricoordinate Boron Units2021

    • Author(s)
      Adachi Yohei、Nabeya Taishi、Kawakami Keigo、Yamaji Kosuke、Jaekle Frieder、Ohshita Joji
    • Journal Title

      Chemistry - A European Journal

      Volume: 27 Issue: 10 Pages: 3306-3314

    • DOI

      10.1002/chem.202004643

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Extended conjugated borenium dimers via late stage functionalization of air-stable borepinium ions2020

    • Author(s)
      Yohei Adachi, Fuka Arai, Frieder Jaekle
    • Journal Title

      Chemical Communications

      Volume: 56 Issue: 38 Pages: 5119-5119

    • DOI

      10.1039/d0cc02514c

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] アントリル基を有する含三配位ホウ素芳香族化合物の合成とフッ化物イオンセンサーへの応用2022

    • Author(s)
      山田航平、安達洋平、大下浄治
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ドナー‐アクセプター型ベンゾ[d]ジチエノ[b,f]ボレピンの合成とその多様な発光特性2022

    • Author(s)
      栗原真歩、安達洋平、中村優志、大下浄治
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] チアボリン環を含む新規p-pi共役系ポリマーの合成2021

    • Author(s)
      坂部充、安達洋平、大下浄治
    • Organizer
      第40回無機高分子研究討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Photophysical properties of twisted bistricyclic aromatic ene with tricoordinate boron2021

    • Author(s)
      Yohei Adachi, Joji Ohshita, Hiroyoshi Naito
    • Organizer
      Pacifichem 2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] チオフェンをベースとする含ホウ素共役系ビルディングユニットの二量体の合成2021

    • Author(s)
      安達 洋平, 野村 隆憲, 田津原 汐音, 内藤 裕義, 大下 浄治
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] ジチエノゲルモールと三配位ホウ素ユニットから成る環状化合物と その特性評価2020

    • Author(s)
      河上啓吾, 大下浄治, 安達洋平, 鍋谷太志
    • Organizer
      第39回無機高分子研究討論会
    • Related Report
      2020 Research-status Report
  • [Presentation] 安定なカチオン性三配位ホウ素ビルディングユニットの合成と物性2020

    • Author(s)
      安達 洋平, Frieder Jaekle, 大下浄治
    • Organizer
      第39回無機高分子研究討論会
    • Related Report
      2020 Research-status Report
  • [Remarks]

    • URL

      https://home.hiroshima-u.ac.jp/orgmtrls/Ohshita_Group/Ohshita_Group-Home.html

    • Related Report
      2019 Research-status Report

URL: 

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

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