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Organic Electron Donors and Acceptors through the Use of Nocovalent Bonding Interaction

Research Project

Project/Area Number 17K05769
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionTohoku University

Principal Investigator

TAKEDA Takashi  東北大学, 多元物質科学研究所, 助教 (80625038)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2018: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords電子アクセプター / 水素結合 / 分子構造 / 酸化還元 / 分子集合体 / 有機電子アクセプター / 結晶構造 / アントラキノン / 光学特性 / 溶媒吸着 / 有機電子ドナー
Outline of Final Research Achievements

This project aimed to propose use of noncovalent bonding interaction to modulate electronic properties of organic electron donors and acceptors. We focused on emergent noncovalent bonding interactions between the substituents in close proximity and designed and synthesized arylsulfonamide-armed anthraquinones for this purpose. Cyclic voltammetry measurement of these compounds revealed that intermolecular hydrogen bonding interaction could modulate electronic properties of anthraquinone. Single crystal structure analyses of these compounds revealed versatile molecular assemblies. Among them, the single crystal of 1,8-disubstituted derivative showed reversible and selective acetonitrile/propionitrile sorption and that of 1,4,5,8-tetrasubstituted derivative formed cage structure, which can include substituted benzene derivatives.

Academic Significance and Societal Importance of the Research Achievements

有機電子ドナー・アクセプターは様々な有機機能性材料の基本ユニットであり、その開発が古くから盛んにおこなわれてきた。有機ドナー・アクセプター類の電子状態の調整は主に「分子のπ電子系コアの置換・拡張」および「π電子系コアの末端部位への電子供与性・求引性置換基の導入」の2種類の方法で達成されている。適切な分子設計により、非共有結合性相互作用が有機電子ドナー・アクセプターの電子状態の調性できることを示した。新たな有機ドナー・アクセプターの開発指針の提示により、有機電子材料開発推進が期待される。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (32 results)

All 2020 2019 2018 2017 Other

All Int'l Joint Research (2 results) Journal Article (11 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 11 results,  Open Access: 2 results) Presentation (19 results) (of which Int'l Joint Research: 8 results,  Invited: 6 results)

  • [Int'l Joint Research] Leibniz Institute of Photonic Technology(ドイツ)

    • Related Report
      2018 Research-status Report
  • [Int'l Joint Research] University of Liverpool(英国)

    • Related Report
      2018 Research-status Report
  • [Journal Article] Versatile Hydrogen-Bonded Assemblies of Twisted Tetra[3,4]thienylene Tetracarboxylic Acid with Selective Solvent Sorption2019

    • Author(s)
      Takashi Takeda, Masataka Ozawa, Tomoyuki Akutagawa
    • Journal Title

      Crystal Growth & Design

      Volume: 19 Issue: 8 Pages: 4784-4792

    • DOI

      10.1021/acs.cgd.9b00664

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dynamic Motion of Twisted π System-Induced Temperature-Dependent Dielectric Response in the Neat Liquid State2019

    • Author(s)
      Takashi Takeda, Masataka Ozawa, and Tomoyuki Akutagawa
    • Journal Title

      J. Phys. Chem. C

      Volume: 123 Issue: 33 Pages: 20152-20159

    • DOI

      10.1021/acs.jpcc.9b06071

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Jumping Crystal of Hydrogen-Bonded Organic Framework Induced by Collective Molecular Motion of Twisted π System2019

    • Author(s)
      Takashi Takeda, Masataka Ozawa, and Tomoyuki Akutagawa
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 58 Issue: 30 Pages: 10345-10352

    • DOI

      10.1002/anie.201905075

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organic Functional Materials Based on Molecular Motion in the Condensed Phases2019

    • Author(s)
      Takeda Takashi
    • Journal Title

      Molecular Science

      Volume: 13 Issue: 1 Pages: A0102

    • DOI

      10.3175/molsci.13.A0102

    • NAID

      130007696983

    • ISSN
      1881-8404
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Thermoresponsive Amphipathic Fluorescent Organic Liquid2018

    • Author(s)
      Takashi Takeda, Shunsuke Yamamoto, Masaya Mitsuishi, Tomoyuki Akutagawa
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 122 Issue: 17 Pages: 9593-9598

    • DOI

      10.1021/acs.jpcc.8b01131

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] C3 Symmetric Hexaphenyltriphenylenehexamide: Molecular Design of Fluorescent Ferroelectrics2018

    • Author(s)
      Takashi Takeda, Jianyun Wu, Nobuaki Ikenaka, Norihisa Hoshino, Ichiro Hisaki, Tomoyuki Akutagawa
    • Journal Title

      ChemistrySelect

      Volume: 3 Issue: 38 Pages: 10608-10614

    • DOI

      10.1002/slct.201802317

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Preparation, Electronic and Liquid Crystalline Properties of Electron-Accepting Azaacene Derivatives2018

    • Author(s)
      Takashi Takeda, Tomohiro Ikemoto, Shunsuke Yamamoto, Wakana Matsuda, Shu Seki, Masaya Mitsuishi, Tomoyuki Akutagawa
    • Journal Title

      ACS Omega

      Volume: 3 Issue: 10 Pages: 13697-13703

    • DOI

      10.1021/acsomega.8b01943

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Selective MeCN/EtCN soprtion and preferential inclusion of substituted benzenes in a cage structure with arylsulfonamide-armed anthraquinones2018

    • Author(s)
      Takashi Takeda, Shin-ichiro Noro, Takayoshi Nakamura, Yasutaka Suzuki, Jun Kawamata, Tomoyuki Akutagawa
    • Journal Title

      CrystEngComm

      Volume: 20 Issue: 1 Pages: 17-24

    • DOI

      10.1039/c7ce01752a

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Host-guest molecular crystals of diamino-4,4-bithiazole and dynamic molecular motions via guest sorption2018

    • Author(s)
      Hiroshi Nishiyama, Takashi Takeda, Norihisa Hoshino, Kiyonori Takahashi, Shin-ichiro Noro, Takayoshi Nakamura, Tomoyuki Akutagawa
    • Journal Title

      Crystal Growth & Design

      Volume: 18 Issue: 1 Pages: 286-296

    • DOI

      10.1021/acs.cgd.7b01236

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Circular polarized luminescence of hydrogen-bonded molecular assemblies of chiral pyrene derivatives2018

    • Author(s)
      Hayato Anetai, Takashi Takeda, Norihisa Hoshino, Yasuyuki Araki, Takehiko Wada, Shunsuke Yamamoto, Masaya Mitsuishi, Hiromu Tsuchida, Tomoki Ogoshi, Tomoyuki Akutagawa
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 122 Issue: 11 Pages: 6323-6331

    • DOI

      10.1021/acs.jpcc.7b12747

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] The emergent intramolecular hydrogen bonding effect on the electronic structures of organic electron acceptors2017

    • Author(s)
      Takashi Takeda, Yasutaka Suzuki, Jun Kawamata, Shin-ichiro Noro, Takayoshi Nakamura, Tomoyuki Akutagawa
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 19 Issue: 35 Pages: 23905-23909

    • DOI

      10.1039/c7cp04402j

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] アリールアミノ基を複数有するアントラキノン類の光学・電子物性2020

    • Author(s)
      武田 貴志、芥川 智行
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Jumping crystal of hydrogen-bonded organic framework2019

    • Author(s)
      Takashi Takeda, Tomoyuki Akutagawa
    • Organizer
      The 13th Japan-China joint symposium on conduction and photoconduction in organic solids and related phenomena
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Jumping crystal of hydrogen-bonded organic framework induced by collective molecular motion of twisted π system2019

    • Author(s)
      Takashi Takeda, Masataka Ozawa, Tomoyuki Akutagawa
    • Organizer
      5th Japan-Taiwan-Singapore-Hong Kong quadrilateral symposium on coordination chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 有機化合物の分子運動に立脚した機能性材料開発2019

    • Author(s)
      武田 貴志
    • Organizer
      第13回分子科学討論会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] テトラ[2,3]チエニレンテトラカルボン酸が形成するHOFとその結晶ジャンプ2019

    • Author(s)
      武田 貴志、小澤 優喬、芥川 智行
    • Organizer
      第28回有機結晶シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Hydrogen bonded molecular crystals of tetrathienylene tetracaboxylic acids with selective solvent sorption and thermosalient behavior2019

    • Author(s)
      Takashi Takeda, Masataka Ozawa, Tomoyuki Akutagawa
    • Organizer
      18th International symposium on novel aromatic compounds
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Hydrogen bonded molecular crystals of tetrathienylene tetracaboxylic acids with selective solvent sorption and thermosalient behavior2019

    • Author(s)
      Takashi Takeda, Masataka Ozawa, Tomoyuki Akutagawa
    • Organizer
      14th International symposium on functional π-electron systems
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] テトラチエニレンテトラカルボン酸が形成する多様な結晶構造と溶媒吸着・サーモサリエント効果2019

    • Author(s)
      武田 貴志、小澤 優喬、芥川 智行
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 有機化合物の分子運動に立脚した新奇機能性材料開発2018

    • Author(s)
      武田 貴志
    • Organizer
      日本化学会低次元光機能材料研究会第7回研究講演会
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] Arylsulfonamide-armed anthraquinone: The emergent hydrogen bonding effect on the organic electronic structure and selective MeCN/EtCN sorption in the crystal2018

    • Author(s)
      Takashi Takeda, Tomoyuki Akutagawa
    • Organizer
      7th EuCheMS Chemistry Congress
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] キラルアルキル鎖を導入したピレンテトラアミドの分子集合と光学特性・強誘電性2018

    • Author(s)
      武田 貴志、姉帯 勇人、星野 哲久、芥川 智行
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] 折れ曲がり構造を有するテトラ[3,4]チエニレンテトラカルボン酸が形成する水素結合ネットワークと選択的な溶媒吸着2018

    • Author(s)
      武田 貴志、小澤 優喬、星野 哲久、芥川 智行
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] 水素結合性および電子受容性部位を有するピラジノキノキサリン誘導体の合成と物性2018

    • Author(s)
      武田 貴志、芥川 智行
    • Organizer
      第12回分子科学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] 有機化合物の集積構造の熱運動性に立脚した新奇バルク機能性材料創製2018

    • Author(s)
      武田 貴志
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] Crystal jumping of alkyl acridone and its dicyanomethylenated derivatives2017

    • Author(s)
      Takashi Takeda, Tomoyuki Akutagawa
    • Organizer
      24th Congress & General Assembly of the International Union of Crystallography 2017
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Arylsulfonamide substituted anthraquinones: unique electronic structures and selective molecular sorption behavior2017

    • Author(s)
      Takashi Takeda, Tomoyuki Akutagawa
    • Organizer
      17th International Symposium on Novel Aromatic Compounds
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Electron-deficient acene-based liquid crystals2017

    • Author(s)
      Takashi Takeda, Tomohiro Ikemoto, Tomoyuki Akutagawa
    • Organizer
      13th International Symposium on Functional pi-Electron Systems
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] PEGエステル基を有するテトラフェニルエチレン:凝集特性を示すAIE液体2017

    • Author(s)
      武田 貴志、山本 俊介、三ツ石 方也、芥川 智行
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] PEGエステル基を有するテトラフェニルエチレン:凝集特性を示すAIE液体2017

    • Author(s)
      武田 貴志、山本 俊介、三ツ石 方也、芥川 智行
    • Organizer
      第11回分子科学討論会
    • Related Report
      2017 Research-status Report

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Published: 2017-04-28   Modified: 2021-02-19  

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