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Synthesis of heterohelicene polymers with one-handed helical structure by intramolecular chain reaction between arynes

Research Project

Project/Area Number 18K05220
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 35010:Polymer chemistry-related
Research InstitutionSeikei University

Principal Investigator

Yokoyama Akihiro  成蹊大学, 理工学部, 教授 (50343637)

Co-Investigator(Kenkyū-buntansha) 大石 智之  成蹊大学, 理工学部, 助教 (80582973)
Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
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アライン / アミド / ヘリセン / ポリアミド / 芳香族アミド
Outline of Final Research Achievements

The formation and intramolecular reaction of the arynes were studied by using the reaction of the model compounds and bases. The model reaction was carried out using potassium hexamethyldisilazide, lithium hexamethyldisilazide, n-butyllithium, and t-butyllithium as bases. In these reactions, the desired intramolecular reaction did not proceed, but the rearrangement reaction and the cleavage of amide linkages occurred as side reactions. Next, heterohelice oligomers with one-handed helical structure were synthesized and their absorption and photoluminescence spectra were studied.

Academic Significance and Societal Importance of the Research Achievements

本研究により明らかとなったアラインとアミド結合の分子内反応は、分子内にアミド結合を有する芳香環に発生させたアラインを利用する今後の研究に役立つと思われる。また本研究で開発した一方向巻きヘテロヘリセン型オリゴマーの合成方法は、ヘテロヘリセンの新たな合成方法として学術的な価値が高い。さらに本研究で明らかにしたヘテロヘリセンの立体構造や紫外・可視光吸収や蛍光発光などの物性は、ヘリセン類似体の研究に大きく寄与すると思われる。

Report

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

    (9 results)

All 2021 2020 2018

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (8 results)

  • [Journal Article] Synthesis of a coronene analogue containing an amide bond by Pd-mediated intramolecular C C bond formation of 2-halogenated 4-(alkylamino)benzoic acid cyclic trimer2021

    • Author(s)
      Yokoyama Akihiro、Ishii Arisa、Ohishi Tomoyuki、Kikkawa Shoko、Azumaya Isao
    • Journal Title

      Tetrahedron Letters

      Volume: 62 Pages: 152704-152704

    • DOI

      10.1016/j.tetlet.2020.152704

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Presentation] ナフタレンユニット間の分子内ビアリール化によるヘリセン類似体の合成検討2020

    • Author(s)
      宇佐美瑠乃・大石智之・横山明弘
    • Organizer
      第69回高分子学会年次大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] N-アルキル化された4-アミノ-5-ヨード-2-メチル安息香酸を用いた直鎖オリゴアミドの合成と分子内結合形成によるヘリセン類似体への変換2020

    • Author(s)
      下田寛貴・大石智之・横山明弘
    • Organizer
      第69回高分子学会年次大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 4-アルキルアミノ安息香酸誘導体から合成した芳香族オリゴアミドのパラジウム触媒を用いた分子内 結合形成による[7]ヘリセン類似体への変換2020

    • Author(s)
      下田 寛貴、大石 智之、横山 明弘
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 臭素とメチル基を有するN-アルキルアミノ安息香酸の縮合による環化三量体の合成とコロネン類似体への変換を目指した分子内ビアリール化の検討2020

    • Author(s)
      藤井 美帆、大石 智之、横山 明弘
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] ヘリセン類似体の合成を目指したナフタレンユニット間結合形成反応の検討2020

    • Author(s)
      宇佐美 瑠乃、大石 智之、横山 明弘
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 臭素を有するp-(アルキルアミノ)安息香酸の環化三量体を用いたコロネン類似体の合成検討2018

    • Author(s)
      石井亜梨沙・大石智之・横山明弘
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Shunsuke Sekine, Tomoyuki Ohishi, Akihiro Yokoyama2018

    • Author(s)
      Synthetic Study of Helicene Analogue via Aryne: Model Reactions
    • Organizer
      Polycondensation 2018
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis of Cyclic Trimer of Brominated p-(Alkylamino)benozic Acid and Its Conversion to Coronene Analogue2018

    • Author(s)
      Arisa Ishii, Tomoyuki Ohishi, Akihiro Yokoyama
    • Organizer
      Polycondensation 2018
    • Related Report
      2018 Research-status Report

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

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