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Synthesis and physical evaluation of polyazulene-doping graphene-nano-ribbons

Research Project

Project/Area Number 19K22185
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 33:Organic chemistry and related fields
Research InstitutionKyoto University

Principal Investigator

Takasu Kiyosei  京都大学, 薬学研究科, 教授 (10302168)

Project Period (FY) 2019-06-28 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2020: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2019: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Keywords多環芳香族炭化水素 / 精密有機合成 / アズレン / 蛍光 / ナノグラフェン / グラフェンナノリボン / ボトムアップ合成 / スピロ環 / 物性 / キラリティ / 遷移金属触媒反応 / 会合状態 / 電子状態 / 有機材料
Outline of Research at the Start

本研究は、過去に例の無いアズレンを核とするグラフェンナノリボンを設計・ボトムアップ合成への挑戦である。すなわち、アズレンを高度に縮環して骨格内に組み込むという独自の発想に基づき、アズレン固有の分極を分子全体に伝播させるとともに、5員環・7員環の幾何構造を活かした新奇なPAHの創成に波及させることを目標とし、最終的には機能性有機材料・薄膜の開発を目指す。

Outline of Final Research Achievements

Polycyclic aromatic hydrocarbons (PAHs) have unique properties such as luminescence in the visible region and electrical conductivity in the solid state, which are derived from delocalized π-electrons in a broadly conjugated system. In this study, we have developed new synthetic methods for PAHs based on the strategy of utilizing distorted molecules. In particular, we have shown that heteroproperanes can be converted into non-alternative hydrocarbons, heteroaromatic compounds, and spirocyclic PAHs by inducing reactions involving the release of strain under appropriate reaction conditions. Through multi-step transformations, nanographene with continuous azulene ring structure was synthesized and its properties were successfully elucidated.

Academic Significance and Societal Importance of the Research Achievements

格子欠陥を高密度にグラフェンやグラフェンナノリボン(GNR)に導入する技術は、それらの機能を劇的に向上もしくは変化させることに直結する。我々が創製したアズレン含有GNRの基礎的性質を調べたかぎり、ベンゼン環のみからなるGNRと様々な点で異なる性質が明らかとなった。我々が開発した「10π電子環状反応による新たなアズレン環構築法」は簡便であることから、今後は原料の種類を変えて、幅・長さ・エッジ構造の異なる連結アズレンを格子欠陥とするGNRを合成し機能を明らかにするとともに、医薬利用を含めたナノデバイスへの応用が期待される。

Report

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

    (7 results)

All 2020 2019

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (5 results) (of which Int'l Joint Research: 4 results,  Invited: 2 results)

  • [Journal Article] Helical Nanographenes Embedded with Contiguous Azulene Units2020

    • Author(s)
      Ogawa Naoki、Yamaoka Yousuke、Takikawa Hiroshi、Yamada Ken-ichi、Takasu Kiyosei
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 31 Pages: 13322-13327

    • DOI

      10.1021/jacs.0c06156

    • NAID

      120006888507

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Polycyclic Spirocarbocycles via Acid-Promoted Ring-Contraction/Dearomative Ring-Closure Cascade of Oxapropellanes2019

    • Author(s)
      Ogawa Naoki、Yamaoka Yousuke、Takikawa Hiroshi、Takasu Kiyosei
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 18 Pages: 7563-7567

    • DOI

      10.1021/acs.orglett.9b02835

    • NAID

      120006767906

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Presentation] New Horizons of Chemistry of 4-Membered Carbocycles2020

    • Author(s)
      Kiyosei Takasu
    • Organizer
      2019 Designing Molecules Workshop and Conference
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Graphene Nanoribbons Embedded Polyazulene Framework2019

    • Author(s)
      Naoki Ogawa, Yousuke Yamaoka, Hiroshi Takikawa, Kiyosei Takasu
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] KHMDS-Promoted Enolate-Olefin Metathesis2019

    • Author(s)
      Kiyosei Takasu, Kazuma Sugimoto, Shun Fujimura, Ken-ichi Yamada, Hiroshi Takikawa, Yousuke Yamaoka
    • Organizer
      The 4th International Symposium on Process Chemistry
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] New Horizons of Chemistry of 4-Membered Carbocycles2019

    • Author(s)
      Kiyosei Takasu
    • Organizer
      2019 Designing Molecules Workshop and Conference
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] オキサプロペランを経る多様な多環芳香族炭化水素の合成2019

    • Author(s)
      小川直希, 山岡庸介, 瀧川紘, 高須清誠
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Research-status Report

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Published: 2019-07-04   Modified: 2022-01-27  

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