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An attempt to synthesize cyclacene using decarbonyl aromatic ring reaction

Research Project

Project/Area Number 17K19123
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Research Field Organic chemistry and related fields
Research InstitutionKyushu University

Principal Investigator

Watanabe Motonori  九州大学, カーボンニュートラル・エネルギー国際研究所, 准教授 (60700276)

Project Period (FY) 2017-06-30 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2018: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2017: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Keywordsシクラセン / アセン / 前駆体法 / ナノチューブ / 環状アセン / π電子系化合物 / カーボンナノチューブ / 有機半導体 / 構造・機能材料 / 有機化学 / ナノ材料 / ナノチューブ・フラーレン / 光物性
Outline of Final Research Achievements

In this research, we aim to synthesize the precursor that can form cyclacene skeleton and achieve the target cyclacene by the reaction that is stimulated by mild condition such heat and/or light energy instead of chemical reaction. When the norbornadiene skeleton was selected as the starting material for the targeted cyclacene skeleton, we succeeded in synthesizing a bromohexacene precursor, which is a planar extension structure of the cyclacene skeleton. However, it was difficult to synthesize a precursor with a small ring size by this method, so reaction with norbornadiene-2,3,5,6-tetradiene was tried, but the corresponding cyclacene precursor could not be synthesized. . In the future, it has become an issue to consider the synthesis of cyclacene skeleton by multistep reaction.

Academic Significance and Societal Importance of the Research Achievements

新規カーボン材料は実用化を見据えた研究が数多くなされ、その分野もバッテリー、キャパシタや半導体等の蓄電・導電材料、太陽電池や光触媒等の光電材料、熱伝材料や分子フィルター等、応用は幅広い。シクラセンはジグザグ型ナノチューブの基本骨格で、この分子の合成法と物性が明らかにされれば選択的ナノチューブの合成が可能となるが、未だ合成が達成されていない化合物である。本研究によりシクラセンへの合成と物性が明らかにされれば、ジグザグ型ナノチューブの基本骨格分野の新領域が開拓される。

Report

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

    (10 results)

All 2018 2017 Other

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

  • [Int'l Joint Research] 台湾東海大学/台湾中央研究院(その他の国・地域)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] 台湾中央研究院化学研究所/台湾東海大学化学系(台湾)

    • Related Report
      2017 Research-status Report
  • [Journal Article] Visible Light-Driven Dye-Sensitized Photocatalytic Hydrogen Production by Porphyrin and its Cyclic Dimer and Trimer: Effect of Multi-Pyridyl-Anchoring Groups on Photocatalytic Activity and Stability2018

    • Author(s)
      M. Watanabe, S. Sun, T. Ishihara, T. Kamimura, M. Nishimura, F. Tani
    • Journal Title

      ACS Appl. Energy Mater.

      Volume: 1 Issue: 11 Pages: 6072-6081

    • DOI

      10.1021/acsaem.8b01113

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and physical properties of brominated hexacene and hole-transfer properties of thin-film transistors2018

    • Author(s)
      Watanabe Motonori、Miyazaki Takaaki、Matsushima Toshinori、Matsuda Junko、Chein Ching-Ting、Shibahara Masahiko、Adachi Chihaya、Sun Shih-Sheng、Chow Tahsin J.、Ishihara Tatsumi
    • Journal Title

      RSC Advances

      Volume: 8 Issue: 24 Pages: 13259-13265

    • DOI

      10.1039/c7ra13632c

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] Physical properties of hexacenes and thin-film state hole-transfer properties2018

    • Author(s)
      Motonori Watanabe
    • Organizer
      The 11th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules, Taichung City, Taiwan, Aug. 25-29. 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of Higher Acene from Soluble Precursors2018

    • Author(s)
      Motonori Watanabe
    • Organizer
      Fuzzy bond Conference, Osaka University, Toyonaka Campus (Japan), Sep. 15, 2018.
    • Related Report
      2018 Annual Research Report
  • [Presentation] Synthesis and physical properties of brominated hexacene and hole-transfer properties of thin-film transistors2018

    • Author(s)
      Motonori Watanabe, Takaaki Miyazaki, Toshinori Matsushima, Junko Matsuda, Ching Ting Chein, Masahiko Shibahara, Chihaya Adachi, Shih Sheng Sun, Tahsin J. Chow, Tatsumi Ishihara
    • Organizer
      29th Symposium on Physical Organic Chemistry. Tokyo Institute of Technology, Ookayama Campus (Japan), Sep. 6-8, 2018.
    • Related Report
      2018 Annual Research Report
  • [Presentation] アセン類の合成法の開発と機能性有機材料・デバイスへの応用2017

    • Author(s)
      渡邊源規
    • Organizer
      九州・山口支部 第29回 若手研究者のためのセミナー
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] ブロモヘキサセンの合成と物性2017

    • Author(s)
      渡邊源規
    • Organizer
      構造有機化学若手研究者 研究会2017
    • Related Report
      2017 Research-status Report
  • [Remarks] Motonori Watanabe homepage

    • Related Report
      2017 Research-status Report

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Published: 2017-07-21   Modified: 2022-02-22  

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