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Creation of High-order Structures Based on Cycloparaphenylene Radical Cations and Dications and Elucidation of their Function

Research Project

Project/Area Number 18K19075
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

KAYAHRA EIICHI  京都大学, 化学研究所, 助教 (10610553)

Project Period (FY) 2018-06-29 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥6,240,000 (Direct Cost: ¥4,800,000、Indirect Cost: ¥1,440,000)
Fiscal Year 2019: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2018: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywordsラジカルカチオン / ジカチオン / 曲面環状π共役分子 / シクロパラフェニレン / 酸化 / 導電性 / スピン / 電荷 / 化学酸化 / 環状π共役分子 / 電子状態 / フラーレン / カーボンナノチューブ
Outline of Final Research Achievements

This study focused on deepening the academic understanding of the spin and charge (de)localization in the oxidized species of cycloparaphenylenes (CPPs) and their derivatives, which are strongly related to the conductivity of CPPs. We clarified the effect of introduction of heteroatom substituents in CPP oxidized species.

Academic Significance and Societal Importance of the Research Achievements

本研究で得られた知見をさらに深化させることで、π共役分子の酸化状態におけるスピンや電荷の振る舞いなど、未解明なまま存在している疑問に対して、多くの体系的な理解を与えることが期待される。さらに、本研究の知見を材料化学分野へ展開していくことで、エレクトロニクス素子としてのポテンシャルが高い環状π共役分子、酸化種を創出出来ると考えられる。

Report

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

    (26 results)

All 2020 2019 2018

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (19 results) (of which Int'l Joint Research: 4 results)

  • [Journal Article] Selective and Gram-Scale Synthesis of [8]Cycloparaphenylene2020

    • Author(s)
      Kawanishi Tatsuya、Ishida Kosuke、Kayahara Eiichi、Yamago Shigeru
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 85 Issue: 4 Pages: 2082-2091

    • DOI

      10.1021/acs.joc.9b02844

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Reactions of Carbon Nanohoop2019

    • Author(s)
      Yamago Shigeru、Kayahara Eiichi
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 77 Issue: 11 Pages: 1147-1158

    • DOI

      10.5059/yukigoseikyokaishi.77.1147

    • NAID

      130007742541

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2019-11-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Size-Dependent Relaxation Processes of Photoexcited [n]Cycloparaphenylenes (n = 5-12): Significant Contribution of Internal Conversion in Smaller Rings2019

    • Author(s)
      Fujitsuka Mamoru、Lu Chao、Zhuang Bo、Kayahara Eiichi、Yamago Shigeru、Majima Tetsuro
    • Journal Title

      The Journal of Physical Chemistry A

      Volume: 123 Issue: 22 Pages: 4737-4742

    • DOI

      10.1021/acs.jpca.9b03334

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Strain-Induced Double Carbon-Carbon Bond Activations of Cycloparaphenylenes (CPPs) by a Platinum Complex and Its Application for the Synthesis of Cyclic Diketones2018

    • Author(s)
      Kayahara, E.; Hayashi, T.; Takeuchi, K.; Ozawa, F.; Ashida, K.; Ogoshi, S.; Yamago, S
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 57 Issue: 35 Pages: 11418-11421

    • DOI

      10.1002/anie.201806591

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Near-Infrared Fluorescence from In-Plane-Aromatic Cycloparaphenylene Dications2018

    • Author(s)
      Masumoto, Y.; Toriumi, N.; Muranaka, A.; Kayahara, E.; Yamago, S.; Uchiyama, M.
    • Journal Title

      J. Phys. Chem. A

      Volume: 122 Issue: 23 Pages: 5162-5167

    • DOI

      10.1021/acs.jpca.8b03105

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Short-step Synthesis of Large Cycloparaphenylenes2018

    • Author(s)
      Kayahara, E.; Cheng, Y.; Yamago, S
    • Journal Title

      Chem. Lett

      Volume: 47 Issue: 9 Pages: 1108-1111

    • DOI

      10.1246/cl.180486

    • NAID

      130007472096

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Physical Properties of Polyfluorinated Cycloparaphenylenes2018

    • Author(s)
      Hashimoto, S.; Kayahara, E.; Mizuhata, Y.; Tokitoh, N.; Takeuchi, K.; Ozawa, F.; Yamago, S.
    • Journal Title

      Org. Lett

      Volume: 20 Issue: 18 Pages: 5973-5976

    • DOI

      10.1021/acs.orglett.8b02715

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] メビウストポロジーを持つ環状パラフェニレン誘導体ジカチオンの合成とその面内芳香族性2020

    • Author(s)
      寺林 智昭, 茅原 栄一, 加藤 立久, 山子 茂
    • Organizer
      日本化学会 第100春季年会 (2020)
    • Related Report
      2019 Annual Research Report
  • [Presentation] 8の字構造を有するシクロパラフェニレンの酸化種の電子状態2020

    • Author(s)
      小野塚洸太, 茅原栄一, 加藤立久, 山子茂
    • Organizer
      日本化学会 第100春季年会 (2020)
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis and Characterization of a Doubly Annulated Cycloparaphenylene and Its Oxidized Species2020

    • Author(s)
      孫連盛, 茅原栄一, 加藤立久, 山子茂
    • Organizer
      日本化学会 第100春季年会 (2020)
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis and Properties of Cycloparaphenylene Radical Cation and Dication2019

    • Author(s)
      Eiichi Kayahara
    • Organizer
      2019 Gordon Research Conference on Photochemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Aromaticity in Cycloparaphenylene Dicaions2019

    • Author(s)
      Eiichi Kayahara
    • Organizer
      First International Conference on Excited State Aromaticity and Antiaromaticity
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Strain-induced Double Carbon-carbon Bond Activations of Cycloparaphenyelens by a Platnum Complex2019

    • Author(s)
      Eiichi Kayahara, Toshiki Hayashi, Shigeru Yamago
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ねじれた構造を持つシクロパラフェニレン誘導体およびその酸化種の合成と同定2019

    • Author(s)
      小野塚洸太, 橋本士雄磨, 茅原栄一, 加藤立久, 山子茂
    • Organizer
      第36回有機合成化学セミナー
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis and Characterization of a Doubly Annulated Cycloparaphenylene and Its Dication2019

    • Author(s)
      Sun Liansheng, Eiichi Kayahara, Shigeru Yamago
    • Organizer
      The 1st Kyoto University - UNIST Joint Symposium on Chemistry and Materials Science
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 環状ヘキサ-2,7-(4,5-ジアリール)アントリレンエチニレンの合成と性質2019

    • Author(s)
      松木洋憲, 茅原栄一, 山子茂, 小林健二
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ねじれた構造を持つシクロパラフェニレン誘導体およびその酸化種の合成と同定2019

    • Author(s)
      小野塚洸太, 橋本士雄磨, 茅原栄一, 加藤立久, 山子茂
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis and Characte- rization of Doubly Annulated Cycloparaphenylenes Having Orthogonal Conjugation2019

    • Author(s)
      Sun Liansheng, Eiichi Kayahara, Shigeru Yamago
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] スピロ構造を有する環状π共役分子の合成2019

    • Author(s)
      小野塚洸太、橋本士雄磨、茅原栄一、山子茂
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] シクロパラフェニレンの励起緩和過程の環サイズ依存性2019

    • Author(s)
      藤塚守、茅原栄一、山子茂、真嶋哲朗
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Syntheses and Properties of Tetraalkoxycycloparaphenylene Radical Cation and Dication2019

    • Author(s)
      Kobayashi Go、Kayahara Eiichi、Yamago Shigeru
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Formation and applications of host-guest complexes formed from tetraalkynyl[10]CPP and fullerenes2019

    • Author(s)
      Sun Liansheng、Kayahara Eiichi、Yamago Shigeru
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] [10]シクロパラフェニレン(CPP) テトラトリフラートからのベンザイン発生を鍵としたCPP誘導体の合成2019

    • Author(s)
      中野雅也、茅原栄一、山子茂
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 遷移金属錯体による炭素-炭素結合活性化を介したシクロパラフェニレンの環拡大反応2019

    • Author(s)
      松尾俊太郎、茅原栄一、山子茂
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] シクロパラフェニレンと1,2,4-トリアゾリン-3,5-ジオン誘導体の環化付加体の変換反応2019

    • Author(s)
      山本晃嗣、茅原栄一、山子茂
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 遷移金属錯体を用いたテトラヒドロキシシクロパラフェニレンの変換反応2018

    • Author(s)
      中野雅也、茅原栄一、山子茂
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Research-status Report

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Published: 2018-07-25   Modified: 2021-12-27  

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