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Synthesis of cyclic p-conjugated polymer based on the carbon-carbon cleavage of cycloparaphenyelens

Research Project

Project/Area Number 18H01962
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionKyoto University

Principal Investigator

Kayahara Eiichi  京都大学, 化学研究所, 助教 (10610553)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥17,160,000 (Direct Cost: ¥13,200,000、Indirect Cost: ¥3,960,000)
Fiscal Year 2020: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2019: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2018: ¥8,580,000 (Direct Cost: ¥6,600,000、Indirect Cost: ¥1,980,000)
Keywords金属錯体 / 曲面環状π共役分子 / 環状π共役高分子 / シクロパラフェニレン / 白金 / 炭素-炭素結合活性化 / トポロジー / メビウス / 曲面状π共役分子 / 環状π共役分子 / メビウストポロジー / ねじれ / アルケン / 環状π共役オリゴマー / 炭素ー炭素結合開裂 / 遷移金属錯体 / アルキン / 炭素ー炭素結合活性化 / 結合活性化
Outline of Final Research Achievements

Here we developed new method for creating cyclic curved π-conjugated molecules and polymers with new frameworks and topologies. We succeeded in elucidating the reactivity originated from the distorted π and σ bonds of cycloparaphenylenes(CPPs),which are readily available cyclic π-conjugated molecule, and the unique reactivity was applied for the synthesis of CPP derivatives and new cyclic π-conjugated molecules.

Academic Significance and Societal Importance of the Research Achievements

近年、環状π共役分子の化学の進展は著しく、その原動力となっている有機合成化学が、本分野の今後の発展の要であることは明白である。本研究は、入手容易なCPPに対する独自の反応設計・反応開発を始点に、有機金属化学、高分子化学といった複合的な観点から環状π共役分子の新しい合成法に成功した。環状π共役分子の合成研究に新しい潮流をつくるにとどまらず、特徴的なトポロジーとπ電子系に由来する物性や機能の発現、新しい有機材料への応用など、新たな融合領域の開拓が期待される。

Report

(4 results)
  • 2021 Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (40 results)

All 2022 2021 2020 2019 2018

All Journal Article (12 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 11 results) Presentation (28 results) (of which Int'l Joint Research: 4 results,  Invited: 6 results)

  • [Journal Article] 1,3-Diradicals Embedded in Curved Paraphenylene Units: Singlet versus Triplet State and In-Plane Aromaticity2021

    • Author(s)
      Miyazawa, Y.; Wang, Z.; Matsumoto, M.; Hatano, S.; Antol, I.; Kayahara, E.; Yamago, S.; Abe, M.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 143 Issue: 19 Pages: 7426-7439

    • DOI

      10.1021/jacs.1c01329

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of a Cyclohexa-2,7-Anthrylene Ethynylene Derivative2021

    • Author(s)
      Matsuki, H.; Okubo, K.; Takaki, Y.; Niihori, Y.; Mitsui, M.; Kayahara, E.; Yamago, S.; Kobayashi, K.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 60 Issue: 2 Pages: 998-1003

    • DOI

      10.1002/anie.202012120

    • NAID

      120006901656

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Twisted [N]Cycloparaphenylenes by Alkene Insertion2021

    • Author(s)
      Terabayashi Tomoaki、Kayahara Eiichi、Mizuhata Yoshiyuki、Tokitoh Norihiro、Nishinaga Toru、Kato Tatsuhisa、Yamago Shigeru
    • Journal Title

      ChemRxiv

      Volume: -

    • DOI

      10.26434/chemrxiv.14547384

    • Related Report
      2020 Annual Research Report
  • [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
      2020 Annual Research Report 2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Syntheses of Tetrasubstituted [10]Cycloparaphenylenes by a Pd-catalyzed Coupling Reaction. Remarkable Effect of Strain on the Oxidative Addition and Reductive Elimination2020

    • Author(s)
      Kayahara, E.; Nakano, M.; Sun, L.; Ishida, K.; Yamago, S.
    • Journal Title

      Chem. Asian J.

      Volume: 15 Issue: 16 Pages: 2451-2455

    • DOI

      10.1002/asia.202000711

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ultrafast Exciton Self‐Trapping and Delocalization in Cycloparaphenylenes: The Role of Excited‐State Symmetry in Electron‐Vibrational Coupling2020

    • Author(s)
      Kim Juno、Kishi Ryohei、Kayahara Eiichi、Kim Woojae、Yamago Shigeru、Nakano Masayoshi、Kim Dongho
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 59 Issue: 39 Pages: 16989-16996

    • DOI

      10.1002/anie.202006066

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [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 Annual Research 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 Annual Research 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 Annual Research 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 Annual Research Report
    • Peer Reviewed
  • [Presentation] 環状白金錯体を用いたデヒドロ[2.2]シクロファン誘導体の合成2022

    • Author(s)
      張逸辰、茅原栄一、山子茂
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 環状白金錯体を用いた環状パラフェニレンジケトンの直接合成2022

    • Author(s)
      森隆博、茅原栄一、加藤立久、山子茂
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ねじれ構造を持つアルケン挿入環状パラフェニレンの合成と物性2021

    • Author(s)
      茅原栄一、寺林智昭、山子茂
    • Organizer
      第31回 基礎有機化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 環状白金錯体を用いたテトラヒドロ[2,2]パラシクロファンの合成2021

    • Author(s)
      張逸辰、寺林智昭、茅原栄一、山子茂
    • Organizer
      第67回有機金属化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 環状パラフェニレンジケトンの還元と生成物の同定2021

    • Author(s)
      森隆博、茅原栄一、加藤立久、山子茂
    • Organizer
      第31回 基礎有機化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] トポロジカルπ共役分子の合成と物性2020

    • Author(s)
      茅原栄一
    • Organizer
      第40回有機合成若手セミナー 明日の有機合成を担う人のために
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] トポロジーに基づく曲面π共役分子の合成2020

    • Author(s)
      茅原栄一
    • Organizer
      2020KIPS若手高分子シンポジウム
    • Related Report
      2020 Annual Research Report
    • Invited
  • [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] 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2019

    • 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2019

    • 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 Species2019

    • 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] 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 Annual Research Report
  • [Presentation] 白金錯体によるシクロパラフェニレンの炭素-炭素結合活性化反応とその応用2018

    • Author(s)
      茅原栄一、林俊輝、山子茂
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 白金錯体によるシクロパラフェニレンの炭素-炭素結合活性化反応2018

    • Author(s)
      茅原栄一、林俊輝、山子茂
    • Organizer
      第65回有機金属化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Highly Efficient Synthesis of Cyclic Curved π-Conjugated Molecules2018

    • Author(s)
      茅原栄一
    • Organizer
      Invited Lecture at University of Munster
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Highly Efficient Synthesis of Cyclic Curved π-Conjugated Molecules2018

    • Author(s)
      茅原栄一
    • Organizer
      Invited Lecture at Justus-Liebig University
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Highly Efficient Synthesis of Cyclic Curved π-Conjugated Molecules2018

    • Author(s)
      茅原栄一
    • Organizer
      Invited Lecture at Heidelberg University
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Highly Efficient Synthesis of Cyclic Curved π-Conjugated Molecules2018

    • Author(s)
      茅原栄一
    • Organizer
      Invited Lecture at Freie University
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] シクロパラフェニレンの反応性を利用した新しい環状曲面π共役分子の合成法の開発2018

    • Author(s)
      茅原栄一、山子茂
    • Organizer
      第118回化学研究所研究発表会
    • Related Report
      2018 Annual Research Report
  • [Presentation] シクロパラフェニレンと 1,2,4-トリアゾリン-3,5-ジオンの環化付加反応2018

    • Author(s)
      山本晃嗣、茅原栄一、山子茂
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Host-guest interaction of redox-responsive [10]cycloparaphenylene derivatives having hydro- and benzoquinone units with fullerenes2018

    • Author(s)
      孫連盛、茅原栄一、山子茂
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research 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 Annual Research Report

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Published: 2018-04-23   Modified: 2023-12-25  

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