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Rational design and synthesis of non-planar nanocarbon molecules based on macrocyclic structures

Research Project

Project/Area Number 17K05772
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

Ikemoto Koki  東京大学, 大学院理学系研究科(理学部), 講師 (30735600)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2019: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsナノカーボン / 大環状分子 / 湾曲 / 芳香族炭化水素 / ジオデシック / 大環分子 / 非平面構造
Outline of Final Research Achievements

Recent years have witnessed an ever-growing interest in the bottom-up synthesis of nanocarbon molecules because it brings about an in-depth understanding of the unique structure-property relationships. However, it remains a formidable challenge to design and synthesize curved nanocarbon molecules in a rational way. To address this challenge, we have introduced a new concept for the design of nanocarbon molecules that used 1,3,5-trisubstituted benzene (phenine) as a basic trigonal planar unit. By adopting a synthetic strategy to utilize coupling reactions between phenine units, we successfully synthesized varios curved nanocarbon molecules including bowl-, saddle-, cylinder- and hemispherical-shaped nanocarbons.

Academic Significance and Societal Importance of the Research Achievements

フラーレンやカーボンナノチューブに代表されるナノカーボンは,強い・軽い・しなやかを兼ね備えた構造材料として幅広い応用が期待されている.しかしながら,これらナノカーボンは様々な構造の「混合物」であり,このことが構造に基づく物性の理解を妨げていた.本研究では,一義的構造を有する「分子」として,湾曲構造を有するナノカーボン分子を合理的に設計・合成するため戦略を確立した.原子レベルで構造が制御されたナノカーボン分子の物理的性質・化学的性質を解き明かすことで,湾曲ナノカーボン分子が有する構造的特長・物性を明らかにすることが出来た.

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (34 results)

All 2020 2019 2018 2017 Other

All Journal Article (12 results) (of which Peer Reviewed: 11 results,  Open Access: 3 results) Presentation (14 results) (of which Int'l Joint Research: 3 results,  Invited: 2 results) Book (2 results) Remarks (5 results) Patent(Industrial Property Rights) (1 results) (of which Overseas: 1 results)

  • [Journal Article] Synthesis of a Hemispherical Geodesic Phenine Framework by a Polygon Assembling Strategy2020

    • Author(s)
      Mio Tatsuru、Ikemoto Koki、Sato Sota、Isobe Hiroyuki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 132 Issue: 16 Pages: 6629-6633

    • DOI

      10.1002/ange.201915509

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A nitrogen-doped nanotube molecule with atom vacancy defects2020

    • Author(s)
      K. Ikemoto, S. Yang, H. Naito, M. Kotani, S. Sato, H. Sato
    • Journal Title

      Nature Communications

      Volume: 11, 1807 Issue: 1 Pages: 1807-1807

    • DOI

      10.1038/s41467-020-15662-6

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Curved phenine normal vectors: Geometric measures of geodesic phenine frameworks2020

    • Author(s)
      Mio, T.; Ikemoto, K.; Isobe, H.
    • Journal Title

      Chem. Asian J.

      Volume: 15 Issue: 8 Pages: 1355-1359

    • DOI

      10.1002/asia.202000271

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Periphery design of macrocyclic materials for organic light-emitting devices with a blue phosphorescent emitter2019

    • Author(s)
      Yoshii, A.; Ikemoto, K.; Izumi, T.; Taka, H.; Kita, H.; Sato, S.; Isobe, H.
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 8 Pages: 2759-2762

    • DOI

      10.1021/acs.orglett.9b00717

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Fluorescence Enhancement of Aromatic Macrocycles by Lowering Excited Singlet State Energies2019

    • Author(s)
      Ikemoto Koki、Tokuhira Toshiki、Uetani Akari、Harabuchi Yu、Sato Sota、Maeda Satoshi、Isobe Hiroyuki
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 85 Issue: 1 Pages: 150-157

    • DOI

      10.1021/acs.joc.9b02379

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Finite phenine nanotubes with periodic vacancy defects2019

    • Author(s)
      Sun Zhe、Ikemoto Koki、Fukunaga Toshiya M.、Koretsune Takashi、Arita Ryotaro、Sato Sota、Isobe Hiroyuki
    • Journal Title

      Science

      Volume: 363 Issue: 6423 Pages: 151-155

    • DOI

      10.1126/science.aau5441

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Structures, and Assembly of Geodesic Phenine Frameworks with Isoreticular Networks of [n]Cyclo-para-phenylenes2019

    • Author(s)
      Sun Zhe、Mio Tatsuru、Ikemoto Koki、Sato Sota、Isobe Hiroyuki
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 84 Issue: 6 Pages: 3500-3507

    • DOI

      10.1021/acs.joc.9b00085

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Fluctuating Carbonaceous Networks with a Persistent Molecular Shape: A Saddle-Shaped Geodesic Framework of 1,3,5-Trisubstituted Benzene (Phenine)2018

    • Author(s)
      Ikemoto Koki、Lin Jennie、Kobayashi Ryo、Sato Sota、Isobe Hiroyuki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 28 Pages: 8555-8559

    • DOI

      10.1002/anie.201803984

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Magneto-electroluminescence effects in the single-layer organic light-emitting devices with macrocyclic aromatic hydrocarbons2018

    • Author(s)
      Pham, S.-T.; Ikemoto, K.; Suzuki, K. Z.; Izumi, T.; Taka, H.; Kita, H.; Sato, S.; Isobe, H.; Mizukami, S.
    • Journal Title

      APL Mater.

      Volume: 6 Issue: 2 Pages: 26103-26103

    • DOI

      10.1063/1.5021711

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] [n]Cyclo-3,6-phenanthrenylenes: Synthesis, structure and fluorescence2017

    • Author(s)
      Tian, Y.; Ikemoto, K.; Sato, S.; Isobe, H.
    • Journal Title

      Chem. Asian J.

      Volume: 12 Issue: 16 Pages: 2093-2097

    • DOI

      10.1002/asia.201700563

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Entropy-driven ball-in-bowl assembly of fullerene and geodesic phenylene bowl2017

    • Author(s)
      Ikemoto, K.; Kobayashi, R.; Sato, S.; Isobe, H.
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 9 Pages: 2362-2365

    • DOI

      10.1021/acs.orglett.7b00899

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] 芳香環で「笊」を編む2017

    • Author(s)
      池本晃喜,佐藤宗太,磯部寛之
    • Journal Title

      月刊化学

      Volume: 72 Pages: 31-35

    • Related Report
      2017 Research-status Report
  • [Presentation] Molecular Design Using Trigonal Planar "Phenine" toward Functional Nanocarbon Molecules2020

    • Author(s)
      Koki Ikemoto
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 平面三方構造「フェナイン」を活用したナノカーボン分子の設計・合成2019

    • Author(s)
      池本晃喜
    • Organizer
      京都大学第4回有機若手ワークショップ
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] サドル状及びフープ状構造を有するジオデシックフェナインフレームワーク2019

    • Author(s)
      池本晃喜,孫哲,美尾樹,Lin Jennie,小林良,佐藤宗太,磯部寛之
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Bowl-shaped and Saddle-shaped Geodesic Phenine Framework2019

    • Author(s)
      Koki Ikemoto, Jennie Lin, Ryo Kobayashi, Sota Sato, Hiroyuki Isobe
    • Organizer
      18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Structural Chemistry and Materials Application of Aromatic Hydrocarbon Macrocycles2019

    • Author(s)
      Ikemoto Koki
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 周期孔をもつ新しいナノチューブの化学合成2019

    • Author(s)
      福永隼也、孫哲、池本晃喜、是常隆、有田亮太郎、佐藤宗太、磯部寛之
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis and Structures of Nanometer-sized Geodesic Phenine Framework2018

    • Author(s)
      Ikemoto Koki、Lin Jennie、Kobayashi Ryo、Sato Sota、Isobe Hiroyuki
    • Organizer
      24th IUPAC International Conference on Physical Organic Chemistry
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 1,3,5-三置換ベンゼン(フェナイン)を構成要素としたサドル状ジオデシック芳香族炭化水素分子の合成と構造2018

    • Author(s)
      池本晃喜、Lin Jennie、小林良、佐藤宗太、磯部寛之
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ジオデシックフェナイン構造体に基づくナノメートルサイズの湾曲芳香族炭化水素分子2018

    • Author(s)
      池本晃喜、Lin Jennie、小林良、佐藤宗太、磯部寛之
    • Organizer
      第5回π造形科学若手研究会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis and Molecular Recognition of Nanometer-sized Geodesic Phenylene Bowl2018

    • Author(s)
      Ikemoto, K.; Kobayashi, R.; Sato, S.; Isobe, H.
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 大環状芳香族炭化水素を用いた高効率有機ELデバイスの開発2017

    • Author(s)
      泉倫生, 薛ジン, 池本晃喜, 高秀雄, 北弘志, 佐藤宗太, 磯部寛之
    • Organizer
      有機EL討論会 第24回例会
    • Related Report
      2017 Research-status Report
  • [Presentation] Aromatic Hydrocarbon Macrocycles for Highly Efficient Single-layer Organic Light-emitting Devices2017

    • Author(s)
      Ikemoto, K.; Xue, J.Y.; Izumi, T.; Yoshii, A.; Tian, Y.; Kobayashi, R.; Koretsune, T.; Akashi, R.; Arita, R.; Taka, H.; Kita, H.; Sato, S.; Isobe, H.
    • Organizer
      ISNA 2017 (17th International Symposium on Novel Aromatics)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] ナノメートルサイズのジオデシックフェニレンボウルの合成と構造2017

    • Author(s)
      池本晃喜,小林良,佐藤宗太,磯部寛之
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] ナノメートルサイズのジオデシックフェニレンボウルの合成と構造2017

    • Author(s)
      池本晃喜
    • Organizer
      第4回π造形科学若手研究会
    • Related Report
      2017 Research-status Report
  • [Book] 化学と工業,"「フェナイン」を用いて巨大湾曲分子を設計・合成する"2019

    • Author(s)
      池本晃喜
    • Total Pages
      2
    • Publisher
      日本化学会
    • Related Report
      2019 Annual Research Report
  • [Book] 化学,“周期孔をもつ筒状分子 フェナインナノチューブ"2019

    • Author(s)
      磯部寛之,池本晃喜,孫哲,佐藤宗太
    • Total Pages
      6
    • Publisher
      化学同人
    • Related Report
      2019 Annual Research Report
  • [Remarks] BEHIND THE PAPER

    • URL

      https://devicematerialscommunity.nature.com/users/381290-koki-ikemoto/posts/64691-a-nitrogen-doped-nanotube-molecule

    • Related Report
      2019 Annual Research Report
  • [Remarks] 世界初 窒素ドープ型ナノチューブ分子登場

    • URL

      https://www.s.u-tokyo.ac.jp/ja/press/2020/6741/

    • Related Report
      2019 Annual Research Report
  • [Remarks] 新しいナノチューブ登場:ベンゼンを連結

    • URL

      https://www.s.u-tokyo.ac.jp/ja/info/6191/

    • Related Report
      2018 Research-status Report
  • [Remarks] Chemical synthesis of nanotubes

    • URL

      https://www.u-tokyo.ac.jp/focus/en/press/z0508_00023.html

    • Related Report
      2018 Research-status Report
  • [Remarks] 新しいナノチューブ登場:ベンゼンを連結

    • URL

      http://www.jst.go.jp/pr/announce/20190111-4/index.html

    • Related Report
      2018 Research-status Report
  • [Patent(Industrial Property Rights)] Finite Phenine Nanotubes with Periodic Vacancy Defects2018

    • Inventor(s)
      H. Isobe, Z. Sun, K. Ikemoto
    • Industrial Property Rights Holder
      H. Isobe, Z. Sun, K. Ikemoto
    • Industrial Property Rights Type
      特許
    • Filing Date
      2018
    • Related Report
      2018 Research-status Report
    • Overseas

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Published: 2017-04-28   Modified: 2021-02-19  

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