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Proposal and development of novel mechanical bonds

Research Project

Project/Area Number 19K22183
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 InstitutionInstitute for Molecular Science (2020)
Nagoya University (2019)

Principal Investigator

SEGAWA Yasutomo  分子科学研究所, 生命・錯体分子科学研究領域, 准教授 (60570794)

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機械的結合 / カテナン / ノット / スピロシラン / 分子トポロジー / メカニカル結合 / トポロジー
Outline of Research at the Start

これまでに、2つの輪が幾何的に連結したカテナン、1つの輪の中に1つの棒が通ったロタキサンの2種類の機械的結合が知られている。しかし、これら機械的結合をもつ化合物の合成には大きな問題点がある。カテナンやロタキサンには大員環が必須だが、大員環形成反応は常に多量化反応と競合する。本研究では、「カテナンでもロタキサンでもない第3の機械的結合」について、その存在の実証および応用展開を行う。

Outline of Final Research Achievements

The purpose of this study was to develop a method for the synthesis of the new type of mechanical bonds. The main focus of our research is the creation of "mechanical bonds composed entirely of aromatic hydrocarbons," which has not been achieved in the past due to synthetic limitations. We developed a new method for the synthesis of mechanical bonds, and conducted research on the synthesis and properties of new catenanes using this method. We have succeeded in synthesizing catenanes and knot molecules composed entirely of benzene rings, using the development of a silicon-based template method.

Academic Significance and Societal Importance of the Research Achievements

本研究成果は、複雑な幾何学構造をもつ芳香族化合物の合成に向けた大きな一歩となる。結び目や絡み目といった幾何学構造を炭素骨格のみで作ることが可能になったことで、芳香族化合物の構造多様性をさらに広げることができる。また、機械的結合は分子機械に欠かせない部分構造であることから、分子機械の設計自由度を大きく上げることにつながる。カテナンの2つの環の間でのエネルギー移動過程やノットの溶液状態における動的挙動や円二色性を実験的に明らかにしたことで、複雑な幾何学構造がもたらす構造的・電子的性質について新たな知見を得た。

Report

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

    (28 results)

All 2021 2020 2019 Other

All Int'l Joint Research (1 results) Journal Article (14 results) (of which Int'l Joint Research: 7 results,  Peer Reviewed: 14 results,  Open Access: 2 results) Presentation (11 results) (of which Int'l Joint Research: 4 results,  Invited: 7 results) Remarks (2 results)

  • [Int'l Joint Research] ネバダ大学リノ校(米国)

    • Related Report
      2020 Annual Research Report
  • [Journal Article] Double-Helix Supramolecular Nanofibers Assembled from Negatively Curved Nanographenes2021

    • Author(s)
      Kato Kenta、Takaba Kiyofumi、Maki-Yonekura Saori、Mitoma Nobuhiko、Nakanishi Yusuke、Nishihara Taishi、Hatakeyama Taito、Kawada Takuma、Hijikata Yuh、Pirillo Jenny、Scott Lawrence T.、Yonekura Koji、Segawa Yasutomo、Itami Kenichiro
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 14 Pages: 5465-5469

    • DOI

      10.1021/jacs.1c00863

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of a zigzag carbon nanobelt2021

    • Author(s)
      Cheung Kwan Yin、Watanabe Kosuke、Segawa Yasutomo、Itami Kenichiro
    • Journal Title

      Nature Chemistry

      Volume: 13 Issue: 3 Pages: 255-259

    • DOI

      10.1038/s41557-020-00627-5

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Exciton Spatial Dynamics and Self-Trapping in Carbon Nanocages2020

    • Author(s)
      Rodr?guez-Hern?ndez Beatriz、Nelson Tammie、Oldani Nicolas、Mart?nez-Mesa Aliezer、Uranga-Pi?a Llinersy、Segawa Yasutomo、Tretiak Sergei、Itami Kenichiro、Fernandez-Alberti Sebastian
    • Journal Title

      The Journal of Physical Chemistry Letters

      Volume: 12 Issue: 1 Pages: 224-231

    • DOI

      10.1021/acs.jpclett.0c03364

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A theoretical study on the strain energy of helicene-containing carbon nanobelts2020

    • Author(s)
      Watanabe Kosuke、Segawa Yasutomo、Itami Kenichiro
    • Journal Title

      Chemical Communications

      Volume: 56 Issue: 95 Pages: 15044-15047

    • DOI

      10.1039/d0cc06373h

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Creation of negatively curved polyaromatics enabled by annulative coupling that forms an eight-membered ring2020

    • Author(s)
      Matsubara Satoshi、Koga Yoshito、Segawa Yasutomo、Murakami Kei、Itami Kenichiro
    • Journal Title

      Nature Catalysis

      Volume: 3 Issue: 9 Pages: 710-718

    • DOI

      10.1038/s41929-020-0487-0

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Nonalternant Aromatic Belt: Methylene-Bridged [6]Cycloparaphenylene Synthesized from Pillar[6]arene2020

    • Author(s)
      Li Yuanming、Segawa Yasutomo、Yagi Akiko、Itami Kenichiro
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 29 Pages: 12850-12856

    • DOI

      10.1021/jacs.0c06007

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of cycloiptycenes from carbon nanobelts2020

    • Author(s)
      Shudo Hiroki、Kuwayama Motonobu、Segawa Yasutomo、Itami Kenichiro
    • Journal Title

      Chemical Science

      Volume: 11 Issue: 26 Pages: 6775-6779

    • DOI

      10.1039/d0sc02501a

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and Structure of [9]Cycloparaphenylene Catenane: An All-Benzene Catenane Consisting of Small Rings2020

    • Author(s)
      Segawa Yasutomo、Kuwayama Motonobu、Itami Kenichiro
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 3 Pages: 1067-1070

    • DOI

      10.1021/acs.orglett.9b04599

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Selective Transformation of Strychnine and 1,2-Disubstituted Benzenes by C?H Borylation2020

    • Author(s)
      Saito Yutaro、Yamanoue Kotono、Segawa Yasutomo、Itami Kenichiro
    • Journal Title

      Chem

      Volume: 6 Issue: 4 Pages: 985-993

    • DOI

      10.1016/j.chempr.2020.02.004

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Six-fold C-H borylation of hexa-peri-hexabenzocoronene2020

    • Author(s)
      Nagase Mai、Kato Kenta、Yagi Akiko、Segawa Yasutomo、Itami Kenichiro
    • Journal Title

      Beilstein Journal of Organic Chemistry

      Volume: 16 Pages: 391-397

    • DOI

      10.3762/bjoc.16.37

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Topological molecular nanocarbons: All-benzene catenane and trefoil knot2019

    • Author(s)
      Segawa Yasutomo、Kuwayama Motonobu、Hijikata Yuh、Fushimi Masako、Nishihara Taishi、Pirillo Jenny、Shirasaki Junya、Kubota Natsumi、Itami Kenichiro
    • Journal Title

      Science

      Volume: 365 Issue: 6450 Pages: 272-276

    • DOI

      10.1126/science.aav5021

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Negatively Curved Warped Nanographene Self-Assembled on Metal Surfaces2019

    • Author(s)
      Urgel JoseI.、Di Giovannantonio Marco、Segawa Yasutomo、Ruffieux Pascal、Scott Lawrence T.、Pignedoli Carlo A.、Itami Kenichiro、Fasel Roman
    • Journal Title

      Journal of the American Chemical Society

      Volume: 141 Issue: 33 Pages: 13158-13164

    • DOI

      10.1021/jacs.9b05501

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Two-step synthesis of a red-emissive warped nanographene derivative via a ten-fold C?H borylation2019

    • Author(s)
      Kato Kenta、Lin Hsing-An、Kuwayama Motonobu、Nagase Mai、Segawa Yasutomo、Scott Lawrence T.、Itami Kenichiro
    • Journal Title

      Chemical Science

      Volume: 10 Issue: 39 Pages: 9038-9041

    • DOI

      10.1039/c9sc03061a

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Ni-Catalyzed α-Selective C?H Borylations of Naphthalene-Based Aromatic Compounds2019

    • Author(s)
      Kamei Toshiyuki、Nishino Soshi、Yagi Akiko、Segawa Yasutomo、Shimada Toyoshi
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 84 Issue: 21 Pages: 14354-14359

    • DOI

      10.1021/acs.joc.9b02333

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthesis of a zigzag carbon nanobelt2021

    • Author(s)
      Kosuke Watanabe・Kwan Yin Cheung・Yasutomo Segawa・Kenichiro Itami
    • Organizer
      3rd ICReDD International Symposium
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of a zigzag carbon nanobelt2021

    • Author(s)
      Kosuke Watanabe・Kwan Yin Cheung・Yasutomo Segawa・Kenichiro Itami
    • Organizer
      2021 #RSCPoster Twitter Conference
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of a zigzag carbon nanobelt2021

    • Author(s)
      Kosuke Watanabe・Kwan Yin Cheung・Yasutomo Segawa・Kenichiro Itami
    • Organizer
      The 4th IRCCS International Symposium
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] MicroED構造有機化学2020

    • Author(s)
      瀬川泰知
    • Organizer
      第一回バーチャル化学フロンティア研究会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] ジグザグ型カーボンナノベルトの合成2020

    • Author(s)
      渡邊 幸佑・Kwan Yin Cheung・瀬川 泰知・伊丹 健一郎
    • Organizer
      第10回CSJ化学フェスタ
    • Related Report
      2020 Annual Research Report
  • [Presentation] 高度に湾曲したπ共役分子の合成戦略2019

    • Author(s)
      瀬川泰知
    • Organizer
      第3回産総研化学研究シンポジウム
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] 様々なトポロジーをもつ新奇芳香族炭化水素の合成2019

    • Author(s)
      瀬川泰知
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] ナノカーボンの有機合成に向けて2019

    • Author(s)
      瀬川泰知
    • Organizer
      野口研究所10周年記念講演会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Strained π-systems bearing nontrivial topology2019

    • Author(s)
      瀬川泰知
    • Organizer
      ITbM-GTR Pre-ISNA Symposium
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 高度に湾曲したπ共役分子の合成戦略2019

    • Author(s)
      瀬川泰知
    • Organizer
      第52回有機金属若手の会夏の学校
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] 高度に湾曲したπ共役分子の合成戦略2019

    • Author(s)
      瀬川泰知
    • Organizer
      第7回慶應有機化学若手シンポジウム
    • Related Report
      2019 Research-status Report
    • Invited
  • [Remarks] ナノグラフェンの二重らせん構造が電子回折で明らかに

    • URL

      https://www.ims.ac.jp/news/2021/03/25_4925.html

    • Related Report
      2020 Annual Research Report
  • [Remarks] ジグザグ型カーボンナノベルトの合成に成功

    • URL

      https://www.ims.ac.jp/news/2021/03/10_4913.html

    • Related Report
      2020 Annual Research Report

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

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