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Development of sigma-conjugated molecules based on perfluorocubane

Research Project

Project/Area Number 21K14608
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionKyoto University (2022)
The University of Tokyo (2021)

Principal Investigator

Akiyama Midori  京都大学, 工学研究科, 助教 (50807055)

Project Period (FY) 2021-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2022: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2021: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywordsキュバン / フッ素 / cubane / fluorination / electron transfer / electron acceptor / σ共役
Outline of Research at the Start

箱型分子であるキュバンが完全にフッ素化されたペルフルオロキュバンは,理論計算により「内部に電子を閉じこめる」と予測されているが,その合成は達成されていなかった。申請者は2019年度~2020年度の科研費(若手研究)課題としてペルフルオロキュバンの合成に取り組み,単離に成功した。本研究ではペルフルオロキュバン内に閉じこめられた電子の挙動,特に分子内電子移動に着目する。具体的には,ペルフルオロキュバン多量体を合成して電子を閉じこめ,この電子が分子全体に非局在化し安定化されることを実証する。

Outline of Final Research Achievements

Perfluorocubane, a fully fluorinated box-shaped molecule, was predicted to "confine electrons inside the box" by theoretical calculations, but its synthesis had not been achieved. The researcher has succeeded in synthesizing perfluorocubane for the first time in the world. In this study, the behavior of an electron inside perfluorocubane was investigated, and an electron inside perfluorocubane was successfully observed. A paper summarizing the results so far was published in Science (Science, 2022, 377, 756.)

Academic Significance and Societal Importance of the Research Achievements

研究対象であるペルフルオロキュバンは,対称性の高い立方体型構造の美しさ,電子を閉じ込めるという新しい機能性から,長らく合成が望まれていた待望の分子である。この化合物を合成し,電子を閉じ込める性質を実現したことは,有機化学や物理化学の教科書を書き換えるほどの学術的意義がある。

Report

(3 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • Research Products

    (11 results)

All 2023 2022 2021 Other

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

  • [Int'l Joint Research] オレゴン大学(米国)

    • Related Report
      2022 Annual Research Report
  • [Journal Article] Electron in a cube: Synthesis and characterization of perfluorocubane as an electron acceptor2022

    • Author(s)
      Sugiyama Masafumi、Akiyama Midori、Yonezawa Yuki、Komaguchi Kenji、Higashi Masahiro、Nozaki Kyoko、Okazoe Takashi
    • Journal Title

      Science

      Volume: 377 Issue: 6607 Pages: 756-759

    • DOI

      10.1126/science.abq0516

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Presentation] Perfluorocubane: A Novel Electron Acceptor2023

    • Author(s)
      Midori Akiyama
    • Organizer
      The 1st Kyoto Advanced Porous Science (KAPS) Symposium
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 電子受容性を有する全フッ素化キュバンの合成と物性評価2023

    • Author(s)
      秋山みどり
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Synthesis and Properties of Fluorinated Cubanes2022

    • Author(s)
      Midori Akiyama, Masafumi Sugiyama, Kenji Komaguchi, Kyoko Nozaki, Takashi Okazoe
    • Organizer
      241st ECS Meeting
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Characterization of Perfluorocubane as an Electron Acceptor2022

    • Author(s)
      Midori Akiyama
    • Organizer
      The 5th NYCU Conference on Advanced Organic Synthesis (CAOS-5)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 全フッ素化キュバンの合成と物性2022

    • Author(s)
      杦山真史・秋山みどり・米澤侑希・野崎京子・岡添隆
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] Synthesis and Properties of Fluorinated Cubanes2022

    • Author(s)
      Akiyama, M; Sugiyama, M.; Komaguchi, K.; Nozaki, K.; Okazoe, T.
    • Organizer
      241st ECS Meeting
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 液相直接フッ素化反応を用いた全フッ素化キュバンの合成2021

    • Author(s)
      杦山真史・秋山みどり・米澤侑希・野崎京子・岡添隆
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2021 Research-status Report
  • [Remarks] プレスリリース

    • URL

      https://www.t.u-tokyo.ac.jp/press/pr2022-08-17-001

    • Related Report
      2022 Annual Research Report
  • [Remarks] 電子を閉じ込める箱: 全フッ素化キュバンの合成

    • URL

      https://www.chem-station.com/blog/2022/09/pfc.html

    • Related Report
      2022 Annual Research Report

URL: 

Published: 2021-04-28   Modified: 2024-01-30  

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