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Synthesis and properties of compounds with a bond length beyond 2Å

Research Project

Project/Area Number 20K21194
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 InstitutionOsaka University

Principal Investigator

Kubo Takashi  大阪大学, 大学院理学研究科, 教授 (60324745)

Project Period (FY) 2020-07-30 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2021: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Fiscal Year 2020: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywords炭素-炭素単結合 / 超結合 / 2Å / 共有結合 / ビラジカル / 炭素-炭素結合 / 炭素ー炭素結合
Outline of Research at the Start

炭素原子間に形成される共有結合は、有機化学において最も基本的で重要な概念である。最近、単結合長の限界とされていた1.8Åを超える炭素-炭素単結合を持つ化合物が複数単離され、限界を超えた単結合が示す性質に注目が集まっている。本研究は、2Åを超える炭素-炭素単結合をもつ化合物を創出し、その特殊な結合状態の電子構造の解明と特異な反応性・物性の探索を通じて、有機化合物の新たな可能性を引き出すことを目的とする。その目的を達成するために、本研究では研究を、①長い結合を持つ化合物の基本骨格の確立、②長い結合の電子構造の解明、③長い結合の共役の構築、④長い結合による新現象の探索、の4つの段階にわけ、遂行する。

Outline of Final Research Achievements

This study aims to explore new possibilities in organic compounds by focusing on the length of single bonds as non-standard states of carbon-carbon bonding, creating compounds with single bonds exceeding 2 Angstrom, elucidating the electronic structure of their unique bonding state, and exploring their distinctive reactivity and physical properties. In fact, successful isolation of compounds with single bonds of 2.04 Angstrom; in length, in five steps starting from commercially available fulorenone, was achieved. Various spectroscopic measurements and quantum chemical calculations revealed that the long single bond has sufficient covalent bonding character. Additionally, in order to investigate interactions between long bonds, attempts were made to synthesize two compounds having long bonds within a molecule, and successful generation of the precursor dianion species was achieved.

Academic Significance and Societal Importance of the Research Achievements

共有結合は有機化学にとって最も根本的な概念であり、炭素‐炭素単結合は共有結合を理解するにあたって最もシンプルなモデルとなる。その炭素‐炭素単結合の限界点を探ることで共有結合とは何か、何をもってどう判断するか、という学術的問いに答えることができる。その限界点にほぼ達した化合物の単離に成功した本研究は、共有結合性の有無をいかにして調べ、得られた測定結果をどのように解釈するべきかを提示できた点で、学術的に非常に意義深いものであると言える。

Report

(4 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • 2020 Research-status Report
  • Research Products

    (19 results)

All 2023 2022 2021 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Open Access: 4 results) Presentation (9 results) (of which Int'l Joint Research: 2 results,  Invited: 7 results) Remarks (2 results)

  • [Journal Article] Closed-shell and open-shell dual nature of singlet diradical compounds2023

    • Author(s)
      Kubo Takashi
    • Journal Title

      Pure and Applied Chemistry

      Volume: 0 Issue: 4 Pages: 363-375

    • DOI

      10.1515/pac-2023-0114

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of a Through-Space Interacting Diradicaloid2023

    • Author(s)
      Kodama Takuya、Hirao Yasukazu、Kubo Takashi
    • Journal Title

      Precision Chemistry

      Volume: 1 Issue: 3 Pages: 183-191

    • DOI

      10.1021/prechem.3c00024

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of π-Extended Thiele’s and Chichibabin’s Hydrocarbons and Effect of the π-Congestion on Conformations and Electronic States2022

    • Author(s)
      Nishiuchi Tomohiko、Aibara Seito、Sato Hiroyasu、Kubo Takashi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 144 Issue: 16 Pages: 7479-7488

    • DOI

      10.1021/jacs.2c02318

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Tunable Solid‐State Thermochromism: Alkyl Chain Length‐Dependent Conformational Isomerization of Bianthrones2022

    • Author(s)
      Hirao Yasukazu、Hamamoto Yosuke、Kubo Takashi
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 17 Issue: 11

    • DOI

      10.1002/asia.202200121

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Biradicaloid Behavior of a Twisted Double Bond2021

    • Author(s)
      Hamamoto Yosuke, Hirao Yasukazu, Kubo Takashi
    • Journal Title

      The Journal of Physical Chemistry Letters

      Volume: 12 Issue: 19 Pages: 4729-4734

    • DOI

      10.1021/acs.jpclett.1c00664

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Spin-Spin Interactions in One‐Dimensional Assemblies of a Cumulene‐Based Singlet Biradical2021

    • Author(s)
      Hirao Yasukazu、Daifuku Yoko、Ihara Keiji、Kubo Takashi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 39 Pages: 21319-21326

    • DOI

      10.1002/anie.202105740

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Long Carbon-Carbon Bonding beyond 2Å in Tris(9-fluorenylidene)methane2021

    • Author(s)
      Kubo Takashi、Suga Yuki、Hashizume Daisuke、Suzuki Hiroki、Miyamoto Tatsuya、Okamoto Hiroshi、Kishi Ryohei、Nakano Masayoshi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 35 Pages: 14360-14366

    • DOI

      10.1021/jacs.1c07431

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of Anthracene‐Based Cyclic π‐Clusters and Elucidation of their Properties Originating from Congested Aromatic Planes2021

    • Author(s)
      Tomohiko Nishiuchi, Kazuki Kisaka, Takashi Kubo
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 10 Pages: 5400-5406

    • DOI

      10.1002/anie.202013349

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] Long carbon-carbon bonding beyond 2 Å in tris(9-fuorenylidene)methane2022

    • Author(s)
      Takashi Kubo
    • Organizer
      The 19th International Symposium on Novel Aromatic Compounds (ISNA-19)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 新分子創造で探る電子対の新しい姿2022

    • Author(s)
      久保 孝史
    • Organizer
      第34回 万有札幌シンポジウム
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] 開殻性有機分子が示す結晶状態での特異な挙動2022

    • Author(s)
      久保 孝史
    • Organizer
      第30回 有機結晶シンポジウム
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] フェナレニルラジカルの高密度共役化2021

    • Author(s)
      久保 孝史
    • Organizer
      第11回化学フェスタ(2021年度)
    • Related Report
      2021 Research-status Report
    • Invited
  • [Presentation] 高密度共役を生み出す物質の開発2021

    • Author(s)
      久保 孝史
    • Organizer
      第14回 物性科学領域横断研究会
    • Related Report
      2021 Research-status Report
    • Invited
  • [Presentation] 結合と非結合の狭間で:一重項ビラジカル種に関する最近の研究2021

    • Author(s)
      久保 孝史
    • Organizer
      2021年度有機合成化学北陸セミナー
    • Related Report
      2021 Research-status Report
    • Invited
  • [Presentation] Duality of Reactivity Characterized by Closed-Shell and Open-Shell Electronic Structure2021

    • Author(s)
      Takashi KUBO
    • Organizer
      PACIFICHEM2021
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 長い炭素間結合を二つ有する化合物の合成検討2021

    • Author(s)
      藤井 匠平、久保 孝史
    • Organizer
      第14回有機π電子系シンポジウ
    • Related Report
      2020 Research-status Report
  • [Presentation] フルオレニル骨格を用いた長い炭素間結合を二つ有する化合物の合成検討2021

    • Author(s)
      藤井 匠平、久保 孝史
    • Organizer
      日本化学会 第101回春季年会
    • Related Report
      2020 Research-status Report
  • [Remarks] 研究室ホームページ

    • URL

      http://www.chem.sci.osaka-u.ac.jp/lab/kubo/

    • Related Report
      2022 Annual Research Report 2021 Research-status Report
  • [Remarks] 研究室HP

    • URL

      http://www.chem.sci.osaka-u.ac.jp/lab/kubo/

    • Related Report
      2020 Research-status Report

URL: 

Published: 2020-08-03   Modified: 2024-01-30  

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