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Elucidation of the interaction between weak electron pairs based on the creation of multi-radical molecules

Research Project

Project/Area Number 21H01918
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 InstitutionOsaka University

Principal Investigator

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

Co-Investigator(Kenkyū-buntansha) 中野 雅由  大阪大学, 基礎工学研究科, 教授 (80252568)
Project Period (FY) 2021-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2023: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2022: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2021: ¥8,970,000 (Direct Cost: ¥6,900,000、Indirect Cost: ¥2,070,000)
Keywords弱い電子対 / 一重項ビラジカル / 共役 / フルオレニル / フェナレニル / マルチラジカル
Outline of Research at the Start

本研究では、①弱い電子対の形成が可能なラジカル種を多数配置した分子系(=マルチラジカル系)を新たに合成し、②弱い電子対の共役を分子構造と電子構造の観点から詳細に明らかにし、③その特殊な電子状態に起因する特徴的な物性・機能性を見出すことで、「弱い電子対が共役した系の物質科学」を確立することを目指す。申請者の実験研究(新規化合物の合成とその物性評価)と研究分担者の理論研究(高精度量子化学計算を用いた解析)という相補的アプローチによって、実験的検証がいまだ不十分な弱い電子対の共役という概念を確立する。

Outline of Final Research Achievements

This study aims to establish "material science of systems with conjugated weak electron pairs" by (1) newly synthesizing molecular systems with many radical species capable of weak electron pair formation (=multiradical systems), (2) clarifying the conjugation of weak electron pairs in detail in terms of molecular and electronic structures, and (3) finding characteristic physical and functional properties that result from their special electronic states. In fact, we attempted to synthesize multimeric forms of fluorenyl radicals, diazafluorenyl radicals, and phenalenyl radicals, and for fluorenyl radicals and phenalenyl radicals, we were able to confirm the structure of the cyclic multimer of the radical precursor. For the phenalenyl cyclic multimer, we were also able to confirm the generation of radicals.

Academic Significance and Societal Importance of the Research Achievements

一重項ビラジカルの研究については、現在、Tobe, Wu, Haley, Chiなど多くの著名な研究者がこの分野に関わり、精力的に研究を行っている。しかし、依然としてマルチラジカル系の例は少なく、弱い電子対の共役という概念は、実験的検証が待たれている状況である。本研究では、新規化合物合成と各種分光測定という研究代表者の実験的アプローチと、研究分担者の助力を得た高精度な理論的アプローチを組み合わせることで、弱い電子対の共役の本質的理解を深めることを目指した。得られているラジカル多量体の電子構造を今後明らかにすることで、「弱い電子対の共役」の科学が一気に進展すると期待できる。

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Annual Research Report
  • 2021 Annual Research Report
  • Research Products

    (33 results)

All 2024 2023 2022 2021 Other

All Int'l Joint Research (1 results) Journal Article (17 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 17 results,  Open Access: 8 results) Presentation (13 results) (of which Int'l Joint Research: 7 results,  Invited: 13 results) Remarks (2 results)

  • [Int'l Joint Research] Aalto University(フィンランド)

    • Related Report
      2023 Annual Research Report
  • [Journal Article] On‐Surface Synthesis of Silole and Disila‐Cyclooctene Derivatives2024

    • Author(s)
      Sun Kewei、Kurki Lauri、Silveira Orlando J.、Nishiuchi Tomohiko、Kubo Takashi、Foster Adam S.、Kawai Shigeki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 63 Issue: 18

    • DOI

      10.1002/anie.202401027

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Enhancing NIR-to-visible photon upconversion in cast solid by introducing bulky substituents in rubrene and by suppressing back energy transfer2023

    • Author(s)
      Sawa Akane、Shimada Shota、Tripathi Neeti、Heck Claire、Tachibana Hiroaki、Koyama Emiko、Mizokuro Toshiko、Hirao Yasukazu、Kubo Takashi、Tamai Naoto、Kuzuhara Daiki、Yamada Hiroko、Kamada Kenji
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 11 Issue: 25 Pages: 8502-8513

    • DOI

      10.1039/d3tc00853c

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and structural evaluation of closed-shell folded and open-shell twisted hexabenzo[5.6.7]quinarene2023

    • Author(s)
      Nishiuchi Tomohiko、Uchida Kazuyuki、Kubo Takashi
    • Journal Title

      Chemical Communications

      Volume: 59 Issue: 48 Pages: 7379-7382

    • DOI

      10.1039/d3cc02157b

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Local probe-induced structural isomerization in a one-dimensional molecular array2023

    • Author(s)
      Kawai Shigeki、Silveira Orlando J.、Kurki Lauri、Yuan Zhangyu、Nishiuchi Tomohiko、Kodama Takuya、Sun Kewei、Custance Oscar、Lado Jose L.、Kubo Takashi、Foster Adam S.
    • Journal Title

      Nature Communications

      Volume: 14 Issue: 1 Pages: 7741-7741

    • DOI

      10.1038/s41467-023-43659-4

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [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] Sterically Frustrated Aromatic Enes with Various Colors Originating from Multiple Folded and Twisted Conformations in Crystal Polymorphs2022

    • Author(s)
      T. Nishiuchi, S. Aibara, T. Yamakado, R. Kimura, S. Saito, H. Sato, T. Kubo
    • Journal Title

      Chemistry A European Journal

      Volume: - Issue: 28 Pages: 202200286-202200286

    • DOI

      10.1002/chem.202200286

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [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] Synergistic Enhancement of Hydrogen-Bonding and Charge-Transfer Interactions in a Crystal of an Anthranol?Acridine Dyad Comprised of a Hydrogen-Bonded Chain Aggregate2022

    • Author(s)
      Hirao Yasukazu、Inobe Honami、Hosoi Katsuma、Kubo Takashi
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 126 Issue: 26 Pages: 10940-10946

    • DOI

      10.1021/acs.jpcc.2c03584

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Properties, and Intermolecular Interactions in the Solid States of π-Congested X-Shaped 1,2,4,5-Tetra(9-anthryl)benzenes2022

    • Author(s)
      Nishiuchi Tomohiko、Takeuchi Shino、Makihara Yuta、Kimura Ryo、Saito Shohei、Sato Hiroyasu、Kubo Takashi
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 95 Issue: 11 Pages: 1591-1599

    • DOI

      10.1246/bcsj.20220257

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis, properties and chemical modification of a persistent triisopropylsilylethynyl substituted tri(9-anthryl)methyl radical2022

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

      Chemical Communications

      Volume: 58 Issue: 20 Pages: 3306-3309

    • DOI

      10.1039/d2cc00548d

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Stacked antiaromaticity in the π‐congested space between the aromatic rings in the anthracene dimer2022

    • Author(s)
      Nishiuchi Tomohiko、Makihara Yuta、Kishi Ryohei、Sato Hiroyasu、Kubo Takashi
    • Journal Title

      Journal of Physical Organic Chemistry

      Volume: 36 Issue: 1

    • DOI

      10.1002/poc.4451

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Molecular and Spin Structures of a Through‐Space Conjugated Triradical System2022

    • Author(s)
      Kodama Takuya、Aoba Mitsuya、Hirao Yasukazu、Rivero Samara Medina、Casado Juan、Kubo Takashi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 61 Issue: 14 Pages: 202200688-202200688

    • DOI

      10.1002/anie.202200688

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [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 Annual Research 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 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Syntheses and Properties of Open-Shell π-Conjugated Molecules2021

    • Author(s)
      Kubo Takashi
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 94 Issue: 9 Pages: 2235-2244

    • DOI

      10.1246/bcsj.20210224

    • NAID

      130008103595

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Presentation] Recent studies on π-expanded trinaphtho[3.3.3]propellane2023

    • Author(s)
      久保 孝史
    • Organizer
      π-Conjugated Molecules and Materials: Beilsten Organic Chemistry Symposium 2023
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Recent studies on π-expanded trinaphtho[3.3.3]propellane2023

    • Author(s)
      久保 孝史
    • Organizer
      Solvation Chemistry and Reactive Molecules (755. WE-Heraeus-Seminar)
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Nature of electron-electron coupling in carbon-carbon contacts beyond 2Å2023

    • Author(s)
      久保 孝史
    • Organizer
      10th Pacific Symposium on Radical Chemistry (PSRC-10)
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 結合と非結合の狭間に備わる特異な性質の解明2023

    • Author(s)
      久保 孝史
    • Organizer
      第33回 万有福岡シンポジウム
    • Related Report
      2023 Annual Research Report
    • Invited
  • [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] Sigmarene: Duality of Reactivity Characterized by Closed-Shell and Open-Shell Electronic Structure2022

    • Author(s)
      Takashi Kubo
    • Organizer
      25th IUPAC Conference on Physical Organic Chemistry (ICPOC25)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 1D-Chain of Organic Radicals and Biradicals with Close π-π-Contact2022

    • Author(s)
      Takashi Kubo
    • Organizer
      UHMob International Conference; Organic Semiconductors: From Principles to Applications
    • 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 Annual Research 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 Annual Research 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 Annual Research Report
    • Invited
  • [Presentation] Duality of Reactivity Characterized by Closed-Shell and Open-Shell Electronic Structure2021

    • Author(s)
      Takashi KUBO
    • Organizer
      PACIFICHEM2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Remarks] 研究室HP

    • URL

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

    • Related Report
      2023 Annual Research 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 Annual Research Report

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Published: 2021-04-28   Modified: 2025-01-30  

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