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Exploration of the Properties of Nonbenzenoid Conjugated Systems based on Intermolecular Interaction and Novel Molecular Design

Research Project

Project/Area Number 21H01916
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 InstitutionKyoto University

Principal Investigator

Fukazawa Aiko  京都大学, 高等研究院, 教授 (70432234)

Project Period (FY) 2021-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥17,680,000 (Direct Cost: ¥13,600,000、Indirect Cost: ¥4,080,000)
Fiscal Year 2023: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2022: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2021: ¥8,450,000 (Direct Cost: ¥6,500,000、Indirect Cost: ¥1,950,000)
Keywords非ベンゼン系共役電子系 / π共役 / 反芳香族 / ペンタレン / ジアザペンタレン / 電子受容体 / フラーレン / 芳香族 / 交差共役系 / ジチエノペンタレン / ペンタフルバレン / 多段階酸化還元系 / 電子受容性 / アザフルバレン / 芳香環 / 反芳香族性 / フルバレン
Outline of Research at the Start

本研究では,基礎科学と材料科学の両面にブレイクスルーをもたらす新しい光・電子機能性有機材料を生み出すことを最終目標とし,特異な電子構造と安定性を兼ね備えた非ベンゼン系共役電子系および分子集合体の創成と機能開拓に取り組む。「効率的合成法の開発」と「弱い芳香環の縮環による安定化」を基盤とし,非ベンゼン系共役電子系における分子間相互作用の本質理解に努めるとともに,めざす物性・機能からバックキャストした独自の分子設計をもとに未踏物性や機能を探求する。

Outline of Final Research Achievements

The intermolecular interactions of pentalenes and 1,4-diazapentalenes having thiophene as a fused ring moiety were analyzed and found to be capable of forming densely stacked structures by reducing exchange repulsion, although the formation of face-centered stacking structures that would manifest stacking aromaticity was not observed. During the course of the synthetic studies of a series of novel antiaromatic compounds, we selendipitiously found that benzothiophene-S,S-dioxide-fused pentalenes form stable complexes with nickel(0).
Furthermore, we have designed the π-conjugated oligomers of pentafulvalene and demonstrated their high electron affinity and robustness against multi-electron reduction close to that of fullerene C60, even in a flat one-dimensional conjugated system.

Academic Significance and Societal Importance of the Research Achievements

現在の有機光・電子機能性有機材料の基本構造はベンゼンや複素芳香環に依存している。これらの物性や機能の限界を打破する上で,異なる構造特性をもつ化合物群に対する物性の探究や機能開拓の試みは必要不可欠であり,本研究で得られた知見はその中でも分子設計や分子間相互作用に対する基礎的な理解を与えるものである。特に,フラーレンに迫る電子受容性を一次元炭化水素で実現できたことは,これまでの電子受容体の設計における常識を打破する成果であり,電子受容体の科学に新たな方向性を示すものといえる。

Report

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

    (27 results)

All 2023 2022 2021

All Journal Article (3 results) (of which Peer Reviewed: 2 results) Presentation (24 results) (of which Int'l Joint Research: 11 results,  Invited: 12 results)

  • [Journal Article] Synthesis and Reactivity of Weiss Diketone Derivative Bearing Four Phenylsulfanyl Groups2022

    • Author(s)
      Yasui Kosuke、Isogai Ryosuke、Fukazawa Aiko
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2022 Issue: 43

    • DOI

      10.1002/ejoc.202201029

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-dimensional fragments of fullerene C60 that exhibit robustness toward multi-electron reduction and pronounced light absorption2022

    • Author(s)
      Masahiro Hayakawa, Naoyuki Sunayama, Shu I. Takagi, Asuka Tamaki, Shigehiro Yamaguchi, Aiko Fukazawa
    • Journal Title

      ChemRxiv

      Volume: -

    • DOI

      10.26434/chemrxiv-2022-9w59c

    • Related Report
      2022 Annual Research Report
  • [Journal Article] Thiophene-fused 1,4-Diazapentalene: A Stable C=N-Containing π-Conjugated System with Restored Antiaromaticity2021

    • Author(s)
      J. Usuba, A. Fukazawa
    • Journal Title

      Chem. Eur. J.

      Volume: 27 Issue: 65 Pages: 16127-16134

    • DOI

      10.1002/chem.202103122

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Presentation] Design of Novel Nonbenzenoid π-Electron Systems toward Unusual Yet Stable Functional Materials2023

    • Author(s)
      Aiko Fukazawa
    • Organizer
      10th International Conference on Advanced Materials & Nanotechnology (AMN10)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 反芳香族炭化水素が配位したニッケル(0)錯体の合成と構造2023

    • Author(s)
      今西 勇文,薄葉 純一,安井 孝介,植竹 裕太,深澤 愛子
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Thiophene-fused Pentalene: Highly Antiaromatic Yet Stable π-Electron Systems without Bulky Substituents2022

    • Author(s)
      Aiko Fukazawa
    • Organizer
      The 19th International Symposium on Novel Aromatic Compounds (ISNA-19)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Design of Novel Nonbenzenoid π-Electron Systems toward Unusual Yet Stable Functional Materials2022

    • Author(s)
      Aiko Fukazawa
    • Organizer
      25th IUPAC International Conference on Physical Organic Chemistry (ICPOC 25)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Exploring Novel Nonbenzenoid π-Electron Systems toward Unusual Yet Stable Functional Materials2022

    • Author(s)
      Aiko Fukazawa
    • Organizer
      UNIST-Kyoto University Symposium
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Thiophene-Fused 1,4-Diazapentalene and Their Derivatives: Nitrogen-Doped 4nπ Electron System with Strong Antiaromaticity2022

    • Author(s)
      Junichi Usuba, Aiko Fukazawa
    • Organizer
      25th IUPAC International Conference on Physical Organic Chemistry (ICPOC 25)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Stereoselective Synthesis and Properties of Electron-Accepting π-Electron Systems Bearing Indenone Azines2022

    • Author(s)
      Shu Takagi, Masahiro Hayakawa, Aiko Fukazawa
    • Organizer
      26th IUPAC International Conference on Physical Organic Chemistry (ICPOC 25)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 強い近赤外吸収をもつ反芳香族化合物の合成2022

    • Author(s)
      薄葉純一,深澤愛子
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Weissジケトンへの硫黄官能基の導入とその位置特異的変換2022

    • Author(s)
      磯貝涼介,安井孝介,深澤愛子
    • Organizer
      第38回有機合成化学セミナー
    • Related Report
      2022 Annual Research Report
  • [Presentation] 含窒素ペンタフルバレンを基本骨格にもつ拡張π共役系の合成,構造および物性2022

    • Author(s)
      安井孝介,深澤愛子
    • Organizer
      第38回有機合成化学セミナー
    • Related Report
      2022 Annual Research Report
  • [Presentation] 第38回有機合成化学セミナー2022

    • Author(s)
      高木 周,早川雅大,深澤愛子
    • Organizer
      基礎有機化学会第2回若手オンラインシンポジウム
    • Related Report
      2022 Annual Research Report
  • [Presentation] 特異な電子構造と安定性をあわせもつ新奇π電子系の創成2022

    • Author(s)
      深澤愛子
    • Organizer
      第955回分子研コロキウム
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] ケタジン骨格を組み込んだビインデニリデンの合成と物性2022

    • Author(s)
      高木 周,早川雅大,深澤愛子
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ベンゼン縮環ペンタフルバレンの官能基化と拡張π電子系への展開2022

    • Author(s)
      早川雅大,砂山尚之,松尾 優,深澤愛子
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 硫黄官能基をもつ Weiss ジケトンの合成とその位置特異的変換2022

    • Author(s)
      磯貝涼介,安井孝介,深澤愛子
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ジアザペンタフルバレンを基本骨格にもつ拡張π電子系の合成,構造および物性2022

    • Author(s)
      安井孝介,深澤愛子
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Thiophene-fused Nonbenzenoid Hydrocarbons: Unusual Yet Stable π-Electron Materials2021

    • Author(s)
      Aiko Fukazawa
    • Organizer
      Symposium on George A. Olah Award in Hydrocarbon or Petroleum Chemistry, ACS Spring Meeting 2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 非ベンゼン系共役電子系のルネサンス2021

    • Author(s)
      深澤愛子
    • Organizer
      近畿化学協会 令和3年度第1回合成フォーラム
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] 新奇π電子系の設計・合成化学と機能探求2021

    • Author(s)
      深澤愛子
    • Organizer
      東京大学物性研 IPPS ワークショップ ISSP WOMEN’s WEEK 2021
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Exploring Novel Nonbenzenoid π-Electron Systems toward Unusual Yet Stable Functional Materials2021

    • Author(s)
      Aiko Fukazawa
    • Organizer
      International Workshop on Materials Science, Osaka Prefecture University
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Exploring Thiophene-fused Nonbenzenoid Hydrocarbons toward Unusual Yet Stable Functional Materials2021

    • Author(s)
      Aiko Fukazawa
    • Organizer
      Yoshida Prize Symposium
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Exploring the Novel π-Electron Scaffolds and Solubilizing Groups toward Organic Semiconducting Materials2021

    • Author(s)
      Aiko Fukazawa
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2021)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Design of Sulfur-Containing π-Electron Systems toward Unusual Yet Stable Functional Materials2021

    • Author(s)
      Aiko Fukazawa
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2021)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 硫黄官能基をもつ Weiss ジケトンの合成と位置特異的変換2021

    • Author(s)
      磯貝涼介,安井孝介,深澤愛子
    • Organizer
      第1回基礎有機化学若手オンラインシンポジウム
    • Related Report
      2021 Annual Research Report

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

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