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Development of dynamic molecular systems using main-group element embedded polycyclic aromatic hydrocarbons

Research Project

Project/Area Number 20K15258
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 InstitutionOsaka University (2021-2022)
Nagoya University (2020)

Principal Investigator

Ando Naoki  大阪大学, 産業科学研究所, 助教 (80848979)

Project Period (FY) 2020-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2021: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2020: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsホウ素 / Lewis酸性 / 配位結合 / 刺激応答性 / Frustrated Lewis Pair / Lewis酸 / 光物性 / 外部刺激応答性 / 刺激応答 / 光学特性 / 典型元素 / 多環芳香族炭化水素 / Lewis酸・塩基平衡 / Lewis酸・塩基相互作用 / π-π相互作用
Outline of Research at the Start

本研究では,典型元素を組み込んだ多環芳香族化合物 (PAH) 間のLewis酸・塩基相互作用とπ-π相互作用を活用し,従来の分子系とは異なる動作原理に基づいた動的分子系の創出を目的とする.また,この分子系を基盤に,従来型の分子系では得られない物性や機能を追求することで,π電子系の機能開拓に挑む.

Outline of Final Research Achievements

In this study, we have explored the dynamic molecular systems using the Lewis acidity of a boron atom as a key essence. The Lewis acid-base equilibrium among the main-group element embedded polycyclic aromatic hydrocarbons (PAHs) was demonstrated by employing the highly Lewis acidic boron-containing PAH bearing a borole substructure. New boron-based acceptor units with olefin-borane interactions were synthesized. Noteworthy is that the donor-π-acceptor compounds with these units exhibited the Frustrated Lewis Pair-type reactivity. Throughout these findings, promising concepts have been presented as the basis for a new dynamic molecular system

Academic Significance and Societal Importance of the Research Achievements

可逆的な結合や相互作用は,動的な特性をもつ材料の開発に必要不可欠な構成要素である.新たな動作原理に基づいた動的分子系(動的化学システム)の創出は,基礎学術見地からの重要性のみならず,スマートマテリアルなどの応用研究を通して,科学技術の飛躍的発展に結びつく可能性を秘めている.本研究では,ホウ素のLewis酸性を活かした動的分子系の基礎となるコンセプトを提案した.これらの成果を利用した新機軸の分子系への展開が期待される.

Report

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

    (18 results)

All 2023 2022 2021 2020

All Journal Article (7 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 7 results) Presentation (10 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Photodissociative Modules that Control Dual‐Emission Properties in Donor?π?Acceptor Organoborane Fluorophores2023

    • Author(s)
      Kawashiro Midori、Mori Tatsuya、Ito Masato、Ando Naoki、Yamaguchi Shigehiro
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 26

    • DOI

      10.1002/anie.202303725

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fluorescent Organic π‐Radicals Stabilized with Boron: Featuring a SOMO?LUMO Electronic Transition2022

    • Author(s)
      Ito Masato、Shirai Shusuke、Xie Yongfa、Kushida Tomokatsu、Ando Naoki、Soutome Hiroki、Fujimoto Kazuhiro J.、Yanai Takeshi、Tabata Kenichi、Miyata Yasuo、Kita Hiroshi、Yamaguchi Shigehiro
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 61 Issue: 25

    • DOI

      10.1002/anie.202201965

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Planarized Phenyldithienylboranes: Effects of the Bridging Moieties and π‐Extension on the Photophysical Properties and Lewis Acidity2022

    • Author(s)
      Sakai Mika、Mori Masayoshi、Hirai Masato、Ando Naoki、Yamaguchi Shigehiro
    • Journal Title

      Chemistry A European Journal

      Volume: 28 Issue: 38

    • DOI

      10.1002/chem.202200728

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Olefin?Borane Interactions in Donor?π?Acceptor Fluorophores that Undergo Frustrated‐Lewis‐Pair‐Type Reactions2022

    • Author(s)
      Oshimizu Ryo、Ando Naoki、Yamaguchi Shigehiro
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 61 Issue: 41

    • DOI

      10.1002/anie.202209394

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fully fused boron-doped polycyclic aromatic hydrocarbons: their synthesis, structure-property relationships, and self-assembly behavior in aqueous media2022

    • Author(s)
      Hiroki Narita, Heekyoung Choi, Masato Ito, Naoki Ando, Soichiro Ogi, Shigehiro Yamaguchi
    • Journal Title

      Chemical Science

      Volume: 13 Issue: 5 Pages: 1484-1491

    • DOI

      10.1039/d1sc06710a

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Boron-Doped Polycyclic π-Electron Systems with an Antiaromatic Borole Substructure That Forms Photoresponsive B?P Lewis Adducts2021

    • Author(s)
      Ando Naoki、Yamada Takuya、Narita Hiroki、Oehlmann Niels N.、Wagner Matthias、Yamaguchi Shigehiro
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 26 Pages: 9944-9951

    • DOI

      10.1021/jacs.1c04251

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Electron-deficient heteroacenes that contain two boron atoms: near-infrared fluorescence based on a push-pull effect2021

    • Author(s)
      Masato Ito, Mika Sakai, Naoki Ando, Shigehiro Yamaguchi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 40 Pages: 21853-21859

    • DOI

      10.1002/anie.202106642

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Presentation] 5,5'-ビチアゾリリデン-4,4'-ジオン誘導体の物性と半導体特性評価2023

    • Author(s)
      山田 澪奈、安藤 直紀、家 裕隆
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] ホウ素ドープ多環芳香族炭化水素の水媒体中での自己集合特性2022

    • Author(s)
      成田 皓樹,Heekyoung Choi, 伊藤 正人, 安藤 直紀, 大城 宗一郎, 山口 茂弘
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] 平面固定ホウ酸化合物の構造とLewis酸性の相関2021

    • Author(s)
      清水悠貴,安藤直紀, 山田卓弥,山口茂弘
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Research-status Report
  • [Presentation] Structure-Lewis Acidity Relationship in Planarized Triarylboranes2021

    • Author(s)
      Yuki Shimizu, Naoki Ando, Takuya Yamada, Shigehiro Yamaguchi
    • Organizer
      Pacifichem 2021
    • Related Report
      2021 Research-status Report
  • [Presentation] ホウ素ドープ多環芳香族炭化水素の構造物性相関と自己集合特性2021

    • Author(s)
      成田皓樹,伊藤正人, 安藤直紀, 大城宗一郎, 山口茂弘
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Research-status Report
  • [Presentation] Hiroki Narita, Masato Ito, Naoki Ando, Soichiro Ogi, Shigehiro Yamaguchi2021

    • Author(s)
      Boron-doped Polycyclic Aromatic Hydrocarbons with Unsymmetric Structures
    • Organizer
      Pacifichem 2021
    • Related Report
      2021 Research-status Report
  • [Presentation] ボロールを含む多環式π電子系の創製とホウ素-リン錯体の光応答性2021

    • Author(s)
      安藤 直紀, 山田 卓弥, 成田 皓樹, Niels Oehlmann, Matthias Wagner, 山口 茂弘
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] ボロール骨格を含む高ルイス酸性多環式化合物の合成と物性2021

    • Author(s)
      清水 悠貴,安藤 直紀, 山口 茂弘
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] オレフィン-ボラン相互作用に基づく刺激応答性ジアリールボリル基の開発2021

    • Author(s)
      大清水 凌,安藤 直紀, 山口 茂弘
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] オレフィン-ホウ素相互作用をもつジアリールボリル基の創製2020

    • Author(s)
      大清水凌,安藤直紀,山口茂弘
    • Organizer
      第47回有機典型元素化学討論会
    • Related Report
      2020 Research-status Report
  • [Patent(Industrial Property Rights)] 有機電子素子用材料、有機電子素子、及び化合物2023

    • Inventor(s)
      家 裕隆、安藤 直紀、山田 澪奈、岡田 壮史、新井 信道
    • Industrial Property Rights Holder
      家 裕隆、安藤 直紀、山田 澪奈、岡田 壮史、新井 信道
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2023-021531
    • Filing Date
      2023
    • Related Report
      2022 Annual Research Report

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Published: 2020-04-28   Modified: 2024-01-30  

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