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Development functional materials by the boron-mediated aromatic ring-forming reactions

Research Project

Project/Area Number 17H03020
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

Shoji Yoshiaki  東京工業大学, 科学技術創成研究院, 准教授 (40525573)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥18,200,000 (Direct Cost: ¥14,000,000、Indirect Cost: ¥4,200,000)
Fiscal Year 2019: ¥5,850,000 (Direct Cost: ¥4,500,000、Indirect Cost: ¥1,350,000)
Fiscal Year 2018: ¥5,850,000 (Direct Cost: ¥4,500,000、Indirect Cost: ¥1,350,000)
Fiscal Year 2017: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Keywordsホウ素 / π電子系分子 / π共役高分子 / ルイス酸 / アルキン / 固体物性 / π共役分子 / 9-ボラフルオレン / 芳香環構築 / 反応機構 / ボラフルオレン
Outline of Final Research Achievements

In this research, we focused on (1) the elucidation of the mechanism of a new boron-mediated aromatic ring construction reaction and (2) the development of π-conjugated functional materials. Through experimental and theoretical studies, we succeeded in the evaluation of the boron-mediated 1,2-carboboration of alkynes and the oxidative deborylation/C-C coupling of the resultant borepin derivatives. We also clarified the structural elements of 9-borafluorenes required for the efficient benzannulation of alkyne derivatives. Using the optimized reaction conditions and substrates, we have developed a dynamic propeller molecule with superb chiral sensing capability and a direct transformation reaction of linear π-conjugated polymers into microporous zigzag-shaped polymers. These findings would be useful for the development of new π-conjugated materials with unique structural and dynamic properties.

Academic Significance and Societal Importance of the Research Achievements

本研究では、独自に見出した、ホウ素化合物による新しいπ電子系骨格構築反応のメカニズムを明らかにするとともに、開発した新反応を用いて、特異な構造特性や動的特性を有するπ電子系機能分子・高分子を開発しました。本研究を通じて、典型元素であるホウ素が織りなす新たな反応化学を開拓することができました。また得られた知見は、有機エレクトロニクスに応用可能な新材料開発にも有用であると期待できます。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (26 results)

All 2020 2019 2018 2017

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Open Access: 1 results) Presentation (20 results) (of which Int'l Joint Research: 3 results,  Invited: 9 results)

  • [Journal Article] Organic Transformations Using Electron-Deficient Boron Compounds2020

    • Author(s)
      Shoji Yoshiaki, Kashida Junki, Fukushima Takanori
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 78 Issue: 3 Pages: 190-203

    • DOI

      10.5059/yukigoseikyokaishi.78.190

    • NAID

      40022181819

    • ISSN
      0037-9980, 1883-6526
    • Year and Date
      2020-03-01
    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Reactivity of Cyclic Borane‐Amidine Conjugated Molecules Formed by Direct 1,2‐Carboboration of Carbodiimides with 9‐Borafluorenes2019

    • Author(s)
      J. Kashida, Y. Shoji, T. Fukushima
    • Journal Title

      Chem. Asian J.

      Volume: 14 Issue: 10 Pages: 1879-1885

    • DOI

      10.1002/asia.201900047

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Theoretical Study on the Mechanism of the Oxidative Deborylation/C-C Coupling Reaction of Borepin Derivatives2019

    • Author(s)
      C. Ozen, Y. Shoji, T. Fukushima, S. Maeda
    • Journal Title

      J. Org. Chem.

      Volume: 84 Issue: 4 Pages: 1941-1950

    • DOI

      10.1021/acs.joc.8b02917

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sensing the chirality of various organic solvents by helically arranged π-blades2018

    • Author(s)
      Y. Shimizu, Y. Shoji, D. Hashizume, Y. Nagata, T. Fukushima
    • Journal Title

      Chem. Commun.

      Volume: 54 Issue: 87 Pages: 12314-12317

    • DOI

      10.1039/c8cc06277c

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Mechanistic Study of Highly Efficient Direct 1,2-Carboboration of Alkynes with 9-Borafluorenes2018

    • Author(s)
      Shoji Yoshiaki、Shigeno Naoki、Takenouchi Kumiko、Sugimoto Manabu、Fukushima Takanori
    • Journal Title

      Chemistry - A European Journal

      Volume: 24 Issue: 50 Pages: 13223-13230

    • DOI

      10.1002/chem.201801818

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Efficient Transformation of Linear Poly(Phenylene Ethynylene)s into Zigzag-Shaped π-Conjugated Microporous Polymers through Boron-Mediated Alkyne Benzannulation2018

    • Author(s)
      Y. Shoji, M. Hwang, H. Sugiyama, F. Ishiwari, K. Takenouchi, R. Osuga, J. N. Kondo, S. Fujikawa, T. Fukushima
    • Journal Title

      Mater. Chem. Front.

      Volume: 2 Issue: 4 Pages: 807-814

    • DOI

      10.1039/c7qm00582b

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Presentation] Synthesis of Boron-Nitrogen Bond-Containing Non-Benzenoid Type π-Conjugated Molecules2020

    • Author(s)
      Junki Kashida, Yoshiaki Shoji, Takanori Fukushima
    • Organizer
      第100回日本化学会春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis of Cyclic Borane-Amidine Conjugated Molecules by 1,2-Carboboration of Carbodiimide with 9-Borafluorene2019

    • Author(s)
      Junki Kashida, Yoshiaki Shoji, Takanori Fukushima
    • Organizer
      18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 9-Borafluorene-Mediated Benzannulation of Alkyne Derivatives: The Mechanism and Applications2019

    • Author(s)
      Yoshiaki Shoji
    • Organizer
      18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 9-ボラフルオレン誘導体に対する歪みアルキンの連続挿入を利用した含ホウ素π共役マクロサイクルの合成2019

    • Author(s)
      村田幸優, 菓子田惇輝, 庄子良晃, 福島孝典
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Development of electron-deficient boron compounds and their organic transformations2019

    • Author(s)
      Yoshiaki Shoji
    • Organizer
      Center for Functional SeNsor & Actuator (CFSN) Seminar
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 9-ボラフルオレン誘導体を用いた歪みアルキンの芳香環化による湾曲πシステムの構築2019

    • Author(s)
      荒井由土、庄子良晃、奥田靖浩、折田明浩、福島孝典
    • Organizer
      第99回日本化学会春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] カルボジイミドの直接的1,2-カルボホウ素化による環状および非環状ボラン-アミジン共役系の構築2019

    • Author(s)
      菓子田惇輝、庄子良晃、福島孝典
    • Organizer
      第99回日本化学会春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ホウ素ルイス酸とπ電子の相互作用に基づく連続反応の開発と展開2018

    • Author(s)
      庄子良晃
    • Organizer
      第2回 触発型有機化学研究会 (AIKOC-2)
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] ホウ素が媒介する連続反応の開発とその展開2018

    • Author(s)
      庄子良晃
    • Organizer
      第53回 反応有機若手の会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 含ホウ素 π 共役マクロサイクルの合成、構造、および反応性2018

    • Author(s)
      馬緤賢太、庄子良晃、福島孝典
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ボラフルオレンを用いた C=N 二重結合の 1,2-カルボホウ素化による含ホウ素-窒素 π 共役系の合成2018

    • Author(s)
      菓子田惇輝、庄子良晃、福島孝典
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 連続的1,2-カルボホウ素化反応を利用したπ共役マクロサイクルの合成2018

    • Author(s)
      馬緤賢太・滋野直樹・庄子良晃・福島孝典
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ホウ素の特性を活かした電子・光電子機能性材料の創製2018

    • Author(s)
      庄子良晃
    • Organizer
      第2回 東工大応用化学系 次世代を担う若手シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] ホウ素と芳香環で組み立てる分子機能の探求2017

    • Author(s)
      庄子良晃
    • Organizer
      ITbM/IGER Chemistry Workshop 2017
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 連続的1,2-カルボホウ素化反応を利用したπ共役マクロサイクルの合成2017

    • Author(s)
      馬緤賢太・滋野直樹・庄子良晃・福島孝典
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] アルキンの芳香環化反応を利用した多孔性高分子の合成2017

    • Author(s)
      黄旻授・杉山陽香・庄子良晃・福島孝典
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] C3対称性プロペラ型π共役分子の不斉認識2017

    • Author(s)
      清水 佑樹・庄子 良晃・橋爪 大輔・福島 孝典
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] プロペラ分子が可能にする高秩序有機薄膜の造形と機能2017

    • Author(s)
      庄子良晃
    • Organizer
      第3回「高次複合光応答」若手の会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 電子欠損性ホウ素化合物の新構造・新反応の探求2017

    • Author(s)
      庄子良晃
    • Organizer
      第49回構造有機化学若手の会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 電子欠損性ホウ素化合物の新構造・新反応2017

    • Author(s)
      庄子良晃
    • Organizer
      第5回慶応有機化学若手シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited

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Published: 2017-04-28   Modified: 2021-02-19  

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