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Synthesis of Bismuth-incorporated Conjugated Systems and Exploration of Their Function

Research Project

Project/Area Number 17K19128
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Research Field Organic chemistry and related fields
Research InstitutionNagoya University

Principal Investigator

Suzuki Katsunori  名古屋大学, 工学研究科, 助教 (60455350)

Research Collaborator YAMASHITA Makoto  
Project Period (FY) 2017-06-30 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2018: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2017: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Keywords共役系 / ビスマス / 第6周期元素 / 芳香族 / ビスマベンゼン / 高周期元素 / ベンゼン / 第6周期元素 / ヘテロベンゼン / 共役系化合物 / 重原子効果
Outline of Final Research Achievements

In this research, to reveal the unique properties derived from heavy atom effect of sixth period main group element and conjugated organic framework, we investigated synthesis and characterization of bismuth-incorporated organic conjugated systems. As a result, we found the substitution of bismabenzene by a reaction with electrophiles and oxidative coupling of bismabenzene. The structures and electronic properties of bismuth-incorporated conjugated systems were revealed by spectroscopic as well as theoretical studies.

Academic Significance and Societal Importance of the Research Achievements

有機共役系化合物は有機発光素子や半導体など有機電子材料としての応用が期待される化合物群である。有機共役系のサイズや置換基の電子的効果によりその物性は様々に変化し、その機能を発現する。本研究では従来の有機共役系の設計とは異なるアプローチとして第6周期元素の導入を提案した。有機共役系の機能に重原子効果を付与することで従来にはない機能を持った共役系がデザインできると期待される。また重原子を含む共役系の研究はほぼ未開拓である。この重原子を含む共役系の化学を世界に先駆けて開拓することが本研究の学術的意義である。

Report

(3 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • Research Products

    (43 results)

All 2019 2018 2017 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (34 results) (of which Int'l Joint Research: 10 results,  Invited: 1 results) Remarks (1 results)

  • [Journal Article] Chlorine-Substituted Germabenzene: Generation and Application as a Precursor for Aryl-Substituted Germabenzenes2019

    • Author(s)
      Kaiya Canon、Suzuki Katsunori、Yamashita Makoto
    • Journal Title

      Organometallics

      Volume: 38 Issue: 3 Pages: 610-613

    • DOI

      10.1021/acs.organomet.8b00938

    • NAID

      120006650163

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chlorine-Substituted 9,10-Dihydro-9-aza-10-boraanthracene as a Precursor for Various Boron- and Nitrogen-Containing π-Conjugated Compounds2019

    • Author(s)
      Ishikawa Yutaro、Suzuki Katsunori、Hayashi Kohei、Nema Shin-ya、Yamashita Makoto
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 6 Pages: 1722-1725

    • DOI

      10.1021/acs.orglett.9b00278

    • NAID

      120006650162

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Monomeric Stannabenzene: Synthesis, Structure, and Electronic Properties2019

    • Author(s)
      Kaiya Canon、Suzuki Katsunori、Yamashita Makoto
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 印刷中 Issue: 23 Pages: 7749-7752

    • DOI

      10.1002/anie.201902639

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dimerization of boryl- and amino-substituted acetylenes by B2C2 four-membered ring formation2018

    • Author(s)
      Kitamura Ryo、Suzuki Katsunori、Yamashita Makoto
    • Journal Title

      Chemical Communications

      Volume: 54 Issue: 46 Pages: 5819-5822

    • DOI

      10.1039/c8cc02122h

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Planar and Bent BN-Embedded p-Quinodimethanes Synthesized by Transmetalation of Bis(trimethylsilyl)-1,4-dihydropyrazines with Chloroborane2018

    • Author(s)
      Noguchi Mao、Suzuki Katsunori、Kobayashi Jun、Yurino Taiga、Tsurugi Hayato、Mashima Kazushi、Yamashita Makoto
    • Journal Title

      Organometallics

      Volume: 37 Issue: 12 Pages: 1833-1836

    • DOI

      10.1021/acs.organomet.8b00294

    • NAID

      120006529615

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A zwitterionic aluminabenzene-alkylzirconiium complex having half-zirconocence structure: synthesis and application for additive-free ethylene polymerization2018

    • Author(s)
      Nakamura Taichi、Suzuki Katsunori、Yamashita Makoto
    • Journal Title

      Chemical Communications

      Volume: 印刷中 Issue: 33 Pages: 4180-4183

    • DOI

      10.1039/c8cc02186d

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Aluminabenzene-Rh and -Ir Complexes: Synthesis, Structure, and Application toward Catalytic C?H Borylation2017

    • Author(s)
      Nakamura Taichi、Suzuki Katsunori、Yamashita Makoto
    • Journal Title

      Journal of the American Chemical Society

      Volume: 139 Issue: 49 Pages: 17763-17766

    • DOI

      10.1021/jacs.7b11127

    • NAID

      120006473512

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Anionic indabenzene: synthesis and characterization2017

    • Author(s)
      Nakamura Taichi、Suzuki Katsunori、Yamashita Makoto
    • Journal Title

      Chemical Communications

      Volume: 53 Issue: 99 Pages: 13260-13263

    • DOI

      10.1039/c7cc08397a

    • NAID

      120006473511

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] 単離可能なスタンナベンゼンの合成及び構造2019

    • Author(s)
      海谷河音、鈴木克規、山下誠
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] N-ヘテロ環カルベンにより安定化されたアザボラアントラセンの合成、構造および反応2019

    • Author(s)
      石川祐太朗、鈴木克規、山下誠
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ホウ素窒素置換アセチレンと有機ホウ素化合物の反応2019

    • Author(s)
      小林明弥、北村亮、鈴木克規、山下誠
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ビ(ビスマベンゼン)の合成、構造および物性2019

    • Author(s)
      難波叶帆、石井拓弥、鈴木克規、山下誠
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ジアニオン性ビ(アルミナベンゼン)の合成と構造2019

    • Author(s)
      久野真揮、鈴木克規、仲村太智、山下誠
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 求電子剤と塩基によるアニオン性アルミナベンゼンの段階的置換反応2018

    • Author(s)
      久野真揮、鈴木克規、仲村太智、山下誠
    • Organizer
      第113回有機合成シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] Reversible B2C2 Four-Membered Ring Formmation by Dimerization of Boryl- and Amino-Substituted Acetylenes2018

    • Author(s)
      Kitamura Ryo、Suzuki Katsunori、Yamashita Makoto
    • Organizer
      The 15th International Symposium on Inorganic Ring Systems (IRIS-15)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Germabenzenes Having Various Aryl Groups by Reaction of in-situ Generated Chlorogermabenzene2018

    • Author(s)
      Kaiya Canon、Suzuki Katsunori、Yamashita Makoto
    • Organizer
      The 15th International Symposium on Inorganic Ring Systems (IRIS-15)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Structure of 9,10-Dihydro-9-aza-10-boraanthracene2018

    • Author(s)
      Ishikawa Yutaro、Nema Shin-ya、Hayashi Kohei、Suzuki Katsunori、Yamashita Makoto
    • Organizer
      The 15th International Symposium on Inorganic Ring Systems (IRIS-15)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Reactions of Anionic Aluminabenzene with Electrophiles2018

    • Author(s)
      Kuno Masaki、Suzuki Katsunori、Nakamura Taichi、Yamashita Makoto
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Reactivity of Bismabenzene2018

    • Author(s)
      Nanba Yasuho、Ishii Takuya、Suzuki Katsunori、Yamashita Makoto
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ビスマベンゼンと求電子剤との反応2018

    • Author(s)
      難波叶帆、石井拓弥、鈴木克規、山下誠
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 無置換9,10-ジヒドロ-9-アザ-10-ボラアントラセンの合成、構造および反応性2018

    • Author(s)
      石川祐太朗、根間慎也、林晃平、鈴木克規、山下誠
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 久野真揮、鈴木克規、仲村太智、山下誠2018

    • Author(s)
      アニオン性アルミナベンゼンと求電子剤の反応
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 海谷河音、鈴木克規、山下誠2018

    • Author(s)
      14族元素上に様々な置換基を持つ高周期14族元素含有ベンゼンの合成
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ビスマベンゼンにおける求電子置換反応の解明2018

    • Author(s)
      難波叶帆、石井拓弥、鈴木克規、山下誠
    • Organizer
      第49回中部化学関係学協会支部連合秋季大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] プルンバベンゼニルアニオンの合成2018

    • Author(s)
      海谷河音、鈴木克規、山下誠
    • Organizer
      第45回有機典型元素化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 塩素置換9-アザ-10-ボラアントラセンの合成とその誘導化2018

    • Author(s)
      石川祐太朗、根間慎也、林晃平、鈴木克規、山下誠
    • Organizer
      第45回有機典型元素化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Heavy Group 13 and 15 Element-Incorporated Heterobenzenes: Synthesis and Characterization2017

    • Author(s)
      Katsunori Suzuki、Taichi Nakamura、Takuya Ishii、Makoto Yamashita
    • Organizer
      International Symposium on Pure & Applied Chemistry 2017
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Catalytic Activity of Aluminabenzene-Rh and -Ir Complexes2017

    • Author(s)
      Taichi Nakamura、Katsunori Suzuki、Yamashita Makoto
    • Organizer
      12th International Conference on Hereroatom Chemistry
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of BCN Graphite Using BN-Containing π-Conjugated Systems as Precursors2017

    • Author(s)
      Jun Kobayashi, Katsunori Suzuki, Yoshiyuki Sugahara, Makoto Yamashita
    • Organizer
      12th International Conference on Hereroatom Chemistry
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] BN含有π共役系化合物を前駆体としたBCNグラファイトの合成と物性評価2017

    • Author(s)
      小林純、鈴木克規、菅原義之、山下誠
    • Organizer
      第6回JACI/GSCシンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] Synthesis of BCN Graphite Using BN-Containing π-Conjugated Systems as a Precursor2017

    • Author(s)
      Jun Kobayashi, Katsunori Suzuki, Yoshiyuki Sugahara, Makoto Yamashita
    • Organizer
      16th International Meeting on Boron Chemistry
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Property of BN-doped Carbon Materials Using BN Containing π-Conjugated Compounds as Precursors2017

    • Author(s)
      Jun Kobayashi, Katsunori Suzuki, Yoshiyuki Sugahara, Makoto Yamashita
    • Organizer
      International ERATO Itami Molecular Nanocarbon Symposium 2017 "The Power of Carbon-based Materials"
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] 嵩高いシリル基で安定化された塩素置換ゲルマベンゼンの合成とその変換反応2017

    • Author(s)
      海谷河音、仲村太智、鈴木克規
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 中性アルミナベンゼン-ルイス塩基付加体の合成と構造2017

    • Author(s)
      仲村太智、鈴木克規、山下誠
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 官能基変換可能なアミノ基とボリン酸部位を持つ9-アザ-10-ボラアントラセンの合成と誘導化2017

    • Author(s)
      石川祐太朗、根間慎也、林晃平、鈴木克規、山下誠
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] BN含有π共役系分子を前駆体としたBNドープグラファイトの合成と物性評価2017

    • Author(s)
      小林純、鈴木克規、菅原義之、山下誠
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] アルミナベンゼン-ジルコニウム錯体の合成、構造およびエチレン重合活性2017

    • Author(s)
      仲村太智、鈴木克規、山下誠
    • Organizer
      第48回中部化学関係学協会支部連合秋季大会
    • Related Report
      2017 Research-status Report
  • [Presentation] クロロ置換ゲルマシクロヘキサジエンの反応を用いたゲルマベンゼン誘導体の合成と性質2017

    • Author(s)
      海谷河音、鈴木克規、山下誠
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 9-アザ-10-ボラアントラセンオリゴマーの合成、構造および光物性2017

    • Author(s)
      石川祐太朗、根間慎也、林晃平、鈴木克規、山下誠
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 無置換9,10-ジヒドロ-9-アザ-10-ボラアントラセンの合成および構造2017

    • Author(s)
      石川祐太朗、根間慎也、林晃平、鈴木克規、山下誠
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 求電子剤との反応を経由するアニオン性アルミナベンゼンの置換反応2017

    • Author(s)
      久野真揮、鈴木克規、仲村太智、山下誠
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 多環式芳香族炭化水素が置換したゲルマベンゼンの合成と性質2017

    • Author(s)
      海谷河音、鈴木克規、山下誠
    • Organizer
      日本化学会 第98春季年会
    • Related Report
      2017 Research-status Report
  • [Remarks] 名古屋大学大学院工学研究科有機元素化学研究室ウェブサイト

    • URL

      http://oec.chembio.nagoya-u.ac.jp/

    • Related Report
      2018 Annual Research Report 2017 Research-status Report

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Published: 2017-07-21   Modified: 2020-03-30  

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