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Synthesis and Properties of pi-Conjugated Compounds Based on Borabenzene-Lewis Base Adducts

Research Project

Project/Area Number 25810029
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionChuo University

Principal Investigator

SUZUKI Katsunori  中央大学, 理工学部, 助教 (60455350)

Co-Investigator(Renkei-kenkyūsha) YAMASHITA Makoto  中央大学, 理工学部, 准教授 (10376486)
Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywords有機ホウ素 / 共役系 / ルイス酸 / ルイス塩基 / 有機アルミニウム / 芳香族 / ジルコニウム錯体 / 有機典型元素 / ボラベンゼン / 機能性材料
Outline of Final Research Achievements

We have investigated the synthetic approach to the conjugated systems by using the Lewis acid-base interaction between borabenzene and pyridine derivatives. In this studies, we also found the novel cyclization reaction of 1,5-bis(silyl)-1,4-diyne with DIBAL-H and dibutyltin dichloride. Using this cyclization, an anionic aluminabenzene was synthesized for the first time. The unique aromatic character described by the resonance structure between aromatic and ambiphilic contributions have been revealed by experimental and theoretical studies. In addition, the first aluminabenzene zirconium complexes were also synthesized and characterized.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (53 results)

All 2015 2014 2013 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Acknowledgement Compliant: 4 results) Presentation (47 results) Remarks (2 results)

  • [Journal Article] An Anionic Aluminabenzene bearing Aromatic and Ambiphilic Contributions2014

    • Author(s)
      Nakamura, T.; Suzuki, K.; Yamashita, M.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 26 Pages: 9276-9279

    • DOI

      10.1021/ja504771d

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Dimesitylboryl- and Amino-Substituted Acetylene Having Butatriene-Type Resonance Contribution2014

    • Author(s)
      Onuma, K.; Suzuki, K.; Yamashita, M.
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 3 Pages: 405-407

    • DOI

      10.1246/cl.141063

    • NAID

      130004868401

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Rhombic Cyclobutadiene with a Boryl/Amino-Substitution Pattern: Boryl Group Migration Induced by Reaction with Water2014

    • Author(s)
      Onuma, K.; Suzuki, K.; Yamashita, M.
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 5 Pages: 1212-1215

    • DOI

      10.1021/acs.orglett.5b00163

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Aluminabenzene-Zirconium Complexes: Intramolecular Coordination of Chloride to Aluminium2014

    • Author(s)
      Nakamura, T.; Suzuki, K.; Yamashita, M.
    • Journal Title

      Organometallics

      Volume: 34 Issue: 5 Pages: 813-816

    • DOI

      10.1021/acs.organomet.5b00073

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] ホウ素、窒素置換シクロブタジエンの反応2015

    • Author(s)
      小沼郁,鈴木克規,山下誠
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] アルミナベンゼン-ジルコニウム錯体の合成と構造2015

    • Author(s)
      仲村太智,鈴木克規,山下誠
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] ジボリルジホスフェンの合成・構造・反応性2015

    • Author(s)
      浅見俊介,岡本匡史,鈴木克規,山下誠
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 1,5-ビスシリル1,4-ジインのヒドロアルミニウム化を経由した含15族高周期ベンゼンの合成2015

    • Author(s)
      石井拓弥,仲村太智,鈴木克規,山下誠
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] ビスシリルピラジンとハロボランの反応によるホウ素、窒素含有共役系の合成2015

    • Author(s)
      野口真緒,百合野大雅,劒隼人,真島和志,鈴木克規,山下誠
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] An Anionic Aluminabenzene: Synthesis, Structure, and Their Transition-Metal Complexes2014

    • Author(s)
      Katsunori Suzuki, Taichi Nakamura, Makoto Yamashita
    • Organizer
      The 2nd International Symposium for Young Chemists on Stimuli-Responsive Chemical Species for the Creation of Functional Molecules
    • Place of Presentation
      大阪
    • Year and Date
      2014-12-09 – 2014-12-10
    • Related Report
      2014 Annual Research Report
  • [Presentation] ホウ素置換ジホスフェンの合成・構造・反応性2014

    • Author(s)
      浅見俊介,岡本匡史,鈴木克規,山下誠
    • Organizer
      第41回有機典型元素化学討論会
    • Place of Presentation
      宇部
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 1,5-ビスシリル1,4-ジインのヒドロアルミニウム化を経由したホスフィニンの合成2014

    • Author(s)
      石井拓弥,仲村太智,鈴木克規,山下誠
    • Organizer
      第41回有機典型元素化学討論会
    • Place of Presentation
      宇部
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] ホウ素、窒素導入アセン骨格を元素ブロックモノマーとした共役系材料の合成研究2014

    • Author(s)
      鈴木克規,根間慎也,山下誠
    • Organizer
      島津新素材セミナー2014
    • Place of Presentation
      東京
    • Year and Date
      2014-10-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 1,4-ジインのヒドロアルミニウム化を用いたホスファベンゼンの効率的合成法の開発2014

    • Author(s)
      石井拓弥,仲村太智,鈴木克規,山下誠
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      東京
    • Year and Date
      2014-10-14 – 2014-10-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] ボラベンゼンの反応性を鍵としたホウ素-窒素含有共役系化合物の合成研究2014

    • Author(s)
      野口真緒,鈴木克規,山下誠
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      東京
    • Year and Date
      2014-10-14 – 2014-10-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] アニオン性アルミナベンゼン配位子を持つZr錯体の合成2014

    • Author(s)
      仲村太智,鈴木克規,山下誠
    • Organizer
      錯体化学会第64回討論会
    • Place of Presentation
      東京
    • Year and Date
      2014-09-18 – 2014-09-20
    • Related Report
      2014 Annual Research Report
  • [Presentation] アニオン性アルミナベンゼンの合成、構造解析およびその反応性2014

    • Author(s)
      仲村太智,鈴木克規,山下誠
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] 窒素ホウ素置換シクロブタジエンの合成と構造2014

    • Author(s)
      小沼郁,鈴木克規,山下誠
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of Boron and Nitrogen Containing pi-Conjugated Molecules Using Transformations of 9-Bora-10-azaanthracene and Borabenzene-Lewis Base Adducts2014

    • Author(s)
      Katsunori Suzuki, Shin-ya Nema, Mao Noguchi, Makoto Yamashita
    • Organizer
      15th International Meeting on Boron Chemistry (IMEBORON-XV)
    • Place of Presentation
      Prague, Czech Republic
    • Year and Date
      2014-08-24 – 2014-08-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis and Structure of B, N-Substituted Cyclobutadiene2014

    • Author(s)
      Kaoru Onuma, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      15th International Meeting on Boron Chemistry (IMEBORON-XV)
    • Place of Presentation
      Prague, Czech Republic
    • Year and Date
      2014-08-24 – 2014-08-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis, Structure, and Photophysical Properties of Chloro-Substituted 9-Aza-10-boraanthracene Derivative2014

    • Author(s)
      Shin-ya Nema, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      15th International Meeting on Boron Chemistry (IMEBORON-XV)
    • Place of Presentation
      Prague, Czech Republic
    • Year and Date
      2014-08-24 – 2014-08-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] ynthesis of B,N Containing pi-Conjugated Compounds Containing Borabenzene2014

    • Author(s)
      Mao Noguchi, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      15th International Meeting on Boron Chemistry (IMEBORON-XV)
    • Place of Presentation
      Prague, Czech Republic
    • Year and Date
      2014-08-24 – 2014-08-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of pi-Conjugated Compounds Using the transformation of 9-Bora-10-azaanthracene and Borabenzene-Lewis Base Adducts2014

    • Author(s)
      Katsunori Suzuki, Shin-ya Nema, Mao Noguchi, Makoto Yamashita
    • Organizer
      248th ACS National Meeting and Exposition
    • Place of Presentation
      San Francisco, USA
    • Year and Date
      2014-08-10 – 2014-08-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] Development of Synthetic Method for Heterabenzenes using anti-Hydroalumination of 1,4-Diyne2014

    • Author(s)
      Takuya Ishii, Taichi Nakamura, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      248th ACS National Meeting and Exposition
    • Place of Presentation
      San Francisco, USA
    • Year and Date
      2014-08-10 – 2014-08-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] Boryl-substituted Diphosphene: Synthesis, Structure, and Physical Properties2014

    • Author(s)
      Shunsuke Asami, Masashi Okamoto, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      248th ACS National Meeting and Exposition
    • Place of Presentation
      San Francisco, USA
    • Year and Date
      2014-08-10 – 2014-08-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis, Characterization, and Reactions of Aluminabenzene2014

    • Author(s)
      Taichi Nakamura, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      248th ACS National Meeting and Exposition
    • Place of Presentation
      San Francisco, USA
    • Year and Date
      2014-08-10 – 2014-08-14
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of Anionic Aluminabenzene Bearing Aromatic and Ambiphilic Resonance Contribution2014

    • Author(s)
      Taichi Nakamura, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      XXVI International Conference on Organometallic Chemistry (ICOMC 2014)
    • Place of Presentation
      札幌
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthetic Approach to Boron- and Nitrogen-Containing Polymer Based on 9-Aza-10-boraanthracene Element-Block2014

    • Author(s)
      katsunori Suzuki, Shin-ya Nema, Makoto Yamashita
    • Organizer
      International Symposium on Polymeric Materials Based on Element-Blocks
    • Place of Presentation
      京都
    • Year and Date
      2014-05-31
    • Related Report
      2014 Annual Research Report
  • [Presentation] ホウ素及び窒素置換基を有するシクロブタジエンの合成と構造2014

    • Author(s)
      小沼郁,鈴木克規,山下誠
    • Organizer
      第67回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      横浜
    • Year and Date
      2014-05-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] ハロゲン置換9-ボラ-10-アザアントラセンの合成と性質2014

    • Author(s)
      根間慎也、鈴木克規、山下誠
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学、名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] ホウ素および窒素置換基を有するシクロブタジエンの合成2014

    • Author(s)
      小沼郁、鈴木克規、山下誠
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学、名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] アニオン性アルミナベンゼンの反応性2014

    • Author(s)
      仲村太智、鈴木克規、山下誠
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学、名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] ホウ素および窒素置換基を有するシクロブタジエンの合成と構造2014

    • Author(s)
      小沼郁、鈴木克規、山下誠
    • Organizer
      第67回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      慶應義塾大学、横浜
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of pi-Conjugated Compounds using transformation of 9-bora-10-azaanthracene and Borabenzene-Lewis Base Adducts2014

    • Author(s)
      Katsunori Suzuki, Shin-ya Nema, Mao Noguchi, Makoto Yamashita
    • Organizer
      248th ACS National Meeting
    • Place of Presentation
      San Francisco, USA
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis, Characterization and Reactions of Aluminabenzene2014

    • Author(s)
      Taichi Nakamura, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      248th ACS National Meeting
    • Place of Presentation
      San Francisco, USA
    • Related Report
      2013 Research-status Report
  • [Presentation] Development of Synthetic Method for Heterabenzenes using anti-Hydroalumination of 1,4-Diyne2014

    • Author(s)
      Takuya Ishii, Taichi Nakamura, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      248th ACS National Meeting
    • Place of Presentation
      San Francisco, USA
    • Related Report
      2013 Research-status Report
  • [Presentation] Boryl-substituted Diphosphene: Synthesis, Structure, and Physical Properties2014

    • Author(s)
      Shunsuke Asami, Masashi Okamoto, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      248th ACS National Meeting
    • Place of Presentation
      San Francisco, USA
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthetic Approach to Aluminabenzne2013

    • Author(s)
      Taichi Nakamura, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      15th Asian Chemical Congress
    • Place of Presentation
      Sentosa, Singapore
    • Related Report
      2013 Research-status Report
  • [Presentation] Cyclobutadiene Cobalt Complex having Push-Pull type Amino and Boryl Substituents2013

    • Author(s)
      Katsunori Suzuki, Kaoru Onuma, Makoto Yamashita
    • Organizer
      15th Asian Chemical Congress
    • Place of Presentation
      Sentosa, Singapore
    • Related Report
      2013 Research-status Report
  • [Presentation] アニオン性アルミナベンゼン: 合成と構造解析2013

    • Author(s)
      仲村太智、鈴木克規、山下誠
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学、東京
    • Related Report
      2013 Research-status Report
  • [Presentation] Aluminacyclohexadiene as a Precursor for Group 13 Elements Incorporated Benzenes2013

    • Author(s)
      Katsunori Suzuki, Taichi Nakamura, Makoto Yamashita
    • Organizer
      6th European Conference on Boron Chemistry (EuroBoron6)
    • Place of Presentation
      Radziejowice, Poland
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of N,B-Substituted Push-Pull type pi System2013

    • Author(s)
      Kaoru Onuma, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      6th European Conference on Boron Chemistry (EuroBoron6)
    • Place of Presentation
      Radziejowice, Poland
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of pi-Conjugated Framework based on 1,4-Azaborine Skeleton2013

    • Author(s)
      Shin-ya Nema, Katsunori Suzuki, Makoto Yamashita
    • Organizer
      6th European Conference on Boron Chemistry (EuroBoron6)
    • Place of Presentation
      Radziejowice, Poland
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis and Properties of Boryl- Substituted Phosphorus Compounds2013

    • Author(s)
      Shunsuke Asami, Masashi Okamoto, Makoto Yamashita, Katsunori Suzuki
    • Organizer
      6th European Conference on Boron Chemistry (EuroBoron6)
    • Place of Presentation
      Radziejowice, Poland
    • Related Report
      2013 Research-status Report
  • [Presentation] 1,4-アザボリン骨格を有するパイ共役系化合物の合成2013

    • Author(s)
      根間慎也、鈴木克規、山下誠
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      タワーホール船堀、東京
    • Related Report
      2013 Research-status Report
  • [Presentation] ホウ素置換ホスフィドおよびジホスフェンの合成と性質2013

    • Author(s)
      浅見俊介、岡本匡史、山下誠、鈴木克規
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      タワーホール船堀、東京
    • Related Report
      2013 Research-status Report
  • [Presentation] 窒素およびホウ素置換基をもったpush-pull型パイ系化合物の合成2013

    • Author(s)
      小沼郁、鈴木克規、山下誠
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      タワーホール船堀、東京
    • Related Report
      2013 Research-status Report
  • [Presentation] アニオン性アルミナベンゼンの合成2013

    • Author(s)
      仲村太智、鈴木克規、山下誠
    • Organizer
      第3回CSJ化学フェスタ2013
    • Place of Presentation
      タワーホール船堀、東京
    • Related Report
      2013 Research-status Report
  • [Presentation] 1,4-アザボリン骨格を有するパイ共役系化合物の合成と性質2013

    • Author(s)
      根間慎也、鈴木克規、山下誠
    • Organizer
      第40回有機典型元素化学討論会
    • Place of Presentation
      近畿大学、東大阪
    • Related Report
      2013 Research-status Report
  • [Presentation] ホウ素、窒素置換アセチレン:Push-pull共役系の新規ビルディングブロック2013

    • Author(s)
      小沼郁、鈴木克規、山下誠
    • Organizer
      第40回有機典型元素化学討論会
    • Place of Presentation
      近畿大学、東大阪
    • Related Report
      2013 Research-status Report
  • [Presentation] アニオン性アルミナベンゼンの合成、構造およびその反応2013

    • Author(s)
      仲村太智、鈴木克規、山下誠
    • Organizer
      第40回有機典型元素化学討論会
    • Place of Presentation
      近畿大学、東大阪
    • Related Report
      2013 Research-status Report
  • [Remarks] 中央大学有機元素化学研究室ホームページ

    • URL

      http://www.chem.chuo-u.ac.jp/~element/

    • Related Report
      2014 Annual Research Report
  • [Remarks] 中央大学山下研究室ホームページ

    • URL

      http://www.chem.chuo-u.ac.jp/~element/

    • Related Report
      2013 Research-status Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

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