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Functionalization of fused quinoxaline derivatives using an aggregated state

Research Project

Project/Area Number 24550146
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Functional materials chemistry
Research InstitutionChiba University

Principal Investigator

MATSUMOTO Shoji  千葉大学, 工学(系)研究科(研究院), 准教授 (50302534)

Co-Investigator(Renkei-kenkyūsha) AKAZOME Motohiro  千葉大学, 大学院工学研究科, 教授 (10261934)
Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Keywordsキノキサリン / 縮環 / キノキサリウム塩 / 蛍光発光 / 固体発光 / 微細構造 / 結晶構造 / 蛍光制御 / πスタック / 色調変化 / デュアル発光 / 分子内塩 / スルホナート / 熱失活 / キノキサリニウム / トリアゾール / アルキル化 / 電子供与性官能基
Outline of Final Research Achievements

I examined the systematic investigation of azole-fused quinoxaline derivatives on their synthesis and fluorescence properties. About the synthetic method, I could achieve the formation of the corresponding products by three methods based on the type of coupling reaction between two azole rings. From the investigation of the fluorescence in solution, I revealed that the introduction of an additional fused benzene, especially on pyrrole moiety, and the substitution of a nitrogen atom had a strong impact on the fluorescence. Through the analyses of the single crystal structure, I found that the interaction with C-H bond in azole moieties constructs the unique crystal packings even though the resembled molecular structures. And the all compounds except for the triazole derivative gave the fluorescence ability in the solid state. Furthermore, I achieved the functionalization of these compounds by introducing the additional substituents.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (21 results)

All 2015 2014 2013 2012 2010 Other

All Journal Article (6 results) (of which Acknowledgement Compliant: 2 results,  Peer Reviewed: 5 results) Presentation (15 results)

  • [Journal Article] Systematic Investigation of Fluorescence Properties of Symmetric and Asymmetric Diazolo[1,2-a:2',1'-c]quinoxaline Derivatives2015

    • Author(s)
      Shoji Matsumoto, Keisuke Sakamoto, Motohiro Akazome
    • Journal Title

      Heterocycles

      Volume: 91 Issue: 4 Pages: 795-814

    • DOI

      10.3987/com-15-13189

    • NAID

      40020423225

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 多様な状態で蛍光発光可能な縮環型有機化合物群の開発2014

    • Author(s)
      松本祥治
    • Journal Title

      Jasco Report

      Volume: 56 Pages: 15-22

    • NAID

      40020079358

    • Related Report
      2014 Annual Research Report
    • Acknowledgement Compliant
  • [Journal Article] Formation of Benzo[c]thiophene-1-aminium Iodide by the Reaction of o-Alkynylbenzothioamide with Iodine2014

    • Author(s)
      Shoji Matsumoto, Daiki Takada, Hirokazu Kageyama, Motohiro Akazome
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 5 Pages: 1082-1085

    • DOI

      10.1016/j.tetlet.2013.12.094

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Fluorescence of Diimidazo[1,2-a:2',1'-c]quinoxalinium Salts Under Various Conditions2013

    • Author(s)
      Shoji Matsumoto, Hajime Abe, Motohiro Akazome
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 78 Issue: 6 Pages: 2397-2404

    • DOI

      10.1021/jo302531g

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Utilization of Carboxylated 1,3-Indandione as an Electron Acceptor in Dye-Sensitized Solar Cells2012

    • Author(s)
      Shoji Matsumoto, Tatsuro Aoki, Tasutaka Suzuki, Motohiro Akazome, Atsushi Betto, Yasumasa Suda
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 85 Issue: 12 Pages: 1329-1331

    • DOI

      10.1246/bcsj.20120208

    • NAID

      130004153018

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Iterative Extension of Thiophene Ring Leading to Head-to-tail-type Oligothiophenes via Stepwise CH Arylation and Halogen Exchange Sequence2010

    • Author(s)
      Shunsuke Tanba, Atsushi Sugie, Naoyuki Masuda, Daiki Monguchi, Nagatoshi Koumura, Kohjiro Hara, Atsunori Mori
    • Journal Title

      Heterocycles

      Volume: 82 (1) Issue: 1 Pages: 505-529

    • DOI

      10.3987/com-13-s(s)12

    • NAID

      120006220730

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 2,2'-ビイミダゾール誘導体からの2種類の発光への置換基による影響2015

    • Author(s)
      松本祥治,松島佳紀,赤染元浩
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市習志野台)
    • Year and Date
      2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] アリールカルボン酸エステルをアクセプターとするドナー-π-アクセプター化合物のメカノクロミズム発現2015

    • Author(s)
      松本祥治,茂木 淳,加藤直希,赤染元浩
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市習志野台)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] ジアゾロ[1,2-a:2',1'-c]キノキサリン誘導体の固体発光と結晶構造2015

    • Author(s)
      松本祥治,赤染元浩
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市習志野台)
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] Novel Fluorophore Consisted of Diimidazo[1,2-a: 2',1'-c]quinoxalinium Salt2014

    • Author(s)
      Shoji Matsumoto, Hajime Abe, Tatsuya Kuroshio, Motohiro Akazome
    • Organizer
      The 9th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-9), The 5th New Phase International Conference on Cutting-Edge Organic Chemistry in Asia (NICCEOCA-5)
    • Place of Presentation
      Petaling Jaya (Malaysia)
    • Year and Date
      2014-12-03
    • Related Report
      2014 Annual Research Report
  • [Presentation] 分子内にアニオン性官能基を有するジイミダゾキノキサリニウム誘導体の合成と物性2014

    • Author(s)
      畠山博樹,黒潮達也,赤染元浩,松本祥治
    • Organizer
      第4回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀(東京都江東区船堀)
    • Year and Date
      2014-10-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] ヨウ素環化反応による環状チオアミジウム塩の生成と反応への利用

    • Author(s)
      松本祥治,高田大貴,赤染元浩
    • Organizer
      第16回ヨウ学会シンポジウム
    • Place of Presentation
      千葉
    • Related Report
      2013 Research-status Report
  • [Presentation] 2,2'-ビイミダゾールおよびベンゾ[d]イミダゾール誘導体の合成と光励起による共役系伸長

    • Author(s)
      松本祥治,趙 宇,赤染元浩
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      岐阜
    • Related Report
      2013 Research-status Report
  • [Presentation] トリアゾピロロキノキサリン誘導体の合成と光学特性

    • Author(s)
      松本祥治,岩本直樹,赤染元浩
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      岐阜
    • Related Report
      2013 Research-status Report
  • [Presentation] Syntheses and Physical Properties of Benzoic Acid Derivatives Bearing an Electron-accepting Group at the Meta Position for Dye-sensitized Solar Cells

    • Author(s)
      Jun Moteki, Motohiro Akazome, Shoji Matsumoto
    • Organizer
      3rd Junior International Conference on Cutting-Edge Organic Chemistry in Asia (Asian Core Program)
    • Place of Presentation
      千葉
    • Related Report
      2013 Research-status Report
  • [Presentation] ジイミダゾ[1,2-a:2',1'-c]キノキサリニウム化合物の構造と光学特性

    • Author(s)
      松本祥治,安部 元,赤染元浩
    • Organizer
      第7回有機π電子系シンポジウム
    • Place of Presentation
      高崎
    • Related Report
      2013 Research-status Report
  • [Presentation] 1,1',5,5'-テトラアリール-2,2'-ビイミダゾール誘導体の合成と光学特性

    • Author(s)
      松本祥治,野呂大樹,赤染元浩
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] 分子内にスルホナートを有するジイミダゾ[1,2-a:2',1'-c]キノキサリニウム塩の合成と物性

    • Author(s)
      松本祥治,黒潮達也,岩本直樹,赤染元浩
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Related Report
      2013 Research-status Report
  • [Presentation] Optical Properties of Diimidazo[1,2-a:2',1'-c]quinoxalines: Relation to the Structural Modification

    • Author(s)
      Shoji Matsumoto, Erdenebolore Batmunkh, Motohiro Akazome
    • Organizer
      The Twelfth International Kyoto Conference on New Aspect of Organic Chemsitry (IKCOC-12)
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Presentation] 1,3-インダンジオン誘導体のヒドラゾン化による吸収波長の長波長化

    • Author(s)
      松本祥治,青木達郎,赤染元浩
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report
  • [Presentation] ジイミダゾ[1,2-a:2',1'-c]キノキサリニウム塩の分子内蛍光消光現象の機構解明

    • Author(s)
      松本祥治,安部 元,赤染元浩
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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