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Controlling solid state photoluminescent properties of bipyrrole derivatives

Research Project

Project/Area Number 15K17848
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Research InstitutionKitakyushu National College of Technology

Principal Investigator

Okawara Toru  北九州工業高等専門学校, 生産デザイン工学科, 講師 (50632650)

Research Collaborator TAKEHARA Kenji  北九州工業高等専門学校, 生産デザイン工学科・物質化学コース, 教授 (50249877)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2017: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords蛍光 / 単結晶X線構造解析 / 複素環化合物 / ビピロール / 長波長シフト / 赤色蛍光 / 固体蛍光 / アルドール縮合 / アルキル基 / 結晶構造解析 / 計算化学 / 分子内水素結合 / 分子間相互作用 / エステル結合 / ビニル基
Outline of Final Research Achievements

Luminescent materials have been widely investigated for both industrial and biochemical applications. Based on the background, we have been focusing on developing novel luminescent bipyrroles. Recently we demonstrated that the solid state emission can be shifted between 400 and 430 nm by changing crystal structure. However, when we started the research, only blue emission of bipyrrole derivatives have been achieved. In 2016, we successfully synthesized the first yellow luminescent bipyrroles via an aldol condensation. π-extension with barbituric acid derivatives resulted in the highest bathochromic shift of the fluorescence wavelength with high quantum yield. Furthermore, using the same approach, red luminescent bipyrroles have also been reported in 2017. The density functional theory calculations revealed that electron-donating groups at the bipyrrole and electron-withdrawing groups at the vinyl terminal are essential to achieve the red fluorescence.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (13 results)

All 2018 2017 2016 2015 Other

All Int'l Joint Research (1 results) Journal Article (4 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 4 results,  Open Access: 2 results,  Acknowledgement Compliant: 3 results) Presentation (6 results) (of which Int'l Joint Research: 2 results) Remarks (2 results)

  • [Int'l Joint Research] ニューヨーク市立大学クイーンズ校(米国)

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Synthesis, crystal structure, and photoluminescent properties of 3,3’,4,4’-tetraethyl-5,5’-divinyl-2,2’-bipyrroles derivatives2017

    • Author(s)
      T. Okawara , R. Kawano, H. Morita, A. Finkelstein, R.Toyofuku, K. Matsumoto, K. Takehara, T. Nagamura, S. Iwasa, S. Kumar
    • Journal Title

      Molecules

      Volume: 22 Issue: 11 Pages: 1816-1816

    • DOI

      10.3390/molecules22111816

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis, Structure, and Spectroscopy of Green to Yellow Fluorescent Divinylbipyrroles2016

    • Author(s)
      Reo Kawano, Tamami Kato, Ryu Fukuda, Toru Okawara, Kenji Takehara, Toshihiko Nagamura
    • Journal Title

      ChemistrySelect

      Volume: 1 Issue: 14 Pages: 4144-4151

    • DOI

      10.1002/slct.201600843

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Conformational Change in Molecular Assembly of Nickel(II) Tetra(n-propyl)porphycene Triggered by Potential Manipulation2016

    • Author(s)
      Soichiro Yoshimoto, Teppei Kawamoto, Toru Okawara, Yoshio Hisaeda, and Masaaki Abe
    • Journal Title

      Langmuir

      Volume: 32 Issue: 51 Pages: 13635-13639

    • DOI

      10.1021/acs.langmuir.6b03782

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Crystal Structure of Bis(acetone-<i>&kappa;</i><i>O</i>)-1,4,8,11-tetraazacyclotetradecane Copper(II) Ditetraphenylborate Acetone Disolvate2015

    • Author(s)
      Chihiro Matsui, Toru Okawara, Toshihiko Nagamura, Kenji Takehara
    • Journal Title

      X-ray Structure Analysis Online

      Volume: 31 Issue: 0 Pages: 53-54

    • DOI

      10.2116/xraystruct.31.53

    • NAID

      130005105085

    • ISSN
      1883-3578
    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] Synthesis and photoluminescent properties of bipyrroles2018

    • Author(s)
      Kiko Kunitake, Toru Okawara, Kenji Takehara, Toshihiko Nagamura
    • Organizer
      平成29年度第5ブロック高専国際シンポジウムInternational Symposium on Innovative Engineering 2018
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Divinylbipyrrole: Influences of Alkyl Groups on Solubility and Photophysical Properties2017

    • Author(s)
      大川原 徹、河野 玲緒、豊福 連二郎、松本 佳奈子、山本竜太郎、竹原 健司
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2017-03-18
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis of Bipyrrole Derivatives: Red Luminescent Organic Solid2017

    • Author(s)
      Toru Okawara, Kiko Kunitake, Kenji Takehara, Toshihiko Nagamura
    • Organizer
      BIT’s 7th Annual World Congress of Nano Science &Technology (Nano S&T-2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 高効率赤色発光ビピロールの合成と発光挙動2016

    • Author(s)
      大川原 徹、河野 玲緒、豊福 連二郎、松本 佳奈子、竹原 健司
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場
    • Year and Date
      2016-09-02
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis, Crystal Structure and Emission Properties of Bipyrroles Having Extended Conjugation Systems2016

    • Author(s)
      大川原徹、石濱航平、河野玲緒、加藤珠実、福田竜、竹原健司
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学、京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 電子不足二重結合を側鎖に有するビピロールの合成とその光物性2016

    • Author(s)
      河野玲緒、加藤珠実、福田竜、竹原健司、大川原徹
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学、京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Remarks] 大川原研究室トップページ

    • URL

      http://c-chem.kct.ac.jp/okawara/okawara_profile.htm

    • Related Report
      2017 Annual Research Report
  • [Remarks] ChemistrySelect誌の表紙に採択されました

    • URL

      https://www.kct.ac.jp/news/h28/h281101-01.html

    • Related Report
      2017 Annual Research Report

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Published: 2015-04-16   Modified: 2022-06-07  

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