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Rational molecular design toward creation of circularly polarized luminescent organic materials

Research Project

Project/Area Number 18K19081
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 33:Organic chemistry and related fields
Research InstitutionKyushu University

Principal Investigator

Shimizu Soji  九州大学, 工学研究院, 准教授 (70431492)

Project Period (FY) 2018-06-29 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥6,240,000 (Direct Cost: ¥4,800,000、Indirect Cost: ¥1,440,000)
Fiscal Year 2019: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Fiscal Year 2018: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Keywords円偏光発光 / キラリティ / 有機環状分子 / ジケトピロロピロール / BODIPY
Outline of Final Research Achievements

In this research project, a cyclic arrangement of chromophore molecules is proposed as a rational molecular design toward prominent circular polarized luminescent organic molecules. In this molecular design, small anisotropy factor (g value) of circular polarized luminescence of organic chromophores due to their inherently large transition electric dipole moments can be improved by canceling transition electric dipole moments along the circumferential direction. On the basis of this molecular design, cyclic oligomers of diketopyrrolopyrrole were synthesized and isolated using size exclusion chromatography. Due to decomposition in chiral columns, optical resolution has not been successful yet. The high theoretical g value based on the TDDFT calculations indicated potential of this molecular design toward creation of circularly polarized organic materials.

Academic Significance and Societal Importance of the Research Achievements

円偏光発光特性を示す有機色素分子は、3次元ディスプレイへの応用など、次世代の光情報技術を担う分子材料として注目されている一方で、優れた円偏光発光特性を示す分子構造についての知見はほとんど示されていない。本研究では円偏光発光の理論式に基づき、色素分子を環状に配列することを提案した。最終的な目的分子の単離には安定性の問題から達成できてはいないが、合成と理論計算の両方から、分子構造と円偏光発光特性の相関について解明し、本研究で提案した分子設計の有用性を示すことができた。

Report

(3 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • Research Products

    (25 results)

All 2020 2019 2018 Other

All Int'l Joint Research (1 results) Journal Article (6 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 6 results) Presentation (18 results) (of which Int'l Joint Research: 6 results)

  • [Int'l Joint Research] Yonsei University(韓国)

    • Related Report
      2019 Annual Research Report
  • [Journal Article] Rational design of pyrrolopyrrole-aza-BODIPY- based acceptor-donor-acceptor triads for organic photovoltaics application2020

    • Author(s)
      Ru Feng、Narumi Sato、Takuma Yasuda、Hiroyuki Furuta、Soji Shimizu
    • Journal Title

      Chemical Communications

      Volume: 56 Issue: 20 Pages: 2975-2978

    • DOI

      10.1039/d0cc00398k

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] aza-BODIPY synthesis towards vis/NIR functional chromophores based on a Schiff base forming reaction protocol using lactams and heteroaromatic amines2019

    • Author(s)
      Shimizu Soji
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 60 Pages: 8722-8743

    • DOI

      10.1039/c9cc03365c

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pyrrolopyrrole Aza-BODIPY Analogues as Near‐Infrared Chromophores and Fluorophores: Red‐Shift Effects of Substituents on Absorption and Emission Spectra2019

    • Author(s)
      Kage Yuto、Karasaki Hideaki、Mori Shigeki、Furuta Hiroyuki、Shimizu Soji
    • Journal Title

      ChemPlusChem

      Volume: 84 Issue: 11 Pages: 1648-1652

    • DOI

      10.1002/cplu.201900226

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] N-Confused Porphyrin-aza-Dipyrrin Chimera: A Versatile Metal Coordination Ligand Using its Unique NH Tautomerism2019

    • Author(s)
      Fukuda Masaya、Mori Shigeki、Furuta Hiroyuki、Shimizu Soji
    • Journal Title

      Chemistry - An Asian Journal

      Volume: 14 Issue: 10 Pages: 1697-1702

    • DOI

      10.1002/asia.201801750

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] 1,3-Dithiole-2-one-Fused Subphthalocyanine and Subporphyrazine: Synthesis and Properties Arising from the 1,3-Dithiole-2-one Units2019

    • Author(s)
      Wang Yemei、Uchihara Koya、Mori Shigeki、Furuta Hiroyuki、Shimizu Soji
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 9 Pages: 3103-3107

    • DOI

      10.1021/acs.orglett.9b00752

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rational Synthesis of Antiaromatic 5,15-Dioxaporphyrin and Oxidation into β,β-Linked Dimers2018

    • Author(s)
      Nishiyama Akihide、Fukuda Masaya、Mori Shigeki、Furukawa Ko、Fliegl Heike、Furuta Hiroyuki、Shimizu Soji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 31 Pages: 9728-9733

    • DOI

      10.1002/anie.201804648

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Pyrrolopyrrole aza-BODIPYs Bearing Electron-Donating Amino Substituents as NIR Fluorophore2020

    • Author(s)
      Yuto Kage, Hideaki Karasaki, Shigeki Mori, Seongsoo Kang, Dongho Kim, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis of Pyrrolopyrrole-aza-BODIPY-based Polymers for Organic Solar Cells2019

    • Author(s)
      Ru Feng, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      The 24th Joint Seminar of the Kyushu Branch of the CSJ and the Busan Branch of the KCS
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Creation of Diketopyrrolopyrrole-based Luminescent Molecules2019

    • Author(s)
      Misaki Kamioka, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      The 24th Joint Seminar of the Kyushu Branch of the CSJ and the Busan Branch of the KCS
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Substitutent Effect and Unique Dual Emission of Pyrrolopyrrole aza-BODIPY2019

    • Author(s)
      Yuto Kage, Shigeki Mori, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Pyrrolopyrrole-aza-BODIPY-based Polymer for Organic Photovoltaic Application2019

    • Author(s)
      Ru Feng, Mayuka Nomura, Akinori Saeki, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of aza-BODIPY Analogues from a Schiff base Forming Reaction and Their Intriguing Optical and Electrochemical Properties2019

    • Author(s)
      Soji Shimizu
    • Organizer
      The 12th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Optical Properties of Circular Diketopyrrolopyrrole2019

    • Author(s)
      Misaki Kamioka, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      1st International Conference on Noncovalenet Interactions (ICNI 2019)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 円偏光発光を指向した環状ジケトピロロピロールの合成と光学特性2019

    • Author(s)
      神岡美咲、古田弘幸、清水宗治
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ピロロピロール-アザ-BODIPYの近赤外発光特性に及ぼす置換基効果2019

    • Author(s)
      鹿毛悠冬、唐崎秀朗、森重樹、古田弘幸、清水宗治
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis of Pyrrolopyrrole-aza-BODIPY-based Triads and Their OPV Application2019

    • Author(s)
      Ru Feng, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 円偏光発光を指向した環状ジケトピロロピロールの合成と光学特性2019

    • Author(s)
      神岡美咲、古田弘幸、清水宗治
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ピロロピロール-アザ-BODIPYの近赤外発光特性と置換基効果2019

    • Author(s)
      鹿毛悠冬、古田弘幸、清水宗治
    • Organizer
      第9回CSJ化学フェスタ
    • Related Report
      2019 Annual Research Report
  • [Presentation] ピロロピロール-アザ-BODIPY二量化による吸収帯の特異な広帯域化2018

    • Author(s)
      鹿毛悠冬、古田弘幸、清水宗治
    • Organizer
      第28回万有福岡シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] ジケトピロロピロール白金錯体の合成と発光特性2018

    • Author(s)
      神岡美咲、古田弘幸、清水宗治
    • Organizer
      第55回化学関連支部合同九州大会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis of Pyrrolopyrrole-aza-BODIPY-based Polymer for Organic Photovoltaic Application2018

    • Author(s)
      Ru Feng, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      第55回化学関連支部合同九州大会
    • Related Report
      2018 Research-status Report
  • [Presentation] ジケトピロロピロールを基盤とした発光性分子の創出2018

    • Author(s)
      神岡美咲、古田弘幸、清水宗治
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis of Pyrrolopyrrole-aza-BODIPY-based Polymer for Organic Photovoltaic Application2018

    • Author(s)
      Ru Feng, Eman Al-Naamani, Akinori Saeki, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Creation of Diketopyrrolopyrrole-based Luminescence Molecules2018

    • Author(s)
      Misaki Kamioka, Hiroyuki Furuta, Soji Shimizu
    • Organizer
      The 13th International Symposium on Organic Reactions
    • Related Report
      2018 Research-status Report

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Published: 2018-07-25   Modified: 2021-02-19  

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