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Development of novel synthetic methodology for circularly polarized electroluminescent molecules by hierarchical supramolecular formation

Research Project

Project/Area Number 18K05262
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 35030:Organic functional materials-related
Research InstitutionKyoto Institute of Technology

Principal Investigator

Yamada Shigeyuki  京都工芸繊維大学, 分子化学系, 准教授 (10612252)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥520,000 (Direct Cost: ¥400,000、Indirect Cost: ¥120,000)
Fiscal Year 2019: ¥520,000 (Direct Cost: ¥400,000、Indirect Cost: ¥120,000)
Fiscal Year 2018: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Keywordsフッ素 / 液晶 / 発光 / 液晶性発光 / 凝集構造 / キラル / 非共有結合性相互作用 / 非共有結合 / 円偏光発光 / 電荷輸送
Outline of Final Research Achievements

The purpose of this research project is to develop and establish a method for synthesizing electric field circularly polarized light emitting molecules with the key to controlling the aggregated structure by changing the liquid crystal phase by designing molecules based on the disk-shaped supramolecules of chiral rod-shaped liquid crystal molecules. Through this study, this researcher was able to develop a chiral liquid crystal luminescent molecule that causes a phase transition by heating and cooling and forms a spiral aggregate structure in the liquid crystal state. this researcher also developed a liquid crystal luminescent molecule with high luminous efficiency by forming a hydrogen-bonding dimer by introducing a carboxy group. Furthermore, we investigated the development of a fluorine-containing tolane-carboxylic acid having a chiral side chain, but did not develop chiral liquid crystallinity even though it had relatively excellent optical properties.

Academic Significance and Societal Importance of the Research Achievements

本研究課題では,らせん状凝集構造とπ共役構造の積層構造を同時かつ精密に構築するために, 液晶分子に注目した。本研究は,棒状分子形状を有するキラル液晶性の低分子化合物に非共有結合性相互作用を利用した階層的な超分子形成により自発的なカラム状凝集構造を誘起し,効率的な電界円偏光発光分子の合成法となる。本研究課題では,二種の有機分子を混ぜるだけで水素結合による超分子形成を実現でき,合成化学的に簡便かつ効率的な合成法となる。本研究で開拓・確立した合成アプローチは3Dディスプレイ材料の開発を加速させ,円偏光デバイスやわが国の科学技術の発展に大きく貢献できる。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (43 results)

All 2021 2020 2019 2018

All Journal Article (11 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 11 results,  Open Access: 6 results) Presentation (32 results) (of which Int'l Joint Research: 10 results,  Invited: 1 results)

  • [Journal Article] Effect of Fluoroalkyl-Substituent in Bistolane-Based Photoluminescent Liquid Crystals on Their Physical Behavior2021

    • Author(s)
      Yamada Shigeyuki, Wang Yizhou, Morita Masato, Zhang Qingzhi, O'Hagan David, Nagata Masakazu, Agou Tomohiro, Fukumoto Hiroki, Kubota Toshio, Hara Mitsuo, Konno Tsutomu
    • Journal Title

      Crystals

      Volume: 11 Issue: 4 Pages: 450-450

    • DOI

      10.3390/cryst11040450

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Fluorine-induced emission enhancement of tolanes via formation of tight molecular aggregates2020

    • Author(s)
      Morita Masato、Yamada Shigeyuki、Konno Tsutomu
    • Journal Title

      New Journal of Chemistry

      Volume: 44 Issue: 17 Pages: 6704-6708

    • DOI

      10.1039/d0nj01268h

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Photoluminescence Liquid Crystals Based on Flexible Chain-Bearing Pentafluorinated Bistolanes2020

    • Author(s)
      Yamada Shigeyuki、Sato Masaya、Konno Tsutomu
    • Journal Title

      Crystals

      Volume: 10 Issue: 7 Pages: 603-603

    • DOI

      10.3390/cryst10070603

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Fluorinated Tolane Dyads with Alkylene Linkage: Synthesis and Evaluation of Photophysical Characteristics2020

    • Author(s)
      Yamada Shigeyuki、Uto Eiji、Agou Tomohiro、Kubota Toshio、Konno Tsutomu
    • Journal Title

      Crystals

      Volume: 10 Issue: 8 Pages: 711-711

    • DOI

      10.3390/cryst10080711

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Development of light-emitting liquid-crystalline polymers with a pentafluorinated bistolane-based luminophore2020

    • Author(s)
      Yamada Shigeyuki、Mitsuda Akira、Adachi Kaoru、Hara Mitsuo、Konno Tsutomu
    • Journal Title

      New Journal of Chemistry

      Volume: 44 Issue: 15 Pages: 5684-5691

    • DOI

      10.1039/d0nj00659a

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] 1,2-Disubstituted 3,3,4,4,5,5-hexafluorocyclopentens as bent light-emitting π-conjugated luminophores2020

    • Author(s)
      Shigeyuki Yamada, Akito Nishizawa, Tomohiro Agou, Toshio Kubota, Tsutomu Konno
    • Journal Title

      Europen Journal of Organic Chemistry

      Volume: 2020 Issue: 7 Pages: 870-877

    • DOI

      10.1002/ejoc.201901794

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and characterization of bent fluorine-containing donor-π-acceptor molecules as intense luminophores with large Stokes shifts2019

    • Author(s)
      Shigeyuki Yamada, Akito Nishizawa, Masato Morita, Takuya Hosokai, Yusuke Okabayashi, Tomohiro Agou, Takaaki Hosoya, Toshio Kubota, Tsutomu Konno
    • Journal Title

      Organic and Biomolecular Chemistry

      Volume: 17 Issue: 28 Pages: 6911-6919

    • DOI

      10.1039/c9ob01300h

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Luminescence Tuning of Fluorinated Bistolanes via Electronic or Aggregated-Structure Control2019

    • Author(s)
      Masato Morita, Shigeyuki Yamada, Tomohiro Agou, Toshio Kubota, Tsutomu Konno
    • Journal Title

      Applied Sciences

      Volume: 9 Issue: 9 Pages: 1905-1905

    • DOI

      10.3390/app9091905

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] 2-Chloroalkoxy-Substituted Pentafluorinated Bistolanes as Novel Light-Emitting Liquid Crystals2019

    • Author(s)
      Shigeyuki Yamada, Kazuya Miyano, Tomohiro Agou, Toshio Kubota, Tsutomu Konno
    • Journal Title

      Crystals

      Volume: 印刷中

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Novel V- and Y‐Shaped Light-Emitting Liquid Crystals with Pentafluorinated Bistolane-Based Luminophores2019

    • Author(s)
      Shigeyuki Yamada, Tsuyoshi Tanaka, Takahiro Ichikawa, Tsutomu Konno
    • Journal Title

      ACS Omega

      Volume: 4 Issue: 2 Pages: 3922-3932

    • DOI

      10.1021/acsomega.8b03543

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Thermoresponsive luminescence properties of polyfluorinated bistolane-type light-emitting liquid crystals2018

    • Author(s)
      Shigeyuki Yamada, Masato Morita, Tomohiro Agou, Toshio Kubota, Takahiro Ichikawa, Tsutomu Konno
    • Journal Title

      Org. Biomol. Chem.

      Volume: 16 Issue: 31 Pages: 5609-5617

    • DOI

      10.1039/c8ob01497c

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] 新規なドナー・アクセプター型フッ素化トラン誘導体の合成と各種物性評価2020

    • Author(s)
      山田重之,片岡光樹,今野 勉
    • Organizer
      第43回フッ素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 種々の連結鎖を有する多フッ素化トランダイアドの合成と光学特性評価2020

    • Author(s)
      山田重之,宇都慧司,今野 勉
    • Organizer
      第43回フッ素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ヘキサフルオロシクロペンテンを屈曲コアとした非対称型発光分子の新規合成とその光学特性評価2020

    • Author(s)
      山田重之,西澤彰人,今野 勉
    • Organizer
      第43回フッ素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 含フッ素ビストラン型発光性液晶分子の開発2020

    • Author(s)
      山田重之,今野 勉
    • Organizer
      2020年日本液晶学会 オンライン研究発表会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 新規な含フッ素トランダイマーの合成と物性評価2020

    • Author(s)
      山田重之,宇都慧司,今野 勉
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] テトラフルオロ安息香酸誘導体を部分構造とした新規なフッ素化トランの合成と物性評価2020

    • Author(s)
      山田重之,片岡光樹,今野 勉
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 新規な含フッ素トランダイマーの合成と物性評価2020

    • Author(s)
      山田重之,宇都慧司,今野 勉
    • Organizer
      日本化学会第100春季年会 (1C3-56)
    • Related Report
      2019 Research-status Report
  • [Presentation] テトラフルオロ安息香酸誘導体を部分構造とした新規なフッ素化トランの合成と物性評価2019

    • Author(s)
      山田重之,片岡光樹,今野 勉
    • Organizer
      日本化学会第100春季年会 (1C3-55)
    • Related Report
      2019 Research-status Report
  • [Presentation] 含フッ素トランダイマーの置換様式が物性に及ぼす影響2019

    • Author(s)
      山田重之,田中剛志,今野 勉
    • Organizer
      第42回フッ素化学討論会 (P61)
    • Related Report
      2019 Research-status Report
  • [Presentation] 多フッ素化ビストラン側鎖をもつ発光性液晶高分子の物性評価2019

    • Author(s)
      山田重之,光田 晶,今野 勉
    • Organizer
      第42回フッ素化学討論会 (P60)
    • Related Report
      2019 Research-status Report
  • [Presentation] ヘキサフルオロシクロペンテンを屈曲コアとしたエンジイン型発光分子の光学特性評価2019

    • Author(s)
      山田重之,西澤彰人,今野 勉
    • Organizer
      第42回フッ素化学討論会 (P59)
    • Related Report
      2019 Research-status Report
  • [Presentation] ヘキサフルオロシクロペンテンを屈曲コアとした発光分子の光学特性評価2019

    • Author(s)
      山田重之,西澤彰人,今野 勉
    • Organizer
      第9回フッ素化学若手の会 (P-51)
    • Related Report
      2019 Research-status Report
  • [Presentation] 含フッ素ビストラン構造を導入した側鎖型発光性液晶ポリマーの新規合成2019

    • Author(s)
      山田重之,光田 晶,今野 勉
    • Organizer
      第9回フッ素化学若手の会 (P-50)
    • Related Report
      2019 Research-status Report
  • [Presentation] 含フッ素ビストラン誘導体の液晶相転移を利用した発光特性変化2019

    • Author(s)
      盛田雅人,山田重之,今野 勉
    • Organizer
      第9回フッ素化学若手の会 (P-49)
    • Related Report
      2019 Research-status Report
  • [Presentation] 分岐構造を有する多フッ素化液晶性発光分子の物性評価2019

    • Author(s)
      山田重之,佐藤公哉,今野 勉
    • Organizer
      第9回フッ素化学若手の会 (P-39)
    • Related Report
      2019 Research-status Report
  • [Presentation] Novel Light-Emitting Liquid Crystals with a Chiral Flexible Unit2019

    • Author(s)
      Shigeyuki Yamada, Kazuya Miyano, Masaya Sato, Tsutomu Konno
    • Organizer
      19th European Symposium on Fluorine Chemistry (M-C23)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Broad PL color-shift of bent-shaped π-conjugated luminophores with fluorinated tolanes2019

    • Author(s)
      Shigeyuki Yamada, Akito Nishizawa, Tsutomu Konno
    • Organizer
      19th European Symposium on Fluorine Chemistry (M-P11)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Light-Emittigng Liquid-Crystalline Polymers Bearing Luminous Pollyfluorinated Bistolane Side Chain2019

    • Author(s)
      Shigeyuki Yamada, Akira Mitsuda, Tsutomu Konno
    • Organizer
      International Conference on Fluorine Chemistry 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Novel Bistolane-based Light-Emitting Liquid Crystals with a Chiral Center2019

    • Author(s)
      Shigeyuki Yamada, Masaya Sato, Tsutomu Konno
    • Organizer
      International Conference on Fluorine Chemistry 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Hexafluorocyclopentene with Tolane Arms as Multi-color Luminophore with Large Stokes Shift2019

    • Author(s)
      Shigeyuki Yamada, Akito Nishizawa, Tsutomu Konno
    • Organizer
      International Conference on Fluorine Chemistry 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Phosphorescent Polyfluorinated Benzil Derivatives and Their Photophysical Properties2019

    • Author(s)
      Shigeyuki Yamada, Takuya Higashida, Takuya Hosokai, Akimi Mizoguchi, Yusuke Okabayashi, Tsutomu Konno
    • Organizer
      日本化学会第99春季年会 (2PB-054)
    • Related Report
      2019 Research-status Report
  • [Presentation] キラル側鎖を有する多フッ素化拡張π共役分子の合成とその液晶ならびに光学特性評価2019

    • Author(s)
      山田重之,佐藤公哉,今野 勉
    • Organizer
      日本化学会第99春季年会 (3H1-47)
    • Related Report
      2019 Research-status Report
  • [Presentation] ヘキサフルオロシクロペンテンを屈曲コアとした拡張π共役分子の新規合成とその高額特性評価2019

    • Author(s)
      山田重之,西澤彰人,今野 勉
    • Organizer
      日本化学会第99春季年会 (3H1-46)
    • Related Report
      2019 Research-status Report
  • [Presentation] キラル側鎖を有する多フッ素化拡張π共役分子の合成とその液晶ならびに光学特性評価2019

    • Author(s)
      山田重之*,○佐藤公哉,今野 勉
    • Organizer
      日本化学会第99春季年会 (3H1-47)
    • Related Report
      2018 Research-status Report
  • [Presentation] Stimulus-responsible Photoluminescence Behavior of Polyfluorinated Bistolane Derivatives2018

    • Author(s)
      Masato Morita, Shigeyuki Yamada*, Tsutomu Konno
    • Organizer
      22nd International Symposium on Fluorine Chemistry (P-43)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Photoluminescence Properties of Novel Polyfluorinated Bistolane Derivatives Containing a Chiral Flexible Chain2018

    • Author(s)
      Kazuya Miyano, Shigeyuki Yamada*, Tsutomu Konno
    • Organizer
      22nd International Symposium on Fluorine Chemistry (P-44)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Light-emitting Liquid Crystals with Reversible Luminescent Behavior via Thermal Phase Transition2018

    • Author(s)
      Shigeyuki Yamada*, Masato Morita, Kazuya Miyano, Tsutomu Konno
    • Organizer
      27th Internationl Liquid Crystal Conference (4-E-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 含フッ素ビストラン構造を分岐末端に導入した新規な発光性液晶分子の創製2018

    • Author(s)
      山田重之*, ○田中剛志, 今野 勉
    • Organizer
      2018日本液晶学会討論会 (PA-22)
    • Related Report
      2018 Research-status Report
  • [Presentation] ビストラン型熱応答性発光分子の合成及びその物性評価2018

    • Author(s)
      ○盛田雅人,山田重之*, 今野 勉
    • Organizer
      第8回CSJ化学フェスタ2018 (P1-034)
    • Related Report
      2018 Research-status Report
  • [Presentation] キラル側鎖を有するビストラン型発光性液晶分子の合成および物性評価2018

    • Author(s)
      ○宮野和也,山田重之*, 今野 勉
    • Organizer
      第8回CSJ化学フェスタ2018 (P1-035)
    • Related Report
      2018 Research-status Report
  • [Presentation] Thermally Responsible Photoluminescent Properties of Bistolane Derivatives2018

    • Author(s)
      Masato Morita, Shigeyuki Yamada,* Tsutomu Konno
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (PB(C)-80)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Luminescent Liquid Crystal Molecules by Changing Primary Structure2018

    • Author(s)
      Kazuya Miyano, Shigeyuki Yamada,* Tsutomu Konno
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (PB(C)-81)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research

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Published: 2018-04-23   Modified: 2022-01-27  

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