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New strategies for the functional fluorescent dyes

Research Project

Project/Area Number 19H03355
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionKyoto Prefectural University

Principal Investigator

Tsubaki Kazunori  京都府立大学, 生命環境科学研究科, 教授 (50303897)

Co-Investigator(Kenkyū-buntansha) 今吉 亜由美  京都府立大学, 生命環境科学研究科, 助教 (20786462)
Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2021: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2020: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Keywords蛍光色素 / 円偏光発光 / オリゴナフタレン / V字型蛍光色素 / インジゴ / CPL / 励起状態 / 光異性化 / 光酸 / 新規蛍光色素 / CPL光学材料 / 基底状態 / 呈色色素
Outline of Research at the Start

呈色/蛍光色素の研究は、実用を強く志向した開発研究が多数を占めるが、今回、我々は①生体を指向した新たな蛍光色素骨格の開発、②蛍光色素の精密配置に基づいた円偏光発光 (CPL) 材料の開発、③色素を用いた新たな有機化学の創出の三点を目標とし、呈色/蛍光色素研究を基盤とした新たな次元の化学へと昇華する。

Outline of Final Research Achievements

In this study, we focused on three points: (1) development of new fluorescent dyes for living organisms, (2) development of circularly polarized luminescent (CPL) materials based on precise arrangement of fluorescent dyes, and (3) creation of new organic chemistry using dyes. As a result, we developed (1) V-shaped fluorescent dyes that strongly glows in cells, (2) CPL materials based on a binaphthol skeleton with many phenylacetylenes, and (3) elucidated the mechanism of isomerization using chiral cross-linked indigos.

Academic Significance and Societal Importance of the Research Achievements

V字型の蛍光色素においては、導入した置換基が分子のLUMOのレベルに大きな影響を与え、幅広い吸収波長、発光波長をもつ化合物の合成が可能である。また導入した置換基のハメット定数から吸収波長、発光波長が予測可能であった。ビナフトールを基本骨格としたCPL活性分子の研究では、二面角とπ系拡張の方向について精査し、より活性の高い分子創出の基礎データを得た。架橋インジゴの研究では、シス-トランスの異性化に加え、キラリティーを導入することで高次の応答分子のデザインを可能にした。

Report

(4 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • Research Products

    (17 results)

All 2022 2021 2020 2019

All Journal Article (5 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 5 results) Presentation (12 results) (of which Int'l Joint Research: 1 results,  Invited: 3 results)

  • [Journal Article] Synthesis and Properties of V-Shaped Xanthene Dyes with Tunable and Predictable Absorption and Emission Wavelengths2022

    • Author(s)
      Yamagami Akari、Kiyotaki Kotaro、Wakabayashi Sae、Egami Naoki、Kawano Kenichi、Futaki Shiroh、Imayoshi Ayumi、Tsubaki Kazunori
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 87 Issue: 5 Pages: 2336-2344

    • DOI

      10.1021/acs.joc.1c02139

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of Bridged Indigos and Their Thermoisomerization and Photoisomerization Behaviors2021

    • Author(s)
      Kanda Junya、Egami Naoki、Sasamori Takahiro、Imayoshi Ayumi、Hosoya Takashi、Tsubaki Kazunori
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 86 Issue: 24 Pages: 17620-17628

    • DOI

      10.1021/acs.joc.1c01726

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] AN ALTERNATIVE APPROACH TO THE DEVELOPMENT OF NEAR-INFRARED FLUORESCENT DYES BASED ON FLUORESCEIN2021

    • Author(s)
      Akane Katori, Akari Yamagami, Sae Wakabayashi, Kouji Kuramochi, Ayumi Imayoshi, Kazunori Tsubaki
    • Journal Title

      HETEROCYCLES

      Volume: 103

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Sign control of circularly polarized luminescence by substituent domino effect in binaphthyl-Eu(III) organometallic luminophores2020

    • Author(s)
      Kaji Daiki、Kitayama Masumi、Hara Nobuyuki、Yoshida Keishiro、Wakabayashi Sae、Shizuma Motohiro、Tsubaki Kazunori、Imai Yoshitane
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 397 Pages: 112490-112490

    • DOI

      10.1016/j.jphotochem.2020.112490

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Optical Properties of L-Shaped Dinaphthofluoresceins with Two Peripheral Hydroxy Groups2020

    • Author(s)
      Tsubaki Kazunori、Yamashita Hikari、Minari Chihiro、Azuma Eriko、Kuramochi Kouji、Imayoshi Ayumi
    • Journal Title

      HETEROCYCLES

      Volume: 101 Issue: 2 Pages: 536-536

    • DOI

      10.3987/com-19-s(f)44

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Presentation] 軸性不斉を有するビアリール類の光学特性の解明2021

    • Author(s)
      ○野田 駿介・藤尾 晋哉・長屋 勇輝・吉田 圭史朗・木元 隆裕・今吉 亜由美・今井 喜胤・椿 一典
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ビナフチルの二面角とCPL特性の関連性の研究2021

    • Author(s)
      ○藤尾晋哉・野田 駿介・長屋 勇輝・酒井 美里・宮崎 貴俊・木元 隆裕・岡田 啓汰・今吉 亜由美・今井 喜胤・椿 一典
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 連結ナフタレンを用いた光学活性分子の合成と機能2021

    • Author(s)
      椿 一典
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] ヘテロ原子を基本骨格に有する新奇 CPP誘導体軍の合成と機能評価2021

    • Author(s)
      若林 沙依、正田 孝明、今吉 亜由美、椿一典
    • Organizer
      日本薬学会141年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Synthesis and evaluation of binaphthol-based functional molecules2020

    • Author(s)
      Kazunori Tsubaki
    • Organizer
      The 5th International Symposium of Quantum Beam Science
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] CPL 特性と立体構造の関連性の解明2020

    • Author(s)
      藤尾 晋哉、長屋 勇輝、木元 隆裕、今吉 亜由美、今井 喜胤、椿 一典
    • Organizer
      第70回 日本薬学会関西支部大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 光酸を鍵とした新規酸触媒反応の開発2020

    • Author(s)
      綿野 真実、平田 瞭、今吉 亜由美、椿 一典
    • Organizer
      第49回 複素環化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] CPL Properties of Dye-connected Oligonaphthalenes2019

    • Author(s)
      Kazunori Tsubaki
    • Organizer
      International Symposium on Circularly Polarized Luminescence and the Related Phenomena
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Functionalization of Oligonaphthalenes by Adding Appropriate Component2019

    • Author(s)
      Masumi Kitayama, Keishiro Yoshida, Ayumi Imayoshi and Kazunori Tsubaki
    • Organizer
      International Symposium on Circularly Polarized Luminescence and the Related Phenomena
    • Related Report
      2019 Annual Research Report
  • [Presentation] 新奇なV字型キサンテン色素の合成2019

    • Author(s)
      岡﨑直樹、鳥居彩芽、山上紅里、今吉亜由美、椿一典
    • Organizer
      第13回 有機π電子系シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] オリゴナフタレンを骨格とした2種のらせん状分子の合成と物性評価2019

    • Author(s)
      北山真珠美,吉田圭史朗,今吉亜由美,椿一典
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] 光酸を利用した新規反応の開発2019

    • Author(s)
      綿野真実,平田瞭,今吉亜由美,椿一典
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Annual Research Report

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Published: 2019-04-18   Modified: 2023-01-30  

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