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Development of Fluorescent Sensors for Water and Their Functional Dye Material Characteristics

Research Project

Project/Area Number 19H02754
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 34030:Green sustainable chemistry and environmental chemistry-related
Research InstitutionHiroshima University

Principal Investigator

Ooyama Yousuke  広島大学, 先進理工系科学研究科(工), 教授 (60403581)

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: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2020: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2019: ¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Keywords蛍光性水センサー / 水 / 光誘起電子移動 / 分子内電荷移動 / 蛍光共鳴エネルギー移動 / 蛍光性水センサーフィルム / 蛍光性センサー
Outline of Research at the Start

本研究では、蛍光性色素の光誘起電子移動(PET)、蛍光共鳴エネルギー移動(FRET)および分子内電荷移動(ICT)特性を利用して試料中や表面の水分を検出・定量化かつ可視化(蛍光発光による画像化)できる蛍光性水センサーを創製し、PET, FRETおよび ICT特性に基づいた水分検出のメカニズムを解明することで、微量水分から高水分領域で使用できる水分検出・定量・可視化蛍光分析法の創成(JISやISOなどの国家・国際規格化)を目的とする。

Outline of Final Research Achievements

Development of fluorescence sensing methods for detection and quantification of water in samples has received considerable attention from the viewpoint of fundamental studies, and is eagerly anticipated in industry because of their potential applications to environmental and quality control monitoring systems. If we can develop organic fluorescent sensors for water, the fluorescence spectroscopic technique utilizing the fluorescent sensors allows the visualization as well as detection and quantification of water content in samples using a highly sensitive and quick flow analysis based on the changes in wavelength, intensity and lifetime of photoluminescence depending on the water content. In this work, we have developed fluorescent sensors for detection, quantification and visualization of water content in solvents, and polymer films doped with fluorescent sensors for water as one of the most promising and convenient functional materials for visualizing moisture and water droplets.

Academic Significance and Societal Importance of the Research Achievements

本研究で開発した蛍光性水センサーの学術的意義は、蛍光発光特性を利用した微量水分から高水分領域の水分検出法という新しい方法論(JISやISOなどの国家・国際規格化)を提供し、水分子を検出・定量・可視化するエポックメイキングな蛍光分析法(概念)を世界に先駆けて具現化するところにある。さらに、本研究の社会的意義は、有機溶媒、ガス、食品および工業製品中の水分検出剤としての用途の他、蛍光性水センサーをポリマー化あるいは分散(固定化)させたフィルム(基板)等を作製し、Society 5.0やSDGsに資する機能性色素材料群に発展(土木・建築・医療・医薬・衛生材料として社会実装)させるところにある。

Report

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

    (42 results)

All 2022 2021 2020 2019 Other

All Journal Article (18 results) (of which Peer Reviewed: 17 results,  Open Access: 11 results) Presentation (14 results) (of which Int'l Joint Research: 9 results,  Invited: 4 results) Book (6 results) Remarks (2 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Development of Fluorescent Sensors and Fluorescent Polymer Films for Detection and Visualization of Water2022

    • Author(s)
      大山陽介
    • Journal Title

      Journal of the Japan Society of Colour Material

      Volume: 95 Issue: 3 Pages: 53-66

    • DOI

      10.4011/shikizai.95.53

    • ISSN
      0010-180X, 1883-2199
    • Year and Date
      2022-03-20
    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Optical and Electrochemical Properties of Benzofuro[2,3-<i>c</i>]carbazoloquinol Fluorescent Dyes2021

    • Author(s)
      Yousuke Ooyama, Kazuki Ohira, Yusuke Kagawa, and Keiichi Imato
    • Journal Title

      Electrochemistry

      Volume: 89 Issue: 6 Pages: 562-566

    • DOI

      10.5796/electrochemistry.21-00082

    • NAID

      130008113604

    • ISSN
      1344-3542, 2186-2451
    • Year and Date
      2021-11-05
    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Polymer films doped with fluorescent sensor for moisture and water droplet based on photo-induced electron transfer2021

    • Author(s)
      Takuma Fumoto, Saori Miho, Yuta Mise, Keiichi Imato and Yousuke Ooyama
    • Journal Title

      RSC Advances

      Volume: 11 Issue: 28 Pages: 17046-17050

    • DOI

      10.1039/d1ra02673a

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis, optical and electrochemical properties of 4,4'-bibenzo[c]thiophene derivatives2021

    • Author(s)
      Kotaro Obayashi, Keiichi Imato, Satoshi Aoyama, Toshiaki Enoki, Seiji Akiyama, Mio Ishida, Seiji Suga, Koichi Mitsudo and Yousuke Ooyama
    • Journal Title

      RSC Advances

      Volume: 11 Issue: 31 Pages: 18870-18880

    • DOI

      10.1039/d1ra01189h

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Development of phenazine-2,3-diol-based photosensitizers: effect of formyl groups on singlet oxygen generation2021

    • Author(s)
      Kazuki Ohira, Keiichi Imato and Yousuke Ooyama
    • Journal Title

      Materials Chemistry Frontiers

      Volume: 5 Issue: 14 Pages: 5298-5304

    • DOI

      10.1039/d1qm00649e

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organohalogenochromism (OHC) of Dyes: D-π-A Pyrazinium Dye2021

    • Author(s)
      Taiki Higashino and Yousuke Ooyama
    • Journal Title

      Chemistry Letters

      Volume: 50 Issue: 8 Pages: 1530-1533

    • DOI

      10.1246/cl.210272

    • NAID

      130008072822

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, photophysical and electrochemical properties of 1,1′,3,3′-tetrasubstituted-4,4′-bibenzo[c]thiophene derivative with different substituents on the thiophene rings2021

    • Author(s)
      Kotaro Obayashi, Taiki Higashino, Keiichi Imato and Yousuke Ooyama
    • Journal Title

      New Journal of Chemistry

      Volume: 45 Issue: 30 Pages: 13258-13261

    • DOI

      10.1039/d1nj02498a

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of 4,4'-bibenzo[c]thiophene fluorophores with substituents on the thiophene rings2021

    • Author(s)
      Kotaro Obayashi, Saori Miho, Masataka Yasui, Keiichi Imato, Seiji Akiyama, Mio Ishida, and Yousuke Ooyama
    • Journal Title

      New Journal of Chemistry

      Volume: 45 Issue: 37 Pages: 17085-17094

    • DOI

      10.1039/d1nj03153h

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of highly sensitive fluorescent sensor and fluorescent sensor-doped polymer films for trace amounts of water based on photo-induced electron transfer2021

    • Author(s)
      Saori Miho, Takuma Fumoto, Yuta Mise, Keiichi Imaousukeo, Seiji Akiyama, Mio Ishida and Y. Ooyama
    • Journal Title

      Materials Advances

      Volume: 2 Issue: 23 Pages: 7662-7670

    • DOI

      10.1039/d1ma00881a

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] 飛沫を可視化する蛍光性フィルムの開発2021

    • Author(s)
      大山陽介
    • Journal Title

      ファインケミカル

      Volume: 50 Pages: 32-38

    • Related Report
      2021 Annual Research Report
  • [Journal Article] Fluorescence sensors for detection of water based on tetraphenylethene?anthracene possessing both solvatofluorochromic properties and aggregation-induced emission (AIE) characteristics2021

    • Author(s)
      Mise Yuta、Imato Keiichi、Ogi Takashi、Tsunoji Nao、Ooyama Yousuke
    • Journal Title

      New Journal of Chemistry

      Volume: 45 Issue: 9 Pages: 4164-4173

    • DOI

      10.1039/d1nj00186h

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Development of fluorescent sensors based on a combination of PET (photo-induced electron transfer) and FRET (Forster resonance energy transfer) for detection of water2020

    • Author(s)
      Jinbo Daisuke、Ohira Kazuki、Imato Keiichi、Ooyama Yousuke
    • Journal Title

      Materials Advances

      Volume: 1 Issue: 3 Pages: 354-362

    • DOI

      10.1039/d0ma00139b

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis, optical and electrochemical properties of propeller-type 3,5,8-trithienyl-BODIPY dyes2020

    • Author(s)
      Tsumura Shuhei、Ohira Kazuki、Hashimoto Kosuke、Imato Keiichi、Ooyama Yousuke
    • Journal Title

      Materials Chemistry Frontiers

      Volume: 4 Issue: 9 Pages: 2762-2771

    • DOI

      10.1039/d0qm00494d

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of optical sensor for water in acetonitrile based on propeller-structured BODIPY-type pyridine-boron trifluoride complex2020

    • Author(s)
      Tsumura Shuhei、Ohira Kazuki、Imato Keiichi、Ooyama Yousuke
    • Journal Title

      RSC Advances

      Volume: 10 Issue: 56 Pages: 33836-33843

    • DOI

      10.1039/d0ra06569b

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Phenazine-based photosensitizers for singlet oxygen generation2020

    • Author(s)
      Imato Keiichi、Ohira Kazuki、Yamaguchi Masakuni、Enoki Toshiaki、Ooyama Yousuke
    • Journal Title

      Materials Chemistry Frontiers

      Volume: 4 Issue: 2 Pages: 589-596

    • DOI

      10.1039/c9qm00685k

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] luorescent sensor for water based on photo-induced electron transfer and Forster resonance energy transfer: anthracene-(aminomethyl)phenylboronic acid ester-BODIPY structure2019

    • Author(s)
      D. Jinbo, K. Imato and Y. Ooyama
    • Journal Title

      RSC Adv.

      Volume: 9 Issue: 27 Pages: 15335-15340

    • DOI

      10.1039/c9ra02686j

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis and Photophysical and Electrochemical Properties of Pyridine-, Pyrazine- and Triazine-based (D-π-)2A Fluorescent Dyes2019

    • Author(s)
      K. Imato, T. Enoki, K. Uenaka and Y. Ooyama
    • Journal Title

      Beilstein J. Org. Chem.

      Volume: 15 Pages: 1712-1721

    • DOI

      10.3762/bjoc.15.167

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Development of an intramolecular charge transfer-type colorimetric and fluorescence sensor for water by fusion with juloidine structure and complexation with boron trifluoride2019

    • Author(s)
      K. Imato, T. Enoki and Y. Ooyama
    • Journal Title

      RSC Adv.

      Volume: 9 Issue: 54 Pages: 31466-31473

    • DOI

      10.1039/c9ra07136a

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Presentation] 微量から高水分量領域の水分検出を可能とするPET/AIE型蛍光性水センサーの分子設計と合成2022

    • Author(s)
      西本 絵美子,三瀬 裕大,今任 景一,今榮 一郎,大山 陽介
    • Organizer
      日本化学会第102回春季年会(オンライン)
    • Related Report
      2021 Annual Research Report
  • [Presentation] 光誘起電子移動を利用した蛍光性水センサーの開発とポリマーフィルム化2022

    • Author(s)
      麓 拓馬,三保 沙織,今任 景一,大山 陽介
    • Organizer
      日本化学会第102回春季年会(オンライン)
    • Related Report
      2021 Annual Research Report
  • [Presentation] PET型蛍光性水センサーの水分検出限界の改善と機能性材料化の検討2021

    • Author(s)
      三保沙織, 大山陽介, 今任景一
    • Organizer
      第45回有機電子移動化学討論会(オンライン)
    • Related Report
      2021 Annual Research Report
  • [Presentation] PET型蛍光性水センサーをドープしたポリマーフィルムの作製と水分の可視化2021

    • Author(s)
      麓 拓馬, 大山陽介, 今任景一
    • Organizer
      第45回有機電子移動化学討論会(オンライン)
    • Related Report
      2021 Annual Research Report
  • [Presentation] Synthesis of phenazine-based photosensitizers for singlet oxygen generation2020

    • Author(s)
      Yousuke Ooyama
    • Organizer
      The 14th International Symposium on Organic Reactions (ISOR-14)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] A Novel PET (Photo-induced Electron Transfer)-Based Sensor for Water and Polymerization2020

    • Author(s)
      Saori Miho, Keiichi Imato and Yousuke Ooyama
    • Organizer
      The 14th International Symposium on Organic Reactions (ISOR-14)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis, Optical and Electrochemical Properties of Phenazine-2,3-diol Dyes2020

    • Author(s)
      Chih-Hsin Yu, Keiichi Imato, Cheng-Liang Liu and Yousuke Ooyama
    • Organizer
      The 14th International Symposium on Organic Reactions (ISOR-14)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis, Optical and Electrochemical Properties of Bibenzo[c]thiophene Derivative2020

    • Author(s)
      Kotaro Obayashi, Keiichi Imato, Seiji Akiyama, Yousuke Ooyama
    • Organizer
      The 14th International Symposium on Organic Reactions (ISOR-14)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of new photosensitizing dyes based on phenazine skeleton and their singlet oxygen generation properties2020

    • Author(s)
      Kazuki Ohira, Keiichi Imato, and Yousuke Ooyama
    • Organizer
      The 14th International Symposium on Organic Reactions (ISOR-14)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Luminescence Properties of Tetraphenylethylene Bearing Four Anthraldehyde Units2020

    • Author(s)
      Yuta Mise, Keiichi Imato and Yousuke Ooyama
    • Organizer
      The 14th International Symposium on Organic Reactions (ISOR-14)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Optical and Electrochemical Properties of Phenanthrodithiophene (Fused-Bibenzo[c]thiophene) Chromophore2019

    • Author(s)
      Y. Ooyama
    • Organizer
      14th International symposium on Functional π-Electron Systems, in Berlin, Germany
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 機能性色素のレドックス制御とオプトエレクトロニクスデバイスへの展開2019

    • Author(s)
      大山 陽介
    • Organizer
      第43回有機電子移動化学討論会, 横浜国立大学教育文化ホール, 神奈川
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Synthesis, Optical and Electrochemical Properties of Fused-Bibenzo[c]thiophene (Phenanthrodithiophene) Derivatives as a New Functional Dye2019

    • Author(s)
      Y. Ooyama
    • Organizer
      The 9th East Asia Symposium on Functional Dyes and Advanced Materials (EAS9); National Taipei University of Technology, Taipei, Taiwan
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Photovoltaic performances of type-II dye-sensitized solar cells based on catechol dyes2019

    • Author(s)
      Y. Ooyama
    • Organizer
      Asian International Symposium -Electrochemistry in 100th Annual Meeting of The Chemical Society of Japan; Tokyo University of Science, Chiba, Japan
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Book] Sustainable and Functional Redox Chemistry; Chapter13 Fluorescent Sensors for Water2022

    • Author(s)
      Yousuke Ooyama
    • Total Pages
      31
    • Publisher
      The Royal Society of Chemistry (RSC)
    • ISBN
      9781839162466
    • Related Report
      2021 Annual Research Report
  • [Book] Progress in the Science of Functional Dyes; Chapter 13 Photodynamic therapy2021

    • Author(s)
      Keiichi Imato and Yousuke Ooyama
    • Total Pages
      23
    • Publisher
      Springer
    • ISBN
      9789813343917
    • Related Report
      2021 Annual Research Report
  • [Book] Progress in the Science of Functional Dyes; Chapter 14 Photoenergy Conversion (Dye-Sensitized Solar Cells)2021

    • Author(s)
      Yousuke Ooyama
    • Total Pages
      72
    • Publisher
      Springer
    • ISBN
      9789813343917
    • Related Report
      2021 Annual Research Report
  • [Book] Progress in the Science of Functional Dyes2021

    • Author(s)
      Yousuke Ooyama and Shigeyuki Yagi (co-editor)
    • Total Pages
      609
    • Publisher
      Springer
    • ISBN
      9789813343917
    • Related Report
      2021 Annual Research Report
  • [Book] 刺激応答性高分子の開発動向 (監修:荏原充宏) 第8章 外部刺激応答性の機能性色素の分子設計 第2編 刺激応答性高分子の設計・合成技術2021

    • Author(s)
      大山陽介,今任 景一
    • Total Pages
      25
    • Publisher
      シーエムシー出版
    • ISBN
      9784781316116
    • Related Report
      2021 Annual Research Report
  • [Book] CSJカレントレビュー第40号 多彩な色素材料の新展開 (日本化学会 編) 9章 分子間相互作用を制御した蛍光性色素のメカノフルオロクロミズム2021

    • Author(s)
      大山陽介
    • Total Pages
      7
    • Publisher
      化学同人
    • ISBN
      4759814000
    • Related Report
      2020 Annual Research Report
  • [Remarks] 広島大学大学院先進理工系科学研究科 機能性色素化学研究室

    • URL

      https://ooyama-lab.hiroshima-u.ac.jp/index_en.html

    • Related Report
      2021 Annual Research Report
  • [Remarks] 広島大学大学院先進理工系科学研究科 機能性色素化学研究室

    • URL

      https://ooyama-lab.hiroshima-u.ac.jp/

    • Related Report
      2020 Annual Research Report 2019 Annual Research Report
  • [Patent(Industrial Property Rights)] 光増感色素、光増感色素の製造方法、色素増感型有機太陽電池用色素、可視光応答型光触媒、及び、光線力学的療法用色素2021

    • Inventor(s)
      大山陽介
    • Industrial Property Rights Holder
      大山陽介
    • Industrial Property Rights Type
      特許
    • Filing Date
      2021
    • Related Report
      2021 Annual Research Report
  • [Patent(Industrial Property Rights)] 化合物、及び該化合物を含有する部材2020

    • Inventor(s)
      大山陽介、秋山誠治
    • Industrial Property Rights Holder
      大山陽介、秋山誠治
    • Industrial Property Rights Type
      特許
    • Filing Date
      2020
    • Related Report
      2020 Annual Research Report

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

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