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Creation and Function of Organic Fluorophores and Phosphors That Exhibit Efficient Emission in the Aggregated States

Research Project

Project/Area Number 15H03795
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional solid state chemistry
Research InstitutionKyoto Institute of Technology

Principal Investigator

Shimizu Masaki  京都工芸繊維大学, 分子化学系, 教授 (10272709)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥10,790,000 (Direct Cost: ¥8,300,000、Indirect Cost: ¥2,490,000)
Fiscal Year 2017: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2016: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2015: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Keywords蛍光 / 燐光 / 分子凝集 / 発光材料 / リン光
Outline of Final Research Achievements

Several luminophores that exhibit efficient fluorescence in the aggregated states such as crystal, powder, and liquid were developed based on the electronic structure of 1,4-bis(donor)-2,5-bis(acceptor)benzenes as a guideline of molecular design. The fluorescent benzene derivatives were applied to the creation of white light-emitting polymers and a fluorescent probe for selective sensing of cysteine. Based on the findings that siloxy and silylmethyloxy groups effectively stabilized the triplet excited states of 1,4-diaroylbenzenes, rare metal-free room temperature phosphorescent materials that emit with high quantum yields and long lifetimes were developed. The phosphors were applied to the sensing of molecular oxygen and temperature.

Academic Significance and Societal Importance of the Research Achievements

固体蛍光材料や蛍光性液体材料の創製は、有機EL、発光性トランジスタ、蛍光分子センサーや電気化学発光素子の進歩に、革新をもたらすことが期待される。特に、蛍光性液体の開発例は極めて少ないので、本研究の成果は光る液体分子材料の開発促進をもたらすものと思われる。また、希少金属を含まない室温燐光材料の開発は、励起三重項状態が酸素分子や温度に極めて敏感なことや細胞毒性が低いと予想されることから、蛍光材料をはるかに凌ぐ感度の酸素センサーや分子温度計として、細胞内などの微小空間への応用展開が期待される。

Report

(4 results)
  • 2018 Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • Research Products

    (31 results)

All 2019 2018 2017 2016 2015

All Journal Article (10 results) (of which Peer Reviewed: 10 results,  Acknowledgement Compliant: 2 results) Presentation (20 results) (of which Int'l Joint Research: 10 results,  Invited: 6 results) Book (1 results)

  • [Journal Article] 4,5-Diaminophthalimides: highly efficient solid-state fluorophores and turn-on type fluorescent probes for hydrazine2019

    • Author(s)
      Shimizu Masaki, Tamagawa Tomokazu, Nishimura Kenta
    • Journal Title

      Materials Chemistry Frontiers

      Volume: 3 Issue: 4 Pages: 563-570

    • DOI

      10.1039/c8qm00578h

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] (Poly)terephthalates with Efficient Blue Emission in the Solid State2018

    • Author(s)
      M. Shimizu, R. Shigitani, T. Kinoshita, H. Sakaguchi
    • Journal Title

      Chemistry - An Asian Journal

      Volume: - Issue: 10 Pages: 1792-1800

    • DOI

      10.1002/asia.201801619

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Use of silylmethoxy groups as inducers of efficient room temperature phosphorescence from precious-metal-free organic luminophores2018

    • Author(s)
      Shimizu Masaki, Kinoshita Takumi, Shigitani Ryosuke, Miyake Yusuke, Tajima Kunihiko
    • Journal Title

      Materials Chemistry Frontiers

      Volume: 2 Issue: 2 Pages: 347-354

    • DOI

      10.1039/c7qm00524e

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Aggregation-induced emission and thermally activated delayed fluorescence of 2,6-diaminobenzophenones2018

    • Author(s)
      Shimizu Masaki, Nakatani Masaki, Nishimura Kenta
    • Journal Title

      Science China Chemistry

      Volume: 61 Issue: 8 Pages: 925-931

    • DOI

      10.1007/s11426-018-9301-6

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Germanium-Bridged 2-Phenylbenzoheteroles as Luminophores Exhibiting Highly Efficient Solid-State Fluorescence2017

    • Author(s)
      Shimizu Masaki, Ryuse Daiki, Kinoshita Takumi
    • Journal Title

      Chemistry A European Journal

      Volume: 23 Issue: 58 Pages: 14623-14630

    • DOI

      10.1002/chem.201703235

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Blue-to-Green Delayed Fluorescence of 2-Aminoisophthalic Acid Diesters Dispersed in Polymer Film2017

    • Author(s)
      Shimizu Masaki、Nakatani Masaki
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2017 Issue: 32 Pages: 4695-4702

    • DOI

      10.1002/ejoc.201700695

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Siloxy Group-Induced Highly Efficient Room Temperature Phosphorescence with Long Lifetime2016

    • Author(s)
      Shimizu Masaki, Shigitani Ryosuke, Nakatani Masaki, Kuwabara Keiko, Miyake Yusuke, Tajima Kunihiko, Sakai Hayato, Hasobe Taku
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 120 Issue: 21 Pages: 11631-11639

    • DOI

      10.1021/acs.jpcc.6b03276

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Aggregation-Induced Orange-to-Red Fluorescence of 2,5-Bis(diarylamino)terephthalic Acid Dithioesters2016

    • Author(s)
      M. Shimizu, H. Fukui, M. Nakatani, H. Sakaguchi
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 36 Issue: 36 Pages: 5950-5956

    • DOI

      10.1002/ejoc.201601067

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Room Temperature Phosphorescence of Crystalline 1,4-Bis(aroyl)-2,5-dibromobenzenes2016

    • Author(s)
      M. Shimizu, A. Kimura, H.Sakaguchi
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 3 Issue: 3 Pages: 467-473

    • DOI

      10.1002/ejoc.201501382

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Native-Chemical-Ligation-Based Turn-on Fluorescent Probe for Selective Detection of Cysteine2016

    • Author(s)
      Shimizu, Masaki Fukui, Hiroki Shigitani, Ryosuke
    • Journal Title

      Journal of the Chinese Chemical Society

      Volume: 63 Issue: 4 Pages: 317-322

    • DOI

      10.1002/jccs.201500466

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] Design and Applications of Highly Luminescent Organic Solids2018

    • Author(s)
      Masaki Shimizu
    • Organizer
      Organic Chemistry Symposium @ IIT Kanpur
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 1,4-ビス(アリールスルホニル)-2,5-ジシロキシベンゼンの蛍光-りん光二重発光性2018

    • Author(s)
      酒井元晴、木下沢泉、清水正毅、三宅祐輔、田嶋邦彦
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 1,4-ビス(ジアリールホスフィニル)-2,5-ビス(シリルメチオキ)ベンゼンの蛍光ーりん光二重発光性2018

    • Author(s)
      長野 翔、木下 沢泉、清水 正毅
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ジアロイルビス(ジシリルメチルオキシ)ベンゼンの蛍光-りん光二重発光性2018

    • Author(s)
      木下沢泉、清水正毅、三宅祐輔、田嶋邦彦
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ジアロイルビス(シリルメチルオキシ)ベンゼンの置換様式がりん光発光に及ぼす影響2018

    • Author(s)
      西村賢汰、木下沢泉、清水正毅
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 固体状態で高効率発光する蛍光材料とレアメタルフリー燐光材料2017

    • Author(s)
      清水正毅
    • Organizer
      第80回白鷺セミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Development of Rare Metal-Free Room Temperature Phosphors2017

    • Author(s)
      Masaki Shimizu
    • Organizer
      The Third International Symposium on Aggregation-Induced Emission
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Replacing Lumogen Red from high optical efficiency Luminescent Solar Concentrators: the example of a red-emitting silafluorene dye2017

    • Author(s)
      Tarita Biver, Federico Gianfaldoni, Andrea Pucci, Masaki Shimizu, Daiki Ryuse
    • Organizer
      The Third International Symposium on Aggregation-Induced Emission
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Design and Characterization of 2,5-Dialkoxyterephthalates as Efficient Blue Emitters in the Solid Statend Characterization of 2,5-Dialkoxyterephthalates as Efficient Blue Emitters in the Solid State2017

    • Author(s)
      Masaki Shimizu, Ryosuke Shigitani, Takumi Kinoshita, and Hiroshi Sakaguchi
    • Organizer
      The 8th International Symposium of Advanced Energy Science-Interdisciplinary Approach to Zero-Emission Energy-
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 室温リン光を示す1,4-ジベンゾイル-2,5-ビス(シリルメチルオキシ)ベンゼン2017

    • Author(s)
      木下 沢泉、鴫谷 亮祐、清水 正毅、三宅 祐輔、田嶋邦彦
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] 固体状態で高効率発光する蛍光材料と室温リン光材料2016

    • Author(s)
      清水正毅
    • Organizer
      第10回有機π電子系シンポジウム
    • Place of Presentation
      あうる京北
    • Year and Date
      2016-12-16
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] イオン性ビス(アリールエテニル)ジメトキシベンゼンの熱および光物性2016

    • Author(s)
      中野慶紀・清水正毅
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2016-11-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] レアメタルを含まない有機分子からの高効率室温リン光2016

    • Author(s)
      鴫谷亮祐・清水正毅・中谷匡希・桑原慶子・三宅祐輔・田嶋邦彦・酒井隼人・羽曾部卓
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2016-11-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] Aggregation-Induced Orange to Red Fluorescence of 2,5-Bis(diarylamino)terephthalic Acid Dithioesters2016

    • Author(s)
      Masaki Shimizu and Hiroshi Sakaguchi
    • Organizer
      The 7th International Symposium to Advanced Energy Science -Frontiers of Zero Emission Energy
    • Place of Presentation
      京都大学
    • Year and Date
      2016-09-05
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ビス(アリールエテニル)ベンゼンを基盤とする発光性イオン液体の開発2016

    • Author(s)
      中野慶紀・清水正毅
    • Organizer
      JACI/GSCシンポジウム
    • Place of Presentation
      ANAクラウンプラザ神戸
    • Year and Date
      2016-06-02
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis and Luminescent Properties of 2,5-Dialkoxyterephthalic Acid Diesters2015

    • Author(s)
      Ryosuke Shigitani and Masaki Shimizu
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Doshisha University, Kyoto, Japan
    • Year and Date
      2015-11-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Organic Chromophores That Exhibit Efficient Visible-Light Emission in the Solid State2015

    • Author(s)
      Masaki Shimizu
    • Organizer
      7th East Asia Symposium on Functional Dyes and Advanced Materials
    • Place of Presentation
      Osaka Prefecture University, Osaka, Japan
    • Year and Date
      2015-09-02
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Design and Characterization of Laterally Substituted D-pi-A Type Biphenyls as Fluorescent Solid2015

    • Author(s)
      Tomokazu Tamagawa and Masaki Shimizu
    • Organizer
      7th East Asia Symposium on Functional Dyes and Advanced Materials
    • Place of Presentation
      Osaka Prefecture University, Osaka, Japan
    • Year and Date
      2015-09-02
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Design and Characterization of 4,5-Diaminophthalic Acid Diesters as Blue Emissive Solids2015

    • Author(s)
      Masaki Shimizu and Tomokazu Tamagawa
    • Organizer
      7th Spanish-Portuguese-Japanese Organic Chemistry Symposium
    • Place of Presentation
      Seville, Spain
    • Year and Date
      2015-06-23
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Fluorescent Properties of Silicon-Bridged Biaryls2015

    • Author(s)
      Masaki Shimizu
    • Organizer
      The 2nd International Symposium on Aggregation-Induced Emission (AIE2)
    • Place of Presentation
      Guangzhou, China
    • Year and Date
      2015-05-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Book] Principles and Applications of Aggregation-Induced Emission2019

    • Author(s)
      Masaki Shimizu
    • Total Pages
      514
    • Publisher
      Springer International Publishing
    • ISBN
      9783319990378
    • Related Report
      2017 Annual Research Report

URL: 

Published: 2015-04-16   Modified: 2020-03-30  

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