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Development of organic solid-state luminescent materials controllable based on two-way mechanism

Research Project

Project/Area Number 24550222
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic industrial materials
Research InstitutionThe University of Tokyo

Principal Investigator

MUTAI Toshiki  東京大学, 生産技術研究所, 助教 (80313112)

Co-Investigator(Renkei-kenkyūsha) YOSHIKAWA Isao  東京大学, 生産技術研究所, 技術専門職員 (10401283)
Project Period (FY) 2012-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords光物性 / 蛍光発光 / 有機固体 / 結晶多形 / ESIPT発光 / 計算化学 / イミダゾピリジン / 集積誘起発光AIE / AIE / 蛍光 / 固体発光 / 分子内水素結合 / 有機結晶 / 高分子薄膜 / 相転移 / 固体発光材料 / 分子軌道計算 / ベンズイミダゾール
Outline of Final Research Achievements

This research showed the validity of the new concept for controlling the solid-state ESIPT luminescence property based on the polymorphism of supramolecular assembly without changing chemical structure of compounds ("fine" control mechanism) by means of X-ray crystallographic analysis and quantum chemical calculation, in addition to the conventional synthetic modification of the electronic state of compounds ("coarse" control mechanism). Combination of the above two controlling mechanisms were confirmed to be useful for tuning the luminescence wavelength gradually and widely, which surely presented considerable potential leading to a valuable designing concept for developing novel organic luminescent materials.

Report

(5 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (37 results)

All 2016 2015 2014 2013 2012 Other

All Journal Article (15 results) (of which Peer Reviewed: 15 results,  Open Access: 2 results,  Acknowledgement Compliant: 3 results) Presentation (20 results) (of which Int'l Joint Research: 1 results,  Invited: 5 results) Book (2 results)

  • [Journal Article] Effects of Semi-flexible Linker on Mechanochromic Photoluminescence of a Bis(Pt-salen) Complex2016

    • Author(s)
      Hirohiko Houjou, Keisuke Yagi, Isao, Yoshikawa, Toshiki Mutai, Koji Araki
    • Journal Title

      Polyhedron

      Volume: 未定 Pages: 123-131

    • DOI

      10.1016/j.poly.2016.04.022

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Aryl-substituted 2-Phenylimidazo[1,2-a]pyridines (PIP) with Various Colors of Excited-State Intramolecular Proton Transfer (ESIPT) Luminescence in the Solid State2016

    • Author(s)
      Toshiki Mutai, Tatsuya Ohkawa, Hideaki Shono, Koji Araki
    • Journal Title

      J. Mater. Chem. C

      Volume: 4 Issue: 16 Pages: 3599-3606

    • DOI

      10.1039/c6tc00376a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Triarylmethane Dye-Conjugated Hexanuclear Zinc Complexes: Photophysical Properties and Cyanide-Selective Anion-Sensing Behavior2015

    • Author(s)
      Saori Takeda, Hiroka Yamada, Toshiki Mutai, Isao Yoshikawa, Hirohiko Houjou
    • Journal Title

      Dyes and Pigments

      Volume: 121 Pages: 372-375

    • DOI

      10.1016/j.dyepig.2015.05.038

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solid-State Characterization of a Fused Salphen-Nickel Metallopolymer Prepared via Transmetalation in a Heterogeneous Reaction System2015

    • Author(s)
      Hirohiko Houjou, Keisuke Yagi, Isao Yoshikawa, Toshiki Mutai, Koji Araki
    • Journal Title

      J. Inorg. Organomet. Polym.

      Volume: 未定 Issue: 4 Pages: 906-911

    • DOI

      10.1007/s10904-015-0187-4

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Colorless, Transparent, Dye-Doped Polymer Films Exhibiting Tunable Luminescence Color: Controlling the Dual-Color Luminescence of 2-(2'-Hydroxyphenyl)imidazo[1,2-a]pyridine Derivatives with the Surrounding Matrix2014

    • Author(s)
      Shintaro Furukawa, Hideaki Shono, Toshiki Mutai, Koji Araki
    • Journal Title

      ACS Appl. Mater. Interfaces

      Volume: 6 Issue: 18 Pages: 16065-16070

    • DOI

      10.1021/am503956t

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Spectroscopic Tracking of Schiff Base Compounds' Hydrogen Bonding Reorganization Associated with Solid-to-Solid Phase Transition2014

    • Author(s)
      3.Satomi Hara, Hirohiko Houjou, Isao Yoshikawa, Hiroyasu Sato, Akihito Yamano, Yukiko Namatame, Toshiki Mutai, Koji Araki
    • Journal Title

      J. Phys. Chem. A

      Volume: 118 Issue: 34 Pages: 6979-6984

    • DOI

      10.1021/jp5063034

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Three-color Polymorph-dependent Luminescence ; Crystallographic Analysis and Theoretical Study on Excited-State Intramolecular Proton Transfer (ESIPT) Luminescence of Cyano-substituted Imidazo[1,2-a]pyridine2014

    • Author(s)
      T.Mutai, H.Shono, Y.Shigemitsu and K.Araki
    • Journal Title

      Crystal Engineering Comminucations

      Volume: 16 Issue: 19 Pages: 3890-3895

    • DOI

      10.1039/c3ce42627k

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Intermolecular Interaction Influence on Solid State Luminescence of Imidazopyrizines : Theoretical Interpretations using FMO-TDDFT and ONIOM Approach2014

    • Author(s)
      Y.Shigemitsu, T.Mutai , H.Houjou and Koji Araki
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 16 Issue: 28 Pages: 14388-14395

    • DOI

      10.1039/c3cp55461a

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Spontaneous helical folding of bis(Ni-salphen) complexes in solution and in the solid state: spectroscopic tracking of the unfolding process induced by Na+ ions2014

    • Author(s)
      Hiroto Achira, Muneyuki Ito, Toshiki Mutai, Isao Yoshikawa, Koji Araki, Hirohiko Houjou
    • Journal Title

      Dalton Trans.

      Volume: 43 Issue: 15 Pages: 5899-5907

    • DOI

      10.1039/c3dt53397b

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Sterically Induced Polymorphism: ON-OFF Control of Excited- state Intramolecular Proton Transfer (ESIPT) Luminescence of 1-Methyl-2-(2'-Hydroxyphenyl)benzimidazole2013

    • Author(s)
      Toshihide Shida, Toshiki Mutai, Koji Araki
    • Journal Title

      CrystEngComm

      Volume: 15 Issue: 47 Pages: 10179-10182

    • DOI

      10.1039/c3ce41742e

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Mechanochromic Luminescent Liquid Crystals Based on a Bianthryl Moiety2013

    • Author(s)
      山根祥吾
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 1 Issue: 15 Pages: 2648-2656

    • DOI

      10.1039/c3tc00861d

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rational Approach to Tuning of Efficient Exciedt-State Intramolecular Proton Transfer (ESIPT) Fluorescence of Imidazo[1,2-a]pyridine in Rigid Matrices by Substituent Groups2013

    • Author(s)
      Toshiki Mutai, Hiroaki Sawatani, Toshihide Shida, Hideaki ShonKoo,ji Araki
    • Journal Title

      J. Org. Chem

      Volume: 78 Issue: 6 Pages: 2482-2489

    • DOI

      10.1021/jo302711t

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Emission of Hydroxyphenylimidazopyridine: Computational Study on Enhanced and Polymorph-Dependent Luminescence in the Solid-State2012

    • Author(s)
      Y. Shigemitsu, T. Mutai, H. Houjou, K. Araki
    • Journal Title

      J. Phys. Chem., A.

      Volume: 116 Issue: 49 Pages: 12041-12048

    • DOI

      10.1021/jp308473j

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Propylamino-connected Fluorescent Terpyridine Dimer and Trimer: Syntheses, Photophysical Properties and Formation of Duplex-Type Complexes with Cd(II)2012

    • Author(s)
      Y. Kamoya, K. Kojima, G. Tanaka, R. Tanaka, T. Mutai, K. Araki
    • Journal Title

      Org. Biomol. Chem.

      Volume: 10 Issue: 44 Pages: 8895-8902

    • DOI

      10.1039/c2ob26609a

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Solid-State Luminescence of Tetraphenylpyrene Derivatives: Mechano / Vapochromic Luminescence of 1,3,6,8-Tetra(4’-carboxyphenyl)pyrene2012

    • Author(s)
      S. Yamaguchi, I. Yoshikawa, T. Mutai and K.Araki
    • Journal Title

      J. Mater. Chem.

      Volume: 22 Issue: 37 Pages: 20065-20070

    • DOI

      10.1039/c2jm33690a

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 有機超分子の発光 ー 分子をどのように集め、光らせるか2016

    • Author(s)
      務台 俊樹
    • Organizer
      第13回日本写真学会光機能性材料セミナー
    • Place of Presentation
      東京工芸大学(東京都中野区)
    • Year and Date
      2016-06-20
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 分子間相互作用部位を有するイミダゾピリジン誘導体の固体ESIPT発光2016

    • Author(s)
      金田 翔平,吉川 功,北條 博彦,務台 俊樹
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Enhanced solid-state ESIPT luminescence of imidazopyridine derivatives: Polymorph dependence and stimuli-responsive behavior2015

    • Author(s)
      Toshiki Mutai, Yasuhiro Shigemitsu, Hdeaki Shono, Tatsuya Ohkawa, Hirotaka Sawatani, Koji Araki
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-19
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 有機超分子の発光化学2015

    • Author(s)
      務台 俊樹
    • Organizer
      大阪市立大学 第74回白鷺セミナー
    • Place of Presentation
      大阪府立大学(大阪府堺市)
    • Year and Date
      2015-10-26
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] イミダゾピリジン誘導体の固体ESIPT発光における置換基効果2015

    • Author(s)
      務台 俊樹, 沢谷 浩隆, 加藤 拓, 吉川 功, 北條 博彦, 荒木 孝二
    • Organizer
      2015光化学討論会
    • Place of Presentation
      大阪市立大学(大阪府大阪市)
    • Year and Date
      2015-09-11
    • Related Report
      2015 Annual Research Report
  • [Presentation] 複数の置換基を導入したフェニルイミダゾピリジン誘導体の固体ESIPT発光2015

    • Author(s)
      加藤 拓,吉川 功,北條博彦,務台俊樹
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部(千葉・船橋)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 結晶多形に依存するESIPT発光 - アルキル基の立体効果による水素結合の制御2014

    • Author(s)
      務台俊樹・志田俊秀・荒木孝二
    • Organizer
      2014光化学討論会
    • Place of Presentation
      北海道大学
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Research-status Report
  • [Presentation] Control of ESIPT Luminescence of 1-Methyl-2-(2'-hydroxyphenyl)benzimidazole by Sterically Induced Polymorphism2014

    • Author(s)
      Toshiki MUTAI, Toshihide SHIDA, Koji ARAKI
    • Organizer
      XXVth IUPAC Photochemistry
    • Place of Presentation
      ボルドー(フランス)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Research-status Report
  • [Presentation] 有機超分子のフォトルミネッセンスとその二元制御

    • Author(s)
      務台 俊樹
    • Organizer
      日本化学会第94春季年会/特別企画「ルミネッセンス・アンサンブル」
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Structure/property relationship of polymorph-dependent ESIPT luminescence

    • Author(s)
      Toshiki MUTAI
    • Organizer
      日本化学会第94春季年会/Asian International Symposium
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] ピレン誘導体のピエゾ/メカノクロミック発光 ― 分子集積構造と発光応答特性

    • Author(s)
      務台 俊樹,山口 真吾,佐瀨 光敬,荒木 孝二
    • Organizer
      2013光化学討論会
    • Place of Presentation
      愛媛大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 2. 結晶中におけるベンズイミダゾール誘導体のESIPT発光 -結晶構造とアルキル基の立体効果

    • Author(s)
      務台 俊樹,志田 俊秀,荒木 孝二
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] フェニルイミダゾピリジン誘導体およびその配位化合物が示す固体発光

    • Author(s)
      務台 俊樹,生野 秀明,荒木 孝二
    • Organizer
      第25回配位化合物の光化学討論会
    • Place of Presentation
      唐津ロイヤルホテル
    • Related Report
      2013 Research-status Report
  • [Presentation] Solid-state ESIPT Luminescence - Multi-color Emission Based on Crystalline Polymorphism

    • Author(s)
      Toshiki Mutai, Koji Araki
    • Organizer
      XXIVth IUPAC Symposium on Photochemistry
    • Place of Presentation
      Coimbra (Portugal)
    • Related Report
      2012 Research-status Report
  • [Presentation] ベンズイミダゾール誘導体のESIPT発光に対するN1-アルキル置換の効果

    • Author(s)
      志田 俊秀, 務台 俊樹, 荒木 孝二
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ
    • Related Report
      2012 Research-status Report
  • [Presentation] Piezo/Mechanochromic Luminescence of p-Substiututed 1,3,6,8-Tetraphenylpyrene Derivatives:

    • Author(s)
      Toshiki Mutai
    • Organizer
      17th Malaysian Chemical Congress (17MCC)
    • Place of Presentation
      Kuala Lumpur, Malaysia
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] 分子内/分子間水素結合に基づくN-置換ベンズイミダゾールの固体発光制御

    • Author(s)
      志田 俊秀, 務台 俊樹, 荒木 孝二
    • Organizer
      第21回有機結晶シンポジウム
    • Place of Presentation
      東工大
    • Related Report
      2012 Research-status Report
  • [Presentation] 外部環境因子による新たな有機固体発光の制御法開発

    • Author(s)
      古川信太郎,生野秀明,務台俊樹,荒木孝二
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大
    • Related Report
      2012 Research-status Report
  • [Presentation] N-置換ベンズイミダゾールの示す有機固相ESIPT発光のON/OFFスイッチング

    • Author(s)
      志田俊秀,務台俊樹,荒木孝二
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大
    • Related Report
      2012 Research-status Report
  • [Presentation] 集積構造変化によるブロモ置換イミダゾピリジンの固相ESIPT発光スイッチング

    • Author(s)
      高橋優佳,沢谷浩隆,務台俊樹,荒木孝二
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大
    • Related Report
      2012 Research-status Report
  • [Book] DOJIN ACADEMIC SERIES 現代光化学2016

    • Author(s)
      水野一彦,宮坂 博,池田 浩 編 (8.2章:務台 俊樹)
    • Publisher
      化学同人
    • Related Report
      2015 Annual Research Report
  • [Book] Packing-Directed Tuning and Switching of Organic Solid-State Luminescence2015

    • Author(s)
      Koji Araki and Toshiki Mutai
    • Publisher
      The Royal Society of Chemistry
    • Related Report
      2014 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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