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Development of highly emissive switching materials with structural changes

Research Project

Project/Area Number 17K05777
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionKanazawa University

Principal Investigator

Maeda Hajime  金沢大学, 物質化学系, 教授 (40295720)

Co-Investigator(Kenkyū-buntansha) 千木 昌人  金沢大学, 物質化学系, 教授 (90135046)
古山 渓行  金沢大学, 物質化学系, 准教授 (30584528)
Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsピレン / ピレノファン / ペリレン / クラウンエーテル / 金属イオン / 蛍光 / エキシマー / スイッチ材料 / ビフェニレン / シクロファン / エキシプレックス / シリルエチニル基 / 光反応 / 光スイッチ / 光二量化反応 / 光二量体 / 有機化学 / 有機工業化学
Outline of Final Research Achievements

We have developed strong fluorescent switching materials whose structures change in response to the external environment and external stimuli. It was found that (1,3) and (1,8)pyrenophanes act as molecules whose fluorescent colors change depending on the solvent and temperature. Crown ether-linked pyrene and perylene formed complexes by recognizing metal ions, and the fluorescent colors changed while maintaining strong fluorescence emission, or they acted as turn-OFF or turn-ON type fluorescent sensors.

Academic Significance and Societal Importance of the Research Achievements

高性能な発光材料の開発は、有機EL、照明、発光ダイオード、インクなどの分野にとって重要である。それぞれの分野で発光材料に求められる性能は異なるが、より強く光る材料の開発が常に求められている。本研究は溶媒、温度、添加物によって可逆的に強い蛍光の色が変わる、色が消える、色がつくという材料の開発を扱ったものであり、工業的に意義深い。また、蛍光強度の増大と長波長化をもたらす分子設計指針を提供するものとして学術的にも意義がある。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (47 results)

All 2020 2019 2018 2017 Other

All Journal Article (17 results) (of which Peer Reviewed: 16 results,  Open Access: 2 results) Presentation (28 results) (of which Int'l Joint Research: 1 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Effects of substituents on absorption and fluorescence properties of trimethylsilylethynyl- and tert-butylethynyl-pyrenes2020

    • Author(s)
      Hajime Maeda, Ryota Ueno, Taniyuki Furuyama, Masahito Segi
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 392 Pages: 112428-112428

    • DOI

      10.1016/j.jphotochem.2020.112428

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions2019

    • Author(s)
      Hajime Maeda, Kazuhiro Tanaka, Mona Aratani, Masahito Segi
    • Journal Title

      Photochemistry and Photobiology

      Volume: 95 Issue: 3 Pages: 762-772

    • DOI

      10.1111/php.13071

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] (1,3)Pyrenophanes containing crown ether moieties as fluorescence sensors for metal and ammonium ions2019

    • Author(s)
      Hajime Maeda, Keigo Nakamura, Taniyuki Furuyama, Masahito Segi
    • Journal Title

      Photochemical & Photobiological Sciences

      Volume: 18 Issue: 10 Pages: 2397-2410

    • DOI

      10.1039/c9pp00239a

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Protonation of Radical Anion Intermediates in Photoallylation and Photoreduction Reactions of 3,3-Diaryl-1,1-dicyano-2-methylprop-1-ene with Allyltrimethylsilane2019

    • Author(s)
      Hajime Maeda, Masayuki Iida, Daisuke Ogawa, Kazuhiko Mizuno
    • Journal Title

      Molecules

      Volume: 24 Issue: 14 Pages: 2677-2677

    • DOI

      10.3390/molecules24142677

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis, fluorescence properties, and conformational analysis of ether-linked (1,8)pyrenophanes2019

    • Author(s)
      Hajime Maeda, Makoto Geshi, Kenji Hirose, Taniyuki Furuyama, Masahito Segi
    • Journal Title

      Tetrahedron

      Volume: 75 Issue: 37 Pages: 130512-130512

    • DOI

      10.1016/j.tet.2019.130512

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Intramolecular photocycloaddition reactions of 2- and 4-(5-arylpent-4-enyl)-1-cyanonaphthalenes2019

    • Author(s)
      Hajime Maeda, Kouhei Enya, Naoki Negoro, Kazuhiko Mizuno
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 374 Pages: 173-184

    • DOI

      10.1016/j.jphotochem.2019.01.033

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Effects of substituents in silyl groups on the absorption, fluorescence and structural properties of 1,3,6,8-tetrasilylpyrenes2018

    • Author(s)
      Maeda Hajime、Suzuki Tsubasa、Segi Masahito
    • Journal Title

      Photochemical & Photobiological Sciences

      Volume: 17 Issue: 6 Pages: 781-792

    • DOI

      10.1039/c8pp00135a

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of silicon-containing macrocyclic compounds by using intramolecular [2+2] photocycloaddition reactions of bis-dimethylsilyl-linked styrenes and stilbenes2018

    • Author(s)
      Hajime Maeda, Ko-ichi Nishimura, Ryu-ichiro Hiranabe, Kazuhiko Mizuno
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 364 Pages: 472-477

    • DOI

      10.1016/j.jphotochem.2018.06.038

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photoinduced three-component coupling reactions of electron deficient alkenes, dienes and active methylene compounds2018

    • Author(s)
      Hajime Maeda, Hiroshi Takayama, Masahito Segi
    • Journal Title

      Photochemical & Photobiological Sciences

      Volume: 17 Issue: 8 Pages: 1118-1126

    • DOI

      10.1039/c8pp00239h

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of pyrenocrown ethers as fluorescent sensors and their recognition ability of metal ions2018

    • Author(s)
      Hajime Maeda, Kenji Hirose, Masahito Segi
    • Journal Title

      Journal of Luminescence

      Volume: 204 Pages: 269-277

    • DOI

      10.1016/j.jlumin.2018.08.032

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Polycyclic Compounds by Using Photocycloaddition Reactions to Aromatic Rings2018

    • Author(s)
      前多 肇,水野一彦
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 76 Issue: 3 Pages: 241-254

    • DOI

      10.5059/yukigoseikyokaishi.76.241

    • NAID

      130006449139

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] ポリチオフェン Ambiphilic Reactivity Reaction Progress Kinetic Analysis(RPKA) エキシプレックス2018

    • Author(s)
      前多 肇
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 76 Issue: 3 Pages: 259-259

    • DOI

      10.5059/yukigoseikyokaishi.76.259

    • NAID

      130006449142

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2017 Research-status Report
  • [Journal Article] Synthesis and Conformational Analysis of 2,11-Dioxa[3.3]metacyclophanes2017

    • Author(s)
      Hajime Maeda, Shinsuke Endo, Takashi Ouchi, Kazuhiko Mizuno, Masahito Segi
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 9 Pages: 1357-1360

    • DOI

      10.1246/cl.170527

    • NAID

      130006067858

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Diastereoselective photocycloaddition reactions of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furans governed by chiral auxiliaries and hydrogen bonding interactions2017

    • Author(s)
      Hajime Maeda, Norihiro Koshio, Yuko Tachibana, Kazuhiko Chiyonobu, Gen-ichi Konishi, Kazuhiko Mizuno
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 349 Pages: 7-17

    • DOI

      10.1016/j.jphotochem.2017.08.052

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Effects of substituents on silicon atoms upon absorption and fluorescence properties of 1,3,6,8-tetrakis(silylethynyl)pyrenes2017

    • Author(s)
      Hajime Maeda, Tomokazu Shoji, Masahito Segi
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 46 Pages: 4372-4376

    • DOI

      10.1016/j.tetlet.2017.10.008

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photo-Fries rearrangement of 1-pyrenyl esters2017

    • Author(s)
      Hajime Maeda, Tomomi Akai, Masahito Segi
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 46 Pages: 4377-4380

    • DOI

      10.1016/j.tetlet.2017.10.007

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Intramolecular Photoreactions of 9-Cyanophenanthrene-Linked Arylcyclopropanes2017

    • Author(s)
      Hajime Maeda, Hisashi Sakurai, Masahito Segi
    • Journal Title

      ACS Omega

      Volume: 2 Issue: 12 Pages: 8697-8708

    • DOI

      10.1021/acsomega.7b01439

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] ペリレンとベンゾクラウンエーテルを連結した分子による金属イオン認識型蛍光センサーの開発2020

    • Author(s)
      橋本陽奈,古山渓行,千木昌人,前多 肇
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ピレンとアルケンをオリゴエチレングリコール鎖で連結した化合物の蛍光と光反応2020

    • Author(s)
      松原良太郎,古山渓行,千木昌人,前多 肇
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 3位にアルケニル基を有する2-シアノナフタレン誘導体の分子内光環化付加反応2020

    • Author(s)
      柳本雅也,古山渓行,千木昌人,前多 肇
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ナフトニトリル誘導体と電子求引基を有する芳香族アルキンとの光環化付加反応2019

    • Author(s)
      山先健太,國松祐希,古山渓行,千木昌人,前多 肇
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ピレンとアルケンをオリゴエチレングリコール鎖で連結した化合物の蛍光と光反応2019

    • Author(s)
      松原良太郎,古山渓行,千木昌人,前多 肇
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 3位にオキサアルケニル基を有する2-シアノナフタレン誘導体の分子内光環化付加反応2019

    • Author(s)
      柳本雅也,古山渓行,千木昌人,前多 肇
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ピレンの並列構造の制御による分子内エキシマー発光の最適化と長波長化2019

    • Author(s)
      中田梨香子,松野 佑,濱塚明宣,古山渓行,千木昌人,前多 肇
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] エチニルピレン―ベンゾクラウンエーテル連結系分子による金属イオン認識型蛍光センサーの開発2019

    • Author(s)
      橋本陽奈,田中一弘,荒谷萌菜,古山渓行,千木昌人,前多 肇
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 並列構造の制御によるピレンの分子内エキシマー発光の最適化と長波長化2019

    • Author(s)
      中田梨香子,松野 佑,濱塚明宣,古山渓行,千木昌人,前多 肇
    • Organizer
      2019年度有機合成化学北陸セミナー
    • Related Report
      2019 Annual Research Report
  • [Presentation] 3位にオキサアルケニル基を導入した2-シアノナフタレン誘導体の分子内光環化付加反応2019

    • Author(s)
      柳本雅也,古山渓行,千木昌人,前多 肇
    • Organizer
      2019年度有機合成化学北陸セミナー
    • Related Report
      2019 Annual Research Report
  • [Presentation] ピレンとシンナモニトリルをオリゴエチレングリコール鎖で連結した化合物の蛍光と光反応2019

    • Author(s)
      松原良太郎,古山渓行,千木昌人,前多 肇
    • Organizer
      日本化学会近畿支部2019年度北陸地区講演会と研究発表会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 1,8-ビス(ピレン-1-イルエチニル)ビフェニレン類の合成とその分子内エキシマー発光2019

    • Author(s)
      中田梨香子,松野 佑,濱塚明宣,古山渓行,千木昌人,前多 肇
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] シアノナフタレン類への芳香族シアノアルキンの光環化付加反応2019

    • Author(s)
      山先健太,古山渓行,千木昌人,前多 肇
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] メチレン鎖で架橋した(2,7)ピレノファンの合成、蛍光、分子認識2019

    • Author(s)
      二重作亮太,古山渓行,千木昌人,前多 肇
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ナフタレン環の1,8a位へのアルケンの分子内光環化付加反応の開発2018

    • Author(s)
      工保優太,中嶋亮太,水野一彦,古山渓行,千木昌人,前多 肇
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] メチレン鎖で架橋した(2,7)ピレノファンの合成と蛍光特性2018

    • Author(s)
      二重作亮太,古山渓行,千木昌人,前多 肇
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] フェナントリルエステルの光フリース転位2018

    • Author(s)
      飯井滉也,古山渓行,千木昌人,前多 肇
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] 1,8-ビス(ピレン-1-イルエチニル)ビフェニレン類の合成とその分子内エキシマー発光2018

    • Author(s)
      中田梨香子,松野 佑,濱塚明宣,古山渓行,千木昌人,前多 肇
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] シアノナフタレン類への芳香族シアノアルキンの光環化付加反応2018

    • Author(s)
      山先健太,國松裕希,古山渓行,千木昌人,前多 肇
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] フェナントリルエステルの光フリース転位反応2018

    • Author(s)
      飯井滉也,古山渓行,千木昌人,前多 肇
    • Organizer
      平成30年度有機合成化学北陸セミナー
    • Related Report
      2018 Research-status Report
  • [Presentation] メチレン鎖で架橋した(2,7)ピレノファンの合成、蛍光、分子認識能2018

    • Author(s)
      二重作亮太,古山渓行,千木昌人,前多 肇
    • Organizer
      平成30年度有機合成化学北陸セミナー
    • Related Report
      2018 Research-status Report
  • [Presentation] Regioselective Intramolecular [2+2] Photocycloaddition of 1-Cyanonaphthalenes Bearing Cycloalkenyl Groups Using Flow Microreactor2018

    • Author(s)
      Kazuhiko Mizuno, Jiro Noguchi, Momoe Nakano, Yasuhiro Nishiyama, Hajime Maeda, Kiyomi Kakiuchi
    • Organizer
      The First International Conference on Automated Flow and Microreactor Synthesis (ICAMS-1)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] ナフタレン環の1,8a位へのアルケンの分子内光環化付加反応の開発2018

    • Author(s)
      工保優太,中嶋亮太,水野一彦,古山渓行,千木昌人,前多 肇
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] フェナントリルエステルの光フリース転位2018

    • Author(s)
      飯井滉也,古山渓行,千木昌人,前多 肇
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 3-(ピレン-1-イル)アクリル酸エステルの分子内および分子間光二量化反応2017

    • Author(s)
      瀬川健太,古山渓行,千木昌人,前多 肇
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] ナフタレン環の1,8a位へのアルケンの分子内光環化付加反応の開発2017

    • Author(s)
      工保優太,中嶋亮太,水野一彦,古山渓行,千木昌人,前多 肇
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] オリゴエチレングリコール鎖で架橋した(1,6)ピレノファン類の合成と蛍光特性2017

    • Author(s)
      斉藤元暉,古山渓行,千木昌人,前多 肇
    • Organizer
      第34回有機合成化学セミナー
    • Related Report
      2017 Research-status Report
  • [Presentation] オリゴエチレングリコール鎖で架橋した(1,6)ピレノファン類の合成と蛍光特性2017

    • Author(s)
      斉藤元暉,古山渓行,千木昌人,前多 肇
    • Organizer
      平成29年度有機合成化学北陸セミナー
    • Related Report
      2017 Research-status Report
  • [Book] 光化学フロンティア:未来材料を生む有機光化学の基礎2018

    • Author(s)
      前多 肇,他42名
    • Total Pages
      436
    • Publisher
      (株)化学同人
    • ISBN
      9784759814194
    • Related Report
      2018 Research-status Report
  • [Remarks] 金沢大学理工研究域物質化学系応用化学コース精密有機合成化学研究室ホームページ

    • URL

      http://kohka.ch.t.kanazawa-u.ac.jp/lab4/lab4.html

    • Related Report
      2019 Annual Research Report 2018 Research-status Report 2017 Research-status Report

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Published: 2017-04-28   Modified: 2021-02-19  

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