Benzocoumarin‐Fused Triskelions Exhibit AIEE Due to Inhibited Molecular Inversion

  • Masafumi Ueda
    Department of Chemistry Graduate of School of Science Kitasato University 1-15-1 Kitazato, Minami-ku Sagamihara Kanagawa 252-0373 JAPAN
  • Midori Kuramochi
    Department of Chemistry Graduate of School of Science Kitasato University 1-15-1 Kitazato, Minami-ku Sagamihara Kanagawa 252-0373 JAPAN
  • Riho Shimizu
    Department of Chemistry Graduate of School of Science Kitasato University 1-15-1 Kitazato, Minami-ku Sagamihara Kanagawa 252-0373 JAPAN
  • Yuki Ohba
    Department of Applied Chemistry Faculty of Engineering Chiba Institute of Technology 2-17-1 Tsudanuma Narashino Chiba 275-0016 JAPAN
  • Norifumi Yamamoto
    Department of Applied Chemistry Faculty of Engineering Chiba Institute of Technology 2-17-1 Tsudanuma Narashino Chiba 275-0016 JAPAN
  • Yasuhiro Mazaki
    Department of Chemistry Graduate of School of Science Kitasato University 1-15-1 Kitazato, Minami-ku Sagamihara Kanagawa 252-0373 JAPAN

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<jats:title>Abstract</jats:title><jats:p>Developing aggregation‐induced emission luminogens (AIEgens) is a unique strategy for alleviating concentration quenching of π‐conjugated organic compounds. This AIE behaviour can be induced not only in organic dyes with rotors but also in invertible π‐conjugated systems. Herein, intramolecular Ullmann coupling was used to synthesize π‐twisted triskelion‐shaped AIEgens (<jats:bold>2F</jats:bold>, <jats:bold>2G</jats:bold>, and <jats:bold>2H</jats:bold>), in which benzo[<jats:italic>f</jats:italic>], [<jats:italic>g</jats:italic>], and [<jats:italic>h</jats:italic>] coumarins were fused into the benzene core to form a helical propeller shape. These structural isomers had unique molecular thicknesses and planarities depending on the fusion mode of the benzocoumarin. The racemic crystals, <jats:italic>PPP</jats:italic> and <jats:italic>MMM</jats:italic>, had different overlapping molecular configurations because of their twisted molecular frameworks. Compounds <jats:bold>2F</jats:bold>, <jats:bold>2G</jats:bold> and <jats:bold>2H</jats:bold> demonstrated weak fluorescence emission in diluted solutions resulting from molecular motions caused by the isomerization process during molecular inversion. By comparison, aggregates exhibited enhanced emission intensity. These π‐twisted triskelions exhibited the characteristics of AIEgens.</jats:p>

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詳細情報 詳細情報について

  • CRID
    1360302866843440000
  • DOI
    10.1002/ejoc.202400015
  • ISSN
    10990690
    1434193X
  • 資料種別
    journal article
  • データソース種別
    • Crossref
    • KAKEN

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