V-shaped fluorophores with a 1-methyl-4,5-bis(arylethynyl)imidazole skeleton displaying solid-state fluorescence, acid responsiveness, and remarkable fluorescence solvatochromism

Youhei Miura, Kotaro Kobayashi, Naoki Yoshioka

研究成果: Article査読

抄録

Novel V-shaped fluorophores with an imidazole skeleton composed of arylethynyl moieties were developed. Their HOMO-LUMO energy gaps were well controlled by the introduction of electron-withdrawing or -donating groups in the aryl moiety. Compounds with different substituents at the 4- and 5-positions were selectively synthesized exploiting the difference in reactivity between the iodo and bromo groups. All compounds synthesized displayed fluorescence not only in solution but also in the solid state. The compound with a donor-acceptor structure displayed a fluorescence maximum with a wavelength over 500 nm and a large Stokes shift of about 150 nm, due to its intramolecular charge transfer character. In the solid state, the synthesized compounds have planar structures, indicating an expansion of π-conjugation. Upon exposure of the compounds in the solid state to acid vapor, the fluorescence of the compounds with acceptor groups was quenched, and that of the others shifted to longer wavelengths.

本文言語English
ページ(範囲)898-905
ページ数8
ジャーナルNew Journal of Chemistry
45
2
DOI
出版ステータスPublished - 2021 1 14

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

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