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Viscosity-Induced Emission of 5-(Diarylmethylene)imidazolone with Extended Conjugation via Attachment of N-Methylpyrrole at the 2-Position.

Masahiro IkejiriAki YoshimizuFumika ShiotaAi NagayamaAki FujisakaYuichi KubokiKazuyuki Miyashita
Published in: Chemical & pharmaceutical bulletin (2024)
We have developed a series of 2-monoaryl-5-diarylmethylene analogs of the green fluorescent protein chromophore to study their viscosity-induced emission (VIE) properties. The analogs were synthesized by a condensation with methyl imidate and N-(diarylmethylene)glycinate. Among the analogs, the N-methylpyrrol-2-yl-substituted analog 1h induced the most remarkable VIE behavior in triglyceride and lipid bilayers probably due to the high π-electron-rich property of the pyrrole ring. The pyrrole substituent in imidazolone analogs can be expected to become a common template for introducing VIE behavior.
Keyphrases
  • molecular docking
  • high glucose
  • diabetic rats
  • quantum dots
  • small molecule
  • fatty acid
  • binding protein
  • protein protein