Synthesis of Fluorogenic Arylureas and Amides and Their Interaction with Amines: A Competition between Turn-on Fluorescence and Organic Radicals on the Way to a Smart Label for Fish Freshness

Molecules. 2021 Mar 5;26(5):1404. doi: 10.3390/molecules26051404.

Abstract

We describe the synthesis of fluorogenic arylureas and amides and their interaction with primary or secondary amines under air and light in organic-aqueous mixtures to give rise to a new class of persistent organic radicals, described on the basis of their electron paramagnetic resonance (EPR), as well as UV-vis, fluorescence, NMR, and quantum mechanics calculations, and their prospective use as multi-signal reporters in a smart label for fish freshness.

Keywords: arylureas; organic radicals; smart label; turn-on fluorescence; volatile amines.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amines / chemistry*
  • Animals
  • Electron Spin Resonance Spectroscopy
  • Fish Products / analysis*
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Food Analysis / methods*
  • Free Radicals / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Perciformes

Substances

  • Amides
  • Amines
  • Fluorescent Dyes
  • Free Radicals