Methoxyquinolone-Benzothiazole Hybrids as New Aggregation-Induced Emission Luminogens and Efficient Fluorescent Chemosensors for Cyanide Ions

Int J Mol Sci. 2024 Nov 30;25(23):12896. doi: 10.3390/ijms252312896.

Abstract

This work describes the synthesis and characterization of new quinolone-benzothiazole hybrids, the study of their aggregation-induced emission (AIE) properties, and the use of these systems as efficient fluorescent probes for cyanide ions. These conjugated derivatives are linked through a double bond favoring electronic communication, and together with their planar geometry, can strongly aggregate under solvophobic environments, leading to aggregation and exhibiting significant AIE behavior. The double bond between electroactive units is prone to nucleophilic addition reactions by cyanide ions, selectively, conducive to turning off the fluorescence properties, making this hybrid system an efficient probe for cyanide ions. These studies were theoretically explained using DFT and TD-DFT calculations.

Keywords: aggregation-induced emission; benzothiazole; chemosensors; cyanide; quinolone.

MeSH terms

  • Benzothiazoles* / chemistry
  • Cyanides* / analysis
  • Cyanides* / chemistry
  • Fluorescent Dyes* / chemistry
  • Ions
  • Molecular Structure
  • Quinolones / chemistry
  • Spectrometry, Fluorescence / methods

Substances

  • Benzothiazoles
  • Fluorescent Dyes
  • Cyanides
  • Quinolones
  • Ions
  • benzothiazole