Synthesis, spectroscopic and DFT studies of novel fluorescent dyes: 3-aminoimidazo[1,2-a]pyridines possessing 4-pyrone moieties

Abstract

A series of novel imidazo[1,2-a]pyridines possessing 4-pyrone ring were synthesized by three-component condensation of 4-pyrone carbaldehydes, 2-aminopyridines and isocyanides. Bismuth (III) chloride was used as a catalyst in these reactions and desired products were synthesized in good yields at a very short period of time under solvent free conditions. UV-Vis absorption and fluorescence emission spectra of these compounds were investigated. It shown that two of these compounds (10f and 10g) exhibit intense fluorescence in dichloromethane. Optimized ground-state molecular geometries and orbital distributions of these two fluorescent dyes were obtained using density functional theory (DFT). Thermogravimetric analysis and electrochemical properties of these compounds were also studied.

Keywords: 4-Pyrone derivatives; Density functional theory (DFT); Fluorescence; Multicomponent reactions; UV–Vis spectra.