Synthesis, characterization, tautomeric structure and solvatochromic behavior of novel 4-(5-arylazo-2-hydroxystyryl)-1-methylpyridinium iodide as potential molecular photoprobe

Abstract

A novel series of the title compound 4-(5-arylazo-2-hydroxystyryl)-1-methylpyridinium iodide 6 has been synthesized via condensation reactions of the arylazosalicylaldehyde derivatives 4a-i with 1-methyl-picolinium iodide 5. The structures of the new arylazo compounds were characterized by 1H NMR, IR, mass spectroscopy, as well as spectral and elemental analyses. The electronic absorption spectra of arylazomerocyanine compounds 6 were measured in different buffer solutions and solvents. The pK's and pK*'s in both the ground and excited states, respectively, were determined for the series and their correlations with the Hammett equation were examined. The results indicated that the title arylazomerocyanine dyes 6 exist in the azo form 6A in both ground and excited states. The substituent and solvent effects (solvatochromism) of the title compound arylazomerocyanine dyes were determined using the Kamlet-Taft equation and subsequently discussed.