Monomethine cyanine dyes with an indole nucleus: Microwave-assisted solvent-free synthesis, spectral properties and theoretical studies

Four asymmetric monomethine indocyanine dyes were rapidly synthesized by the condensation of indole quaternary salts with 2-methylthio quinoline quaternary salt in the presence of triethylamine under solvent-free, microwave irradiation. The effects of microwave power and irradiation time on yield were examined. The products were identified using elemental analysis, IR, MS, UV-Vis spectra, H-1 and C-13 NMR. The absorption of the dyes was investigated both experimentally and theoretically. Calculations performed using a combination of the time-dependent density functional theory (TD-DFT) and the polarizable continuum model (PCM) reproduced the pi -> pi* type absorption bands of the dyes. Multiple linear regression, applied to the theoretical absorption maxima in different solvents, fitted well with experimental data. Resonance frequency calculations were undertaken to study the IR spectra of the dyes and the calculated results were in good accordance with experimental values. (C) 2009 Elsevier Ltd. All rights reserved.