Bischromophoric styrylpyridinium dyes: Spectroscopic properties of 1,3-bis-[4-( p- N, N-dialkylaminostyryl)pyridinyl]propane dibromides

Abstract

The photophysical properties of newly synthesized bischromophoric solvatochromic stilbazolium dyes, 1,3-bis-[4-( p- N, N-dialkylaminostyryl)pyridinyl]propane dibromides (C1–C9), were studied in a series of solvents and their spectroscopic properties were compared with structurally related, monochromophoric styrylpyridinium dyes (SP1–SP9). The position of the UV–vis absorption spectra maximum of novel dyes is only slightly solvent polarity dependent in contrast to the fluorescence spectra that show pronounced solvatochromic effect demonstrated by a large Stokes shifts. The influence of the solvent on absorption and emission spectra, and the solvatochromic properties observed for both ground and first excited states for all the dyes were used for the evaluation of their excited state dipole moments. The ground state dipole moments of both mono- and bischromophoric dyes were established by applying ab initio calculations. The calculations and measurements unexpectedly show that the bischromophoric dyes are characterized by ground state dipole moments being equal to about half of that characterizing their monomeric equivalents, while the excited state dipole moments of bischromophoric dyes are about 10–25% higher in comparison to their monomeric equivalents.