Solvatochromic behaviours and structure-spectra relationships of 4-carboxyl-2,6-dinitrophenylazohydroxynaphthalenes

Comprehensive electronic absorption spectra of a new dye series, 4-carboxyl-2,6-dinitrophenylazohydroxynaphthalenes have been investigated in solvents of varying polarities. The solvent dependent UV-vis spectral shifts were analysed using some solvent physical parameters such as refractive index, dielectric function, hydrogen bonding acceptor ability, orientation of polarization and others. The observed spectral shifts were correlated with different solute-solvent interaction mechanisms using simple and multiple linear regression analyses. The results of the curve fitting coefficients enabled us to classify the various interactions of solvents with the dyes and relate the solvatochromic behaviours to the substituent effects on the dye molecules. Charge-transfer complexation occurring between one of the congeners and N,N'-dimethylformamide was extensively studied and discovered to be both concentration- and temperature-dependent. The electronic character and the chemical nature of the solvents as well as the chemical nature of the other substituents, apart from the common hydroxyl group, are important factors for the observed solvatochromic properties of the 4-carboxyl-2, 6-dinitrophenylazohydroxynaphthalenes. (C) 2009 Elsevier B.V. All rights reserved.