Abstract
Five mono-azo dyes were synthesized using different diazotized aromatic amines followed by coupling with 1, 3-dihydroxy-2-naphthoate and characterized by proton and carbon NMR and elemental analysis. DFT optimized geometries of all the dyes suggest that dyes are present in the hydrazone form in the ground state and not in the azo form. They showed strong negative absorption solvatochromism and were studied using various solvent polarity scales and multilinear regression analysis using Kamlet – Taft and Catlan scales. Dyes are weakly fluorescent in solvents. Dyes were compared with a parallel series of dyes using 2-naphthol and azo dyes based on benzothiazole unit to investigate the effect of hydroxyl naphthalene ester moiety on the photophysical properties. Solvatochromism was used to calculate the excited state dipole moment, linear and nonlinear optical properties of these dyes. The excited state dipole moments found higher than the ground state dipole moments in case of dye 3a, 3b and 3c while lower than the dyes 3d and 3e respectively. The dyes were also found to be sensitive to pH. Positive and negative values are found for second hyperpolarizability. All these features indicates that present dyes have potential for the advanced applications such as third order nonlinear optical materials.
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