Solvatochromism of naringenin in aqueous alcoholic mixtures

Abstract

The spectral change of naringenin in binary mixtures of water with methanol, ethanol or 1-propanol was studied by UV-Vis spectrophotometry at 25°C. The effect of the solvent was investigated by analysis of the electron transition energy at the maximum absorption wavelength as a function of the Kamlet and Taft parameters of the mixtures by means of linear solvation energy relationships. The nonlinear response of the solvatochromism was explained based on solute-solvent and solvent-solvent interactions. The possible preferential solvation of naringenin by each of the solvents was studied through a modified preferential solvation model that considers the hydrogen bonding interactions between the prior solvents due to solvent-solvent interactions. The preferential solvation parameters and local mole fraction distribution around the solute were calculated. The results indicated that naringenin prefers to be more solvated by the complex solvating species and organic solvents than water.