Preferential Solvation in Carbonyl-Twisted PRODAN Derivatives.

The Rosés and Bosch model for preferential solvation is used to analyze the fluorescence behavior of two PRODAN derivatives in binary solvents with one or two protic components. The preferential solvation results suggest that the excited PRODAN derivatives form two H-bonds. The model allows for determining the characteristics of the singly H-bonded excited states. They show red-shifted fluorescence but relatively little quenching. In contrast, the doubly H-bonded excited states are significantly quenched when the protic solvent is a strong H-bond donor (large SA value). With two protic solvents there is little preferential interaction even though the solvents have very different H-bond-forming ability.