Differential Behavior of Amino–Imino Constitutional Isomers in Nonlinear Optical Processes

A detailed study of the “blocked” amino–imino tautomers derived from N-acridine-substituted 2-aminobenzothiazole—and their effect on the nonlinear optical response—is presented. The synthesis, characterization, and nonlinear optical properties of these frozen tautomers, namely, N-methyl-N-(2-nitroacridin-6-yl)-2-aminobenzothia-zole and 3-methyl-N-(7-nitroacridin-3-yl)-2-iminobenzothiazole, are reported. A theoretical model based on valence–bond theory is also proposed and used to analyze the effects of the nuclear configuration corresponding to each frozen tautomer structure. In the present case, the aromatic form and the allylic-anion-like system of the NCN group inherent to each isomer are crucial for understanding and analyzing the different responses of each “blocked” tautomer.