TDDFT study on excited state intramolecular proton transfer mechanism in 2-amino-3-(2'-benzazolyl)-quinolines.

The intramolecular proton transfer reaction of the 2-amino-3-(2'-benzoxazolyl)-quinoline (ABO) and 2-amino-3-(2'-benzothiazolyl)-quinoline (ABT) molecules in both S0 and S1 states at B3LYP/6-311++G(d,p) level in ethanol solvent have been studied to reveal the deactivation mechanism of the tautomers of the two molecules from the S1 state to the S0 state. The results show that the tautomers of ABO and ABT molecules may return to the S0 state by emitting fluorescence. In addition, the bond lengths, angles and infrared spectra are analyzed to confirm the hydrogen bonds strengthened upon photoexcitation, which can facilitate the proton transfer process. The frontier molecular orbitals (MOs) and natural bond orbital (NBO) are also calculated to indicate the intramolecular charge transfer which can be used to explore the tendency of ESIPT reaction. The potential energy surfaces of the ABO and ABT molecules in the S0 and S1 states have been constructed. According to the energy potential barrier of 9.12kcal/mol for ABO molecule and 5.96kcal/mol for ABT molecule, it can be indicated that the proton transfer may occur in the S1 state.