Effects of substitution and conjugation on ESIPT behavior of Schiff base derivatives

The excited-state proton transfer (ESIPT) behavior of organic fluorophores has been of great interest due to their unique photophysical properties. In this work, we have focused on the excited state kinetic behavior of four Schiff base organic molecules (i.e. CPMP, CPMMP, CPMDP, and CPMN) in acetonitrile solvents. The electron-donating of substituents and conjugation effects on the photophysical properties and ESIPT process of the Schiff base derivatives are investigated by theoretical methods. The results show that the hydrogen bonds are all enhanced in the excited states, which could provide the impetus for the ESIPT process. To further reveal the reaction process of ESIPT, we have scanned the potential energy curves of the ESIPT process and compared the potential barriers. It is found that the stronger the substituents give electrons and the conjugation effects the more favorable the excited state proton transfer (ESIPT). In the meantime, this study paves the way for the development of new Schiff base materials based on ESIPT.