Exploring the influence of intermolecular hydrogen bonding on the fluorescence properties of HQCT and HQPH fluorescent chemosensors

Abstract

Recently, two trace water detection probes, 8-hydroxyquinoline-2-carboxaldehyde thiosemicarbazone(HQCT) and 8-hydroxyquinoline-2-carboxaldehyde (pyridine-2-carbonyl)-hydrazine(HQPH) have been successfully designed in the experiment. The original intramolecular proton transfer can be prevented by the water molecules, leading to fluorescence quenching. In order to investigate the fluorescence quenching mechanism, the effect of water molecules on the excited state proton transfer process will be studied in detail. In this contribution, the six models have been optimized and the related analysis have been carried out. When water molecules are involved in the proton transfer process, the energy barrier decreases significantly and the conversion of the enol structure to the keto structure is accelerated. Moreover, the intermolecular hydrogen bonding, not participating in the proton transfer process, can facilitate the proton transfer process by affecting the distribution of the electrostatic potential within the molecule, which in turn lowers the energy barrier for proton transfer.