Substituent effect on ESIPT and hydrogen bond mechanism of N-(8-Quinolyl) salicylaldimine: A detailed theoretical exploration

The effects of substituent on excited-state intramolecular proton transfer (ESIPT) and hydrogen bonding of N-(8-Quinolyl) salicylaldimine (QS) have been studied by theoretical calculation with DFT and TDDFT. The representative electron-withdrawing nitryl and electron-donating methoxyl were selected to analyze the effects on geometries, intramolecular hydrogen bond interaction, absorption/fluorescence spectra, and the ESIPT process. The configurations of the three molecules (QS, QS-OMe and QS-NO2) were optimized in the ground and excited states. The structure parameters, infrared spectra, hydrogen bond interactions, frontier molecular orbitals, absorption/fluorescence spectra, and potential curves have cross-validated the current results. The results show that the introduction of substituent results in a bathochromic-shift of the absorption and fluorescence spectra with large Stokes shift, and is more beneficial to the ESIPT process. The current work will be beneficial to the improvement of ESIPT properties and deepen understanding of the mechanism of ESIPT process. (C) 2020 Elsevier B.V. All rights reserved.

Automated summary

The study investigated the effects of substituents on N-(8-quinolyl) salicylaldimine (QS) through theoretical calculations, revealing that the introduction of substituents leads to a bathochromic-shift in absorption and fluorescence spectra, and is more beneficial for the ESIPT process.