Exploration of intramolecular charge transfer in para-substituted nitrobenzofurazan: Experimental and theoretical analyses

[Display omitted] •A joint experimental and theoretical study on structural and optoelectronic properties of para-substituted NBD.•The optical and electrochemical properties of a para-substituted NBD were theoretically predicted.•NBO, QTAIM, NCI and RDG analyses were computed to understand the nature and type of intermolecular interactions stabilizing our system. The present work aims at exploring the high electrophilic character of 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole (NBD-Cl) toward the morpholine group by an SNAr reaction in acetonitrile or water (thereafter referred to as NBD-Morph). The electron-donating ability of the morpholine causes intra-molecular charge transfer (ICT). In this report, we present a comprehensive study on the optical characteristics using UV–Vis, photoluminescence (cw-PL) and its time-resolved (TR-PL) to determine the properties of the emissive intramolecular charge transfer (ICT) in the NBD-Morph donor–acceptor system. An exhaustive theoretical investigation utilizing the density functional theory (DFT) and its extension TD-DFT methods is an essential complement of experiments to rationalize and understand the molecular structure and related properties. The findings from QTAIM, ELF, and RDG analyses establish that the bonding between morpholine and NBD moieties is of the electrostatic or hydrogen bond type. In addition, the Hirshfeld surfaces have been established to explore the types of interactions. Further, the non-linear optical (NLO) responses of the compound have been examined. The structure–property relationships obtained through the combined experimental and theoretical offer valuable insights for designing efficient NLO material.