4-Diphenylaminobenzaldehyde-formulated isonicotinohydrazide for the rapid recognition of Cu2+ ions; Application of RGB tool, pharmaceutical samples, and DFT studies

Abstract

High copper concentrations have been linked to several harmful illnesses in humans and negatively affect the kidneys and liver. The design and synthesis of simple and effective chemosensors for recognizing copper (Cu2+) ions are extremely significant. However, most of the colorimetric chemosensors have been developed using an intramolecular charge transfer binding mechanism based on donor-acceptor conjugation systems. This study aimed to fabricate a novel Schiff base colorimetric chemosensor, N'-(4-(diphenylamine) benzylidene) isonicotinohydrazide (DPBA-INH), with high sensitivity and selectivity towards copper ions in the semi-aqueous medium (DMSO: H2O, 7:3, v/v). The synthesized receptor DPBA-INH was distinguished using various spectroscopic methods, including NMR analysis, Fourier transform infrared spectroscopy, HRMS, and ultraviolet-visible (UV–vis) spectroscopy. When exposed to sunlight, the receptor DPBA-INH with Cu2+ ion complexation exhibited a color change from orange to pale yellow. A Job's plot and electrospray ionization mass spectra confirmed the presence of complexation at a stoichiometric binding proportion of the receptor to Cu2+ ions of 1:1. The receptor DPBA-INH interacts with Cu2+ ions in a 1:1 stoichiometric manner with a detection limit of 1.40 × 10−7 M. The experimental results were supported by a theoretical DFT study. Moreover, the receptor effectively measured Cu2+ ions in pharmaceutical samples and test strip analyses. Furthermore, the rapid colorimetric recognition of Cu2+ ions in a semi-aqueous medium was achieved using DPBA-INH, which was demonstrated to be an excellent receptor. Notably, DPBA-INH was employed to detect copper ions in real water samples.