Selective recognition of Pb(II) and Cr(III) by novel maleic hydrazide-based 1,2,3-triazole linked derivatives

Abstract

The present report describes the application of versatile and stereospecific Copper(I) catalyzed alkyne-azide cycloaddition (CuAAC) reaction to synthesize two novel maleic hydrazide appended 1,2,3-triazole based chemosensors (5 and 6) as selective probes for Pb(II) and Cr(III) recognition. Maleic hydrazide is a plant growth regulator known to prevent cell division. The probes were characterized via IR, NMR (1H and 13C) spectroscopy and mass spectrometry; and subsequently explored for their ion sensing behavior in DMSO as solvent media via UV–Vis spectroscopy. The probe 5 displayed peak at 312 nm accompanied by a smaller peak at 258 nm; whereas the probe 6 exhibited peaks at 274 nm, 284 nm and 294 nm. Furthermore, the association constants for probe 5 were determined to be 0.61×105M−1 and 0.20×106M−1 for Pb(II) and Cr(III) respectively; and for probe 6 the association constant values for Pb(II) and Cr(III) were 0.46×106M−1 and 0.76×106M−1 respectively. Structural optimization of both the probes was carried out using DFT with hybrid density functional (B3LYP)/6–311G++(d,p)basis set of theory and LANL2DZ basis set was utilized to optimize the representative 5+metal complex . Subsequent docking analysis of 5 and 6 was carried out with leukotriene b4 via AutoDock Vina to get perceptions about their potential anti-inflammatory properties, wherein the binding energies of the probes 5 and 6 were observed to be -8.3 and -9.6 kcal/mol respectively.