Hydrazones derivatives from halo-pyridinol: Synthesis and DFT-based theoretical exploration

Three novel halo-pyridinol-based hydrazone derivatives were synthesized successfully for their virtual optoelectronic properties. These are (E)-2-((2-chloropyridin-3-yl)oxy)-N'-(4-fluorobenzylidene)acetohydrazide (CPFH), (E)-N'-(4-chlorobenzylidene)-2-((2-chloropyridin-3-yl)oxy)acetohydrazide (CCPH), and (E)-2-((2-chloropyridin-3-yl)oxy)-N'-(4-methylbenzylidene)acetohydrazide (CPMH). All these compounds have been extensively characterized using nuclear magnetic resonance and infrared spectroscopic techniques. Additionally, their optoelectronic behavior was investigated using quantum chemical calculations with the omega B97XD/6-31+g(d,p) approach. Various properties of the synthesized compounds were explored using density functional theory (DFT) calculations, including NBO (natural bond orbital), NLO (non-linear optical properties), NPA (natural population analysis), and FMO (frontier molecular orbital) analyses. Furthermore, photophysical properties of these compounds were studied using a time-dependent DFT (TD-DFT) approach at the omega B97xd/6-31+g(d,p) level. The DFT investigations showed that compound CPMH possesses higher stabilization energy than CCPH and CPFH.