Spectral analysis and DFT investigation of some benzopyran analogues and their self-assemblies with graphene

Abstract

Spectroscopic analysis and different quantum mechanical studies of four phramaceutically active flavanoid compounds, 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one (genistein) (F1), 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one (apigenin) (F2), 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one (baicalein) (F3) and 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one (fisetin) (F4) are reported in this manuscript using DFT/B3LYP/6-311++G(d,p) level of theory. Simulated IR spectrum of these compounds was compared with experimentally available data, and essential functional group assignments were made. NBO studies helped to study the various intramolecular electron delocalisation possible in the molecule. We also report the frontier orbital properties and other derived local energy descriptors which talks about the relative stability and reactivity of the compounds. The photovoltaic efficiency of the compounds was studied from the simulated electronic spectra. The compound was found to interact with graphene, to form molecular self-assembly. These self-assemblies showed tremendous enhancement in various physicochemical properties when compared with its constituents. Biological activity of the compounds were predicted using molecular docking studies.