Synthesis, spectral characterization, crystal examination, DFT method and molecular docking studies of 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-(thiophen-2-yl)-1H-phenanthro[9,10-d]imidazole

Abstract

We report a novel synthesis of 1-(2,3-dihydrobenzo[b][1,4]dioxin-7-yl)-2-(thiophen-2-yl)-1H-phenanthro [9,10-d]imidazole ( DDTP ) compound are conveniently found in one pot reaction. The novel compound DDTP had been characterized by FT-IR, 1 H-NMR and 13 C-NMR spectral techniques. The compound was also confirmed by single crystal XRD. The geometrical structure were optimized by density functional theory (DFT) method at B3LYP/6-31G (d,p) level of theory. The optimized geometrical parameters obtained by DFT calculation are in good agreement with single crystal XRD data. The stability and charge delocalization of the molecule were also studied by natural bond orbital (NBO) analysis. The HOMO-LUMO energies describe the charge transfer takes place within the molecule. Molecular electrostatic potential has been analyzed. The reported molecule used as a potential NLO material since it has high μβ 0 value. Hirshfeld surface analysis was carried out to detect the intermolecular interactions in the crystal structure. Molecular docking studies are performed to analyst the biological activity of the DDTP compound against standard drugs namely tetracycline, fluconazole and adriamycin with E.coli DNA gyrase, Cytochrome P450 14 alpha-sterol dimethylase (CYP51) and oxidised quinone reductase-2 inhibitors.