Photophysical and biological aspects of α, β‐unsaturated ketones: Experimental and in silico approach

Abstract In this work, four fluorinated α, β ‐unsaturated ketones named as 3‐(3‐bromophenyl)−1‐(3‐(trifluoromethyl)phenyl)prop‐2‐en‐1‐one (1), 3‐(4‐methoxyphenyl)−1‐(3‐(trifluoromethyl)phenyl) prop‐2‐en‐1‐one (2), 3‐(3‐bromo‐5‐chloro‐2‐hydroxyphenyl)‐1‐(3‐(trifluoromethyl)phenyl) prop‐2‐en‐1‐one (3) and 3‐(2‐hydroxy‐5‐methylphenyl)‐1‐(3‐(trifluoromethyl)phenyl)prop‐2‐en‐1‐one (4) were synthesized by Claisen–Schmidt reaction. The synthesized molecules were then characterized through ultraviolet‐visible spectroscopy (UV‐Vis), Fourier transform infrared (FTIR), 1 H‐NMR, 13 C‐NMR, and mass spectrometry. The antioxidant potential, Urease inhibition, and interaction of compounds 1 – 4 with Salmon sperm DNA were experimentally explored and supported by molecular docking studies. The synthesized compounds strongly interact with SS‐DNA through intercalative mode. It was noticed that compound 1 served as potent Urease inhibitor while compound 4 as better antioxidant among synthesized compounds. Moreover, frontier molecular orbitals, nonlinear optical (NLO) properties, natural bond orbitals, molecular electrostatic potential, natural population analysis, and photophysical properties of synthesized compounds were accomplished through density functional theory and time‐dependent density functional theory. The band gap of all the compounds have been worked out using Taucs method. In addition to that, a precise comparative account of UV and IR data obtained from theoretical and experimental findings showed good agreement between theoretical and experimental data. The findings of our studies reflected that compounds 1 – 4 possess better NLO properties than Urea standard and the band gap data also reflected their prospective use towards optoelectronic materials. The better NLO behavior of compounds was attributed to the noncentrosymmetric structure of synthesized compounds.