Copper(I)‐catalysed synthesis of symmetrical perfluoroterphenyl analogues; fluorescence, antioxidant and molecular docking studies

Abstract

AbstractPentafluoroaryl analogues have been found to exhibit para specific nucleophilic aromatic substitution (SNAr). Herein, we describe the use of SNAr chemistry to create luminous perfluorinated symmetrical terphenyls. Both of SNAr chemistry and copper(I)‐catalysed decarboxylative cross‐coupling were applied for the synthesis of the perfluorinated symmetrical terphenyls in high yields from the corresponding derivatives of aryl iodide and potassium salt of fluorobenzoate. A series of perfluorinated symmetrical terphenyls with different para alkoxy chains were synthesized. The synthesized perfluorinated terphenyl adducts were confirmed via elemental analysis, Fourier‐transform infrared (FTIR), proton (1H) carbon‐13 (13C) and fluorine‐19 (19F) nuclear magnetic resonance (NMR) spectra. The absorbance and fluorescence spectra showed solvatochromic activities. The new synthesized fluoroterphenyl hybrids were screened against antioxidant inspection over DPPH (2,2‐diphenyl‐1‐picrylhydrazyl) performance, in assessment of vitamin C and butylated hydroxytoluene (BHT) as standard drugs exposed that fluoroterphenyl hybrid covering decyl hydrocarbons exhibited highest effectiveness through half maximal inhibitory concentration (IC50) values of 21.74 μg/ml. Additionally, molecular docking procedures of the synthesized fluoroterphenyl hybrids were employed by using protein data bank (PDB ID: 5IKQ). The docking simulation displayed convenient and recognized findings with the antioxidant examination.