Cu(I)-catalyzed Synthesis of Symmetrical Perfluoroterphenyl Analogues; Fluorescence, Antioxidant and Molecular Docking studies.

Abstract

Pentafluoroaryl analogues have been found to exhibit para specific nucleophilic aromatic substitution (SN Ar). Herein, we describe the use of SN Ar chemistry to create luminous perfluorinated symmetrical terphenyls. Both of SN Ar chemistry and Cu(I)-catalyzed decarboxylative cross-coupling were applied for the synthesis of those 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, FT-IR, 1 H/13 C NMR, and 19 F NMR spectra. The absorbance and fluorescence spectra showed solvatochromic activities. The new synthesized fluoroterphenyl hybrids were screened against antioxidant inspection over DPPH performance, in assessment to Vitamin C and BHT as standard drugs exposed that fluoroterphenyl hybrid covering decyl hydrocarbons exhibited highest effectiveness through IC50 values 21.74 μg/mL. Additionally, molecular docking procedures of the synthesized fluoro-terphenyl hybrids were employed by using (PDB ID: 5IKQ) protein. The docking simulation was displayed convenient and recognized findings with the antioxidant examination.