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

Pentafluoroaryl analogues have been found to exhibit para specific nucleophilic aromatic substitution (S_N Ar). Herein, we describe the use of S_N Ar chemistry to create luminous perfluorinated symmetrical terphenyls. Both of S_N Ar 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 (¹ H) carbon-13 (¹³ C) and fluorine-19 (¹⁹ F) 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.