Synthesis of (thio)alkyloxy-substituted perfluorinated terphenyl derivatives: Optical properties, molecular docking and antioxidant activity

Abstract

Nucleophilic aromatic substitution (SNAr) has been known to be a strongly para-selective reaction for various multifunctional perfluoroaryls. In the current study, we report the application of SNAr chemistry to synthesize different derivatives of optically active symmetrical and asymmetrical perfluorinated fluoroterphenyl analogues. The synthesis procedures include a Cu-assisted decarboxylation of perfluorinated fluorobenzoate derivatives and SNAr reaction to produce (thio)alkyloxy-substituted perfluorinated fluoroterphenyls in respectable yield and superb purity starting from the potassium salt of perfluorobenzoate and aryl iodide. The synthesized adducts were inspected by FT-IR and 1H/13C/19F NMR spectroscopy. The optical properties of the synthesized perfluorinated adducts were explored. The absorption and fluorescence spectra showed solvatochromic properties. The DPPH procedure was utilized to inspect the synthesized perfluoroterphenyl analogues for their antioxidant activity. The results demonstrated that the perfluoroterphenyl adducts with asymmetrical hydrocarbon chain exhibited maximum efficiency over an IC50 =10.25±0.24 µg/mL. Moreover, the perfluoroterphenyl adducts were employed in molecular docking using (PDB: 5IKQ) protein.