Synthesis, molecular docking and antioxidant activity of new fluorescent tetrafluoroterphenyl analogues.

Nucleophilic aromatic substitution (S N Ar) chemistry has been applied to develop many functionalized pentafluorobenzene derivatives. Those compounds are highly specific at the para position of the fluorinated ring. Therefore, they are typical adducts for the preparation of antioxidant molecular systems. In this context, we report the use of S N Ar chemistry as a suitable and simple synthetic approach for fluorescent antioxidant perfluorinated materials bearing ether bonds of various para-substituted alkoxy chains in high purity and excellent yields. The fluoroterphenyl core was prepared via alkylation, decarboxylated through Cu(I)-assisted, and cross-coupled by potassium salt of fluorobenzoate followed by reaction with different alcohols. The structures of the synthesized fluoroterphenyl adducts were proved by FT-IR, 1 H NMR, 13 C NMR, and 19 F NMR. The emission plus absorption spectra showed solvatochromism. In contrast to ascorbic acid and BHT as references, newly prepared tetrafluoroterphenyl analogues were investigated toward antioxidant examination through the DPPH process, which revealed that tetrafluoroterphenyl analogue containing the decyl chain had the highest activity over IC 50 value =22.36±0.19 g/mL. Also, using the protein (PDB ID: 5IKQ) through molecular docking strategies of the produced tetrafluoroterphenyl analogues were used. The antioxidant investigations and docking results were offered convergent results to each other.