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

Nucleophilic aromatic substitution (SNAr) 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 SNAr chemistry as a suitable and simple approach for the synthesis of fluorescent antioxidant perfluorinated materials bearing ether bonds in various para‐substituted alkoxy chains and with high purity and excellent yields. The fluoroterphenyl core was prepared via alkylation, Cu(I)‐assisted decarboxylation, and cross‐coupling using the potassium salt of fluorobenzoate, followed by the reaction with different alcohols. The structures of the synthesized fluoroterphenyl adducts were investigated using FT‐IR, 1H NMR, 13C NMR, and 19F NMR spectroscopy. The emission spectra and absorption spectra showed solvatochromism. The newly prepared tetrafluoroterphenyl analogues were investigated by antioxidant examination using the 2,2‐diphenyl‐1‐picrylhydrazyl assay. Results were compared with ascorbic acid and butylated hydroxytoluene as references, and revealed that the tetrafluoroterphenyl analogues containing a decyl chain had the highest activity, with an IC50 value of 22.36 ± 0.19 g/ml. The produced tetrafluoroterphenyl analogues were used in molecular docking strategies with a Protein Data Bank protein ID 5IKQ. The antioxidant investigations and docking results were convergent. The fluorinated decyl hydrocarbon sequence on the tetrafluoro‐terphenyl hybrid demonstrated prominent antioxidant results (IC50 = 22.36 ± 0.19 μg/ml). The high binding score for the decyl hybrid S = −10.6436 kcal/mol with the root mean square deviation of 1.1514 using molecular docking stimulation.