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

Alaa M AlqahtaniHana M AbumelhaRua B AlnomanMatokah M AbualnajaHatun H AlshariefAhmed HameedAbdalaziz M AlmontsheryNashwa M El-Metwaly
Published in: Luminescence : the journal of biological and chemical luminescence (2023)
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 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 IC 50 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.
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