Synthesis of Fluoro and Cyanoaryl-Containing Pyrene Derivatives and their Optical and Electrochemical Properties

Mono- and 1,6-disubstituted pyrene derivatives bearing perfluorotoluene or perfluorobenzonitrile moieties were synthesized by nucleophilic substitution processes. The compounds were characterized by NMR, UV-vis, photoluminescence (PL), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltametry (CV) and density functional theory (DFT) calculations. It was found that derivatives substituted with perfluorobenzonitrile showed better thermal stability, stronger electron withdrawing ability and better fluorescence properties than the corresponding perfluorotoluyl-pyrene systems