Dendronized azochromophores with aromatic and perfluoroaromatic fragments: Synthesis and properties demonstrating ArArF interactions

Abstract Syntheses of four new dendronized azochromophores were performed from 2-(2-amino-5-nitrophenoxy)ethanol, 2-[methyl(phenyl)amino]ethanol, 3,5-bis(benzyloxy)benzoic acid and 3,5-bis[(pentafluorophenyl)methoxy]benzoic acid using azo coupling reaction and ester formation reaction in presence of N,Nʹ -dicyclohexylcarbodiimide and 4-(dimethylamino)pyridine. Arene-perfluoroarene (Ar Ar F ) interactions are demonstrated in single crystal structure of dendronized azochromophore between pentafluorophenyl fragment and acceptor part of the azochromophore. The effect of Ar Ar F interactions becomes apparent in thermal and nonlinear optical properties of the chromophores. Glass transition temperatures of synthesized azochromophores are in the range from 37 to 60 °C. Nonlinear optical properties of synthesized azochromophores were characterized by second harmonic intensity measurements in corona poled thin films of pure amorphous solids. Nonlinear optical coefficient d 33 values for molecular glasses containing single azochromophore were in the range from 20.2 to 50.5 pm⋅V −1 .