6533b7d5fe1ef96bd1263aad

RESEARCH PRODUCT

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

Valdis KamparsAndrejs TokmakovsSergey BelyakovMartins RutkisEdgars NitissLauma Laipniece

subject

Process Chemistry and TechnologyGeneral Chemical Engineering02 engineering and technologyAzo couplingChromophore010402 general chemistry021001 nanoscience & nanotechnologyPhotochemistry01 natural sciencesAcceptor0104 chemical sciencesAmorphous solidchemistry.chemical_compoundchemistryPyridine0210 nano-technologyGlass transitionSingle crystalBenzoic acid

description

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 ArF) interactions are demonstrated in single crystal structure of dendronized azochromophore between pentafluorophenyl fragment and acceptor part of the azochromophore. The effect of Ar ArF 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 d33 values for molecular glasses containing single azochromophore were in the range from 20.2 to 50.5 pm⋅V−1.

https://doi.org/10.1016/j.dyepig.2018.10.035