Structure-property relationship studies in a class of discotic liquid crystals

ORGN 369

Piotr Kaszynski1, Monika Sienkowska1, John M. Farrar1, Wiktor Piecek1, Paul A. Heiney2, and Fan Zhang2. (1) Department of Chemistry, Vanderbilt University, Nashville, TN 37235, (2) Department of Physics and Astonomy, University of Pennsylvania, Philadelphia, PA 19104-6323
In the context of our studies of liquid crystalline radicals, we focused on a class of discotic liquid crystals containing phenanthrene, benzocinnoline, pyrene, tetraazapyrene, and carbazole as rigid cores with alkoxyphenyl substituents. These compounds were prepared by Suzuki coupling of the corresponding tetrabromo derivatives and arylboronic esters. Their thermal behavior was studied as a function of the core structure and the number of alkoxy substituents on the phenyl rings. These studies showed that at least two alkoxy groups are required for the introduction of liquid crystalline behavior. Liquid crystalline properties were characterized by optical microscopy, DSC, and XRD. In addition, carbazole and pyrene-based liquid crystals were investigated for their photoconductive properties.