H-Bond-Stabilized Triphenylene-Based Columnar Discotic Liquid Crystals

A 1,3,5-benzenetrisamide with three pending hexaalkoxytriphenylene groups has been synthesized as an example of an interesting class of intermolecular H-bond-stabilized columnar discotic liquid crystalline materials. The material forms a plastic hexagonal discotic phase that does not crystallize on cooling from the isotropic phase, even after annealing for a few days at room temperature. X-ray and computational studies provide a detailed model for the organization of this material. The charge carrier mobility, 0.12 cm2 V-1 s-1 at 180 C, is the highest ever reported for liquid crystalline triphenylene systems, and even increases with temperature. The factors responsible for this behavior are discussed.