High Hole Mobility in Triindole-Based Columnar phases: Removing the Bottleneck of Homogeneous Macroscopic Orientation

We report the synthesis, mesomorphic behavior, and mobility values of a series of highly ordered N-substituted triindole-based columnar liquid crystals. Shortening the length of N-alkylic substituents from N-dodecyl to N-methyl chains results in a drastic approach of the disks within the columns and in an impressive increase in charge carrier mobility. An study of aggregation in solution provide insights into the intermolecular forces responsible of the reduction of the intrastack distance as the size of the N-alkyl chains is decreased and offer evidence of stabilization of the columns by the contribution of cooperative CH-pi interactions. The materials presented here exhibit mobility values, even in totally misaligned columnar phases, that may compete with those of the best polycrystalline organic semiconductors, without the need of costly vacuum evaporation processes.