Semiconducting and electropolymerizable liquid crystalline carbazole-containing porphyrin-core dendrimers

Abstract

The self-assembly of liquid crystals (LCs) is an important method to control the organization of single molecules into periodically nanostructured phases that have found applications in organic electronics. Herein, we report a new family of LC porphyrin-core dendrimers bearing carbazole moieties at the periphery of the dendrimer. These compounds are synthetic light-harvesting antennas, which exhibit intramolecular energy transfer from the carbazole moieties to the central porphyrin core. We also demonstrate that it is possible to deposit spherical polymeric nanoparticles on ITO electrodes via electrochemical crosslinking of peripheral carbazole units. Moreover, the porphyrin-core dendrimers exhibit discotic nematic phases with excellent film-forming properties and a strong tendency towards defect-free homeotropic alignment. Charge mobility studies reveal promising semiconductor properties with high hole mobility values. Therefore, such carbazole-containing LC dendrimers exhibit a unique combination of interesting properties, opening the way for the preparation of new optoelectronic materials.