Discotic mesophase materials are increasingly interesting as potential molecular electronic materials, owing to the high charge mobilities which have been observed in linear, cofacial aggregates of disk-like molecules, such as triphenylenes, hexabenzocoronenes, phthalocyanines, and certain modified perylene-bisimide dyes. Among these dyes, the phthalocyanines are one of the most interesting for applications requiring high light absorptivity, e.g. for organic photovoltaic applications. The challenge has been to design side chains for these molecules which impart solubility in common solvents, and help direct their self-organization into linear aggregate columnar structures, with the proper orientation for the proposed technological application. This talk will focus on our recent efforts to develope new Pc-based discotic materials (inspired by the initial work done in collaboration with David O'Brien), and will discuss how coherence in the aggregate materials is enhanced by the proper choice of side chain, the choice of atom at the attachment point to the Pc core, and the inclusion of either polymerizable, or hydrogen-bonding functional groups in the side chains themselves.