Abstract: Polycyclic aromatic dyes have been widely studied as self-organizing building blocks due to their intrinsic shape-anisotropy and propensity to microphase segregate from flexible side-chains. Most of the reported mesomorphic dyes, however, are based on a single type of design. A rather symmetric polycyclic aromatic core, often disc-shaped, is symmetrically substituted with peripheral flexible side-chains. Clearly, this design imposes limitations on the number and properties of available core structures and on the materials properties that can be achieved. Our recent work has focused on the development of new design criteria for less conventional self-organizing polycyclic aromatic dyes that include board-shaped core structures, donor-acceptor-type polycyclic aromatic dyes, and side-chain free but conformationally flexible dyes. Materials derived from these new dyes display new mesophases, in addition to the conventional columnar mesophases, and show unusual properties, such as temperature dependent fluorescence and selective charge transport of electrons and holes.