I will discuss new results from our group's ongoing studies to explore new or otherwise underutilized aromatic topologies as viable organic electronic materials. As a proof of principle, I will present a detailed study with two ten pi electron aromatic motifs, that of the cyclic polyene methano[10]annulene and of the more classical aromatic, naphthalene. Thiophene-based semiconductors derived from the annulene show much greater propensities to transport charge as deduced from the structural changes that accompany electrochemical oxidation. Using this principle as a guide, the design and synthesis of new organic electronic platforms will be addressed.