A comparative study of conjugated polymers derived from the two 10 electron circuits of naphthalene and methano[10]annulene is presented.The annulene topology allows for a greater degree of intrapolymer charge delocalization, a key structural parameter for enhancing theperformance of organic semiconductors. Molecular design and synthesis based upon unusual aromatic cores will enable facile transportproperties that would not ordinarily be realized under the 6 electron aromatic paradigm.