The promise of semiconducting materials with tunable electronic and optical properties that share the same mechanical flexibility, low production costs and ease of processing displayed by traditional polymers fuels the intense interest seen in developing devices employing conjugated polymers (CPs). Many examples of -conjugated systems have been studied and reported in the literature, of which Rasmussen and coworkers have advanced the field with their work involving N-alkyl, N-aryl, and N-acyl-dithieno[3,2-b:2',3'-d]pyrroles (DTPs). Using DTP as a template current investigations are targeting two analogues: pyrrolo[3,2-d:4,5-d’]bisthiazole (PBTz) and difuro[3,2-b:2’,3’-d]pyrroles (DFP). In comparison to polymers of DTP, the electron-deficient nature of thiazoles is known to stabilize HOMO levels of PBTz-based polymers. Furan-based oligomers exhibit many of the properties displayed by DTPs and it is a reasonable assumption that the properties of DFPs would be comparable to DTPs. The synthesis and characterization of PBTz and DFPs and a comparison to DTP-based materials will be presented.