Thiophene-based materials have been examined for many different industrial uses due to their attractive optical and electronic properties. In recent years, oligothiophenes have received additional attention as both models for parent polymers and as active materials in devices such as field effect transistors (FETs), light emitting diodes (LEDs), photovoltaic cells, and spintronics. Oligomers incorporating N-functionalized dithieno[3,2-b:2'3'-d]pyrrole (DTP) units have been shown to exhibit enhanced electronic and optical properties, including high solution fluorescence efficiencies (up to 53%). Due to the N-functionalized side chains, these oligomers also exhibit desirable solubility characteristics allowing processing by either solution or vapor deposition techniques. To further investigate the potential of DTP-based materials, a series of DTP oligomers are being synthesized as models of larger polymeric systems and as potential FET materials. These oligomers will additionally contain alkyl groups, which will end-cap the á-positions to enhance stability and control solid-state organization.