Oligomeric dithieno[3,2-b:2'3'-d]pyrroles: Precursors for new conjugated systems and models of effective conjugation length

ORGN 453

Adam R. Wohl, adam.wohl@ndsu.edu and Seth C. Rasmussen, seth.rasmussen@ndsu.edu. Department of Chemistry and Molecular Biology, North Dakota State University, Fargo, ND 58105
Thiophene-based materials have been examined for industrial uses due to their desirable optical and electronic properties. Currently, oligothiophenes are receiving additional attention as both model systems for parent polymers and as active materials in a wide array of 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 quantum yields. To further study the DTP-based materials, two series of DTP oligomers are being prepared. The first series of discrete DTP oligomers contain alkyl end-groups which cap the á-positions to enhance stability and control solid-state organization. This series is of interest as both models of polymeric systems and potential FET materials. A second set of oligomers are being prepared as precursors to new DTP-based polyarylenevinylenes. The synthesis and characterization of both oligomeric series will be presented.