ORGN 615 |
| The semiconducting properties of conjugated oligomers and polymers makes them attractive materials for use in organic field effect transistors, light emitting diodes, solar cells and sensors. While the delocalization of discrete conjugated radical ions serves as a one-dimensional model for conduction in conjugated polymers, other polymer chains surround the segments of a polymeric conjugated chain in a thin film device and interchain interactions have a strong influence on the electronic structure of the material. The importance of interchain hopping between cofacially stacked arenes in conjugated materials led us to propose an extension of these models into the second-dimension by preparation and analysis of well-defined oligoarenes held in a permanent cofacial arrangement. Ketalization of diarene-fused bicyclo[4.4.1]undecanone restricts the conformation of the bicycle so that the two seven-membered rings adopt pseudo-chair conformations and the fused arene rings are held in a stacked arrangement. Installation of oligomeric conjugated arms (thiophenes, phenylenes, phenylene ethynylenes) on the fused rings of the core provide a family of model compounds to investigate the effect of stacking on the evolution of electronic structure in materials consisting of close-packed pi-electron-rich conjugated chains. |
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Materials, Devices, and Switches
8:00 AM-12:00 PM, Thursday, 30 March 2006 Georgia World Congress Center -- Georgia Ballroom 2, Oral
Division of Organic Chemistry |