ORGN 188 |
| Marcia M. Payne and John E. Anthony. Department of Chemistry, University of Kentucky, Chemistry/Physics Building, Lexington, KY 40503 |
| Organic semiconductors offer certain advantages over traditional hydrogenated-amorphous silicon devices, in that they offer the possibility for low-temperature processing such as spin-coating and the choice of flexible plastics as substrate. Pentacene and other acenes are one group of these materials, and have proven useful in field-effect transistor and light-emitting diode geometries, although pentacene has drawbacks resulting from inefficient packing. We have synthesized functionalized silylethynylated pentacenes that pack more efficiently in the solid state, providing greater stability and a decreased bandgap. With these observations, we propose a functionalized heptacene as a synthetic target, with the idea of creating a material with superior solid-state packing, resulting in good oxidative stability and a diminishingly small bandgap, due to excellent pi-overlap. One method that we have tried in this pursuit has been to synthesize the pentacene core with affixed o-diynes at each end which can subsequently be cyclized using Bergman conditions. Through a second route, we have synthesized a tetrahydro-7,16-bis(triisopropylsilylethynyl)heptacene, which requires only the double dehydrogenation to achieve our target. Attempts at accomplishing this transformation will be presented. |
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Functional pi-Electronic Systems
8:00 PM-10:00 PM, Sunday, March 23, 2003 Convention Center -- Hall G, Poster
Division of Organic Chemistry |