Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 32, Pages 9878-9889Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200801549
Keywords
density functional calculations; luminescence; phosphorus heterocycles; semiconductors; sulfur heterocycles
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Funding
- Fonds der Chernischen Industrie
- BMBF
- Deutsche Forschungsgerriemschaft (DFG)
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- Hungarian Scientific Research Fund [T 049258]
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Benzo-condensed dithieno[3,2-b:2',3'-d]phospholes have been synthesized that allow convenient tuning of properties that are essential for application as semiconductor materials in organic field-effect transistor (OFET) devices. The versatile reactivity of the trivalent phosphorus atom in these heteropentacenes provides access to a series of materials that show different photophysical properties, significantly different organization in the solid state, and distinctly different electrochemical properties that can be achieved by simple chemical modifications. The materials show strong photoluminescence in solution and in the solid state that depends oil the electronic nature of the phosphorus center. Electrochemical studies revealed that the phosphorus atom intrinsically furnishes materials with n-channel or ambipolar behavior, also depending oil its electronic nature. The experimental data were verified by DFT quantum chemical calculations and suggest that the phosphorus-based heteropentacenes could be excellent candidates for n-channel OFET semiconductor materials.
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