Pentacene has good semi-conducting properties but its practical use in organic thin film transistor (OTFT), organic photovoltaic (OPV) and organic light emitting diode (OLED) applications is limited due to its relative ease of oxidation and its low solubility. Recently, a combined experimental and computational study for a large series of pentacene derivatives revealed that HOMO-LUMO gaps and photo-oxidative resistances are strongly influenced by both steric and electronic substituent effects as well as the positional location of each substituent.<i> Alkylthio and arylthio substitutents provide for both smaller HOMO-LUMO gaps and enhanced photooxidative resistances. Inspired by our emerging understanding of substituent effects in pentacenes, we now report the rational design, synthesis and characterization of numerous new pentacene derivatives, all of which possess truly exceptional photooxidative resistances. They are all prime candidates for thin-film electronic device applications using low cost manufacturing techniques. Their field effect transistor properties have been measured and are described.<i> Kaur I.; Jia W.; Kopreski R. P.; Selvarasah S.; Dokmeci M. R.; Pramanik C.; McGruer N. E.; Miller G. P. J. Am. Chem. Soc. 2008, 130 (48), 16274-16286.

Rational design of pentacene derivatives with truly exceptional 
photooxidative resistances

240th National Meeting (2010)

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Rational design of pentacene derivatives with truly exceptional photooxidative resistances