Recent research interests in the use of organic semiconductors as an alternative source for green energy have sparked widespread studies into the optimization of such devices for practical and efficient use and application in semiconductor indrustry. Pentacene and pentacene derivatives are promising candidates for organic semiconductors because they exhibit similar conduction mechanisms to inorganic semiconductors.The research was performed to chemically control the chemoselective oxidation of 6,13-Bis(decylthio)pentacene, a thio substitued pentacene derivative. The products of oxidation: 6-(decylsulfinyl)-13-decylthio)pentacene and 6,13-Bis(decylsulfinyl)pentacene were characterized  by nmr, uv, mass spectra, and elctrochemical techniques. The half�life of 6-(decylsulfinyl)-13-decylthio)pentacene was  longer ( 2900min) compared to the starting material and 6,13-Bis(decylsulfinyl)pentacene. However, both products had similar HOMO-LUMO gaps as determined by cyclic voltametry. Using 0.5 equiv of mCPBA gave the maximum yield ( 72%) of  6-(decylsulfinyl)-13-decylthio)pentacene. This product was  a better semiconductor due to higher stablity.

Chemoselective oxidation of 6,13-bis(decylthio)pentacene

243rd National Meeting (2012)

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