Synthesis and characterization of electron-deficient pentacenes |
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Authors: | Swartz Christopher R Parkin Sean R Bullock Joseph E Anthony John E Mayer Alex C Malliaras George G |
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Institution: | Department of Chemistry, University of Kentucky, Lexington, 40506-0055, USA. |
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Abstract: | structure: see text]. Halogen functional groups on pentacene can be used both as synthetic handles for further functionalization as well as to tune the pi-stacking in these systems. The halogenated pentacene derivatives described here (X = Br, X' = H, and X = X' = F) are all stable and soluble, with reduction potentials significantly lower than that of the parent functionalized pentacene (X = X' = H). The bromopentacenes could be further elucidated to pentacene nitriles, further decreasing the acene's reduction potential, while the charge-carrier mobility in the fluorinated systems was shown to scale with the degree of fluorine substitution. |
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