Synthesis and Characterization of Electron-Deficient Pentacenes
Organic Letters2005Vol. 7(15), pp. 3163–3166
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Christopher R. Swartz, Sean Parkin, Joseph E. Bullock, John E. Anthony, Alex C. Mayer, George G. Malliaras
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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