Synthesis and characterization of electron-deficient pentacenes

(Chemical Equation Presented) Halogen functional groups on pentacene can be used both as synthetic handles for further functionalization as well as to tune the π-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.