Synthesis and characterization of electron-deficient pentacenes.
[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.
Swartz
Christopher R
CR
Department of Chemistry, University of Kentucky, Lexington, 40506-0055, USA.
Parkin
Sean R
SR
Bullock
Joseph E
JE
Anthony
John E
JE
Mayer
Alex C
AC
Malliaras
George G
GG