Synthesis and characterization of electron-deficient pentacenes

Christopher R. Swartz, Sean R. Parkin, Joseph E. Bullock, John E. Anthony, Alex C. Mayer, George G. Malliaras

Research output: Contribution to journalArticlepeer-review

271 Scopus citations


(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.

Original languageEnglish
Pages (from-to)3163-3166
Number of pages4
JournalOrganic Letters
Issue number15
StatePublished - Jul 21 2005

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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