2,9-Dibromopentacene: Synthesis and the role of substituent and symmetry on solid-state order

Toshihiro Okamoto, Colin Reese, Michelle L. Senatore, Ming L. Tang, Ying Jiang, Sean R. Parkin, Zhenan Bao

Research output: Contribution to journalArticlepeer-review

10 Scopus citations


We have developed an effective synthetic route for 2,9-dibromopentacene, opening up new possibilities for future derivatization of pentacene. We also present the fundamental properties. Thin-film and single-crystal field-effect transistor results demonstrate a decrease in apparent charge transport efficiency with decreasing symmetry. The trend in symmetry was further correlated to single-crystal structural analysis, which implied that reduction in symmetry also reduced solid-state order. It is likely that this reduction in order is responsible for the diminished performance in the solid-state films and crystal, despite a reduction in overall tilt angle of the molecules relative to one another. Combined with previous studies, this work provides a more complete perspective on the interplay of symmetry, energetic, and intermolecular interactions in the macroscopic properties of solid-state organic electronic materials.

Original languageEnglish
Pages (from-to)2447-2451
Number of pages5
JournalSynthetic Metals
Issue number23-24
StatePublished - Dec 2010

Bibliographical note

Funding Information:
Z.B. acknowledges partial financial support from the Global Climate and Energy Project (GCEP) and an AFSOR Grant.


  • High hole mobility
  • OFETs
  • Selective synthesis
  • Substituted pentacene

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Condensed Matter Physics
  • Mechanics of Materials
  • Mechanical Engineering
  • Metals and Alloys
  • Materials Chemistry


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