Efficient Synthesis of a Novel, Twisted and Stable, Electroluminescent "Twistacene"

Hieu M. Duong, Michael Bendikov, Daniel Steiger, Qichun Zhang, Gursel Sonmez, Jeffrey Yamada, Fred Wudl

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155 Citations (Scopus)

Abstract

(Equation presented) A twistacene, 6,8,15,17-tetraphenyl-1.18,4.5,9.10,13. 14-tetrabenzoheptacene (3), was synthesized using a mild and novel bisbenzyne precursor. It was characterized by X-ray crystallography, NMR, UV-vis, and IR spectroscopies, as well as cyclic voltammetry and DFT calculations. The heptacene derivative possesses a nonpropeller twist topology and is unusually stable for a highly conjugated oligoacene. In addition, it is fluorescent, with a quantum efficiency of 15%. Distortion from planarity, mostly due to the phenyl substituents, causes only marginal changes in electronic properties and is beneficial for redox reversibility, which is required for efficient OLED devices.

Original languageEnglish
Pages (from-to)4433-4436
Number of pages4
JournalOrganic Letters
Volume5
Issue number23
DOIs
Publication statusPublished - Nov 13 2003

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Duong, H. M., Bendikov, M., Steiger, D., Zhang, Q., Sonmez, G., Yamada, J., & Wudl, F. (2003). Efficient Synthesis of a Novel, Twisted and Stable, Electroluminescent "Twistacene". Organic Letters, 5(23), 4433-4436. https://doi.org/10.1021/ol035751v