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

Research output: Contribution to journalArticle

147 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

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X ray crystallography
X Ray Crystallography
Organic light emitting diodes (OLED)
Ultraviolet spectroscopy
Quantum efficiency
Discrete Fourier transforms
Electronic properties
Cyclic voltammetry
crystallography
Oxidation-Reduction
quantum efficiency
Infrared spectroscopy
Spectrum Analysis
topology
Nuclear magnetic resonance
Topology
Derivatives
Equipment and Supplies
nuclear magnetic resonance
causes

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

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

Efficient Synthesis of a Novel, Twisted and Stable, Electroluminescent "Twistacene". / Duong, Hieu M.; Bendikov, Michael; Steiger, Daniel; Zhang, Qichun; Sonmez, Gursel; Yamada, Jeffrey; Wudl, Fred.

In: Organic Letters, Vol. 5, No. 23, 13.11.2003, p. 4433-4436.

Research output: Contribution to journalArticle

Duong, HM, 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, vol. 5, no. 23, pp. 4433-4436. https://doi.org/10.1021/ol035751v
Duong, Hieu M. ; Bendikov, Michael ; Steiger, Daniel ; Zhang, Qichun ; Sonmez, Gursel ; Yamada, Jeffrey ; Wudl, Fred. / Efficient Synthesis of a Novel, Twisted and Stable, Electroluminescent "Twistacene". In: Organic Letters. 2003 ; Vol. 5, No. 23. pp. 4433-4436.
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