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

doi:10.1021/ol035751v

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

Weizmann Institute of Science, Israel

Research output: Contribution to journal › Article › peer-review

160 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 language	English
Pages (from-to)	4433-4436
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	23
DOIs	https://doi.org/10.1021/ol035751v
Publication status	Published - Nov 13 2003

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol035751v

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title = "Efficient Synthesis of a Novel, Twisted and Stable, Electroluminescent {"}Twistacene{"}",

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.",

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T1 - Efficient Synthesis of a Novel, Twisted and Stable, Electroluminescent "Twistacene"

AU - Duong, Hieu M.

AU - Bendikov, Michael

AU - Steiger, Daniel

AU - Zhang, Qichun

AU - Sonmez, Gursel

AU - Yamada, Jeffrey

AU - Wudl, Fred

PY - 2003/11/13

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AB - (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.

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