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 | |
| Publication status | Published - Nov 13 2003 |
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ASJC Scopus subject areas
- Molecular Medicine
Cite this
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 journal › Article
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TY - JOUR
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
Y1 - 2003/11/13
N2 - (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.
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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U2 - 10.1021/ol035751v
DO - 10.1021/ol035751v
M3 - Article
VL - 5
SP - 4433
EP - 4436
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 23
ER -