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
C2 - 14602018
AN - SCOPUS:0344065646
VL - 5
SP - 4433
EP - 4436
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 23
ER -