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

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4433-4436

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

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC COMPOUND;

ARTICLE; CYCLIC POTENTIOMETRY; INFRARED SPECTROSCOPY; LUMINESCENCE; MATHEMATICAL COMPUTING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM CHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 0344065646     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035751v     Document Type: Article

References (27)

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16. Yang, Y.; Xu, Q.; Duong, H. M.; Wudl, F. Manuscript is in preparation.
17. 1H NMR (ODCB, 400 K, 500 MHz) δ 8.56 (s, 2H), 7.98 (d, 4H, J = 7.93 Hz), 7.71 (s, 4H), 7.68 (d, 4H, J = 7.93 Hz), 7.33-7.41 (m, 20H), 7.24 (t, 4H, J = 7.93 Hz); elemental analysis found C 95.12, H 4.76; calcd C 95.39, H 4.61; MALDI-TOF MS found 830.2940, calcd 830.2974.
18. For details, see Supporting Information.
19. For preparation of 4, see: Bock, H.; Nick, S.; Ruppert, K. Z. Naturforsch. 1995, 50, 595.
20. Bisbenzyne precursor 5 is a modification from the benzyne motif of: Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211.
21. Hart, H.; Dong, O. J. Org. Chem. 1986, 51, 979.
22. Netka, J.; Crump, S. L.; Rickborn, B. J. Org. Chem. 1986, 51, 1189.
23. Winling, A.; Russell, R. A. J. Chem. Soc., Perkin Trans. 1 1998, 3921.
24. This notation refers to bisbenzyne precursor where both arynes are promoted in one reaction.
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26. (b) Ferguson, G.; Parvez. M. Acta Crystallogr. 1979, B35, 2419.
27. See 3a in Supporting Information.