Three-step synthesis of end-substituted pentacenes

Journal of Organic Chemistry

Volumn 72, Issue 25, 2007, Pages 9776-9778

  Stone, Matthew T ^a   Anderson, Harry L ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLATION; PENTACENES; TRIMETHYLSILYL SUBSTITUENTS;

ORGANIC SOLVENTS; OXIDATION; SOLUBILITY; SYNTHESIS (CHEMICAL);

OLEFINS;

1,4,8,11 TETRAPHENYL 2,3,9,10 TETRAKIS(METHOXYCARBONYL)PENTACENE; BENZENE DERIVATIVE; CARBONYL DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; METHYL GROUP; ORGANIC SOLVENT; PHENYL GROUP; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG; ZIRCONIUM DERIVATIVE;

ALKYNYLATION; ARTICLE; OXIDATION; SOLUBILITY; SYNTHESIS;

EID: 36849071904     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7017284     Document Type: Article

References (28)

1. Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891-4945.
2. Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048.
3. Payne, M. M.; Parkin, S. R.; Anthony, J. E.; C., K. C.; Jackson, T. N. J. Am. Chem. Soc. 2005, 127, 4986-4987.
4. Wolak, M. A.; Jang, B. B.; Paulis, L. C.; Kafafi, Z. H. J. Phys. Chem. B 2004, 108, 5492-5499.
5. Sheraw, C. D.; Jackson, T. N.; Eaton, D. L.; Anthony, J. E. Adv. Mater. 2003, 15, 2009-2011.
6. Miao, Q.; Chi, X.; Xiao, S.; Zeis, R.; Lefenfeld, M.; Siegrist, T.; Steigerwald, M. L.; Nuckolls, C. J. Am. Chem. Soc. 2006, 128, 1340-1345.
7. Payne, M. M.; Parkin, S. R.; Anthony, J. E. J. Am. Chem. Soc. 2005, 127, 8028-8029.
8. Payne, M. M.; Delcamp, J. H.; Parkin, S. R.; Anthony, J. E. Org. Lett. 2004, 6, 1609-1612.
9. Kobayashi, K.; Shimaoka, R.; Kawahata, M.; Yamanaka, M.; Yamaguchi, K. Org. Lett. 2006, 8, 2385-2388.
10. Stone, M. T.; Anderson, H. L. Chem. Commun. 2007, 2387-2389.
11. Kivelson, S.; Chapman, O. L. Phys. Rev. B. 1983, 28, 7236-7242.
12. Lowe, J. P.; Kafafi, S. A. J. Phys. Chem. 1986, 90, 6602-6610.
13. Houk, K. N.; Lee, P. S.; Nendel, M. J. Org. Chem. 2001, 66, 5517-5521.
14. Bendikov, M.; Duong, H. M.; Starkey, K.; Houk, K. N.; Carter, E. A.; Wudl, F. J. Am. Chem. Soc. 2004, 126, 7416-7417.
15. Maulding, D. R.; Roberts, B. G. J. Org. Chem. 1969, 34, 1734-1736.
16. Vets, N.; Smet, M.; Dehaen, W. Synlett 2005, 217-222.
17. Swartz, C. R.; Parkin, S. R.; Bullock, J. E.; Anthony, J. E.; Mayer, A. C.; Malliaras, G. G. Org. Lett. 2005, 7, 3163-3166.
18. Jiang, J. Y.; Kaafarani, B. R.; Neckers, D. C. J. Org. Chem. 2006, 71, 2155-2158.
19. Takahashi, T.; Kitamura, M.; Shen, B.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 12876-12877.
20. Takahashi, T.; Li, S.; Huang, W. Y.; Kong, F. Z.; Nakajima, K.; Shen, B. J.; Ohe, T.; Kanno, K. J. Org. Chem. 2006, 71, 7967-7977.
21. Gopalsamuthiram, V.; Wulff, W. D. J. Am. Chem. Soc. 2004, 126, 13936-13937.
22. A thermally driven retro-Diels-Alder reaction to produce substituted pentacenes from thin films of the corresponding p-chloranil pentacence adduct is reported in the patent: Yoshitoku, N.; Kazuto, O. (Asahi Kasei Co.). Jpn. Kokai Tokkyo Koho 2005232136, 2005.
23. Regioselectivity of Diels-Alder adduct 5 was assumed on the basis of ref 24.
24. Zhou, X.; Kitamura, M.; Shen, B. J.; Nakajima, K.; Takahashi, T. Chem. Lett. 2004, 33, 410-411.
25. Chan, S. H.; Lee, H. K.; Wang, Y. M.; Fu, N. Y.; Chen, X. M.; Caid, Z. W.; Wong, H. N. C. Chem. Commun. 2005, 66-68.
26. Reichwagen, J.; Hopf, H.; Desvergne, J. P.; Del Guerzo, A.; Bouas-Laurent, H. Synthesis 2005, 3505-3507.
27. Herwig, P. T.; Mullen, K. Adv. Mater. 1999, 11, 480-+.
28. Weidkamp, K. P.; Afzali, A.; Tromp, R. M.; Hamers, R. J. J. Am. Chem. Soc. 2004, 126, 12740-12741.