Unexpected photooxidation of H-bonded tetracene

Organic Letters

Volumn 10, Issue 10, 2008, Pages 2007-2010

  Liang, Zhixiong ^a   Zhao, Wei ^a   Wang, Shenglong ^b   Tang, Qin ^a   Lam, Sheung Chuen ^a   Miao, Qian ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^b NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 58149178492     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800620s     Document Type: Article

References (32)

1. (a) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99-117.
2. (b) Dodabalapur, A. Mater. Today 2006, 9, 24-30.
3. (c) Jang, J. Mater. Today 2006, 9, 46-52.
4. (a) Facchetti, A. Mater. Today 2007, 10, 28-37.
5. (b) Murphy, A. R.; Fréchet. J. M. J. Chem. Rev. 2007, 107, 1066-1096.
6. (c) Anthony, J. E Chem. Rev. 2006, 106 (12), 5028-5048.
7. (a) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104 (11), 4891-4945.
8. (b) References 2b and 2c.
9. Yamada, M.; Ikemoto, I.; Kuroda, H. Bull. Chem. Soc. Jpn. 1988, 61, 1057-1062.
10. Maliakal, A.; Raghavachari, K.; Katz, H.; Chandross, E.; Siegrist, T. Chem. Mater. 2004, 16, 4980-4986.
11. (a) Aubry, J.-M.; Pierlot, C.; Rigaudy, J.; Schmidt, R. Acc. Chem. Res. 2003, 36, 668-675.
12. (b) Greer, A. Acc. Chem. Res. 2003, 39, 797-804.
13. Ono, K.; Totani, H.; Hiei, T.; Yoshino, A.; Saito, K.; Eguchi, K.; Tomura, M.; Nishida, J.; Yamashita, Y. Tetrahedron 2007, 63, 9699-9704.
14. (a) Chan, S. H.; Lee. H. K.; Wang, Y. M.; Fu, N. Y.; Chen, X. M.; Cai, Z. W.; Wong, H. N. C. Chem. Commun. 2005, 66-68.
15. (b) Zhou, X.; Kitamura, M.; Shen, B.; Nakajima, K.; Takahashi, T. Chem. Lett. 2004, 33, 410-411.
16. Bjarneson, D. W.; Petersen, N. O. J. Photochem. Photobiol, A: Chem. 1992, 63, 327-335.
17. (a) Coropceanu, V.; Cornil, J.; da Silva Filho, D, A.; Olivier, Y.; Silbey, R.; Bredas, J.-L. Chem. Rev. 2007, 107 (4), 926-952. (b) Reference 2.
18. (a) Bushey, M. L.; Hwang, A.; Stephens, P. W.; Nuckolls, C. J. Am. Chem. Soc. 2001, 123, 8157-8158.
19. (b) Lightfoot, M. P.; Mair, F. S.; Pritchard, R. G.; Warren, J. E. Chem. Commun. 1999, 1945-1946.
20. (c) Yang, E.; Fan, J.; Geib, S. J.; Stoner, T. C.; Hopkins, M. D.; Hamilton, A. D. J. Chem. Soc. Chem. Commun. 1995, 1251.
21. Direct bromination of tetracene yields 5, 11-dibromotetracene or a mixture of isomers, see:
22. (a) Avlasevich, Y.; Müllen. K. Chem. Commun. 2006, 4440-4442.
23. (b) Kyushin, S.; Ishikita, Y.; Matsumoto, H.; Horiuchi, H.; Hiratsuka, H. Chem. Lett. 2006, 35, 64-65.
24. Dihydrotetracene was previously synthesized by a different method, see:
25. 3 to reduce quinone to dihydro-arene, see:
26. (b) Shahlai. K.; Hart, H. J. Org. Chem. 1991, 56, 6905-6912.
27. For example of dehydrogenation by CuO, see: Satchell, M. P.; Stacey, B. E. J. Chem. Soc. 1971, 468.
28. Mason, R. Acta Crystallogr. 1964, 17. 547.
29. Lim, S.-H.; Bjorklund, T. G.; Spano, F. C.; Bardeen, C. J. Phys. Rev. Lett. 2004, 92, 107402.
30. 2 via H-bonds, see: Adam, W.; Peters, E. M.; Peters, K.; Prein, M.; von Schnering, H. G. J. Am. Chem. Soc. 1995, 117, 6686-6690.
31. DFT optimization was performed using: Frisch, M. J.; Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
32. Kavallieratos, K.; Bertao, C. M.; Crabtree, R. H. J. Org. Chem. 1999, 64, 1675-1683.