Synthesis and characterization of electron-deficient pentacenes

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3163-3166

  Swartz, Christopher R ^a   Parkin, Sean R ^a   Bullock, Joseph E ^a   Anthony, John E ^a   Mayer, Alex C ^b   Malliaras, George G ^b  

^a UNIVERSITY OF KENTUCKY   (United States)

^b Cornell University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 23044444783     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050872b     Document Type: Article

References (23)

1. Meng, H.; Bendikov, M.; Mitchell, G.; Helgeson, R.; Wudl, F.; Bao, Z.; Siegrist, C.; Kloc, C.-H. Adv. Mater. 2003, 15, 1090.
2. Sakamoto, Y.; Suzuki, T.; Kobayashi, M.; Gao, Y.; Fukai, Y.; Inoue, Y.; Sato, F.; Tokito, S. J. Am. Chem. Soc. 2004, 126, 8138.
3. Payne, M. M.; Delcamp, J. H.; Parkin, S. R.; Anthony, J. E. Org. Lett. 2004, 6, 3325.
4. See for example: (a) Weck, M.; Dunn, A. R.; Matsumoto, K.; Coates, G. W.; Lobkovsky, E. B.; Grubbs, R. H. Angew. Chem., Int. Ed. 1999, 38, 2741.
5. (b) Ponzini, F.; Zagha, R.; Hardcastle, K.; Siegel, J. S. Angew. Chem., Int. Ed. 2000, 39, 2323.
6. (c) Gillard, R. E.; Stoddart, J. F.; White, A. J. P.; Williams, B. J.; Williams, D. J. J. Org. Chem. 1996, 61, 4504.
7. Ried, W.; Anthöfer, F. Angew. Chem. 1953, 65, 601.
8. Perepichka, D. F.; Bendikov, M.; Meng, H.; Wudl, F. J. Am. Chem. Soc. 2003, 125, 10190.
9. (a) Cava, M. P.; Shirley, R. L. J. Am. Chem. Soc. 1960, 82, 654.
10. (b) Cava, M. P.; Napier, D. R. J. Am. Chem. Soc. 1957, 79, 1701.
11. For the use of this reaction in the synthesis of pentacenequinone, see: Miller, G. P.; Mack, J.; Briggs, J. Proc. Electrochem. Soc. 2001, 11, 202.
12. Anthony, I. J.; Wege, D. Aust. J. Chem. 1996, 49, 1263.
13. Coe, P. L.; Croll, B. T.; Patrick, C. R. Tetrahedron 1967, 23, 505.
14. (a) Funk, R. L.; Young, E. R. R.; Williams, R. M.; Flanagan, M. F.; Cecil, T. L. J. Am. Chem. Soc. 1996, 118, 3291.
15. (b) Miller, G. P.; Mack, J.; Briggs, J. Org. Lett. 2000, 2, 3983.
16. Jones, B. A.; Ahrens, M. J.; Yoon, M.-H.; Facchetti, A.; Marks, T.; Wasielewski, M. R. Angew. Chem., Int. Ed. 2004, 43, 6363.
17. (a) Eberhardt, W.; Hanack, M. Synthesis 1998, 1760.
18. (a) Sakamoto, T.; Ohsawa, K. J. Chem. Soc., Perkin Trans. 1 1999, 2323.
19. (b) Zanon, J.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 2890.
20. Sheraw, C. D.; Jackson, T. N.; Eaton, D. L.; Anthony, J. E. Adv. Mater. 2003, 15, 2009.
21. Crystallography was also performed on bromopentacenes 4 and 5; the structural data is presented in Supporting Information.
22. For a detailed theoretical treatment, see: Brédas, J. L.; Calbert, J. P.; da Silva Filho, D. A.; Cornil, J. Proc. Nat. Acad. Sci. U.S.A. 2002, 99, 5804.
23. Miao, Q.; Lefenfeld, M.; Nguyen, T.-Q.; Siegrist, T.; Kloc, C.; Nuckolls, C. Adv. Mater. 2005, 17, 407.