Hexathiapentacene: Structure, molecular packing, and thin-film transistors

Journal of the American Chemical Society

Volumn 128, Issue 49, 2006, Pages 15576-15577

  Briseno, Alejandro L ^a,b   Miao, Qian ^a   Ling, Mang Mang ^b   Reese, Colin ^b   Meng, Hong ^c   Bao, Zhenan ^b   Wudl, Fred ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Stanford University   (United States)

^c DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HEXATHIAPENTACENE; SULFUR DERIVATIVE; TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; DEVICE; ELECTRONICS; FILM; MASS SPECTROMETRY; MOLECULAR INTERACTION; SEMICONDUCTOR; STRUCTURE ANALYSIS; TEMPERATURE; THERMOGRAVIMETRY; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 33845430762     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066088j     Document Type: Article

References (27)

1. (a) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14.
2. (b) Forrest, S. R. Nature 2004, 428, 911-918.
3. (c) Meng, H.; Sun, F.; Goldfinger, M. B.; Gao, F.; Londono, D. J.; Marshal, W. J.; Blackman, G. S.; Dobbs, K. D.; Dalen, E.; Keys, D. E. J. Am. Chem. Soc. 2006, 128, 9304-9105.
4. (d) Cahen, D.; Modes, G. Adv. Mater. 2002, 14 (11), 789.
5. Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891-4945.
6. (a) Kelley, T. W.; Boardman, L. D.; Dunbar, T. D.; Muyres, D. V.; Pellerites, M. J.; Smith, T. P. J. Phys. Chem. B 2003, 107, 5877-5881.
7. (b) Klauk, H.; Gundlach, D. J.; Nichols, J. A.; Jackson, T. N. IEEE Trans. Electron. Devices 1999, 46, 1259.
8. (c) Klauk, H.; Halik, M.; Schieschang, V. Z.; Schimd, G.; Radilik, W.; Weber, W. J. Appl. Phys. 2002, 92, 5259.
9. (a) Mas-Torrent, M.; Rovira, C. J. Mater. Chem. 2006, 16, 433-436.
10. (b) Mas-Torrent, M.; Durkut, M.; Hadley, P.; Ribas, X.; Rovira, C. J. Am. Chem. Soc. 2004, 126, 984-985.
11. (c) Naraso Nishida, J.; Kumaki, D.; Tokito, S.; Yamashita, Y. J. Am. Chem. Soc. 2006, 128, 9598-9599.
12. Goodings, E. P.; Mitchard, D. A.; Owen, G. J. Chem. Soc. Perkin Trans. 1 1972, 1310-1314.
13. A U.S. patent on thioacenes is available (20050285156), but no crystal structure is yet deposited in the Cambridge Structural Database (CSD).
14. Meng, H.; Bendikov, M.; Mitchell, G.; Helgeson, R.; Wudl, F.; Bao, Z.; Siegrest, T.; Kloc, Ch.; Chen, C.-H. Adv. Mater. 2003, 15, 1090-1093.
15. For examples of S-S bond lengths and intermolecular S⋯S distances in aliphatic and aromatic disulfides, see: Riga, J.; Verbist, J.; Wudl, F.; Kruger, A. J. Chem. Phys. 1978, 69(7), 3221-3231.
16. (a) Arduengo, A. J.; Burgess, E. M. J. Am. Chem. Soc. 1977, 99, 2376-2378.
17. (b) Arduengo, A. J.; Constantine, A. S. Chem. Rev. 1994, 94, 1215-1237.
18. Hutchison, K.; Srdanov, G.; Hicks, R.; Yu, H.; Wudl, F.; Strassner, T.; Nendel, M.; Houk, K. N. J. Am. Chem. Soc. 1998, 120, 2989-2990.
19. (a) Perrin, C. L.; Kim, Y.-J.; Kuperman, J. J. Phys. Chem. A 2001, 105, 11383-11387.
20. (b) Bjernemose, J. K.; Frandsen, E.; Jensen, F.; Pedersen, C. Th. Tetrahedron 2003, 59, 10255-10259.
21. Moon, H.; Zeis, R.; Borkent, E.-J.; Besnard, C.; Lovinger, A. J.; Siegrist, T.; Kloc, Ch.; Bao, Z. J. Am. Chem. Soc. 2004, 126, 15322-15323.
22. (a) Kobayashi, K.; Shimaoka, R.; Kawahata, M.; Yamanaka, M.; Yamaguchi, K. Org. Lett. 2006, 8, 2385-2388.
23. (b) Kobayashi, K.; Masu, H.; Shuto, A.; Yamaguchi, K. Chem. Mater. 2005, 17, 6666-6673.
24. (c) 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.
25. Sheraw, C. D.; Jackson, T. N.; Eaton, D. L.; Anthony, J. E. Adv. Mater. 2003, 15, 2009-2011.
26. Cho, D. M.; Parkin, S. R.; Watson, M. D. Org. Lett. 2005, 7, 1067-1068.
27. Curtis, M. D.; Cao, J.; Kampf, J. W. J. Am. Chem. Soc. 2004, 126, 4318-4328.