Cruciform π-systems for molecular electronics applications

Journal of the American Chemical Society

Volumn 125, Issue 20, 2003, Pages 6030-6031

  Klare, Jennifer E ^a   Tulevski, George S ^a   Sugo, Kenji ^a   De Picciotto, Anat ^a   White, Kiley A ^a   Nuckolls, Colin ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; BENZOXAZOLE DERIVATIVE; PHENYL GROUP; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; DEVICE; ELECTRODE; ELECTRONICS; FILM; MICHAEL ADDITION; MOLECULAR MECHANICS; MOLECULE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; THICKNESS;

EID: 0037613542     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0350942     Document Type: Article

References (44)

1. In mechanically broken junctions: Reed, M. A.; Zhou, C.; Muller, C. J.; Burgin, T. P.; Tour. J. M. Science 1997, 278, 252-254.
2. In electromigrated junctions: (a) Park, H.; Lim, A. K. L.; Alivisatos, A. P.; Park, J.; McEuen, Paul L. Appl. Phys. Lett. 1999, 400, 301-303. (b) Park, J.; Pasupathy, A. N.; Goldsmith, J. I.; Chang, C.; Yalsh, Y.; Petta, J. R.; Rinkoski, M.; Sethna, J. P.; Abruha, H. D.; McEuen, P. L.; Ralph, D. C. Nature 2002, 417, 722-725. (c) Liang, W.; Shores, M. P.; Bockrath, M.; Long, J. R.; Park, H. Nature 2002, 417, 725-729.
3. In electromigrated junctions: (a) Park, H.; Lim, A. K. L.; Alivisatos, A. P.; Park, J.; McEuen, Paul L. Appl. Phys. Lett. 1999, 400, 301-303. (b) Park, J.; Pasupathy, A. N.; Goldsmith, J. I.; Chang, C.; Yalsh, Y.; Petta, J. R.; Rinkoski, M.; Sethna, J. P.; Abruha, H. D.; McEuen, P. L.; Ralph, D. C. Nature 2002, 417, 722-725. (c) Liang, W.; Shores, M. P.; Bockrath, M.; Long, J. R.; Park, H. Nature 2002, 417, 725-729.
4. In electromigrated junctions: (a) Park, H.; Lim, A. K. L.; Alivisatos, A. P.; Park, J.; McEuen, Paul L. Appl. Phys. Lett. 1999, 400, 301-303. (b) Park, J.; Pasupathy, A. N.; Goldsmith, J. I.; Chang, C.; Yalsh, Y.; Petta, J. R.; Rinkoski, M.; Sethna, J. P.; Abruha, H. D.; McEuen, P. L.; Ralph, D. C. Nature 2002, 417, 722-725. (c) Liang, W.; Shores, M. P.; Bockrath, M.; Long, J. R.; Park, H. Nature 2002, 417, 725-729.
5. In monolayer devices: (a) Aviram, A.; Ratner, M. A. Chem. Phys. Lett. 1974, 29, 277-283. (b) Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550-1552. (c) Zhitenev, N. B.; Meng, H.; Bao, Z. Phys. Rev. Lett. 2002, 88, 226801/1-226801/4.
6. In monolayer devices: (a) Aviram, A.; Ratner, M. A. Chem. Phys. Lett. 1974, 29, 277-283. (b) Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550-1552. (c) Zhitenev, N. B.; Meng, H.; Bao, Z. Phys. Rev. Lett. 2002, 88, 226801/1-226801/4.
7. In monolayer devices: (a) Aviram, A.; Ratner, M. A. Chem. Phys. Lett. 1974, 29, 277-283. (b) Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550-1552. (c) Zhitenev, N. B.; Meng, H.; Bao, Z. Phys. Rev. Lett. 2002, 88, 226801/1-226801/4.
8. For SAMs of linear aromatics, see for example: (a) reference 3. (b) Allara, D. L.; Dunbar, T. D.; Weiss, P. S.; Bumm, L. A.; Cygan, M. T.; Tour, J. M.; Reinerth, W. A.; Yao, Y.; Kozaki, M.; Jones, L., II. Ann. N. Y. Acad. Sci. 1998, 852, 349-370. (c) Schumm, J. S.; Pearson, D. L.; Jones, L., II; Hara, R.; Tour, J. M. Nanotechnology, 1996, 7, 430-433. (d) Holmlin, R. E.; Ismagilov, R. F.; Haag, R.; Mujica, V.; Ratner, M. A.; Rampi, M. A.; Whitesides, G. M. Angew. Chem., Int. Ed. 2001, 40, 2316-2320. (e) Tour, J. M. Acc. Chem. Res. 2000, 33, 791-804.
9. For SAMs of linear aromatics, see for example: (a) reference 3. (b) Allara, D. L.; Dunbar, T. D.; Weiss, P. S.; Bumm, L. A.; Cygan, M. T.; Tour, J. M.; Reinerth, W. A.; Yao, Y.; Kozaki, M.; Jones, L., II. Ann. N. Y. Acad. Sci. 1998, 852, 349-370. (c) Schumm, J. S.; Pearson, D. L.; Jones, L., II; Hara, R.; Tour, J. M. Nanotechnology, 1996, 7, 430-433. (d) Holmlin, R. E.; Ismagilov, R. F.; Haag, R.; Mujica, V.; Ratner, M. A.; Rampi, M. A.; Whitesides, G. M. Angew. Chem., Int. Ed. 2001, 40, 2316-2320. (e) Tour, J. M. Acc. Chem. Res. 2000, 33, 791-804.
10. For SAMs of linear aromatics, see for example: (a) reference 3. (b) Allara, D. L.; Dunbar, T. D.; Weiss, P. S.; Bumm, L. A.; Cygan, M. T.; Tour, J. M.; Reinerth, W. A.; Yao, Y.; Kozaki, M.; Jones, L., II. Ann. N. Y. Acad. Sci. 1998, 852, 349-370. (c) Schumm, J. S.; Pearson, D. L.; Jones, L., II; Hara, R.; Tour, J. M. Nanotechnology, 1996, 7, 430-433. (d) Holmlin, R. E.; Ismagilov, R. F.; Haag, R.; Mujica, V.; Ratner, M. A.; Rampi, M. A.; Whitesides, G. M. Angew. Chem., Int. Ed. 2001, 40, 2316-2320. (e) Tour, J. M. Acc. Chem. Res. 2000, 33, 791-804.
11. For SAMs of linear aromatics, see for example: (a) reference 3. (b) Allara, D. L.; Dunbar, T. D.; Weiss, P. S.; Bumm, L. A.; Cygan, M. T.; Tour, J. M.; Reinerth, W. A.; Yao, Y.; Kozaki, M.; Jones, L., II. Ann. N. Y. Acad. Sci. 1998, 852, 349-370. (c) Schumm, J. S.; Pearson, D. L.; Jones, L., II; Hara, R.; Tour, J. M. Nanotechnology, 1996, 7, 430-433. (d) Holmlin, R. E.; Ismagilov, R. F.; Haag, R.; Mujica, V.; Ratner, M. A.; Rampi, M. A.; Whitesides, G. M. Angew. Chem., Int. Ed. 2001, 40, 2316-2320. (e) Tour, J. M. Acc. Chem. Res. 2000, 33, 791-804.
12. For SAMs of linear aromatics, see for example: (a) reference 3. (b) Allara, D. L.; Dunbar, T. D.; Weiss, P. S.; Bumm, L. A.; Cygan, M. T.; Tour, J. M.; Reinerth, W. A.; Yao, Y.; Kozaki, M.; Jones, L., II. Ann. N. Y. Acad. Sci. 1998, 852, 349-370. (c) Schumm, J. S.; Pearson, D. L.; Jones, L., II; Hara, R.; Tour, J. M. Nanotechnology, 1996, 7, 430-433. (d) Holmlin, R. E.; Ismagilov, R. F.; Haag, R.; Mujica, V.; Ratner, M. A.; Rampi, M. A.; Whitesides, G. M. Angew. Chem., Int. Ed. 2001, 40, 2316-2320. (e) Tour, J. M. Acc. Chem. Res. 2000, 33, 791-804.
13. (a) Both the prone and vertical orientations are reported in: Ulman. A. Acc. Chem. Res. 2001, 34, 855-63. (b) A largely vertical conformation for a number of aromatic molecules: Tour, J. M.; Jones, L.; Pearson, D. L.; Lamba, J. J. S.; Burgin, T. P.; Whitesides, G. W.; Allara, D. L.; Parikh, A. N.; Sundar, V. A. J. Am. Chem. Soc. 1995, 117, 9529-9534.
14. (a) Both the prone and vertical orientations are reported in: Ulman. A. Acc. Chem. Res. 2001, 34, 855-63. (b) A largely vertical conformation for a number of aromatic molecules: Tour, J. M.; Jones, L.; Pearson, D. L.; Lamba, J. J. S.; Burgin, T. P.; Whitesides, G. W.; Allara, D. L.; Parikh, A. N.; Sundar, V. A. J. Am. Chem. Soc. 1995, 117, 9529-9534.
15. Nuzzo, R. G.; Allara, D. L. J. Am. Chem. Soc. 1983, 105, 4481-4483.
16. So, Y.; Zaleski, J. M.; Murlick, C.; Ellaboudy, A. Macromolecules 1996, 29, 2783-2795.
17. Hirohashi, R.; Hishiki, Y.; Ishikawa, S. Polymer 1970, 11, 297-308.
18. Osaheni, J. A.; Jenekhe, S. A.; Burns, A.; Du, G.; Joo, J.; Wang, Z.; Epstein, A. J.; Wang, C. Macromolecules 1992, 25, 5828-5835.
19. (a) Wolfe, J.; Arnold, F. E. Macromolecules 1981, 14, 909-915.
20. (b) Perry, R. J.; Wilson, B. D.; Miller, R. J. J. Org. Chem. 1992, 57, 2883-2887.
21. (c) Seha, V. Z.; Weis, C. D. Helv. Chim. Acta, 1980, 63, 413-419.
22. (d) Fuxen, C.; Azzam, W.; Arnold, R.; Witte, G.; Teflort, A.; Wöll, C. Langmuir 2001, 17, 3689-3695.
23. Similar cyclizations to produce single oxazole rings have been effected using: (a) Phosphites: Leyshon, L. J.; Saunders, D. G. J. Chem. Soc. Chem. Commun. 1972, 1608-1609. (b) Phosphites: Takeuchi, H.; Shunichi, Y.; Ozaki, T.; Hagiwara, S.; Eguchi, S. J. Org. Chem. 1989, 54, 431-434. (c) Phosphines: Gololobov, Y. G.; Gusar, N. I.; Chaus, M. P. Tetrahedron 1985, 41, 793-799.
24. Similar cyclizations to produce single oxazole rings have been effected using: (a) Phosphites: Leyshon, L. J.; Saunders, D. G. J. Chem. Soc. Chem. Commun. 1972, 1608-1609. (b) Phosphites: Takeuchi, H.; Shunichi, Y.; Ozaki, T.; Hagiwara, S.; Eguchi, S. J. Org. Chem. 1989, 54, 431-434. (c) Phosphines: Gololobov, Y. G.; Gusar, N. I.; Chaus, M. P. Tetrahedron 1985, 41, 793-799.
25. Similar cyclizations to produce single oxazole rings have been effected using: (a) Phosphites: Leyshon, L. J.; Saunders, D. G. J. Chem. Soc. Chem. Commun. 1972, 1608-1609. (b) Phosphites: Takeuchi, H.; Shunichi, Y.; Ozaki, T.; Hagiwara, S.; Eguchi, S. J. Org. Chem. 1989, 54, 431-434. (c) Phosphines: Gololobov, Y. G.; Gusar, N. I.; Chaus, M. P. Tetrahedron 1985, 41, 793-799.
26. (a) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635-646.
27. (b) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406.
28. (a) Bernard, M.; Ford, W. T. J. Org. Chem. 1983, 48, 326-332.
29. (b) Charette, A. B.; Boezio, A. A.; Janes, M. K Org. Lett. 2000, 2, 3777-3779.
30. Lindgren, B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888-893.
31. (a) Allara, D. L.; Nuzzo, R. G. Langmuir 1995, 8, 45-52.
32. (b) Allara, D. L.; Nuzzo, R. G. Langmuir 1995, 1, 52-66.
33. For SAMs from cyano groups on: (a) Au and Cu, see: Steiner, U. B.; Caseri, W. R.; Suter, U. W. Langmuir 1992, 8, 2771-2777. (b) Ni, see: Hemminger, J. C.; Muetterties, E. L.; Somorjai, G. A. J. Am. Chem. Soc, 1979, 101, 62-67.
34. For SAMs from cyano groups on: (a) Au and Cu, see: Steiner, U. B.; Caseri, W. R.; Suter, U. W. Lungmuir 1992, 8, 2771-2777. (b) Ni, see: Hemminger, J. C.; Muetterties, E. L.; Somorjai, G. A. J. Am. Chem. Soc, 1979, 101, 62-67.
35. Frey, S.; Stadler, V.; Heister, K.; Eck, W.; Zharnikov, M.; Grunze, M.; Zeysing, B.; Terfort, A. Langmuir 2001, 17, 2408-2415.
36. (a) Briggs, D.; Seah, M. P. Practical Surface Analysis; Wiley: Chichester, 1983.
37. (b) Bain, C. D.; Whitesides, G. M. J. Phys. Chem. 1989, 93, 1670-1673.
38. (c) Laibinis, P. E.; Bain, C. D.; Whitesdies, G. M. J. Phys. Chem. 1991, 95, 7017-7021.
39. (d) Nuzzo, R. G.; Finnie, K. R.; Haasch, R. Langmuir 2000, 16, 6968-6976.
40. (e) Noble-Luginbuhl, A. R.; Nuzzo, R. G. Langmuir 2001, 17, 3937-3944.
41. The length of the molecule from sulfur to carbon is calculated from energy minimized structures generated using MacroModel v7.0 and the MMFFs* forcefield (Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467). To these lengths is added 0.24 nm for the sulfur-gold bond length (from ref 5b).
42. (a) Hegedus, L. S.; Odle, R. R.; Winton, P. M.; Weider, P. R. J. Org. Chem. 1982, 47, 2607-2613.
43. (b) Maryanoff, C. A. Spectroscopy of Oxazoles. In Heterocyclic Compounds; Turchi, I. J., Ed.; John Wiley & Sons: New York3, 1986; Vol. 45, pp 358-359.
44. Advancing contact angle for ester-terminated SAMs are 67° and for methyl-terminated SAMs are 114° (Bain, C. D.; Troughton, B. E.; Tao, Y.; Evall, J.; Whitesides, G. M.; Nuzzo, R. N. J. Am. Chem. Soc. 1989, 111, 321-335). If has both a methyl-ester and an aliphatic component.