Chemical reactions with upright monolayers of cruciform π-systems

Langmuir

Volumn 20, Issue 23, 2004, Pages 10068-10072

  Klare, Jennifer E ^a   Tulevski, George S ^a   Nuckolls, Colin ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ANILINES; CYCLIZATION; MOLECULAR ELECTRONICS; TRIMERIC STRUCTURES;

ALDEHYDES; CARBOXYLIC ACIDS; CRYSTAL STRUCTURE; DERIVATIVES; DIMERS; PHENOLS; SELF ASSEMBLY; SUBSTRATES;

MONOLAYERS;

ALDEHYDES; CARBOXYLIC ACIDS; CRYSTAL STRUCTURE; DIMERS; MONOLAYERS; PHENOLS; SUBSTRATES;

EID: 9144258024     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la0479152     Document Type: Article

References (67)

1. For reactions in aliphatic SAMs, see: (a) Kakkar, A. K. Chem Rev 2002, 102, 3579-3587.
2. (b) Flink, S.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Adv. Mater. 2000, 12, 1315-1328.
3. (c) Ulman, A. Chem. Rev. 1996, 96, 1533-1554.
4. (d) Chapman, R. G.; Ostuni, E.; Van, L.; Whitesides, G. M. Langmuir 2000, 16, 6927-6936.
5. (e) Yan, L.; Zhao, X.-M.; Whitesides, G. M. J. Am. Chem. Soc. 1998, 120, 6179-6180.
6. (f) Yan, L.; Huck, W. T. S.; Zhao, X.-M.; Whitesides, G. M. Langmuir 1999, 15, 1208-1214.
7. (g)Akamatsu, K.; Hasegawa, J.; Nawafune, H.; Katayama, H.; Ozawa, F. J. Mater. Chem. 2002, 12, 2862-2865.
8. (h) Chan, E. W. L.; Yu, L. Langmuir 2002, 18, 311-313.
9. (i) Shon, Y. S.; Choo, H. C. R. Chim. 2003, 6, 1009-1018.
10. (j) Lee, J, K.; Lee, K. B.; Kim, D. J.; Choi, I. S. Langmuir 2003, 19, 8141-8143.
11. (k) Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20, 1051-1053.
12. (l) Lee, J. K.; Chi, Y. S.; Choi, I. S. Langmuir 2004, 20, 3844-3847.
13. (m) Chechik, V.; Crooks, R. M.; Stirling, C. J. M. Adv. Mater. 2000, 12, 1161-1171.
14. (n) Sullivan, T. P.; Huck, W. T. S. Eur. J. Org. Chem. 2003, 17-29.
15. (a) Rosink, J. J. W. M.; Blauw, M. A.; Geerligs, L. J.; van der Drift, E.; Rousseeuw, B. A. C.; Radelaar, S.; Sloof, W. G.; Fakkeldij, E. J. M. Langmuir 2000, 16, 4547-4553.
16. (b) Rosink, J. J. W. M.; Blauw, M. A.; Geerligs, L. J.; Van der Drift, E.; Rousseeuw, B. A. C.; Radelaar, S. Opt. Mater. 1998, 9, 416-422.
17. (c) Onipko, A. I.; Berggren, K. F.; Klymenko, Y. O.; Malysheva, L. I.; Rosink, J. J. W. M.; Geerligs, L. J.; van der Drift, E.; Radelaar, S. Phys. Rev. B 2000, 61, 11118-11124.
18. Klare, J. E.; Tulevski, G. S.; Sugo, K.; de Picciotto, A.; White, K. A.; Nuokolls, C. J. Am. Chem. Soc. 2003, 125, 6030-6031.
19. Other upright aromatic monolayers: (a) de Boer, B.; Meng, H.; Perepichka, D. F.; Zheng, J.; Frank, M. M.; Chabal, Y. J.; Bao, Z. Langmuir 2003, 19, 4272-4284.
20. (b) Zhu, L.; Tang, H.; Harima, Y.; Yamashita, K.; Aso, Y.; Otsubo, T. J. Mater. Chem. 2002, 12, 2250-2254.
21. (c) Tao, Y.-T.; Wu, C.-C.; Eu, J.-Y.; Lin, W.-L.; Wu, K.-C.; Chen, C.-H. Langmuir 1997, 13, 4018-4023.
22. (a) Yang, C.-J.; Jenekhe, S. A. Macromolecules 1996, 28, 1180-1196.
23. (b) Yang, C. J.; Jenekhe, S. A. Chem. Mater. 1991, 3, 878-887.
24. For similar examples to synthesize benzoxazoles, see: (a) Leyshon, L. J.; Saunders, D, G. J. Chem. Soc. Chem. Comm. 1971, 1608 -;
25. (b) Takeuchi, H.; Yanagida, S.; Ozaki, T.; Hagiwara, S.; Eguchi, S. J. Org. Chem. 1989, 54, 431-434.
26. (c) Gololobov, Y. G.; Gusar, N. I.; Chaus, M. P. Tetrahedron 1985, 41, 793-799.
27. (a) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635-646.
28. (b) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1406.
29. (a) Bernard, M.; Ford, W. T. J. Org. Chem. 1988, 48, 326-332.
30. (b) Charette, A. B.; Boezio, A. A.; Janes, M. K. Org. Lett. 2000, 2, 3777-3779.
31. Typical reaction conditions to yield benzoxazoles: (a) Wolfe, J. F.; Arnold, F. E. Macromolecules 1981,14, 909-915.
32. (b) Perry, R. J.; Wilson, B. D.; Miller, R. J. J. Org. Chem. 1992, 57, 2883-2887.
33. (c) Seha, Z.; Weis, C. D. Helv. Chim. Acta 1980, 63, 413-419.
34. For details of the synthesis and characterization of the materials used in this study, see the Supporting Information.
35. (a) Muraki, M.; Mizoguch, T. Chem. Pharm. Bull. 1971, 19, 1708-.
36. (b) Flatt, A. K.; Yao, Y. X.; Maya, F.; Tour, J. M. J. Org. Chem. 2004, 69, 1752-1755.
37. See the Supporting Information for the synthesis of 3.
38. Handbook of Liquid Crystals; Demus, D., Ed.; Wiley-VCH: Weinheim, 1998; Vol. 1: Fundamentals.
39. Jonkheijm, P.; Hoeben, F. J. M.; Kleppinger, R.; Van Herrikhuyzen, J.; Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2003, 125, 15941-15949.
40. (a) Burgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1970, 53, 1747-1764.
41. (b) Burgi, H. B.; Dunitz, J. D. Helv. Chim. Acta 1971, 54, 1255-1260.
42. Haselbach, E.; Heilbronner, E. Helv. Chim. Acta 1968, 31, 16-21.
43. Morley, J. O. J. Chem. Soc., Perkin Trans. 2 1995, 731-734.
44. Henderson, J. I.; Feng, S.; Bein, T.; Kubiak, C. P. Langmuir 2000, 16, 6183-6187.
45. Angell, M. A,; Zeppenfeld, A. C.; Yoshimoto, K.; Cogan, E. B.; Page, C. J. Chem. Mater. 1996, 8, 591.
46. Using methods similar to: (a) Nuzzo, R. G.; Zegarski, B. R.; Dubois, L. H. J. Am. Chem. Soc. 1987, 109, 733-740.
47. (b) Laibinis, P. E.; Nuzzo, R. G.; Whitesides, G. M. J. Phys. Chem. 1992, 96, 5097-5105.
48. Bain, C. D.; Troughton, E. B.; Tao, Y. T.; Evall, J.; Whitesides, G. M.; Nuzzo, R. G. J. Am. Chem. Soc. 1989, 111, 321-335.
49. The experimental procedures used for the inline condensation reactions can be found in the Supporting Information.
50. The length of the molecule was estimated using MacroModel: 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.
51. (a) Schreiber, F. Prog. Surf. Sci. 2000, 65, 151-256.
52. (b) Ulman, A. Acc. Chem. Res. 2001, 34, 855-863.
53. (a) 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. NY Acad. Sci. 1998, 852, 349-370.
54. (b) Chabinyc, M. L.; Chen, X.; Holmlin, R. E.; Jacobs, H.; Skulason, H.; Frisbie, C. D.; Mujica, V.; Ratner, M. A.; Rampi, M. A.; Whitesides, G. M. J. Am. Chem. Soc. 2002, 124, 11730-11736.
55. (c) Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550-1552.
56. (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.
57. (e) Metzger, R. M.; Panetta, C. A. New J. Chem. 1991, 15, 209-221.
58. (a) Cui, X. D.; Primak, A.; Zarate, X.; Tomfohr, J.; Sankey, O. F.; Moore, A. L.; Moore, T. A.; Gust, D.; Harris, G.; Lindsay, S. M. Science 2001, 294, 571-574.
59. (b) Lindsay, S. M. Jpn. J. Appl. Phys., Part 1 2002, 41, 4867-4870.
60. Gimzewski, J. K.; Joachim, C. Science 1999, 283, 1683-1688.
61. (a) Zhitenev, N. B.; Erbe, A.; Meng, H.; Bao, Z. Nanotech. 2003, 14, 254-257.
62. (b) Reed, M. A.; Zhou, C.; Muller, C. J.; Burgin, T. P.; Tour, J. M. Science 1997, 278, 252-254.
63. (c) Zhitenev, N. B.; Meng, H.; Bao, Z. Phys. Rev. Lett. 2002, 88, 226801/226801-226801/226804.
64. (d) Park, H.; Lim, A. K. L.; Alivisatos, A. P.; Park, J.; McEuen, P. L. Appl. Phys. Lett. 1999, 75, 301-303.
65. (e) Heath, J. R.; Ratner, M. A. Phys. Today 2003, 56, 43-49.
66. (f) Liang, W.; Shores, M. P.; Bockrath, M.; Long, J. R.; Park, H. Nature 2002, 417, 725-729.
67. (g) Chen, J.; Wang, W.; Klemic, J.; Reed, M. A.; Axelrod, B. W.; Kaschak, D. M.; Rawlett, A. M.; Price, D. W.; Dirk, S. M.; Tour, J. M.; Grubisha, D. S.; Bennett, D. W. Ann. NY Acad. Sci. 2002, 960, 69-99.