Mixed azide-terminated monolayers: A platform for modifying electrode surfaces

Langmuir

Volumn 22, Issue 6, 2006, Pages 2457-2464

  Collman, James P ^a   Devaraj, Neal K ^a   Eberspacher, Todd P A ^a   Chidsey, Christopher E D ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENES; AZIDE-TERMINATED MONOLAYERS; ELECTRODE SURFACES; GRAZING-ANGLE INFRARED (IR);

ELECTRODES; GOLD COMPOUNDS; INFRARED RADIATION; PARAFFINS; SURFACE TREATMENT; X RAY PHOTOELECTRON SPECTROSCOPY;

MONOLAYERS;

AZIDE;

ARTICLE; CHEMISTRY; ELECTROCHEMISTRY; ELECTRODE; INSTRUMENTATION; METHODOLOGY; SPECTROSCOPY; SURFACE PROPERTY;

AZIDES; ELECTROCHEMISTRY; ELECTRODES; SPECTRUM ANALYSIS; SURFACE PROPERTIES;

EID: 33645507742     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la052947q     Document Type: Article

References (42)

1. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Chem. Rev. 2005, 105 (4), 1103-1169.
2. Chidsey, C. E. D.; Bertozzi, C. R.; Putvinski, T. M.; Mujsce, A. M. J. Am. Chem. Soc. 1990, 112 (11), 4301-6.
3. Yousaf, M. N.; Mrksich, M. J. Am. Chem. Soc. 1999, 121 (17), 4286-4287.
4. Wollman, E. W.; Kang, D.; Frisbie, C. D.; Lorkovic, I. M.; Wrighton, M. S. J. Am. Chem. Soc. 1994, 116 (10), 4395-404.
5. Frey, B. L.; Corn, R. M. Anal. Chem. 1996, 68 (18), 3187-3193.
6. Collman, J. P.; Devaraj, N. K.; Chidsey, C. E. D. Langmuir 2004, 20 (4), 1051-1053.
7. Rostovtsev, V. V.; Green, L. O.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41 (14), 2596-2599.
8. Kolb, H. C.; Finn, M. O.; Sharpless, K. B. Angew. Chem., Int. Ed 2001, 40(11), 2004-2021.
9. Lummerstorfer, T.; Hoffmann, H. J. Phys. Chem. B 2004, 108 (13), 3963-3966.
10. Lee, J. K.; Chi, Y. S.; Choi, I. S. Langmuir 2004, 20 (10), 3844-3847.
11. Devaraj, N. K.; Miller, G. P.; Ebina, W.; Kakaradov, B.; Collman, J. P.; Kool, E. T.; Chidsey, C. E. D. J. Am. Chem. Soc. 2005, 127 (24), 8600-8601.
12. Zirbs, R.; Kienberger, F.; Hinterdorfer, P.; Binder, W. H. Langmuir 2005, 21 (18), 8414-8421.
13. van Steenis, D. J. V. C.; David, O. R. P.; van Strijdonck, G. P. F.; van Maarseveen, J. H.; Reek, J. N. H. Chem. Commun. 2005, (34), 4333-4335.
14. Joralemon, M. J.; O'Reilly, R. K.; Matson, J. B.; Nugent, A. K.; Hawker, C. J.; Wooley, K. L. Macromolecules 2005, 38 (13), 5436-5443.
15. Riva, R.; Schmeits, S.; Stoffelbach, F.; Jerome, C.; Jerome, R.; Lecomte, P. Chem. Commun. 2005, (42), 5334-5336.
16. Malkoch, M.; Thibault, R. J.; Drockenmuller, E.; Messerschmidt, M.; Voit, B.; Russell, T. P.; Hawker, C. J. J. Am. Chem. Soc. 2005, 127 (42), 14942-14949.
17. Helms, B.; Mynar, J. L.; Hawker, C. J.; Frechet, J. M. J. J. Am. Chem. Soc. 2004, 126 (46), 15020-15021.
18. Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2004, 43 (30), 3928-3932.
19. Li, H.; Cheng, F.; Duft, A. M.; Adronov, A. J. Am. Chem. Soc. 2005, 127 (41), 14518-14524.
20. Barriga, S.; Marcos, C. F.; Riant, O.; Torroba, T. Tetrahedron 2002, 58 (49), 9785-9792.
21. Huang, J. Y.; Hemminger, J. C. J. Am. Chem. Soc. 1993, 115 (8), 3342-3343.
22. Bain, C. D.; Whitesides, G. M. J. Am. Chem. Soc. 1989, 111 (18), 7164-75.
23. Strong, L.; Whitesides, G. M. Langmuir 1988, 4 (3), 546-58.
24. Bain, C. D.; Biebuyck, H. A.; Whitesides, G. M. Langmuir 1989, 5 (3), 723-7.
25. He, Z.; Bhattacharyya, S.; Cleland, W. E., Jr.; Hussey, C. L. J. Electroanal. Chem. 1995, 397 (1-2), 305-10.
26. Porter, M. D.; Bright, T. B.; Allara, D. L.; Chidsey, C. E. D. J. Am. Chem. Soc. 1987, 109 (12), 3559-68.
27. Snyder, R. O.; Strauss, H. L.; Elliger, C. A. J. Phys. Chem. 1982, 86 (26), 5145-50.
28. Lieber, E.; Rao, C. N. R.; Chao, T. S.; Hoffman, C. W. W. Anal. Chem. 1957, 29, 916-18.
29. Laibinis, P. E.; Bain, C. D.; Whitesides, G. M. J. Phys. Chem. 1991, 95 (18), 7017-21.
30. Assuming that the sulfur atoms were at the same level as the gold and the nitrogen atoms at the solid vacuum interface, one can calculate that the azide coverage is approximately 43%, which is in good agreement with the electrochemical data.
31. Fazio, F.; Bryan, M. C.; Blixt, O.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124 (48), 14397-14402.
32. Bryan, M. C.; Fazio, F.; Lee, H. K.; Huang, C. Y.; Chang, A.; Best, M. D.; Calarese, D. A.; Blixt, C.; Paulson, J. C.; Burton, D.; Wilson, I. A.; Wong, C. H. J. Am. Chem. Soc. 2004, 126 (28), 8640-8641.
33. Seo, T. S.; Bai, X. P.; Ruparel, H.; Li, Z. M.; Turro, N. J.; Ju, J. Y. Proc. Natl. Acad. Sci. U.S.A. 2004, 101 (15), 5488-5493.
34. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67 (9), 3057-3064.
35. Link, A. J.; Vink, M. K. S.; Tirrell, D. A. J. Am. Chem. Soc. 2004, 126 (34), 10598-10602.
36. Ueda, J.; Takai, M.; Shimazu, Y.; Ozawa, T. Arch. Biochem. Biophys. 1998, 357(2), 231-239.
37. Zareie, M. H.; Erdem, G.; Oner, C.; Oner, R.; Ogus, A.; Piskin, E. Int. J. Biol. Macromol. 1996, 19 (1), 69-73.
38. Chechik, V.; Stirling, C. J. M., Langmuir 1997, 13 (24), 6354-6356.
39. Templeton, A. C.; Hostetler, M. J.; Kraft, C. T.; Murray, R. W. J. Am. Chem. Soc. 1998, 120 (8), 1906-1911.
40. Gawalt, E. S.; Mrksich, M. J. Am. Chem. Soc. 2004, 126 (47), 15613-15617.
41. Zhou, Z.; Fahmi, C. J. J. Am. Chem. Soc. 2004, 126 (29), 8862-8863.
42. Lewis, W. G.; Magallon, F. G.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2004, 126 (30), 9152-9153.