Controlled amine functionality in self-assembled monolayers via the hidden amine route: Chemical and electronic tunability

Journal of Physical Chemistry B

Volumn 110, Issue 15, 2006, Pages 8002-8009

  Ofir, Yuval ^a   Zenou, Noemi ^a   Goykhman, Ilya ^a   Yitzchaik, Shlomo ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ATOMIC FORCE MICROSCOPY; BROMINE; ELECTRONIC PROPERTIES; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROXYLATION; MICROELECTRONICS; SPECTROSCOPIC ANALYSIS; SUBSTITUTION REACTIONS; X RAY PHOTOELECTRON SPECTROSCOPY;

ATTENUATED TOTAL REFLECTION; BROMINE MOIETY; CONTACT ANGLE WETTABILITY; CONTROLLED AMINE FUNCTIONALITY; HYDROXYLATED SURFACES; MOLECULAR NANOELECTRONICS APPLICATIONS; PHTHALIMIDE; SURFACE TRANSFORMATION; VARIABLE ANGLE SPECTROSCOPIC ELLIPSOMETRY;

MONOLAYERS;

EID: 33646394590     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp057251k     Document Type: Article

References (81)

1. Ulman, A. Chem. Rev. 1996, 96, 1533-1554.
2. Sagiv, J. J. Am. Chem. Soc. 1980, 102, 92-98.
3. Nuzzo, R.; Allara, D. J. Am. Chem. Soc. 1983, 105, 4481-4483.
4. (a) Plueddemann, E. P. In Silane Coupling Agents; Plenum: New York, 1991.
5. (b) Silanes and Other Coupling Agents; Mittal, K. L., Ed.; VSP: Leiden, The Netherlands, 1992.
6. (c) Ulman, A. In An Introduction to Ultrathin Organic Films from Langmuir - Blodgett to Self-Assembly; Academic Press: New York, 1991.
7. Yitzchaik, S.; Marks, T. J. Acc. Chem. Res. 1996, 29, 197-202.
8. (a) Burtman, V.; Zelichenok, A.; Yitzchaik, S. Angew. Chem., Int. Ed. 1999, 38, 2041-2045.
9. (b) Burtman, V.; Ofir Y.; Yitzchaik, S. Langmuir 2001, 17, 2137-2142.
10. (a) Cohen, R.; Zenou, N.; Cahen, D.; Yitzchaik, S. Chem. Phys. Lett. 1997, 279, 270-274.
11. (b) Ray, S. G.; Cohen, H.; Naaman, R.; Liu, H.; Waldeck, D. H. J. Phys. Chem. B 2005, 109, 14064-14073.
12. (c) Gershewitz, O.; Grinstein, M.; Sukenik, C. N.; Regev, K.; Ghabboun, J.; Cahen, D. J. Phys. Chem. B 2004, 108, 664-672.
13. (a) Aizenberg, J.; Black, A. J.; Whitesides, G. M. Nature 1999, 398, 495-498.
14. (b) Travaille, A. M.; Kaptijn, L.; Verwer, P.; Hulsken, B.; Elemans, J. A. A.; Nolte, W. R. J. M.; van Kempen, H. J. Am. Chem. Soc. 2003, 125, 11571-11577.
15. Sfez, R.; De-Zhong, L.; Turyan, I.; Mandler, D.; Yitzchaik, S. Langmuir 2001, 17, 2556-2559.
16. Trammell, B.; Ma, C. L.; Luo, H.; Jin, D.; Hillmyer, M. A.; Carr, P. W. Anal. Chem. 2002, 74, 4634-4639.
17. Aqua, T.; Naaman, R.; Daube, S. S. Langmuir 2003, 19, 10573-10580.
18. (a) Culha, M.; Stokes, D.; Allain, L. R.; Vo-Dinh, T. Anal. Chem. 2003, 75, 6196-6201.
19. (b) Qian, X.; Metallo, S. J.; Choi, I. S.; Wu, H.; Liang, M. N.; Whitesides, G. M. Anal. Chem. 2002, 74, 1805-1810.
20. (c) Oren, R.; Sfez, R.; Korbakov, N.; Shabtai, K.; Cohen, A.; Erez, H.; Dormann, A.; Cohen, H.; Shappir, J.; Spira, M. E.; Yitzchaik, S. J. Biomater. Sci., Polym. Ed. 2004, 15, 1355-1374.
21. (a) Lee, B.-w.; Clark, N. A. Langmuir 1998, 14, 5495-5501.
22. (b) Saito, N.; Hayashi, K.; Sugimura, H.; Takai, O. Langmuir 2003, 19, 10632-10634.
23. (c) Hong, L.; Sugimura, H.; Furukawa, T.; Takai, O. Langmuir 2003, 19, 1966-1969.
24. (d) Sugimura, H.; Hanji, T.; Hayashi, K.; Takai, O. Ultramicroscopy 2002, 97, 221-226.
25. (e) Lee, W.; Kim, E. R.; Lee, H. Langmuir 2002, 18, 8375-8380.
26. (f) Piner, R. D.; Zhu, J.; Xu, F.; Hong, S. H.; Mirkin, C. A. Science 1999, 283, 661-663.
27. (g) Liu, G. Y.; Xu, S.; Qian, Y. Acc. Chem. Res. 2000, 53, 457-466.
28. (h) Hoeppener, S.; Maoz, R.; Sagiv, J. Nano Lett. 2003, 3, 761-767.
29. Sugimura, H.; Nakagiri, N. J. Am. Chem. Soc. 1997, 119, 9226-9229.
30. Amoa, I. B.; Sutherland, T. C.; Li, C. Z.; Silerova, R.; Kraatz, H. B. J. Phys. Chem. B 2004, 108, 704-714.
31. (a) Azzaroni, O.; Schilardi, P. L.; Salvarezza, R. C. Electrochim. Acta 2003, 48, 3107-3114.
32. (b) Hoeppener, S.; Maoz, R.; Cohen, S. R.; Chi, L.; Fuchs, H.; Sagiv, J. Adv. Mater. 2002, 14, 1036-1041.
33. Liu, S.; Maoz, R.; Schmid, G.; Sagiv, J. Nano Lett. 2002, 2, 1055-1060.
34. (a) Kallury, K. M. R.; MacDonald, P. M.; Thompson, M. Langmuir 1994, 10, 492-499.
35. (b) Bierbaum, K.; Kinzler, M.; Woll, Ch.; Grunze, M.; Hahner, G.; Heid, S.; Effenberger, F. Langmuir 1995, 11, 512-518.
36. (c) Kallury, K. M. R.; Krull, U. J.; Thompson, M. Anal. Chem. 1988, 60, 169-172.
37. (d) Sugimura, H.; Hozumi, A.; Kameyama, T.; Takai, O. Surf. Interface Anal. 2002, 34, 550-554.
38. Moon, J. H.; Shin, J. W.; Kim, S. Y.; Park, J. W. Langmuir 1996, 12, 4621-4624.
39. (a) Ek, S.; Iiskola, E. I.; Niinisto, L.; Vaittinen, J.; Pakkanen, T. T.; Keranen, J.; Auroux, A. Langmuir 2003, 19, 10601-10609.
40. (b) Ek, S.; liskola, E. I.; Niinisto, L. Langmuir 2003, 19, 3461-3471.
41. Blumel, J. J. Am. Chem. Soc. 1995, 117, 2112-2113.
42. (a) Hayashi, K.; Saito, N.; Sugimura, H.; Takai, O.; Nakagiri, N. Ultramicroscopy 2002, 97, 151-156.
43. (b) Sugimura, H.; Hayashi, K.; Saito, N.; Nakagiri, N.; Takai, O. Appl. Surf. Sci. 2002, 188, 403-410.
44. Rudkevich, E.; Savage, D. E.; Cai, W.; Bean, J. C.; Sullivan, J. S.; Nayak, S.; Kuech, T. F.; McCaughan, L.; Lagally, M. G. J. Vac. Sci. Technol., A 1997, 15, 2153-2157.
45. (a) Kleinfeld, D.; Kahler, K. H.; Hockberger, P. E. J. J. Neurosci. 1988, 8, 4098-4120.
46. (b) Dulcey, C. S.; Georger, J. H.; Krauthamer, V.; Stenger, D. A.; Fare, T. L.; Calvert, J. M. Science 1991, 252, 551-554.
47. (c) Stenger, D. A.; Georger, J. H.; Dulcey, C. S.; Hickman, J. J.; Rudolph, A. S.; Nielsen, T. B.; McCort, S. M.; Calvert, J. M. J. Am. Chem. Soc. 1992, 114, 8435-8442.
48. (d) Balachander, N.; Sukenik, C. N. Langmuir 1990, 6, 1621-1627.
49. (d) Hu, J.; Wang, M.; Weier, H. U. G.; Frantz, P.; Kolbe, W.; Ogletree, D. F.; Salmeron, M. Langmuir 1996, 12, 1697-1700.
50. Vansant, E. F.; van der Voort, P. K.; Vrancken, C. Characterization and Chemical Modification of the Silica Surface; Elsevier: Amsterdam, 1995; Vol. 93, Chapters 8 & 9.
51. (a) Yoshida, W.; Castro, R. P.; Jou, J.-D.; Cohen, Y. Langmuir 2001, 17, 5882-5888.
52. (b) Krasnoslobodtsev, A. V.; Smirnov, S. N. Langmuir 2002, 18, 3181-3184.
53. Horr, T. J.; Arora, P. S. Colloids Surf., A 1997, 126, 113-121.
54. Stevens, M. J. Langmuir 1999, 15, 2773-2778.
55. Haller, I. J. Am. Chem. Soc. 1978, 100, 8050-8055.
56. (a) Durfor, D. N.; Turner, D. C.; Georger, J. H.; Peek, B. M.; Stenger, D. A. Langmuir 1994, 10, 148-152.
57. (b) Petri, D. F. S.; Wenz, G.; Schunk, P.; Schimmel, T. Langmuir 1999, 15, 4520-4523.
58. Brandow, S. L.; Chen, M.-S.; Aggarwal, R.; Ducley, C. S.; Calvert, J. M.; Dressick, W. J. Langmuir 1999, 15, 5429-5432.
59. Greene, T. W. Protective Groups in. Organic Chemistry; Wiley-Interscience: New York, 1981; Chapter 7.
60. Heid, S.; Effenberg, F.; Bierbaum, K.; Grunze, M. Langmuir 1996, 12, 2118-2120.
61. Kobayashi, S.; Nishikawa, T.; Takenobu, T.; Mori, S.; Shimoda, T.; Mitani, T.; Shimotani, H.; Yoshimoto, N.; Ogawa, S.; Iwasa, Y. Nat. Mater. 2004, 3, 317-322.
62. Vilan, A.; Shanzer, A.; Cahen, D. Nature 2000, 404, 166-168.
63. Prutton, M. Introduction to Surface Physics; Oxford University Press-. Oxford, 1994.
64. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
65. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
66. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7 ed.; Gaussian, Inc: Pittsburgh, PA, 1998.
67. (a) Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023.
68. (b) De Proft, F.; Martin, J. M. L.; Geerlings, P. Chem. Phys. Lett. 1996, 250, 393-401.
69. See http://www.cscs.cn/molekel/.
70. Heise, A.; Stamm, M.; Rauscher, M.; Duschner, H.; Menzel, H. Thin Solid Films 1998, 199, 327-329.
71. March, J. Advanced Organic chemistry, 4th ed.; Wiley-Interscience: New York, 1992; Chapter 0-58.
72. Wolfe, S.; Hasan, S. K. Can. J. Chem., 1970, 48, 3572-3579.
73. Osby, J. O.; Martin, M. G.; Ganem, B. Tetrahedron Lett. 1984, 25, 2093-2096.
74. Heise, A.; Menzel, H.; Yim, H.; Foster, H. D.; Wieringa, R. H.; Schoeuten, A. J.; Erb, V.; Stamm, M. Langmuir 1997, 13, 723-728.
75. Oliveira, O. N.; Taylor, D. M.; Lewis, T. J.; Salvagno, S.; Stirling, C. J. M. J. Chem. Soc., Faraday Trans. 1 1989, 85, 1009-1018.
76. The dipole moment direction is graphed from plus to minus.
77. Chosen to be 2.5 for the calculations, as is found in references to be between 2 and 3. See ref 7 and (a) Takahagi, T.; Saiki, A.; Sakaue, H.; Shingubara, S. Jpn. J. Appl. Phys., Part I 2003, 42, 157-161.
78. (b) Gu, D.; Sistiabudi, R.; Dey, S. K. J. Appl. Phys. 2005, 97, 123710.
79. (c) Campbell, L. H.; Kjess, J. D.; Martin, R. L.; Smith, D. L.; Barashkov, N. N.; Ferraris, J. P. Appl. Phys. Lett. 1997, 71, 3528-3530.
80. Bruening, M.; Cohen, R.; Guillemoles, J. F.; Moav, T.; Libman, J.; Shanzer, A.; Cahen, D. J. Am. Chem. Soc. 1997, 119, 5720-5728.
81. Allena, G. C.; Sorbelloa, F.; Altavilla, C.; Castorina, A.; Ciliberto, E. Thin Solid Films 2005, 483, 306-311.