Organization-induced charge redistribution in self-assembled organic monolayers on gold

Journal of Physical Chemistry B

Volumn 109, Issue 29, 2005, Pages 14064-14073

  Ray, S G ^a   Cohen, H ^a   Naaman, R ^a   Liu, Haiying ^b,c   Waldeck, D H ^b  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c MICHIGAN TECHNOLOGICAL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONTACT POTENTIAL DIFFERENCE (CPD); DIPOLE-DIPOLE INTERACTION; LOW-ENERGY PHOTOELECTRON SPECTROSCOPY (LEPS); TWO-PHOTON PHOTOELECTRON SPECTROSCOPY;

CHARGE TRANSFER; ELECTRIC POTENTIAL; ELECTRONIC STRUCTURE; GOLD; PHOTOELECTRON SPECTROSCOPY; SELF ASSEMBLY; X RAY PHOTOELECTRON SPECTROSCOPY;

MONOLAYERS;

EID: 23844469076     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp050398r     Document Type: Article

References (57)

1. (a) Gurney, R. W. Phys. Rev. 1935, 47, 479.
2. (b) Ueba, H. Surf. Sci. 1991, 242, 266.
3. (c) Albano, E. V. Appl. Surf. Sci. 1982, 14, 183.
4. (d) Lang, N.; Kohn, W. Phys. Rev. B 1970, 1, 4555.
5. Kruger, J.; Bach, U.; Oraetzel, M. Adv. Mater. 2000, 12, 447.
6. (a) Katz, H. E.; Johnson, J.; Lovinger, A. J.; Li, W. J. Am. Chem. Soc. 2000, 122, 7787.
7. (b) Appleyard, S. F. J.; Day, S. R.; Pickford, R. D.; Willis, M. R. J. Mater. Chem. 1999, 10, 169.
8. (c) Campbell, I. H.; Rubin, S.; Zawodzinski, T. A.; Kress, J. D.; Martin, R. L.; Smith, D. L. Phys Rev. B 1996, 54, 14321.
9. (a) Dmitriev, S. G.; Kogan, S. M. Sov. Phys., Solid State 1979, 21, 17.
10. (b) Kim, C. W.; Villagran, J. C.; Even, U.; Thompson, J. J. Chem. Phys. 1991, 94, 3974.
11. Briggs, D.; Seah, M. P. Practical Surface Analysis, 2nd ed.; Wiley: New York, 1994; Vol. 1.
12. (a) Ishii, H.; Sugiyama, K.; Ito, E.; Seki, K. Adv. Mater. 1999, 11, 605.
13. (b) Broughton, J. Q.; Perry, D. L. Surf. Sci. 1978, 74, 307.
14. (c) Brundle, C. R. Surf. Sci. 1975, 48, 99.
15. (d) Gadzuk, J. W. Phys. Rev. B 1976, 14, 2267.
16. Mönch, W. Semiconductor Surfaces and Interfaces, 3rd ed.; Springer: New York, 2001; Chapter 14.
17. Ishii, H.; Sugiyama, K.; Ito, E; Seki, K. Adv. Mater. 1999, 11, 605.
18. Yaliraki, S. N.; Roitberg, A. E.; Gonzalez, C.; Mujica, V.; Ratner, M. A. J. Chem. Phys. 1999, 111, 6997.
19. Vilan, A.; Shanzer, A.; Cahen, D. Nature 2000, 404, 166.
20. Campbell, I. H.; Kress, J. D.; Martin, R. L.; Smith, D. L.; Barashkov, N. N.; Ferraris, J. P. Appl. Phys. Lett. 1997, 71, 3528.
21. Hill, I. G.; Milliron, D.; Schwartz, J.; Kahn, A. Appl. Surf. Sci. 2000, 166, 354.
22. Collier, C. P.; Wong, E. W.; Belohradsky, M.; Raymo, F. M.; Stoddart, J. F.; Kuekes, P. J.; Williams, R. S.; Heath, J. R. Science 1999, 285, 391.
23. Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550.
24. Vuillaume, D.; Chen, B.; Metzger, R. M. Langmuir 1999, 15, 4011.
25. Punkka, E.; Rubner, R. F. J. Electron. Mater. 1992, 21, 1057.
26. See for example: Yamamori, A.; Hayashi, S.; Koyama, T.; Taniguchi, Y. Appl. Phys. Lett. 2001, 78, 3343-3345.
27. Crone, B. K.; Davids, P. S.; Campbell, I. H.; Smith, D. L. J. Appl. Phys. 2000, 87, 1974.
28. Wu, D. G.; Cahen, D.; Graf, P.; Naaman, R.; Nitzan, A.; Shvarts, D. Chem-Eur. J. 2001, 7, 1743.
29. Nitzan, A.; Benjamin, I. Acc. Chem. Res. 1999, 32, 854.
30. Hutchison, G. R.; Ratner, M. A.; Marks, T. J.; Naaman, R. J. Phys. Chem. B 2001, 705, 2881.
31. Vager, Z.; Naaman, R. Chem. Phys. 2002, 281, 305.
32. Lvov, V. S.; Naaman, R.; Tiberkevich, V.; Vager, Z. Chem. Phys. Lett. 2003, 381, 650.
33. Boker, R. D.; McConnell, H. M. J. Phys. Chem. 1993, 97, 13419.
34. Möhwald, H. Annu. Rev. Phys. Chem. 1990, 41, 441.
35. Alloway, D. M.; Hofmann, M.; Smith, D. L.; Gruhn, N. E.; Graham, A. L.; Colorado, R., Jr.; Wysocki, V. H.; Lee, T. R.; Lee, P. A.; Armstrong, N. R. J. Phys. Chem. B 2003, 107, 11690.
36. (a) Naaman, R.; Vager, Z. Ace. Chem. Res. 2003, 36, 291.
37. (b) Naaman, R.; Haran, A.; Nitzan, A.; Evans, D.; Galperin, M. J. Phys. Chem. B 1998, 102, 3658.
38. Kronik, L.; Shapira, Y. Surf. Sci. Rep. 1999, 37, 1.
39. Cohen, H.; Nogues, C; Zon, L; Lubomirsky, I. J. Appl. Phys. 2005, 97, 113701.
40. Liu, H.; Yamamoto, H.; Wei, J.; Waldeck, D. H. Langmuir 2003, 19 (6), 2378.
41. Bibart, R. T.; Vogel, K. W.; Drueckhammer, D. G. J. Org. Chem. 1999, 64, 2903.
42. Yamamoto, H.; Liu, H.; Waldeck, D. H. J. Chem. Soc., Chem. Commun. 2001, 1032.
43. Wei, J.; Liu, H.; Dick, A. R.; Yamamoto, H.; He, Y.; Waldeck, D. H. J. Am. Chem. Soc. 2002, 124, 9591.
44. Ron, H.; Matlis, S.; Rubinstein, I. Langmuir 1998, 14, 1116-1121.
45. For samples l and 5, some extra carbon was detected. We attributed this result to incomplete adsorption of the studied molecules, with other hydrocarbons adsorbed at the"open" areas. Alternatively, the extra carbon may be associated with hydrocarbons adsorbed on top of the studied layer. Obviously, with diluted dipolar molecules, the measured WF should be affected; most likely, it is reduced in magnitude. Experimentally, we could not differentiate this effect from the main one of charge transfer, which acts in the same direction. A rough estimate would suggest that the dipole magnitude of perfect monolayers might increase in the case of molecules 1 and 5 by a factor of two, at most Note that such corrections do not contradict any of the conclusions.
46. To achieve a high level of quantification, we used repetitive XPS scans over many hours (up to 24 h in some cases), while the WF measurements were always less than 1 h, usually the early 10-20 min of each experiment. On a time scale of ∼5 h of irradiation, relative changes in atomic concentrations, AIII, were in most samples less than 5%. In samples 5 and 12, we observed a bit higher degradation rates, about 8-10% during 5-6 h of irradiation. It is stressed that the WF measurements were also repeated. We could, therefore, directly quantify the influence of degradation on the measured WF and, hence, eliminate these effects by extrapolating to time zero when necessary.
47. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363.
48. Pu, J.; Thomson, J. D.; Xidos, J. D.; Li, J.; Zhu, T.; Hawkins, G. D.; Chuang. Y.-Y.; Fast, P. L.; Liotard, D. A.; Rinaldi, D.; Gao, J.; Cramer, C. J. ; Truhlar, D. G. GAMESSPLUS, version 4.3.1; University Of Minnesota: Minneapolis, MN, 2004; based on GAMESS as described in ref 36.
49. Zhu, J. L. T.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. A 1998, 702, 1820.
50. For references describing the standard abbreviations and basic ab initio methods, see the following: (a) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab initio Molecular Orbital Theory; Wiley-Interscience: New York, 1986.
51. (b) Clark, T. A Handbook of Computational Chemistry; Wiley-Interscience: New York, 1985.
52. Wu, D.; Ghabboun, J.; Martin, J.; Cahen, D. J. Phys. Chem. B 2001, 705, 12011.
53. 2≈ 2.2.
54. The electron is bound by both the image potential from the metal and the molecular potential. For similarly sized molecules and film dielectric properties, the image potential with the gold should be similar and the BE shifts would correlate with the electron affinity of the molecules, i.e., the LUMO in the limit of Koopmans theorem. For details, please see: (a) Wang, H.; Dutton, G.; Zhu, X.-Y. J. Phys. Chem. B 2000, 104, 10332-10338.
55. (b) Zhu, X.-Y. Amu. Rev. Phys. Chem. 2002, 53, 221-247.
56. Beamson, G.; Briggs, D. High-Resolution XPS of Organic Polymers. The Scienta ESCA300 Database; Wiley & Sons: Chichester, U.K., 1992.
57. Crispin, X.; Geskin, V.; Crispin, A.; Cornil, J.; Lazzaroni, R.; Salaneck, W. R.; Brèdas, J.-L. J. Am. Chem. Soc. 2002, 124, 8131.