Lattice structure of self-assembled monolayers of dialkyl sulfides and calix[4]arene sulfide adsorbates on Au(111) revealed by atomic force microscopy

Langmuir

Volumn 15, Issue 17, 1999, Pages 5541-5546

  Schönherr, Holger ^a   Vancso, G Julius ^a   Huisman, Bart Hendrik ^a   Van Veggel, Frank C J M ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ANNEALING; AROMATIC COMPOUNDS; ATOMIC FORCE MICROSCOPY; GOLD; HIGH TEMPERATURE OPERATIONS; MOLECULAR DYNAMICS; MONOLAYERS; SULFUR COMPOUNDS; VAN DER WAALS FORCES;

ADSORBATES; ALKANETHIOLS; CALIXARENE SULFIDE; DIALKYL SULFIDES; INTERMOLECULAR VAN DER WAALS INTERACTIONS; SELF ASSEMBLED MONOLAYERS;

CRYSTAL LATTICES;

EID: 0039707921     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la981787y     Document Type: Article

References (71)

1. (a) Ulman, A. An Introduction to Ultrathin Organic Films: From Langmuir-Blodgett to Self-Assembly;Academic Press: New York, 1991.
2. (b) Bishop, A. R.; Nuzzo, R. G. Curr. Opinion Colloid Interface Sci. 1996, 1, 127.
3. (c) Dubois, L. H.; Nuzzo, R. G. Annu. Rev. Phys. Chem. 1992, 43, 437.
4. (d) Ulman, A. Chem. Rev. 1996, 96, 1533.
5. (a) Frisbie, C. D.; Rozsnyai, L. F.; Noy, A.; Wrighton, M. S.; Lieber, C. M. Science 1994, 265, 2071.
6. (b) Noy, A.; Vezenov, D. V.; Lieber, C. M. Annu. Rev. Mater. Sci. 1997, 27, 381.
7. Carpick, R. W.; Salmeron, M. Chem. Rev. 1997, 97, 1163.
8. (a) Rubinstein, I.; Steinberg, S.; Tor, Y.; Shanzer, A.; Sagiv, J. Nature 1988, 332, 426.
9. (b) Rubinstein, I.; Steinberg, S.; Tor, Y.; Shanzer, A.; Sagiv, J. Nature 1989, 337, 217.
10. (c) Rubinstein, I.; Steinberg, S.; Tor, Y.; Shanzer, A.; Sagiv, J. Nature 1989, 337, 514.
11. (d) Turyan, I.; Mandler, D. Anal. Chem. 1994, 66, 58.
12. (e) Gafni, Y.; Weizman, H.; Libman, J.; Shanzer, A.; Rubinstein, I. Eur. J. Chem. 1996, 2, 759.
13. Kepley, L. J.; Crooks, R. M.; Ricco, A. J. Anal. Chem. 1992, 64, 3191.
14. Schierbaum, K.-D.; Weiss, T.; Thoden van Velzen, E. U.; Engbersen, J. F. J.; Reinhoudt, D. N.; Göpel, W. Science 1994, 265, 1413.
15. (a) Mrksich, M.; Grunwell, J. R.; Whitesides, G. M. J. Am. Chem. Soc. 1995, 117, 12009.
16. (b) Mrksich, M.; Sigal, G. B.; Whitesides, G. M. Langmuir 1995, 11, 561.
17. (c) Huisman, B.-H.; Kooyman, R. P. H.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Adv. Mater. 1996, 8, 561.
18. (d) Sigal, G. B.; Mrksich, M.; Whitesides, G. M. Langmuir 1997, 13, 561.
19. (a) Kumar, A.; Whitesides, G. M. Science 1994, 263, 60.
20. (b) Kumar, A.; Biebuyck, H. A.; Whitesides, G. M. Langmuir 1994, 10, 1498.
21. (a) Nuzzo, R. G.; Fusco, F. A.; Allara, D. L. J. Am. Chem. Soc. 1987, 109, 2358.
22. (b) Nuzzo, R. G.; Zegarsky, B. R.; Dubois, L. H. J. Am. Chem. Soc. 1987, 109, 733.
23. (a) Batchelder, D. N.; Evans, S. D.; Freeman, T. L.; Häussling, L.; Ringsdorf, H.; Wolf, H. J. Am. Chem. Soc. 1994, 116, 1050.
24. (b) Chan, K.; Kim, T.; Schoer, J. K.; Crooks, R. M. J. Am. Chem. Soc. 1995, 117, 5875.
25. Allara, D. L. Biosensors Bioelectronics 1995, 10, 771.
26. Lavrich, D. J.; Wetterer, S. M.; Bernasek, S. L.; Scoles, G. J. Phys. Chem. B 1998, 102, 3456.
27. Troughton, E. B.; Bain, C. D.; Whitesides, G. M.; Nuzzo, R. G.; Allara, D. L.; Porter, M. D. Langmuir 1988, 4, 365.
28. (a) Thoden van Velzen, E. U.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 3597.
29. (b) Thoden van Velzen, E. U.; Engbersen, J. F. J.; de Lange, P. J.; Many, J. W. G.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6853.
30. (c) Huisman, B.-H.; Rudkevich, D. M.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Am. Chem. Soc. 1996, 119, 3523.
31. Huisman, B.-H. Ph.D. Thesis, University of Twente, 1998.
32. Beulen, M. W. J.; Huisman, B.-H.; van der Heiden, P. A.; van Veggel, F. C. J. M.; Simons, M. G.; Biemond, E. M. E. F.; de Lange, P. J.; Reinhoudt, D. N. Langmuir 1986, 12, 6170.
33. A recent paper by Porter et al. (Zhong, C. J.; Brush, R. C.; Anderegg, J.; Porter, M. D. Langmuir 1999, 15, 518) showed that impurities were indeed the origin of the observations initially attributed to the carbon-sulfur bond cleavage.
34. Schönherr, H.; Vancso, G. J.; Huisman, B.-H.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Langmuir 1997, 13, 1567.
35. Touzov, I.; Gorman, C. B. Langmuir 1997, 13, 4850.
36. Dishner, M. H.; Hemminger, J. C.; Feher, F. J. Langmuir 1996, 12, 6176.
37. Hiesgen, R.; Schonherr, H.; Kumar, S.; Ringsdorf, H.; Meissner, D. Submitted.
38. Trevor, J. L.; Lykke, K. R.; Pellin, M. J.; Hanley, L. Langmuir 1998, 14, 1664.
39. Manne, S.; Butt, H.-J.; Gould, C. A. C.; Hansma, P. K. Appl. Phys. Lett. 1990, 56, 1758.
40. Chidsey, C. E. D.; Loiacono, D. N. Langmuir 1990, 6, 682.
41. Snétivy, D.; Vancso, G. J. Langmuir 1993, 9, 2253.
42. Schönherr, H.; Vancso, G. J. Langmuir 1997, 13, 3769.
43. Jaschke, M.; Schönherr, H.; Wolf, H.; Butt, H.-J.; Bamberg, E.; Besocke, M. K.; Ringsdorf, H. J. Phys, Chem. 1996, 100, 2290.
44. Larsen, N. B.; Biebuyck, H. A.; Delamarche, E.; Michel, B. J. Am. Chem. Soc. 1997, 119, 3017.
45. (a) Schönenberger, C.; Sondag-Huethorst, J. A. M.; Jorritsma, J.; Fokkink, L. G. Langmuir 1994, 10, 611.
46. (b) Poirier, G. E. Langmuir 1997, 13, 2019.
47. Dishner, M. H.; Hemminger, J. C.; Feher, F. J. Langmuir 1997, 13, 2318.
48. Poirier, G. E. Chem. Rev. 1997, 97, 1117.
49. In the XPS analyses of samples prepared at 60 °C the amount of sulfur bound to gold was found to increase significantly as compared to samples prepared at room temperature, e.g. for SAMs of adsorbate 1, 100% of the sulfur atoms bound (60 °C) vs 86% bound (RT) (further details can be found: Huisman, B.-H.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Pure Appl. Chem. 1998, 70, 1985). In addition, the number of defects in the alkyl portion of the molecules can be expected to be significantly reduced for samples prepared at elevated temperatures. Assembly at elevated temperatures was previously shown to improve the quality of n-alkanethiol SAMs: Delamarche, E.; Michel, B.; Gerber, Ch.; Anselmetti, D.; Güntherodt, H.-J.; Wolf, H.; Ringsdorf, H. Langmuir 1994, 10, 2869.
50. In the XPS analyses of samples prepared at 60 °C the amount of sulfur bound to gold was found to increase significantly as compared to samples prepared at room temperature, e.g. for SAMs of adsorbate 1, 100% of the sulfur atoms bound (60 °C) vs 86% bound (RT) (further details can be found: Huisman, B.-H.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Pure Appl. Chem. 1998, 70, 1985). In addition, the number of defects in the alkyl portion of the molecules can be expected to be significantly reduced for samples prepared at elevated temperatures. Assembly at elevated temperatures was previously shown to improve the quality of n-alkanethiol SAMs: Delamarche, E.; Michel, B.; Gerber, Ch.; Anselmetti, D.; Güntherodt, H.-J.; Wolf, H.; Ringsdorf, H. Langmuir 1994, 10, 2869.
51. Alves, C. A.; Porter, M. D. Langmuir 1993, 9, 3507.
52. (a) Widrig, C. A.; Alves, C. A.; Porter, M. D. J. Am. Chem. Soc. 1991, 113, 2805.
53. (b) Camillone, N., III; Chidsey, C. E. D.; Liu, G.-y.; Putvinski, T. M.; Scoles, G. J. Chem. Phys. 1991, 94, 8493.
54. Pan, J.; Tao, N.; Lindsay, S. M. Langmuir 1993, 9, 1556.
55. Delamarche, E.; Michel, B.; Hang, H.; Gerber, Ch. Langmuir 1994, 10, 4103.
56. (e) Poirier, G. E.; Tarlov, M. J. Langmuir 1994, 10, 2853.
57. (f) Delamarche, E.; Michel, B.; Gerber, Ch.; Anselmetti, D.; Güntherodt, H.-J.; Wolf, H.; Ringsdorf, H. Langmuir 1994, 10, 2869.
58. (g) Touzov, I.; German, C. B. J. Phys. Chem. 1997, 101, 5263.
59. Liu, G.-Y.; Fenter, P.; Chidsey, C. E. D.; Ogletree, D. F.; Eisenberger, P.; Salmeron, M. J. Chem. Phys, 1994, 101, 4301.
60. (a) Schönherr, H.; Vancso, G. J, Polym. Prepr. 1998, 39 (2), 904.
61. (b) Schönherr, H.; Vancso, G. J. ACS Symp. Ser. Submitted.
62. Sellers, H.; Ulman, A.; Shnidman, Y.; Eilers, J. E. J. Am. Chem. Soc. 1993, 115, 9389.
63. Fenter, P.; Eberhardt, A.; Liang, K. S.; Eisenberger, P. J. Chem. Phys. 1997, 106, 1600.
64. Ulman, A.; Eilers, J. E.; Tillman, N. Langmuir 1989, 5, 1147.
65. Strong, L.; Whitesides, G. M. Langmuir 1988, 4, 546.
66. Jung, C.; Dannenberger, O.; Xu, Y.; Buck, M.; Grunze, M. Langmuir 1998, 14, 1103.
67. (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
68. (b) Calixarenes: A Versatile Class of Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991.
69. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
70. (a) Nelles, G.; Schönherr, H.; Jaschke, M.; Wolf, H.; Schaub, M.; Küther, J.; Tremel, W. ; Bamberg, E.; Ringsdorf, H.; Butt, H.-J. Langmuir 1966, 14, 808.
71. (b) Nelles, G.; Schönherr, H.; Vancso, G. J.; Butt, H.-J. Appl. Phys. A 1998, 66, S1261.