Insertion of individual dendrimer molecules into self-assembled monolayers on gold: a mechanistic study

Langmuir

Volumn 16, Issue 20, 2000, Pages 7757-7763

  Friggeri, Arianna ^a   Schönherr, Holger ^a,b   Van Manen, Henk Jan ^a   Huisman, Bart Hendrik ^a,c   Vancso, G Julius ^a   Huskens, Jurriaan ^a   Van Veggel, Frank C J M ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b Stanford University   (United States)

^c PHILIPS RESEARCH LABORATORIES   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; ALCOHOLS; ATOMIC FORCE MICROSCOPY; DISSOCIATION; ELECTROCHEMISTRY; GOLD; MOLECULES; MONOLAYERS; ORGANIC SOLVENTS; RATE CONSTANTS; SURFACES; WETTING;

DENDRIMER MOLECULE; DICHLOROMETHANE; IMMERSION; INSERTION PROCESS; SELF ASSEMBLED MONOLAYERS; THIOLS; WETTABILITY;

SULFUR COMPOUNDS;

EID: 0343279240     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la000529+     Document Type: Article

References (44)

1. (a) Cooper, E.; Leggett, G. J. Langmuir 1999, 15, 1024.
2. (b) Collard, D. M.; Fox, M. A. Langmuir 1991, 7, 1192.
3. (c) Koega, R. R.; Schlenoff, J. B. Langmuir 1998, 14, 5469.
4. (d) Schlenoff, J. B.; Li, M.; Ly, H. J. Am. Chem. Soc. 1995, 117, 12528.
5. (e) Chidsey, C. E. D.; Bertozzi, C. R.; Putvinski, T. M.; Mujsce, A. M. J. Am. Chem. Soc. 1990, 112, 4301.
6. (f) Hickman, J. J.; Ofer, D.; Zou, C.; Wrighton, M. S.; Laibinis, P. E.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 1128.
7. (g) Kondoh, H.; Kodama, C.; Sumida, H.; Nozoye, H. J. Chem. Phys. 1999, 111, 1175.
8. (h) Lin, P.-H.; Guyot-Sionnest, P. Langmuir 1999, 15, 6825.
9. (i) Bumm, L. A.; Arnold, J. J.; Cygan, M. T.; Dunbar, T. D.; Burgin, T. P.; Jones II, L.; Allara, D. L.; Tour, J. M.; Weiss, P. S. Science 1996, 271, 1705.
10. (j) Ishida, A.; Majima, T. Chem. Commun. 1999, 1299.
11. The process of desorption of adsorbed thiol/thiolate/disulfide molecules followed by the insertion of sulfide molecules present in solution, will be referred to as the thiol-sulfide, or thiol-dendrimer 1 exchange process throughout the paper.
12. Chung, C.; Lee, M. J. Electroanal. Chem. 1999, 468, 91.
13. (a) Frommer, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1298.
14. (b) Magonov, S. N.; Whangbo, M.-H. Surface Analysis with STM and AFM; VCH: Weinheim, Germany, 1996.
15. (a) Poirier, G.E.; Pylant, E.D. Science 1996, 272, 1145.
16. (b) Yamada, R.; Uosaki, K. Langmuir 1997, 13, 5218.
17. (c) Tamada, K.; Hara M.; Sasabe, H.; Knoll, W. Langmuir 1997, 13, 1558.
18. (a) Poirier, G. E.; Tarlov, M. J. Langmuir 1994, 10, 2853.
19. (b) Delamarche, E.; Michel, B.; Gerber, Ch.; Anselmetti, D.; Güntherodt, H.-J.; Wolf, H.; Ringsdorf, H. Langmuir 1994, 10, 2869.
20. (c) Delamarche, E.; Michel, B.; Biebuyck, H. A.; Gerber, Ch. Adv. Mater. 1996, 8 719.
21. (a) Liu, G.-Y.; Fenter, P.; Chidsey, C. E. D.; Ogletree D. F.; Eisenberger, P.; Salmeron, M. J. Chem. Phys. 1994, 101, 4301.
22. (b) Wolf, H.; Ringsdorf, H.; Delamarche, E.; Takami, T.; Kang, H.; Michel, B.; Gerber, Ch.; Jaschke, M.; Butt, H. J.; Bamberg, E. J. Phys. Chem. 1995, 99, 7102.
23. (c) Jaschke, M.; Schönherr, H.; Wolf, H.; Butt, H.-J.; Bamberg, E.; Besocke, M. K.; Ringsdorf, H. J. Phys. Chem. 1996, 100, 2290.
24. (d) Nelles, G.; Schönherr, H.; Jaschke, M.; Wolf, H.; Schaub, M.; Küther, J.; Tremel, W.; Bamberg, E.; Ringsdorf, H.; Butt, H.-J. Langmuir 1998, 14, 808 and references herein.
25. Hierlemann, A.; Campbell, J. K.; Baker, L. A.; Crooks, R. M.; Ricco, A. J. J. Am. Chem. Soc. 1998, 120, 5323.
26. Lackowski, W. M.; Campbell, J. K.; Edwards, G.; Chechik, V.; Crooks, R. M. Langmuir 1999, 15, 7632.
27. Huisman, B.-H.; Schönherr, H.; Huck, W. T. S.; Friggeri, A.; van Manen, H.-J.; Menozzi, E.; Vancso, G. J.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 1999, 38, 2248.
28. For recent papers on the formation of SAMs of dendritic structures see: (a) Zhang, L.; Huo, F.; Wang, Z.; Wu, L.; Zhang, X.; Höppener, S.; Lifeng, C.; Fuchs, H.; Zhao, J.; Niu, L.; Dong, S. Langmuir 2000, 16, 3813.
29. (b) Tokuhisa, H.; Zhao, M.; Baker, L. A.; Phan, V. T.; Dermody, D. L.; Garcia, M. E.; Peez, R. F.; Crooks, R. M.; Mayer, T. M. J. Am. Chem. Soc. 1998, 120, 4492.
30. (c) Gorman, C. B.; Miller, R. L.; Chen, K.-Y.; Bishop, A. R.; Haasch, R. T.; Nuzzo, R. G. Langmuir 1998, 14, 3312.
31. Wooley, K. L.; Hawker, C. J.; Fréchet, J. M. J. J. Chem. Soc., Perkin Trans. 1 1991, 1059.
32. Schönherr, H.; Vancso, G. J.; Huisman, B.-H.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Langmuir 1999, 15, 5541.
33. (a) Boukamp, B. A. Equivalent Circuit version 4.55, Department Chemical Technology, University of Twente, Enschede, The Netherlands, 1996.
34. (b) Boukamp, B. A. Solid State Ionics 1986, 18, 136.
35. (c) Boukamp, B. A. Solid State Ionics 1986, 20, 31.
36. Lindholm-Sethson, B. Langmuir 1996, 12, 3305.
37. Nahir, T. M.; Bowden, E. F. Electrochim. Acta 1994, 39, 2347.
38. The width of the dendrimer wedges appears to be larger than in reality, due to tip convolution.
39. Electrochemical resistance is a very sensitive, if not the most sensitive, measure for the defects present in monolayers. See: Finklea, H. O. In Electroanalytical Chemistry; Bard, A. J., Rubinstein, I., Eds.; Marcel Dekker: New York, 1996; Vol. 19, pp 109-335.
40. 2 corresponds to approximately a 4% desorption of thiols in the SAM.
41. 3 ohm, this approximation is well founded.
42. The error in the rate constant was determined by varying k as far as the calculated R values remained within the experimental error bars.
43. Since the maximum coverage of dendrimer molecules obtained in these experiments was very small <1%, no assumptions regarding the resistance of a dendrimer molecule with respect to that of a thiol molecule were made.
44. In a previous paper (see ref 10) defect formation was thought to be the rate-determining step of the metallodendrimer insertion process; however, quantitative studies had not been carried out at the time. Moreover, different experimental conditions (e.g., solvent, alkanethiol SAM) have been used in this paper.