Intra- and intermonolayer hydrogen bonding in amide-functionalized alkanethiol self-assembled monolayers on gold nanoparticles

Langmuir

Volumn 16, Issue 24, 2000, Pages 9527-9532

  Boal, Andrew K ^a   Rotello, Vincent M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; GOLD; HYDROGEN BONDS; INFRARED SPECTROSCOPY; NANOSTRUCTURED MATERIALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARAFFINS; SYNTHESIS (CHEMICAL);

ALKANETHIOLS;

MONOLAYERS;

EID: 0034316836     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la0012384     Document Type: Article

References (50)

1. (a) Schmid, G.; Bäumle, M.; Geerkens, M.; Heim, I.; Osemann, C.; Sawitowski, T. Chem. Soc. Rev. 1999, 28, 179-485.
2. (b) Schmid, G.; Chi, L. F. Adv. Mater. 1998, 10, 515-526.
3. (a) Templeton, A. C.; Wuelfing, W. P.; Murray, R. W. Acc. Chem. Res. 2000, 33, 27-36.
4. (b) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. Liu, J.; Xu, R. L.; Kaifer, A. E. Langmuir 1998, 14, 7337-7339.
5. (b) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. Liu, J.; Xu, R. L.; Kaifer, A. E. Langmuir 1998, 14, 7337-7339.
6. (a) Alivastos, A. P.; Barbara, P. F.; Castleman, A. W.; Chang, J.; Dixon, D. A.; Klein, M. L.; McLendon, G. L.; Miller, J. S.; Ratner, M. A.; Rossky, P. J.; Stupp, S. I.; Thompson, M. E. Adv. Mater. 1998, 10, 1297-1336.
7. (b) Alivisatos, A. P.; Johnsson, K. P.; Peng, X. G.; Wilson, T. E.; Loweth, C. J.; Bruchez, M. P.; Schultz, P. G. Nature 1996, 382, 609-611.
8. (c) Mann, S.; Shenton, W.; Li, M.; Connolly, S.; Fitzmaurice, D. Adv. Mater. 2000, 12, 147-150.
9. (a) Bruchez, M., Jr.; Moronne, M.; Gin, P.; Weiss, S.; Alivisatos, A. P. Science 1998, 281, 2013-2016.
10. (b) Chan, W. C. W.; Nie, S. Science 1998, 281, 2016-2018.
11. Brousseau, L. C., III; Zhao, Q.; Shultz, D. A.; Feldheim, D. L. J. Am. Chem. Soc. 1998, 120, 7645-7646.
12. Boal, A. K.; Rotello, V. M. J. Am. Chem. Soc. 1999, 121, 4914-4915.
13. Watson, K. J.; Zhu, J.; Nguyen, S. T.; Mirkin, C. A. J. Am. Chem. Soc. 1999, 121, 402-403.
14. Li, H.; Luk, Y.-Y.; Mrkish, M. Langmuir 1999, 15, 4957-4959.
15. (a) Mucic, R. C.; Storhoff, J. J.; Mirkin, C. A.; Letsinger, R. L. J. Am. Chem. Soc. 1998, 120, 12674-12675.
16. (b) Niemeyer, C. M.; Bürger, W.; Peplies, J. Angew. Chem., Int. Ed. 1998, 37, 2265-2268.
17. (c) Brousseau, L. C.; Novak, J. P.; Marinakos, S. M.; Feldheim, D. L. Adv. Mater. 1999, 11, 447-449.
18. (d) Mirkin, C. A.; Letsinger, R. L.; Mucic, R. C.; Storhoff, J. J. Nature 1996, 382, 607-609.
19. (e) Alivisatos, A. P.; Johnsson, K. P.; Pneg, X.; Wilson, T. E.; Lowteh, C. J.; Bruchez, M. P., Jr.; Schultz, P. G. Nature 1996, 382, 609-611.
20. (f) Boal, A. K.; Ilhan, F.; DeRouchey, J. E.; Thurn-Albrecht, T.; Russell, T. P.; Rotello, V. M. Nature 2000, 404, 746-748.
21. Hosteller, M. J.; Templeton, A. C.; Murray, R. W. Langmuir 1999, 15, 3782-3782.
22. Boal, A. K.; Rotello, V. M. J. Am. Chem. Soc. 2000, 122, 734-735.
23. (a) Tam-Chang, S.-W.; Biebuych, H. A.; Whitesides, G. M.; Jeon, N.; Nuzzo, R. G. Langmuir 1995, 11, 4371-4382.
24. (b) Clegg, R. S.; Hutchison, J. E. Langmuir 1996, 12, 5239-5243.
25. (c) Chechin, V.; Schönherr, H.; Vansco, G. J.; Stirling, C. J. M. Langmuir 1998, 14, 3003-3010.
26. (a) Clegg, R. S.; Reed, S. M.; Hutchison, J. E. J. Am. Chem. Soc. 1998, 120, 2486-2487.
27. (b) Clegg, R. S.; Reed, S. M,; Smith, R. K.; Barron, B. L.; Rear, J. A.; Hutchison, J. E. Langmuir 1999, 15, 8876-8883.
28. Clegg, R. S.; Hutchison, J. E. J. Am. Chem. Soc. 1999, 121, 5319-5327.
29. Intramonolayer refers to interactions between monolayer molecules on the same colloid, while intermonolayer refers to properties arising between monolayer interactions between two or more colloids, that is, interdigitation.
30. The only other example of deep internal functionality in a nanoparticle-based SAM did not investigate chain length dependencies on monolayer structure: Johnson, S. R.; Evans, S. D.; Mahon, S. W.; Ulman, A. Langmuir 1997, 13, 51-57.
31. (a) Bain, C. D.; Troughton, E. B.; Tao, Y.-T.; Evall, J.; Whitesides, G. M.; Nuzzon, R. G. J. Am. Chem. Soc. 1989, 111, 321-335.
32. (b) Ulman, A. An Introduction to Ultrathin Organic Films; Academic Press: Boston, 1991.
33. (a) Luedtke, W. D.; Landman, U. J. Phys. Chem. 1996, 100, 13323-13329.
34. (b) Hosteller, M. J.; Stokes, J. J.; Murray, R. W. Langmuir 1996, 12, 3604-3612.
35. We are currently investigating similar phenomena in π-stacking and π-stacking/hydrogen-bonding multivalent systems and will report these results in due course.
36. It is important to note that the chain lengths of each thiol were the same to avoid the overall SAM length from influencing monolayer properties.
37. Brust, M.; Walker, M.; Bethell, D.; Schiffrin, D. J.; Whyman, R. Chem. Commun. 1994, 801-802.
38. Internal functionality is known to decrease molecular density in alkanethiol SAMs formed on gold surfaces, see: (a) Evans, S. D.; Goppert-Berarducci, K. E.; Urankar, E.; Gerenser, L. J.; Ulman, A.; Snyder, R. G. Langmuir 1991, 7, 2700-2709.
39. (b) Sabapathy, R. C.; Bhattacharyya, S.; Leavy, M. C.; Cleland, W. E., Jr.; Hussey, C. L. Langmuir 1998, 14, 124-136.
40. Hostetler, M. J.; Wingate, J. E.; Zhong, C.-J.; Harris, J. E.; Vachet, R. W.; Clark, M. R.; Londono, J. D.; Green, S. J.; Stokes, J. J.; Wignal, G. D.; Glish, G. L.; Porter, M. D.; Evans, N. D.; Muray, R. W. Langmuir 1998, 14, 17-30.
41. - would result in increased particle size.
42. For an example of unequally sized nanoparticles self-organized in two-dimensional arrays by alkane interdigitation, see: Kiely, C. J.; Fink, J.; Brust, M.; Bethell, D.; Schiffrin, D. J. Nature 1998, 396, 444-446.
43. For an example of nanoparticle aggregation by terminal hydrogen-bonding functionality, see: Johnson, S. R:; Evans, S. D.; Brydson, R. Langmuir 1998, 14, 6639-6647.
44. (a) Badia, A.; Singh, S.; Demers, L.; Cuccia, L.; Brown, G. R.; Lennox, R. B. Chem. Eur. J. 1996,2, 359-363.
45. (b) Badia, A.; Gao, W.; Singh, S.; Demers, L.; Cuccia, L.; Reven, L. Langmuir 1996, 12, 1262-1269.
46. (c) Badia, A.; Cuccia, L.; Demers, L.; Morin, F.; Lennox, R. B. J. Am. Chem. Soc. 1997, 119, 2682-2692.
47. The NH peak in colloid 1 was too broad to be observed.
48. For a similar result of amide proton deshielding upon increased hydrogen bonding due to tight packing in an amide-functionalized dendrimer, see: Stevelmans, S.; van Hest, J. C. M.; Jansen, J. F. G. A.; van Boxtel, D. A. F. J.; de Brabander-van den Berg, E. M. M.; Meier, E. W. J. Am. Chem. Soc. 1996, 118, 7398-7399.
49. Pattison, F. L. M.; Stothers, J. B.; Woolford, R. G. J. Am. Chem. Soc. 1956, 78, 2255-2259.
50. Appleton, D.; Duguid, A. B.; Lee, S.-K.; Ha, Y.-J.; Ha, H.-J.; Leeper, F. J. J. Chem. Soc., Perkin Trans. 1 1998, 89-101.