Individual supramolecular host-guest interactions studied by dynamic single molecule force spectroscopy

Journal of the American Chemical Society

Volumn 122, Issue 20, 2000, Pages 4963-4967

  Schönherr, Holger ^a   Beulen, Marcel W J ^a   Bügler, Jürgen ^a   Huskens, Jurriaan ^a   Van Veggel, Frank C J M ^a   Reinhoudt, David N ^a   Vancso, G Julius ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CYCLODEXTRIN; FERROCENE DERIVATIVE; GOLD; RECEPTOR;

ARTICLE; ATOMIC FORCE MICROSCOPY; COMPLEX FORMATION; MOLECULAR INTERACTION; SPECTROSCOPY;

EID: 0034709391     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994040i     Document Type: Article

References (39)

1. Binnig, G.; Quate, C. F.; Gerber, Ch. Phys. Rev. Lett. 1986, 56, 933.
2. (a) Frommer, J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1298-1328.
3. (b) Magonov, S. N.; Whangbo, M.-H. Surface Analysis with STM and AFM; VHC, Weinheim 1996.
4. (a) Florin, E.-L.; Moy, V. T.; Gaub, H. E. Science 1994, 264, 415-417.
5. (b) Moy, V. T.; Florin, E.-L.; Gaub, H. E. Science 1994, 266, 257-259.
6. (c) Lee, G. U.; Chrisey, L. A.; Colton, R. J. Science 1994, 266, 771-773.
7. (d) Dammer, U.; Popescu, O.; Wagner, P.; Anselmetti, D.; Güntherodt, H.-J.; Misevic, G. N. Science 1995, 267, 1173-1175.
8. (e) Rief, M.; Gautel, M.; Oesterhelt, F.; Fernandez, J. M.; Gaub, H. E. Science 1997, 276, 1109-1112.
9. (f) Rief, M.; Oesterhelt, F.; Heymann, B.; Gaub, H. E. Science 1997, 275, 1295-1297.
10. (g) Lee, G. U.; Kidwell, D. A.; Colton, R. J. Langmuir 1994, 10, 354-357.
11. (h) Ros, R.; Schwesinger, F.; Anselmetti, D.; Kubon, M.; Schäfer, R.; Plückthun, A.; Tiefenauer, L. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 7402-7405 and references therein.
12. Other experimental work on force spectroscopy has been carried out by optical tweezers (Kuo, S. C.; Sheetz, M. P. Science 1993, 260, 232-234.) and biomembrane force probe techniques (see ref 5).
13. For unbinding kinetics which are slow compared to the rate of pulling force, a pronounced rate dependence of the unbinding forces has been predicted theoretically: (a) Evans, E.; Ritchie, K. Biophys. J. 1997, 72, 1541-1555. These predictions were recently supported by experimental data: (b) Merkel, R.; Nassoy, P.; Leung, A.; Ritchie, K.; Evans, E. Nature 1999, 397, 50-53.
14. For unbinding kinetics which are slow compared to the rate of pulling force, a pronounced rate dependence of the unbinding forces has been predicted theoretically: (a) Evans, E.; Ritchie, K. Biophys. J. 1997, 72, 1541-1555. These predictions were recently supported by experimental data: (b) Merkel, R.; Nassoy, P.; Leung, A.; Ritchie, K.; Evans, E. Nature 1999, 397, 50-53.
15. b (a) Szejtli, J.; Osa, T. Comprehensive Supramolecular Chemistry, Vol 3, Cyclodextrins; Elsevier Science Publishers: Oxford 1996. (b) Green, N. M.; Toms, E. J. Biochem. J. 1973, 133, 687.
16. b (a) Szejtli, J.; Osa, T. Comprehensive Supramolecular Chemistry, Vol 3, Cyclodextrins; Elsevier Science Publishers: Oxford 1996. (b) Green, N. M.; Toms, E. J. Biochem. J. 1973, 133, 687.
17. b (a) Szejtli, J.; Osa, T. Comprehensive Supramolecular Chemistry, Vol 3, Cyclodextrins; Elsevier Science Publishers: Oxford 1996. (b) Green, N. M.; Toms, E. J. Biochem. J. 1973, 133, 687.
18. Ashton, P. R.; Königer, R.; Stoddart, J. F.; Alker, D.; Harding, V. D. J. Org. Chem. 1996, 61, 903-908.
19. Guillo, F.; Hamelin, B.; Jullien, L.; Canceill, J.; Lehn, J. M.; Derobertis, L.; Driguez, H. Bull. Soc. Chim. Fr. 1995, 132, 857-866.
20. Beulen, M. W. J.; Bügler, J.; de Jong, M. R.; Lammerink, B.; Huskens, J.; Schönherr, H.; Vancso, G. J.; Boukamp, B. A.; Wieder, H.; Offenhäuser, A.; Knoll, W.; van Veggel, F. C. J. M.; Reinhoudt D. N. Chem. Eur. J. 2000, 6, 1176-1183.
21. (a) Schönherr, H.; Vancso, G. J.; Huisman, B.-H.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Langmuir 1999, 15, 5541-5546.
22. (b) Beulen, M. W. J.; Bügler, J.; Lammerink, B.; Geurts, F. A. J.; Biemond, E. M. E. F.; van Leerdam, K. G. C.; van Veggel, F. C. J. M.; Engbersen, J. F. J.; Reinhoudt, D. N. Langmuir 1998, 14, 6424-6429.
23. Schönherr, H.; Hruska, Z.; Vancso, G. J. Macromolecules 1998, 31, 3679-3685.
24. Tortonese, M.; Kirk, M. Proc. SPIE 1997, 3009, 53-60.
25. (a) Reference 6a.
26. (b) Inoue, Y.; Wada, T. In Advances in Supramolecular Chemistry; Jai Press: Stanford, CA, 1997; Vol. 4, p 55.
27. (c) D'Souza, V. T.; Lipkowitz, K. B. Chem. Rev. 1998, 98, 1741-1742.
28. For details on our concept see: Thoden van Velzen, E. U.; Engbersen, J. F. J.; de Lange, P. J.; Mahy, J. W.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6853-6862.
29. 6-Ferrocenyl-hexanethiol was synthesized according to a literature procedure (Creager, S. E.; Rowe, G. K. J. Electroanal. Chem. 1994, 370, 203-211). 1,8-ANS, 2-hydroxy-ethanethiol, and hexadecanethiol were purchased from Aldrich and used as received.
30. 4 for monolayers of different ratios of the two adsorbates in the adsorption solution (1-100% 6-ferrocenyl-hexanethiol).
31. 14 monolayer is due to host-guest interactions and is not a result of an aspecific interaction, for example, with the alkyl chains. (a) For a fundamental discussion on EIS see: Flink, S.; Boukamp, B. A.; van den Berg, A.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Am. Chem. Soc. 1998, 120, 4652-4657.
32. 14 SAMs, proving the importance of accessibility for the ferrocene units. (a) Noy, A.; Frisbie, C. D.; Rozsnyai, L. F.; Wrighton, M. S.; Lieber, C. M. J. Am. Chem. Soc. 1995, 117, 7943-7951. (b) Sinniah, S. K.; Steel, A. B.; Miller, C. J.; Reutt- Robey, J. E. J. Am. Chem. Soc. 1996, 118, 8925-8931.
33. 14 SAMs, proving the importance of accessibility for the ferrocene units. (a) Noy, A.; Frisbie, C. D.; Rozsnyai, L. F.; Wrighton, M. S.; Lieber, C. M. J. Am. Chem. Soc. 1995, 117, 7943-7951. (b) Sinniah, S. K.; Steel, A. B.; Miller, C. J.; Reutt-Robey, J. E. J. Am. Chem. Soc. 1996, 118, 8925-8931.
34. 1/2.
35. The number of pull-offs was reduced by 20-30% for each cycle, which may be attributed to irreversible damage of the β-CD SAM and/or the tip.
36. The autocorrelation function of the histogram of the second cycle, after washing the 1,8-ANS away, again proved a quantized rupture force of 56 pN. Furthermore, the few pull-offs sometimes observed in the AFM measurements in the presence of 1,8-ANS are also multiples of 56 pN.
37. -3 N/m), and a tip radius (R = 100 nm) were experimentally determined. The following parameters for the SAMs were assumed: Young's modulus E = 0.5 GPa, Poisson's ratio v = 0.3. The number of ferrocene-terminated molecules in the contact area between the tip and the mixed SAMs can be estimated to be ∼14-28 molecules, based on 1-2% of ferrocene-terminated thiol in the SAM (see ref 12).
38. In high resolution scanning electron microscopy (SEM) images of modified tips the granular nature of the gold coating is readily seen (Schönherr, H. Ph.D. Thesis, University of Twente, 1999).
39. In the ultrafast unloading regime only viscous factional drag retards the separation (see ref 5).