Controlling the morphology of aggregates of an amphiphilic synthetic receptor through host-guest interactions

Langmuir

Volumn 22, Issue 14, 2006, Pages 5994-5997

  Suksai, Chomchai ^a,b   Gómez, Sergio Figueiras ^c   Chhabra, Anjali ^d   Liu, Jingyuan ^a   Skepper, Jeremy N ^a   Tuntulani, Thawatchai ^b   Otto, Sijbren ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b CHULALONGKORN UNIVERSITY   (Thailand)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^d INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; AGGREGATES; HYDROPHOBICITY; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; SELF ASSEMBLY; TRANSMISSION ELECTRON MICROSCOPY;

AGGREGATION BEHAVIOR; AMPHIPHILIC RECEPTOR; HYDROPHOBIC CAVITY; WATER-SOLUBLE AMPHIPHILIC RECEPTORS;

MORPHOLOGY;

EID: 33746563430     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la0609470     Document Type: Article

References (41)

1. For a review, see (a) Kunitake, T. Angew. Chem., Int. Ed. Engl. 1992, 31, 709.
2. For selected recent examples, see (b) Abel, E.; De Wall, S. L.; Edwards, W. B.; Lalitha, S.; Covey, D. F.; Gokel, G. W. Chem. Commun. 2000, 433.
3. (c) Hartgerink, J. D.; Beniash, E.; Stupp, S. I. Science 2001, 294, 1684.
4. (d) Zhou, S. Q.; Burger, C.; Chu, B.; Sawamura, M.; Nagahama, N.; Toganoh, M.; Hackler, U. E.; Isobe, H.; Nakamura, E. Science 2001, 291, 1944.
5. (e) Pochan, D. J.; Chen, Z. Y.; Cui, H. G.; Hales, K.; Qi, K.; Wooley, K. L. Science 2004, 306, 94.
6. (f) Boerakker, M. J.; Hannink, J. M.; Bomans, P. H. H.; Frederik, P. M.; Nolle, R. J. M.; Meijer, E. M.; Sommerdijk, N. A. J. M. Angew. Chem., Int. Ed. 2002, 41, 4239.
7. (g) Vriezema, D. M.; Hoogboom, J.; Velonia, K.; Takazawa, K.; Christianen, P. C. M.; Maan, J. C.; Rowan, A. E.; Nolle, R. J. M. Angew. Chem., Int. Ed. 2003, 42, 772.
8. Johnsson, M.; Wagenaar, A.; Engberts, J. B. F. N. J. Am. Chem. Soc. 2003, 125, 757.
9. Hu, Z. J.; Jonas, A. M.; Varshney, S. K.; Gohy, J. F. J. Am. Chem. Soc. 2005, 127, 6526.
10. (a) Yin, H. Q.; Huang, J. B.; Lin, Y. Y.; Zhang, Y. Y.; Qiu, S. C.; Ye, J. P. J. Phys. Chem. B 2005, 109, 4104.
11. (b) Gao, L. C.; Shi, L. Q.; Zhang, W. Q.; An, Y. L.; Liu, Z.; Li, G. Y.; Meng, Q. B. Macromolecules 2005, 38, 4548.
12. (a) Menger, F. M.; Williams, D. Y. Tetrahedron Lett. 1986, 27, 2579.
13. (b) Fetter, R. C.; Salek, J. S. J. Am. Chem. Soc. 1987, 109, 7897.
14. (c) Petter, R. C.; Salek, J. S.; Sikorski, C. T.; Kumaravel, G.; Lin, F. T. J. Am. Chem. Soc. 1990, 112, 3860.
15. (d) Arimori, S.; Nagasaki, T.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2 1995, 679.
16. (e) Ravoo, B. J.; Darcy, R. Angew. Chem., Int. Ed. 2000, 39, 4324.
17. (f) Donohue, R.; Mazzaglia, A.; Ravoo, B. J.; Darcy, R. Chem. Commun. 2002, 2864.
18. (g) Falvey, P.; Lim, C. W.; Darcy, R.; Revermann, T.; Karst, U.; Giesbers, M.; Marcelis, A. T. M.; Lazar, A.; Coleman, A. W.; Reinhoudt, D. N.; Ravoo, B. J. Chem-Eur. J. 2005, 11, 1171.
19. (h) Jeon, Y. J.; Bharadwaj, P. K.; Choi, S. W.; Lee, J. W.; Kim, K. Angew. Chem., Int. Ed. 2002, 41, 4474.
20. (i) Lee, H. K.; Park, K. M.; Jeon, Y. J.; Kim, D.; Oh, D. H.; Kim, H. S.; Park, C. K.; Kim, K. J. Am. Chem. Soc. 2005, 127, 5006.
21. (j) Liu, Y.; Xu, J.; Craig, S. L. Chem. Commun. 2004, 1864.
22. (k) Lim, C. W.; Ravoo, B. J.; Reinhoudt, D. N. Chem. Commun. 2005, 5627.
23. (a) Otto, S. J. Mater. Chem. 2005, 75, 3357.
24. (b) Otto, S. Curr. Opin. Drug Discovery Dev. 2003, 6, 5090.
25. (a) Otto, S.; Furlan, R. L. E.; Sanders, J. K. M. Science 2002, 297, 590.
26. (b) Brisig, B.; Sanders, J. K. M.; Otto, S. Angew. Chem., Int. Ed. 2003, 42, 1270.
27. (c) Otto, S.; Kubik, S. J. Am. Chem. Soc. 2003, 125, 7804.
28. (d) Corbett, P. T.; Tong, L. H.; Sanders, J. K. M.; Otto, S. J. Am. Chem. Soc. 2005, 127, 8902.
29. (e) Corbett, P. T.; Sanders, J. K. M.; Otto, S. J. Am. Chem. Soc. 2005, 127, 9390.
30. (f) Vial, L.; Sanders, J. K. M.; Otto, S. New J. Chem. 2005, 29, 1001.
31. (g) West, K. R.; Bake, K. D.; Otto, S. Org. Lett. 2005, 7, 2615.
32. The low water solubility of 3 precludes the use of aqueous conditions. Using DMSO as the solvent as well as the oxidizing agent gave the best results. For references on the DMSO-mediated oxidation of thiols, see (a) Yiannios, C. N.; Karabinos, J. V. J. Org. Chem. 1963, 28, 3246.
33. (b) Wallance, T. J. J. Am. Chem. Soc. 1964, 86, 2018.
34. (c) Wallance, T. J.; Mahon, J. J. J. Am. Chem. Soc. 1964, 86, 4099.
35. (d) Wallance, T. J.; Mahon, J. J. J. Org. Chem. 1965, 30, 1502.
36. The assignment of the stereoisomers is based on structural correlations through reequilibration experiments (Supporting Information).
37. The discrepancy between the results from DLS and electron microscopy is most likely an artifact of the analysis of the DLS data, which is based on the assumption that the aggregates are spherical. Electron microscopy shows that this assumption is not valid in this case.
38. The fact that 4 is able to template the formation of Ib in DMSO solution is probably because in this solvent the alkyl chain is not occupying the cavity of the receptor.
39. app) therefore contains contributions from the interactions between host and guest as well as contributions associated with the reorganization of the aggregates.
40. (a) Jiang, J. Q.; Tong, X.; Zhao, Y. J. Am. Chem. Soc. 2005, 127, 8290.
41. (b) Goodwin, A. P.; Mynar, J. L.: Ma, Y. Z.; Fleming, G. R.; Frechet, J. M. J. J. Am. Chem. Soc. 2005, 127, 9952.