Self-assembly of [n]rotaxanes bearing dendritic stoppers

Journal of the American Chemical Society

Volumn 118, Issue 48, 1996, Pages 12012-12020

  Amabilino, David B ^a   Ashton, Peter R ^a   Balzani, Vincenzo ^c   Brown, Christopher L ^a   Credi, Alberto ^c   Fréchet, Jean M J ^b   Leon, Jeffrey W ^b   Raymo, Françisco M ^a   Spencer, Neil ^a   Stoddart, J Fraser ^a   Venturi, Margherita ^c  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b Department of Population Medicine and Diagnostic Sciences   (United States)

^c Dipartimento di Chimica   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; ELECTROCHEMISTRY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; SPECTROPHOTOMETRY; TECHNIQUE;

EID: 16944364302     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja962113h     Document Type: Article

References (58)

1. (a) Ashton, P. R.; Ballardini, R.; Balzani, V.; Bělohradský, M.; Gandolfi, M. T.; Philp, D.; Prodi, L.; Raymo, F. M.; Reddington, M. V.; Spencer, N.; Stoddart, J. F.; Venturi, M.; Williams, D. J. J. Am. Chem. Soc. 1996, 118, 4931-4951.
2. (b) Asakawa, M.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Bělohradský, M.; Gandolfi, M. T.; Kocian, O.; Prodi, L.; Raymo, F. M.; Stoddart, J. F.; Venturi, M. J. Am. Chem. Soc. In press.
3. (a) Lindsey, J. S. New J. Chem. 1991, 15, 153-180.
4. (b) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319.
5. (c) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 25, 37-44.
6. (d) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229-2260.
7. (e) Raymo, F. M.; Stoddart, J. F. Curr. Op. Coll. Interface Sci. 1996, 1, 116-126.
8. (f) Philp, D.; Stoddart J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196.
9. (a) Dietrich-Buchecker, C. O.; Sauvage J.-P. Bioorg. Chem. Front. 1991, 2, 195-248.
10. (b) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162.
11. (c) Gibson, H. W.; Marand, H. Adv. Mater. 1993, 5, 11-21.
12. (d) Gibson, H. W.; Bheda, M. C.; Engen., P. T. Prog. Polym. Sci. 1994, 19, 843-945.
13. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828.
14. (f) Bělohradský, M.; Raymo, F. M.; Stoddart, J. F. Collect. Czech. Chem. Commun. 1996, 61, 1-43.
15. (a) Ozin, G. A. Adv. Mater. 1992, 4, 612-649.
16. (b) Merkle, R. C. Nanotechnology 1993, 4, 86-90.
17. (c) Mann, S. Science 1993, 365, 499-505.
18. (d) Wibur, J. L.; Kumar, A.; Kim, E.; Whitesides, G. M. Adv. Mater. 1994, 6, 600-604.
19. (e) Drexler, K. E. Annu. Rev. Biophys. Biomol. Struct. 1994, 23, 377-405.
20. (f) Kumar, A.; Abbot, N. L.; Kim, E.; Biebuyck, A.; Whitesides, G. M. Acc. Chem. Res. 1995, 28, 219-226.
21. (g) Bowes, C. L.; Ozin, G. A. Adv. Mater. 1996, 8, 13-28.
22. (a) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1304-1319.
23. (b) Balzani, V.; Scandola, F. Supramolecular Photochemistry, Horwood: Chichester, 1991, Chapter 12.
24. (c) Bissell, R. A.; de Silva, A. P.; Gunaratne, H.; Lynch, P. L. M.; Maguire, G. E. M.; Sandanayake, K. R. A. S. Chem. Soc. Rev. 1992, 21, 187-195.
25. (d) Lehn, J.-M. Science 1993, 260, 1762-1763.
26. (e) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202.
27. (f) Beer, P. D. Chem. Commun. 1996, 689-696.
28. (a) Tomalia, D. A.; Naylor, A. M.; Goddard, W. A., III Angew. Chem., Int. Ed. Engl. 1990, 29, 138-17.
29. (b) Kim, Y. H. Adv. Mater. 1992, 4, 764-766.
30. (c) Newkome, G. R.; Moorefield, C. N.; Baker, G. R. Aldrichim. Acta 1992, 25, 31-38.
31. (d) Mekelburger, H. B.; Jaworek, W.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1571-1576.
32. (e) van der Made, A. W.; van Leeuwen, P. W. N. M.; de Wielde, J. C.; Brandes, R. Adv. Mater. 1993, 5, 466-468.
33. (f) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193-313.
34. (g) Tomalia, D. A. Adv. Mater. 1994, 6, 529-539.
35. (h) Rajca, A. Adv. Mater. 1994, 6, 605-607.
36. Issbemer, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413-2420.
37. (j) Fréchet, J. M. J. Science 1994, 263, 1710-1715.
38. For examples of dumbbell-shaped two directional dendrimers, see: (a) Newkome, G. R.; Baker, G. R.; Saunders, M. J.; Russo, P. S.; Gupta, V. K.; Yao, Z.; Miller, J. E.; Bouillion, K. J. Chem. Soc., Chem. Commun. 1986, 752-753.
39. (b) Newkome, G. R.; Baker, G. R.; Arai, S.; Saunders, M. J.; Russo, P. S.; Theriot, K. J.; Moorefield, C. N.; Rogers, L. E.; Miller, J. E.; Lieux, T. R.; Murray, M. E.; Phillips, B.; Pascal, L. J. Am. Chem. Soc. 1990, 112, 8458-8465.
40. (c) Newkome, G. R.; Moorefield, C. N.; Baker, G. R.; Behera, R. K.; Escamilla, G. H.; Saunders, M. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 917-919.
41. (d) Newkome, G. R.; Lin, X.; Yaxiong, C.; Escamilla, G. H. J. Org. Chem. 1993, 58, 3123-3129.
42. 4, respectively. The remaining compounds - i.e. the polycationic rotaxanes - are indicated by numbers, followed by the counterions.
43. Anelli, P. L.; Spencer, N.; Stoddart, J. F. J. Am. Chem. Soc. 1991, 113, 5131-5133.
44. (a) Sutherland, I. O. Annu. Rep. NMR Spectrosc. 1971, 4, 71-235.
45. (b) Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
46. Mahamadi, F.; Richards, N. G. K.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, D.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comp. Chem. 1990, 11, 440-467.
47. The approximate end-to-end lengths of the rotaxanes were calculated as the distances between two points located in space at the most remote site of the surface of the dendritic stopper and laying on the mean plane defined by the polycationic thread.
48. Anelli, P. L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M. T.; Goodnow, T. T.; Kaifer, A. E.; Philp, D.; Pietraszkiewicz, M.; Prodi, L.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 193-218.
49. Ballardini, R.; Gandolfi, M. T.; Prodi, L.; Ciano, M.; Balzani, V.; Kohnke, F. H.; Shahriari-Zavareh, H.; Spencer, N.; Stoddart, J. F. J. Am. Chem. Soc. 1989, 111, 7052-7078.
50. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Practical Organic Chemistry; Longman: New York, 1989.
51. Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638-7647.
52. We wish to acknowledge the use of the EPSRC's Chemical Database Service at Daresbury. The United Kingdom Chemical Database Service: Fletcher, D. A., McMeeking, R. F., Parkin, D. J. Chem. Inf. Comput. Sci. 1996, 36, 746-749.
53. 3D Search and Research using Camdridge Structural Database: Allen, F. H., Kennard, O. Chem. Design Automation News 1993, 8(1), 1, 31-37.
54. As a result of the poor parametrization of the hexafluorophosphate counterions within the Amber* forcefield resident in Macromodel 5.0, acetate counterions were used instead.
55. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrckson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129.
56. Polygen Corporation, 200 Fifth Avenue, Waltham, MA 02254.
57. Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Compounds; Academic Press: London, 1965.
58. Armaroli, N.; Balzani, V.; Barigelletti, F.; De Cola, L.; Flamigni, L.; Sauvage, J.-P.; Hemmert, C. J. Am. Chem. Soc. 1994, 116, 5211-5217.