An acid-base switchable [2]rotaxane

Journal of Organic Chemistry

Volumn 67, Issue 26, 2002, Pages 9175-9181

  Elizarov, Arkadij M ^a   Chiu, Sheng Hsien ^a   Stoddart, J Fraser ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICALLY ADDRESSABLE; DUMBBELL SHAPED COMPONENT;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON IRRADIATION;

RING OPENING POLYMERIZATION;

1,2 BIS(PYRIDINIUM)ETHANE; ACID; AMINE; AMMONIA; BASE; CHEMICAL COMPOUND; DIBENZO[24]CROWN 8; ETHANE; PROTON; ROTAXANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL PARAMETERS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037184773     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020373d     Document Type: Article

References (59)

1. (a) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414.
2. (b) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348-3391.
3. (c) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Venturi, M. Acc. Chem. Res. 2001, 34, 445-455.
4. (d) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Venturi, M. Struct. Bonding 2001, 99, 163-188.
5. (e) Harada, A. Acc. Chem, Res. 2001, 34, 456-464.
6. (f) Schalley, C. A.; Beizai, K.; Vögtle, F. Acc. Chem. Res. 2001, 34, 465-476.
7. (g) Hugel, T.; Holland, N. B.; Cattani, A.; Moroder, L.; Seitz, M.; Gaub, H. E. Science 2002, 296, 1103-1106.
8. (a) Introduction to Molecular Electronic Devices; Petty, M. C., Bryce, M. R., Bloor, D., Eds.; Oxford University Press: New York, 1995.
9. (b) Molecular Electronics; Jortner, J., Ratner, M., Eds.; Blackwell Science: Oxford, UK, 1997.
10. (c) Molecular Electronics: Science and Technology; Aviram, A., Ratner, M., Eds.; New York Academy of Sciences: New York, 1998.
11. (d) Wong, E. W.; Collier, C. P.; Belohradsky, M.; Raymo, F. M.; Stoddart, J. F.; Heath, J. R. J. Am. Chem. Soc. 2000, 122, 5831-5840.
12. (e) Collier, C. P.; Mattersteig, G.; Wong, E. W.; Luo, Y.; Beverly, K.; Sampaio, J.; Raymo, F. M.; Stoddart, J. F.; Heath, J. R. Science 2000, 289, 1172-1175.
13. (f) Collier, C. P.; Jeppesen, J. O.; Luo, Y.; Perkins, J.; Wong, E. W.; Heath, J. R.; Stoddart, J. F. J. Am. Chem. Soc. 2001, 123, 12632-12641.
14. (g) Luo, Y.; Collier, C. P.; Jeppesen, J. O.; Nielsen, K. A.; Delonno, E.; Ho, G.; Perkins, J.; Tseng, H.-R.; Yamamoto, T.; Stoddart, J. F.; Heath, J. R. CHEMPHYSCHEM 2002, 3, 519-525.
15. (a) Ashton, P. R.; Glink, P. T.; Stoddart, J. F.; Tasker, P. A.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 729-736.
16. (b) Solladie, N.; Chambron, J.-C.; Sauvage, J.-P. J. Am. Chem. Soc. 1999, 121, 3684-3692.
17. (c) Brouwer, A. M.; Frochot, C.; Gatti, F. G.; Leigh, D. A.; Mottier, L.; Paolucci, F.; Roffia, S.; Wurpel, G. W. H. Science 2001, 291, 2124-2128.
18. (a) Ashton, P. R.; Goodnow, T. T.; Kaifer, A. E.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 1396-1399.
19. (b) Vögtle, F.; Jager, R.; Handel, M.; Ottens-Hildebrandt, S. Pure Appl. Chem. 1996, 68, 225-232.
20. (c) Fujita, M.; Ogura, K. Coord. Chem. Rev. 1996, 148, 249-264.
21. (d) McArdle, C. P.; Van, S.; Jennings, M. C.; Puddephatt, R. J. J. Am. Chem. Soc. 2002, 124, 3959-3965.
22. Anelli, P.-L.; Spencer, N.; Stoddart, J. F. J. Am. Chem. Soc. 1991, 113, 5131-5133.
23. (a) Ashton, P. R.; Philp, D.; Spencer, N.; Stoddart, J. F. J. Chem. Soc., Chem. Commun. 1992, 1125-1128.
24. (b) Cao, J.; Fyfe, M. C. T.; Stoddart, J. F. J. Org. Chem. 2000, 65, 1937-1946.
25. (c) Loeb, S. J.; Wisner, J. A. Chem. Commun. 2000, 1939-1940.
26. (d) Furusho, Y.; Hasegawa, T.; Tsuboi, A.; Kihara, N.; Takata, T. Chem. Lett. 2000, 18-19.
27. (e) Mahoney, J. M.; Shukla, R.; Marshall, R. A.; Beatty, A. M.; Zajicek, J.; Smith, B. D. J. Org. Chem. 2002, 67, 1436-1440.
28. (a) Anelli, P.-L.; Asakawa, M.; Ashton, P. R.; Bissell, R. A.; Clavier, G.; Górski, R.; Kaifer, A. E.; Langford, S. J.; Mattersteig, G.; Menzer, S.; Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Williams, D. J. Chem. Eur. J. 1997, 3, 1113-1135.
29. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Baxter, I.; Credi, A.; Fyfe, M. C. T.; Gandolfi, M. T.; Gómez-López, M.; Martínez-Díaz, M.-V.; Piersanti, A.; Spencer, N.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1998, 120, 11932-11942.
30. (c) Wurpel, G. W. H.; Brouwer, A. M.; van Stokkum, I. H. M.; Farran, A.; Leigh, D. A. J. Am. Chem. Soc. 2001, 123, 11327-11328.
31. Bissell, R. A.; Córdova, E.; Kaifer, A. E.; Stoddart, J. F. Nature 1994, 369, 133-137.
32. Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Dress, K. R.; Ishow, E.; Kleverlaan, C. J.; Kocian, O.; Preece, J. A.; Spencer, N.; Stoddart, J. F.; Venturi, M.; Wegner, S. Chem. Eur. J. 2000, 6, 3558-3674.
33. (a) Ashton, P. R.; Campbell, P. J.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Philp, D.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1865-1871.
34. (b) Ashton, P. R.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Schiavo, C.; Spencer, N.; Stoddart, J. F.; Tasker, P. A.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1996, 2, 709-728.
35. (c) Kolchinski, A. G.; Busch, D. H.; Alcock, N. W. J. Chem. Soc., Chem. Commun. 1995, 1289-1291.
36. (d) Bryant, W. S.; Guzei, I. A.; Rheingold, A. L.; Merola, J. S.; Gibson, H. W. J. Org. Chem. 1998, 63, 7634-7639.
37. (e) Kihara, N.; Yuya, T.; Kawasaki, H.; Takata, T. Chem. Lett. 2000, 506-507.
38. (f) Duggan, S. A.; Fallon, G.; Langford, S. J.; Lau, V. L.; Satchell, J. F.; Paddon-Row, M. N. J. Org. Chem. 2001, 66, 4419-4426.
39. (g) Gibson, H. W.; Yamaguchi, N.; Hamilton, L.; Jones, J. J. Am. Chem. Soc. 2002, 124, 4653-4665.
40. Martínez-Díaz, M.-V.; Spencer, N.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1997, 36, 1904-1907. This reference describes an "all-or-nothing" molecular switch. For many applications (e.g., colorimetric indicators, sensors, logic gates, etc.) small switching ratios are all that is required. However, when it comes to converting chemical energy into mechanical energy in an efficient manner, an "all-or-nothing" switch is a highly desirable goal.
41. (a) Loeb, S. J.; Wisner, J. A. Angew. Chem., Int. Ed. 1998, 37, 2838-2840.
42. (b) Loeb, S. J.; Wisner, J. A. Chem. Commun. 1998, 2757-2758.
43. (c) Loeb, S. J.; Wisner, J. A. Chem. Commun. 2000, 845-846.
44. For recent reviews on dynamic chemistry see: Greig, L. M.; Philp, D. Chem. Soc. Rev. 2001, 30, 287-302.
45. (b) Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898-952.
46. (a) Cantrill, S. J.; Rowan, S. J.; Stoddart, J. F. Org. Lett. 1999, 1, 1363-1366.
47. (b) Ibukuro, F.; Fujita, M.; Yamagichi, Y.; Sauvage, J.-P. J. Am. Chem. Soc. 1999, 121, 11014-11015.
48. (c) Kidd, T. J.; Leigh, D. A.; Wilson, A. J. J. Am. Chem. Soc. 1999, 121, 1599-1600.
49. (d) Furusho, Y.; Hasegawa, T.; Tsuboi, A.; Kihara, N.; Takata, T. Chem. Lett. 2000, 18-19.
50. (e) Glink, P. T.; Oliva, A. I.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. 2001, 40, 1870-1875.
51. 3CN.
52. +-Hmellip;O] hydrogen bonding that is at stake in the former recognition site compared with the weaker [C-H⋯O] interactions that characterize the latter recognition site.
53. 6.
54. 6 recorded in the presence and in the absence of DB24C8, respectively.
55. 1H NMR spectroscopy.
56. 3.)
57. -.
58. 1H NMR spectrum as shown in Figure 3b.
59. Attalla, M. I.; McAlpine, N. S.; Summers, L. A. Z. Naturforsch. B 1984, 39, 74-78.