A three-pole supramolecular switch

Journal of the American Chemical Society

Volumn 121, Issue 16, 1999, Pages 3951-3957

  Ashton, Peter R ^a   Balzani, Vincenzo ^b   Becher, Jan ^c   Credi, Alberto ^b   Fyfe, Matthew C T ^d   Mattersteig, Gunter ^d   Menzer, Stephan ^e   Nielsen, Mogens B ^d   Raymo, Françisco M ^d   Stoddart, J Fraser ^d   Venturi, Margherita ^b   Williams, David J ^e  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

TETRATHIAFULVALENE DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; ELECTROCHEMISTRY; ELECTRON TRANSPORT; MOLECULAR INTERACTION; POTENTIOMETRY; SPECTROSCOPY;

EID: 0033612015     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984341c     Document Type: Article

References (65)

1. (a) Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, 1995.
2. (b) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393-401.
3. (c) Reinhoudt, D. N.; Stoddart, J. F.; Ungaro, R. Chem. Eur. J. 1998, 4, 1349-1351.
4. Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247.
5. Deans, R.; Niemz, A.; Breinlinger, E. C.; Rotello, V. M. J. Am. Chem. Soc. 1997, 119, 10863-10864.
6. (a) Mirzoian, A.; Kaifer, A. E. Chem. Eur. J. 1997, 3, 1052-1058.
7. (b) Wang, Y.; Mendoza, S.; Kaifer, A. E. Inorg. Chem. 1998, 37, 317-320.
8. (a) Collin, J.-P.; Gaviña, P.; Sauvage, J.-P. Chem. Commun. 1996, 2005-2006.
9. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Boyd, S. E.; Credi, A.; Gandolfi, M. T.; Gómez-López, M.; Iqbal, S.; Philp, D.; Preece, J. A.; Prodi, L.; Ricketts, H. G.; Stoddart, J. F.; Tolley, M. S.; Venturi, M.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1997, 3, 152-170.
10. (c) Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Mattersteig, G.; Matthews, O. A.; Montalti, M.; Spencer, N.; Stoddart, J. F.; Venturi, M. Chem. Eur. J. 1997, 3, 1992-1996.
11. (d) Devonport, W.; Blower, M. A.; Bryce, M. R.; Goldenberg, L. M. J. Org. Chem. 1997, 62, 885-887.
12. (a) Bissell, R. A.; Cordóva, E.; Kaifer, A. E.; Stoddart, J. F. Nature 1994, 369, 133-137.
13. (b) Collin, J.-P.; Gaviña, P.; Sauvage, J.-P. New J. Chem. 1997, 21, 525-528.
14. (c) 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.
15. (a) Livoreil, A.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. J. Am. Chem. Soc. 1994, 116, 9399-9400.
16. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Menzer, S.; Pérez-García, L.; Prodi, L.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11171-11197.
17. (c) Càrdenas, D. J.; Livoreil, A.; Sauvage, J.-P. J. Am. Chem. Soc. 1996, 118, 11980-11981.
18. (d) Livoreil, A.; Sauvage, J.-P.; Armaroli, N.; Balzani, V.; Flamigni, L.; Ventura, B. J. Am. Chem. Soc. 1997, 119, 12114-12124.
19. (e) Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Hamers, C.; Mattersteig, G.; Montalti, M.; Shipway, A. N.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Venturi, M.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. 1998, 37, 333-337.
20. (a) Hünig, S.; Kiesslich, G.; Quast, H.; Scheutzow, D. Liebigs Ann. Chem. 1973, 310-323.
21. (b) Schukat, G.; Fanghänel, E. J. Prakt. Chem. 1985, 327, 767-774.
22. (c) Jøgensen, T.; Hansen, T. K.; Becher, J. Chem. Soc. Rev. 1994, 23, 41-51.
23. (d) Bryce, M. R.; Devonport, W.; Moore, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1761-1763.
24. (a) Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1991, 1584-1586.
25. (b) 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.
26. Schukat, G.; van Hinh, L.; Fanghänel, E. Z. Chem. 1976, 16, 360-361.
27. 6, another dication that is bound strongly by 1/5DN38C10. See: Ashton, P. R.; Chrystal, E. J. T.; Mathias, J. P.; Parry, K. P.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Tetrahedron Lett. 1987, 28, 6367-6370.
28. 2+.
29. Other crystallographic analyses of tetrathiafulvalenium dications have been reported hitherto. See: (a) Scott, B. A.; La Placa, S. J.; Torrance, J. B.; Silverman, B. D.; Welber, B. J. Am. Chem. Soc. 1977, 99, 6631-6639. (b) Zhilyaeva, E. I.; Lyubovskaya, R. N.; Rozenberg, L. P.; Shibaeva, R. P.; Khidekel, M. L. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1984, 33, 632-634. (c) Brunn, K.; Endres, H.; Weiss, J. Z. Naturforsch. 1988, 43b, 224-230. (d) Jones, P. G. Z. Naturforsch. 1989, 44b, 243-244. (e) Abboud, K. A.; Clevenger, M. B.; de Oliveira, G. F.; Talham, D. R. J. Chem. Soc., Chem. Commun. 1993, 1560-1562.
30. Other crystallographic analyses of tetrathiafulvalenium dications have been reported hitherto. See: (a) Scott, B. A.; La Placa, S. J.; Torrance, J. B.; Silverman, B. D.; Welber, B. J. Am. Chem. Soc. 1977, 99, 6631-6639. (b) Zhilyaeva, E. I.; Lyubovskaya, R. N.; Rozenberg, L. P.; Shibaeva, R. P.; Khidekel, M. L. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1984, 33, 632-634. (c) Brunn, K.; Endres, H.; Weiss, J. Z. Naturforsch. 1988, 43b, 224-230. (d) Jones, P. G. Z. Naturforsch. 1989, 44b, 243-244. (e) Abboud, K. A.; Clevenger, M. B.; de Oliveira, G. F.; Talham, D. R. J. Chem. Soc., Chem. Commun. 1993, 1560-1562.
31. Other crystallographic analyses of tetrathiafulvalenium dications have been reported hitherto. See: (a) Scott, B. A.; La Placa, S. J.; Torrance, J. B.; Silverman, B. D.; Welber, B. J. Am. Chem. Soc. 1977, 99, 6631-6639. (b) Zhilyaeva, E. I.; Lyubovskaya, R. N.; Rozenberg, L. P.; Shibaeva, R. P.; Khidekel, M. L. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1984, 33, 632-634. (c) Brunn, K.; Endres, H.; Weiss, J. Z. Naturforsch. 1988, 43b, 224-230. (d) Jones, P. G. Z. Naturforsch. 1989, 44b, 243-244. (e) Abboud, K. A.; Clevenger, M. B.; de Oliveira, G. F.; Talham, D. R. J. Chem. Soc., Chem. Commun. 1993, 1560-1562.
32. Other crystallographic analyses of tetrathiafulvalenium dications have been reported hitherto. See: (a) Scott, B. A.; La Placa, S. J.; Torrance, J. B.; Silverman, B. D.; Welber, B. J. Am. Chem. Soc. 1977, 99, 6631-6639. (b) Zhilyaeva, E. I.; Lyubovskaya, R. N.; Rozenberg, L. P.; Shibaeva, R. P.; Khidekel, M. L. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1984, 33, 632-634. (c) Brunn, K.; Endres, H.; Weiss, J. Z. Naturforsch. 1988, 43b, 224-230. (d) Jones, P. G. Z. Naturforsch. 1989, 44b, 243-244. (e) Abboud, K. A.; Clevenger, M. B.; de Oliveira, G. F.; Talham, D. R. J. Chem. Soc., Chem. Commun. 1993, 1560-1562.
33. Other crystallographic analyses of tetrathiafulvalenium dications have been reported hitherto. See: (a) Scott, B. A.; La Placa, S. J.; Torrance, J. B.; Silverman, B. D.; Welber, B. J. Am. Chem. Soc. 1977, 99, 6631-6639. (b) Zhilyaeva, E. I.; Lyubovskaya, R. N.; Rozenberg, L. P.; Shibaeva, R. P.; Khidekel, M. L. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1984, 33, 632-634. (c) Brunn, K.; Endres, H.; Weiss, J. Z. Naturforsch. 1988, 43b, 224-230. (d) Jones, P. G. Z. Naturforsch. 1989, 44b, 243-244. (e) Abboud, K. A.; Clevenger, M. B.; de Oliveira, G. F.; Talham, D. R. J. Chem. Soc., Chem. Commun. 1993, 1560-1562.
34. Cooper, W. F.; Kenny, N. C.; Edmonds, J. W.; Nagel, A.; Wudl, F.; Coppens, P. J. Chem. Soc., Chem. Commun. 1971, 889-890.
35. 2+, see: Trsic, M.; Laidlaw, W. G. Int. J. Quantum Chem. 1982, 21, 557-563.
36. -1 in MeCN at 298 K.
37. 4+·TTF(0) complex.
38. Credi, A.; Montalti, M.; Balzani, V.; Langford, S. J.; Raymo, F. M.; Stoddart, J. F. New J. Chem. 1998, 1061-1065.
39. 2+ is reversible in the macrocyclic polyether's presence and irreversible in its absence.
40. - concentration.
41. 2+ within its cavity; after the first oxidation process, dissociation of the complex takes place so that the second oxidation process occurs on the free macrocyclic polyether.
42. -1) can be neglected under the experimental conditions employed.
43. A further state, originating from the oxidation of 1/5DN38C10, is less important, because such a process is not totally reversible.
44. (a) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202.
45. (b) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566.
46. (c) Ward, M. D. Chem. Ind. (London) 1997, 640-645.
47. (d) Balzani, V.; Gómez-López, M.; Stoddan, J. F. Acc. Chem. Res. 1998, 31, 405-414.
48. (e) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619.
49. (f) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71.
50. (a) de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. Chem. Commun. 1996, 2399-2400.
51. (b) Credi, A.; Balzani, V.; Langford, S. J.; Stoddart, J. F. J. Am. Chem. Soc. 1997, 119, 2679-2681.
52. (c) Fabbrizzi, L.; Licchelli, M.; Pallavicini, P.; Parodi, L. Angew. Chem., Int. Ed. 1998, 37, 800-802.
53. Balzani, V.; Credi, A.; Venturi, M. Coord. Chem. Rev. 1998, 171, 3-16.
54. Rouvray, D. Chem. Br. 1998, 34 (2), 26-29.
55. (a) Montalti, M.; Ballardini, R.; Prodi, L.; Balzani, V. Chem. Commun. 1996, 2011-2012.
56. (b) Ashton, P. R.; Ballardini, R.; Balzani, V.; Gómez-López, M.; Lawrence, S. E.; Martínez-Díaz, M.-V.; Montalti, M.; Piersanti, A.; Prodi, L.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1997, 119, 10641-10651.
57. (c) Ishow, E.; Credi, A.; Balzani, V.; Spadola, F.; Mandolini, L. Chem. Eur. J. 1999, 5, 984-989.
58. Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 239-258.
59. SHELXTL PC, V. 5.03, Siemens Analytical X-ray Instruments, Inc., Madison, WI, 1994.
60. Gaussian 94, Revision D.3, Gaussian, Inc., Pittsburgh, PA, 1995.
61. Spartan, V. 4.1, Wavefunction, Inc., Irvine, CA, 1995.
62. Amabilino, D. B.; Ashton, P. R.; Balzani, V.; Brown, C. L.; Credi, A.; Fréchet, J.-M. J.; Leon, J. W.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; Venturi, M. J. Am. Chem. Soc. 1996, 118, 12012-12020.
63. Phillips, D.; Meech, S. R. J. Photochem. 1983, 23, 193-217.
64. Dawson, W. R.; Windsor, M. W. J. Phys. Chem. 1968, 72, 3251-3260.
65. Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Non-aqueous Systems; Dekker: New York, 1970.