Hydrogen-bonded complexes of aromatic crown ethers with (9-anthracenyl)methylammonium derivatives. Supramolecular photochemistry and photophysics. PH-controllable supramolecular switching

Journal of the American Chemical Society

Volumn 119, Issue 44, 1997, Pages 10641-10651

  Ashton, Peter R ^c   Ballardini, Roberto ^a   Balzani, Vincenzo ^b   Gómez López, Marcos ^c,e   Lawrence, Simon E ^d   Victoria Martinez Diaz M ^c   Montalti, Marco ^b   Piersanti, Arianna ^b   Prodi, Luca ^a   Fraser Stoddart, J ^c,e   Williams, David J ^d  

^a Istituto di Fotochimica e Radiazioni d'Alta Energia   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^d IMPERIAL COLLEGE LONDON   (United Kingdom)

^e UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; CROWN ETHER;

ARTICLE; COMPLEX FORMATION; CRYSTALLOGRAPHY; HYDROGEN BOND; PH; PHOTOCHEMISTRY; PHYSICS;

EID: 16944362561     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9715760     Document Type: Article

References (74)

1. (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood: Chichester, 1991.
2. (b) Balzani, V. Tetrahedron 1992, 48, 10443-10514.
3. (c) Wasielewski, M. R.; O'Neil, M. P.; Gosztola, D.; Niemezyck, M. P.; Svec, W. A. Pure Appl. Chem. 1992, 64, 1319-1325.
4. (d) Bissell, R. A.; de Silva, A. P.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; McCoy, C. P.; Sandanayake, K. R. A. S. Top. Curr. Chem. 1993, 168, 223-264.
5. (e) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202.
6. (f) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, 1995.
7. (a) Balzani, V.; Scandola, F. In Comprehensive Supramolecular Chemistry; Reinhoudt, D. N., Ed.; Pergamon Press: Oxford, England, 1996; Vol. 10, pp 687-746.
8. (b) Feringa, L. B.; Jager, W. F.; de Lange, B. Tetrahedron 1993, 49, 8267-8309.
9. (c) de Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 24, 992-996.
10. (d) 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.
11. (e) Scandola, F.; Bianozzi, C. A.; Balzani, V. Chim. Ind. (Milan) 1995, 78, 1221-1231.
12. (f) Balzani, V.; Credi, A.; Scandola, F. Chim. Ind. (Milan) 1997, 79, 751-759.
13. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017-7036.
14. (a) Shinkai, S.; Ishihara, M.; Ueda, K.; Manabe, O. J. Chem. Soc., Perkin Trans. 2 1985, 511-518.
15. (b) Sutherland, I. O. Chem. Soc. Rev. 1986, 15, 63-91.
16. (c) Stoddart, J. F. Top. Stereochem. 1988, 17, 207-288.
17. (d) Gokel, G. W. Crown Ethers and Cryptands; The Royal Society of Chemistry: London, 1991.
18. (e) Lindoy, L. F. The Chemistry of Macrocyclic Ligands; Cambridge University Press: Cambridge, 1989.
19. (f) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1995, 95, 2529-2586.
20. For interesting applications, see: (a) Izatt, R. M.; Nielsen B. L.; Christensen, J. J.; Lamb, J. D. J. Membrane Sci. 1981, 9, 263-271. (b) Reetz, M. T.; Huff, J.; Rudolf, J.; Toeller, K.; Deege, A.; Goddard, R. J. Am. Chem. Soc. 1994, 116, 11588-11584. (c) Izatt, R. M.; Wang. T.; Hathaway, J. K.; Zhang, X. X.; Curtis, J. C.; Bradshaw, J. S.; Zhu, C. Y.; Huszthy, P. J. Inclusion Phenom. 1994, 17, 157-175 and refrences therein.
21. For interesting applications, see: (a) Izatt, R. M.; Nielsen B. L.; Christensen, J. J.; Lamb, J. D. J. Membrane Sci. 1981, 9, 263-271. (b) Reetz, M. T.; Huff, J.; Rudolf, J.; Toeller, K.; Deege, A.; Goddard, R. J. Am. Chem. Soc. 1994, 116, 11588-11584. (c) Izatt, R. M.; Wang. T.; Hathaway, J. K.; Zhang, X. X.; Curtis, J. C.; Bradshaw, J. S.; Zhu, C. Y.; Huszthy, P. J. Inclusion Phenom. 1994, 17, 157-175 and refrences therein.
22. For interesting applications, see: (a) Izatt, R. M.; Nielsen B. L.; Christensen, J. J.; Lamb, J. D. J. Membrane Sci. 1981, 9, 263-271. (b) Reetz, M. T.; Huff, J.; Rudolf, J.; Toeller, K.; Deege, A.; Goddard, R. J. Am. Chem. Soc. 1994, 116, 11588-11584. (c) Izatt, R. M.; Wang. T.; Hathaway, J. K.; Zhang, X. X.; Curtis, J. C.; Bradshaw, J. S.; Zhu, C. Y.; Huszthy, P. J. Inclusion Phenom. 1994, 17, 157-175 and refrences therein.
23. Kolchinski, A. G.; Busch, D. H.; Alcock, N. W. J. Chem. Soc., Chem. Commun. 1995, 1289-1291.
24. (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, 1865-1869.
25. (b) Ashton, P. R.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Schiavo, C.; Stoddart, J. F.; Tasker, P. A.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1869-1871.
26. (c) Glink, P. T.; Schiavo, C.; Stoddart, J. F.; Williams, D. J. Chem. Commun. 1996, 1483-1490.
27. (d) 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.
28. (e) 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.
29. (f) Ashton, P. R.; Glink, P. T.; Martínez-Díaz, M.-V.; Stoddart, J. F.; White, J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1930-1933.
30. (g) Ashton, P. R.; Glink, P. T.; Menzer, S.; Stoddart, J. F.; Tasker, P. A.; White, A. J. P.; Williams, D. J. Tetrahedron Lett. 1996, 37, 6217-6220.
31. (h) Ashton, P. R.; Collins, A. N.; Fyfe, M. C. T.; Glink, P. T.; Menzer, S.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 59-62.
32. (i) Ashton, P. R.; Collins, A. N.; Fyfe, M. C. T.; Menzer, S.; Stoddart, J.F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 735-739.
33. (j) Feiters, M. C.; Fyfe, M. C. T.; Martínez-Díaz, M.-V.; Menzer, S.; Nolle, R. J. M.; Stoddart, J. F.; Van Kan, P. J. M.; Williams, D. J. J. Am. Chem. Soc. 1997, 119, 8119-8120.
34. (a) Balzani, V.; Moggi, L.; Scandola, F. in Supramolecular Photochemistry; Balzani, V., Ed.; Reidel: Dordrecht, 1987; pp 1-28.
35. (b) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood: Chichester, 1991; Chapter 12.
36. (c) Campagna, S.; Denti, G.; Serroni, S.; Juris, A.; Venturi, M.; Ricevuto, V.; Balzani, V. Chem. Eur. J. 1995, 1, 211-221.
37. (d) Barigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.-P.; Sauvage, J.-P.; Sour, A. New J. Chem. 1995, 19, 793-798.
38. (e) Parola, A. J.; Pina, F.; Ferreira, E.; Maestri, M.; Balzani, V.; J. Am. Chem. Soc. 1996, 118, 11610-11616.
39. (f) Gómez-López, M.; Preece, J. A.; Stoddart, J. F. Nanotechnology 1996, 7, 183-192.
40. (g) 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.
41. (h) Credi, A.; Balzani, V.; Langford, S. J.; Stoddart, J. F. J. Am. Chem. Soc. 1997, 119, 2679-2681.
42. (i) Pina, F.; Melo, M. J.; Maestri, M.; Ballardini, R.; Balzani, V. J. Am. Chem. Soc. 1997, 119, 2679-2681.
43. (j) Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kunitake, M.; Nakashima, N. J. Am. Chem. Soc. 1997, 119, 7605-7606.
44. (a) Aoyama, Y.; Asakawa, M.; Matsui, Y.; Ogoshi, H. J. Am. Chem. Soc. 1991, 113, 6233-6240.
45. (b) Král, V.; Springs, S. L.; Sessler, J. L. J. Am. Chem. Soc. 1995, 117, 8881-8882.
46. (c) Roberts, J. A.; Kirby, J. P.; Nocera, D. G. J. Am. Chem. Soc. 1995, 117, 8051-8052.
47. (d) Lewis, F. D.; Yang, J.-S.; Stem, C. L. J. Am. Chem. Soc. 1996, 118, 2772-2773.
48. (e) Arimura, T.; Brown, C. T.; Springs, S. L.; Sessler, J. L. Chem. Commun. 1996, 2293-2294.
49. Montalti, M.; Ballardini, R.; Prodi, L.; Balzani, V. Chem. Commun. 1996, 2011-2012.
50. (a) Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry; Dekker: New York, 1993.
51. (b) Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Compounds; Academic Press: London, 1965.
52. (c) Jaffé, H. H.; Orchin, M. Theory and Applications of Ultraviolet Spectroscopy; Wiley: New York, 1964.
53. (a) 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.
54. (b) Ballardini, R.; Gandolfi, M. T.; Prodi, L.; Ciano, M.; Balzani, V.; Kohnke, F.; Shariari-Zavariah, H.; Spencer, N.; Stoddart, J. F. J. Am. Chem. Soc. 1989, 111, 7072-7078.
55. Connors, K. A. Binding Constants, Wiley, New York, 1987.
56. For a recent example of how pH can effect the topology of supramolecular systems, see: Shimizu, T.; Kogiso, M.; Masuda, M. J. Am. Chem. Soc. 1997, 119, 6209-6210 and references cited therein.
57. (a) Pages, F.; Desvergne, J.-P.; Bouas-Laurent, H.; Marsau, P.; Lehn, J.-M.; Kotzyba-Hilbert, F.; Albrecht-Gary, A.-M.; Al-Joubbeh, M. J. Am. Chem. Soc. 1989, 111, 8672-8680.
58. (b) Desvergne, J.-P.; Pages, P.; Bouas-Laurent, H.; Marsau, P. Pure Appl. Chem. 1992, 64, 1231-1238.
59. (c) Balzani, V.; Ballardini, R.; Gandolfi, M. T.; Prodi, L. In Frontiers in Supramolecular Organic Chemistry and Photochemistry, Schneider, H.-J., Dürr, H., Eds.; VCH: Weinheim, 1991; pp 371-391.
60. (d) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Kotzyba-Hilbert, F.; Lehn, J.-M.; Prodi, L. J. Am. Chem. Soc. 1994, 116, 5741-5746.
61. Schill, G. Catenanes, Rotaxanes and Knots; Academic Press: New York, 1971.
62. (a) Ashton, P. R.; Bissell, R. A.; Spencer, N.; Stoddart, J. P.; Tolley, M. S. Synlett 1992, 914-918.
63. (b) Ashton, P. R.; Bissell, R. A.; Górski, R.; Philp, D.; Spencer, N.; Stoddart, J. F.; Tolley, M. S. Synlett 1992, 919-922.
64. (c) Ashton, P. R.; Bissell, R. A.; Spencer, N.; Stoddart, J. F.; Telley, M. S. Synlett 1992, 923-926.
65. (d) Bissell, R. A.; Córdova, E.; Kaifer, A. E.; Stoddart, J. F. Nature (London) 1994, 369, 133-137.
66. (e) Amabilino, D. B.; Ashton, P. R.; Boyd, S. E.; Gómez-López, M.; Hayes, W.; Stoddart, J. F. J. Org. Chem. 1997, 62, 3062-3075.
67. (f) 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. P.; Tolley, M. S.; Williams, D. J. Chem. Eur. J. 1997, 3, 1113-1135.
68. Martínez-Díaz, M.-V.; Spencer, N.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1997, 36, 1904-1907.
69. Asakawa, M.; Ashton, P. R.; Brown, C. L.; Fyfe, M. C. T.; Menzer, S.; Pasini, D.; Scheuer, C.; Spencer, N.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1997, 3, 1136-1150.
70. Helgeson, R. C.; Tarnowski, T. L.; Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1977, 99, 6411-6418.
71. Colquhoun, H. M.; Goodings, E. P.; Maud, J. M.; Stoddart, J. F.; Wolstenholme, J. B.; Williams, D. J. J. Chem. Soc., Perkin Trans. 2 1985, 607-624.
72. 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.
73. Credi, A.; Prodi, L. Spectrochimica Acta, Part A, in press.
74. SHELXTL PC version 5.03, Siemens Analytical X-Ray Instruments Inc., Madinson, WI, 1994.