Simple mechanical molecular and supramolecular machines: Photochemical and electrochemical control of switching processes

Chemistry - A European Journal

Volumn 3, Issue 1, 1997, Pages 152-170

  Ashton, Peter R ^a   Ballardini, Roberto ^b   Balzani, Vincenzo ^c   Boyd, Sue E ^a   Credi, Alberto ^c   Gandolfi, Maria T ^c   Gómez López, Marcos ^a   Iqbal, Sayeedha ^a   Philp, Douglas ^a   Preece, Jon A ^a   Prodi, Luca ^c   Ricketts, Howard G ^a   Stoddart, J Fraser ^a   Tolley, Malcolm S ^a   Venturi, Margherita ^c   White, Andrew J P ^d   Williams, David J ^d  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

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

^c UNIVERSITY OF BOLOGNA   (Italy)

^d IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

luminescence; photochemistry; redox chemistry; self assembly; self complexation; template syntheses

Indexed keywords

EID: 0030979932     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030123     Document Type: Article

References (140)

1. V. Balzani, L. Moggi, F. Scandola, in Supramolecular Photochemistry (Ed.: V. Balzani), Reidel, Dordrecht, 1987, p. 1.
2. a) J.-M. Lehn, Angew. Chem. Int. Ed. Engl. 1988, 27, 89;
3. b) ibid. 1990, 29, 1304.
4. Molecular Electronic Devices (Eds.: F. L. Carter, R. E. Siatkowsky, H. Woltjien), North Holland, Amsterdam, 1988.
5. V. Balzani, F. Scandola, Supramolecular Photochemistry, Horwood, Chichester, 1991, ch. 12.
6. H. Kuhn, in Molecular Electronics (Ed.: P. I. Lazaraev), Kluwer, Dordrecht, 1991, p. 175.
7. K. E. Drexler, Nanosystems: Molecular Machinery, Manufacturing, and Computation, Wiley, New York, 1992.
8. a) D. Bradley, Science 1993, 259, 890;
9. b) P. Ball, L. Garwin, Nature 1992, 355, 761.
10. a) J. S. Lindsey, New J. Chem. 1991, 15, 153;
11. b) J. P. Mathias, C. T. Seto, G. M. Whitesides, Science 1991, 254, 1312;
12. c) J. F. Stoddart, Host - Guest Interactions: From Chemistry to Biology, Ciba Foundation Symposia No. 158, Wiley, Chichester, 1991, 5;
13. d) D. Philp, J. F. Stoddart, Synlett 1991, 445;
14. e) J. F. Stoddart, Chem. Aust. 1992, 59, 576;
15. f) D. B. Amabilino, J. F. Stoddart, Pure Appl. Chem. 1993, 65, 2351;
16. g) C. L. Hill, X. Zhang, Nature 1995, 373, 324;
17. h) N. Branda, R. M. Grotzfeld, C. Valdes, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85;
18. i) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37;
19. j) J. A. Preece, J. F. Stoddart, Molecular Engineering for Advanced Materials, Kluwer Academic, 1995, Dordrecht, p. 1;
20. k) D. Philp, J. F. Stoddart, Angew. Chem. Ed. Int. Engl. 1996, 35, 1154.
21. a) M. Ahlers, W. Muller, A. Reichert, H. Ringsdorf, J. Venzmer, Angew. Chem. Int. Ed. Engl. 1990, 29, 1269;
22. b) C. T. Imrie, Trends Polym. Sci. 1995, 3, 22;
23. c) J. Adersch, S. Diele, P. Goring, J.-A. Schroter, C. Tschierske, J. Chem. Soc. Chem. Commun. 1995, 107;
24. d) D. D. Lasic, Angew. Chem. Int. Ed. Engl. 1994, 33, 1685;
25. e) N. Kimizuka, T. Handa, I. Ichinose, T. Kunitake, ibid. 1994, 33, 2483.
26. a) A. Terfort, G. von Kiedrowski, D. Sievers, Angew. Chem. Int. Ed. Engl. 1992, 31, 654;
27. b) D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221;
28. c) M. M. Conn, E. A. Wintner, J. Rebek, Jr., Angew. Chem. Int. Ed. Engl. 1994, 33, 1577;
29. d) J. Rebek, Jr., Sci. Am. 1994, 369, 221.
30. a) G. M. Whitesides, Angew. Chem. Int. Ed. Engl. 1990, 29, 1209;
31. b) D. Seebach, ibid. 1990, 29, 1320;
32. c) G. W. Gokel, J. C. Medina, C. Li, Synlett 1991, 677.
33. a) G. Schill, Catenanes, Rotaxanes and Knots, Academic Press, New York, 1971;
34. b) C. O. Dietrich-Buchecker, J.-P. Sauvage, J.-M. Kern, J. Am. Chem. Soc. 1984, 106, 3043;
35. c) D. M. Walba, Tetrahedron 1985, 41, 3161;
36. d) P. R. Ashton, T. T. Goodnow, A. E. Kaifer, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1989, 28, 1396;
37. e) P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, J. Am. Chem. Soc. 1992, 114, 193;
38. f) D. B. Amabilino, P. R. Ashton, C. L. Brown, E. Córdova, L. A. Godínez, T. T. Goodnow, A. E. Kaifer, S. P. Newton, M. Pietraszkiewicz, D. Philp, F. M. Raymo, A. S. Reder, M. T. Rutland, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, ibid. 1995, 117, 1271;
39. g) D. B. Amabilino, P. L. Anelli, P. R. Ashton, G. R. Brown, E. Córdova, E. A. Godínez, W. Hayes, A. E. Kaifer, D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, M. S. Tolley, D. J. Williams, ibid. 1995, 117, 11142;
40. h) C. A. Hunter, Ibid. 1992, 114, 5303;
41. i) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. Int. Ed. Engl. 1992, 31, 1619;
42. j) F. J. Carter, C. A. Hunter, R. J. Shannon, J. Chem. Soc. Chem. Commun. 1994, 1277;
43. k) M. Fujita, F. Ibukuro, H. Hagihara, K. Ogura, Nature 1994, 367, 720;
44. l) A. G. Johnston, D. A. Leigh, R. J. Pritchard, M. D. Deegan, Angew. Chem. Int. Ed. Engl. 1995, 34, 1209;
45. m) A. G. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, ibid. 1995, 34, 1212.
46. a) P. R. Anelli, N. Spencer, J. F. Stoddart, J. Am. Chem. Soc. 1991, 113, 5131;
47. b) P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synlett 1994, 789;
48. c) J.-C. Chambron, V. Heitz, J.-P. Sauvage, J. Am. Chem. Soc. 1993, 115, 12378;
49. d) H. W. Gibson, M. C. Bheda, P. Engen, Y. X. Shen, J. Sze, H. Zhang, M. D. Gibson, Y. Delaviz, S.-H. Lee, S. Liu, L. Wang, D. Nagvekar, J. Rancourt, E. T. Taylor, J. Org. Chem. 1994, 59, 2186;
50. e) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852;
51. f) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781;
52. g) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739;
53. h) P. R. Ashton, J. Huff, S. Menzer, I. W. Parsons, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 31.
54. a) H.Ogino, J. Am. Chem. Soc. 1981, 103, 1303;
55. b) P. E. Anelli, P. R. Ashton, N. Spencer, A. M. Z. Slawin, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1991, 30, 1036;
56. c) A. Harada, J. Li, M. Kamachi, Nature 1992, 356, 325;
57. d) G. Wenz, B. Keller, Angew. Chem. Ed. Int. Engl. 1992, 31, 197;
58. e) A. Harada, J. Li, M. Kamachi, Nature 1993, 364, 516;
59. f) H. Ogino, New. J. Chem. 1993, 17, 683;
60. g) P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1994, 181;
61. h) G. Wenz, Angew. Chem. Ed. Int. Engl. 1994, 33, 803;
62. i) H. Sleiman, P. Baxter, J.-M. Lehn, K. Rissanen, J. Chem. Soc. Chem. Commun. 1995, 715.
63. E. Wasserman, Sci. Am. 1962, 207, 94.
64. J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995.
65. a) D. J. Cram. Angew. Chem. Int. Ed. Engl. 1988, 27, 1009;
66. b) D. J. Cram, Science 1983, 219, 1177.
67. a) C. J. Pedersen, J. Am. Chem. Soc. 1967, 89, 7017;
68. b) C. O. Dietrich-Buchecker, J.-P. Sauvage, Chem. Rev. 1987, 87, 795;
69. c) C. J. Pedersen, Angew. Chem. Int. Ed. Engl. 1988, 27, 1021;
70. d) D. H. Busch, J. Incl. Phenom. Molec. Recog. 1992, 12, 389;
71. e) S. Anderson, H. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469;
72. f) R. Hoss, F. Vögtle, Angew. Chem. Int. Ed. Engl. 1994, 33, 375.
73. a) D. B. Amabilino, P. R. Ashton, A. S. Reder, N. Spencer, J. F. Stoddart, Angew. Chem. Int. Ed. Engl. 1994, 33, 1286;
74. b) J.-F. Nierengaten, C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1994, 116, 375;
75. c) D. Armspach, P. R. Ashton, C. P. Moore, N. Spencer, J. F. Stoddart, T. J. Wear, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1993, 32, 854;
76. d) D. Armspach, P. R. Ashton, R. Ballardini, V. Balzani, A. Godi, C. P. Moore, L. Prodi, N. Spencer, J. F. Stoddart, M. S. Tolley, T. J. Wear, D. J. Williams, Chem. Eur. J. 1995, 1, 33.
77. P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, D. J. Williams, A. J. P. White, Synthesis 1994, 1344.
78. D. B. Amabilino, P. R. Ashton, G. R. Brown, W. Hayes, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1994, 2479.
79. For discussions of π-π interactions involving experimental and computational approaches, see a) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525; b) W. L. Jorgensen, D. L. Severance, ibid. 1990, 112, 4768; c) F. Cozzi, M. Cinquini, R. Annuziata, T. Dwyer, J. S. Siegel, ibid. 1993, 115, 5330; d) C. A. Hunter, Angew. Chem. Int. Ed. Engl. 1993, 32, 1584.
80. For discussions of π-π interactions involving experimental and computational approaches, see a) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525; b) W. L. Jorgensen, D. L. Severance, ibid. 1990, 112, 4768; c) F. Cozzi, M. Cinquini, R. Annuziata, T. Dwyer, J. S. Siegel, ibid. 1993, 115, 5330; d) C. A. Hunter, Angew. Chem. Int. Ed. Engl. 1993, 32, 1584.
81. For discussions of π-π interactions involving experimental and computational approaches, see a) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525; b) W. L. Jorgensen, D. L. Severance, ibid. 1990, 112, 4768; c) F. Cozzi, M. Cinquini, R. Annuziata, T. Dwyer, J. S. Siegel, ibid. 1993, 115, 5330; d) C. A. Hunter, Angew. Chem. Int. Ed. Engl. 1993, 32, 1584.
82. For discussions of π-π interactions involving experimental and computational approaches, see a) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525; b) W. L. Jorgensen, D. L. Severance, ibid. 1990, 112, 4768; c) F. Cozzi, M. Cinquini, R. Annuziata, T. Dwyer, J. S. Siegel, ibid. 1993, 115, 5330; d) C. A. Hunter, Angew. Chem. Int. Ed. Engl. 1993, 32, 1584.
83. For discussions of hydrogen-bonding interactions, inclusive of C-H ⋯ O and T-type interactions, see a) S. K. Burley, G. A. Petsko, Science 1985, 229, 2; b) G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290; c) C. B. Aakeroy, K. R. Seddon, Chem. Soc. Rev. 1993, 397; d) S. Paliwell, S. Geib, C. S. Wilcox, J. Am. Chem. Soc. 1994, 116, 4497; e) G. R. Desiraju, Angew. Chem. Int. Ed. Eng. 1995, 34, 2311; f) M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665, and references cited therein.
84. For discussions of hydrogen-bonding interactions, inclusive of C-H ⋯ O and T-type interactions, see a) S. K. Burley, G. A. Petsko, Science 1985, 229, 2; b) G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290; c) C. B. Aakeroy, K. R. Seddon, Chem. Soc. Rev. 1993, 397; d) S. Paliwell, S. Geib, C. S. Wilcox, J. Am. Chem. Soc. 1994, 116, 4497; e) G. R. Desiraju, Angew. Chem. Int. Ed. Eng. 1995, 34, 2311; f) M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665, and references cited therein.
85. For discussions of hydrogen-bonding interactions, inclusive of C-H ⋯ O and T-type interactions, see a) S. K. Burley, G. A. Petsko, Science 1985, 229, 2; b) G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290; c) C. B. Aakeroy, K. R. Seddon, Chem. Soc. Rev. 1993, 397; d) S. Paliwell, S. Geib, C. S. Wilcox, J. Am. Chem. Soc. 1994, 116, 4497; e) G. R. Desiraju, Angew. Chem. Int. Ed. Eng. 1995, 34, 2311; f) M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665, and references cited therein.
86. For discussions of hydrogen-bonding interactions, inclusive of C-H ⋯ O and T-type interactions, see a) S. K. Burley, G. A. Petsko, Science 1985, 229, 2; b) G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290; c) C. B. Aakeroy, K. R. Seddon, Chem. Soc. Rev. 1993, 397; d) S. Paliwell, S. Geib, C. S. Wilcox, J. Am. Chem. Soc. 1994, 116, 4497; e) G. R. Desiraju, Angew. Chem. Int. Ed. Eng. 1995, 34, 2311; f) M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665, and references cited therein.
87. For discussions of hydrogen-bonding interactions, inclusive of C-H ⋯ O and T-type interactions, see a) S. K. Burley, G. A. Petsko, Science 1985, 229, 2; b) G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290; c) C. B. Aakeroy, K. R. Seddon, Chem. Soc. Rev. 1993, 397; d) S. Paliwell, S. Geib, C. S. Wilcox, J. Am. Chem. Soc. 1994, 116, 4497; e) G. R. Desiraju, Angew. Chem. Int. Ed. Eng. 1995, 34, 2311; f) M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665, and references cited therein.
88. For discussions of hydrogen-bonding interactions, inclusive of C-H ⋯ O and T-type interactions, see a) S. K. Burley, G. A. Petsko, Science 1985, 229, 2; b) G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290; c) C. B. Aakeroy, K. R. Seddon, Chem. Soc. Rev. 1993, 397; d) S. Paliwell, S. Geib, C. S. Wilcox, J. Am. Chem. Soc. 1994, 116, 4497; e) G. R. Desiraju, Angew. Chem. Int. Ed. Eng. 1995, 34, 2311; f) M. Nishio, Y. Umezawa, M. Hirota, Y. Takeuchi, Tetrahedron 1995, 51, 8665, and references cited therein.
89. The concept of molecular switches has been around for three decades, since the Nobel Laureate R. P. Feynman (Sat. Rev. 1960, 43, 45) proposed storing information in molecules. While K. E. Drexler (Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992) has proposed many molecular devices based on chemical systems, the chemist has been constructing molecular assemblies and supramolecular arrays that possess switching functions. See, for example, a) R. A. Bissell, A. P. de Silva, H. Q. M. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187; b) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; c) S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1011; d) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. García, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657; e) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345; f) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483; g) S. H. Kawai, S. L. Gilat, R. Poniset, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275; h) S. H. Kawai, S. L. Gilat, J.-M. Lehn, ibid. 1995, 1, 284.
90. The concept of molecular switches has been around for three decades, since the Nobel Laureate R. P. Feynman (Sat. Rev. 1960, 43, 45) proposed storing information in molecules. While K. E. Drexler (Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992) has proposed many molecular devices based on chemical systems, the chemist has been constructing molecular assemblies and supramolecular arrays that possess switching functions. See, for example, a) R. A. Bissell, A. P. de Silva, H. Q. M. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187; b) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; c) S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1011; d) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. García, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657; e) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345; f) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483; g) S. H. Kawai, S. L. Gilat, R. Poniset, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275; h) S. H. Kawai, S. L. Gilat, J.-M. Lehn, ibid. 1995, 1, 284.
91. The concept of molecular switches has been around for three decades, since the Nobel Laureate R. P. Feynman (Sat. Rev. 1960, 43, 45) proposed storing information in molecules. While K. E. Drexler (Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992) has proposed many molecular devices based on chemical systems, the chemist has been constructing molecular assemblies and supramolecular arrays that possess switching functions. See, for example, a) R. A. Bissell, A. P. de Silva, H. Q. M. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187; b) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; c) S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1011; d) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. García, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657; e) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345; f) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483; g) S. H. Kawai, S. L. Gilat, R. Poniset, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275; h) S. H. Kawai, S. L. Gilat, J.-M. Lehn, ibid. 1995, 1, 284.
92. The concept of molecular switches has been around for three decades, since the Nobel Laureate R. P. Feynman (Sat. Rev. 1960, 43, 45) proposed storing information in molecules. While K. E. Drexler (Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992) has proposed many molecular devices based on chemical systems, the chemist has been constructing molecular assemblies and supramolecular arrays that possess switching functions. See, for example, a) R. A. Bissell, A. P. de Silva, H. Q. M. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187; b) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; c) S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1011; d) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. García, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657; e) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345; f) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483; g) S. H. Kawai, S. L. Gilat, R. Poniset, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275; h) S. H. Kawai, S. L. Gilat, J.-M. Lehn, ibid. 1995, 1, 284.
93. The concept of molecular switches has been around for three decades, since the Nobel Laureate R. P. Feynman (Sat. Rev. 1960, 43, 45) proposed storing information in molecules. While K. E. Drexler (Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992) has proposed many molecular devices based on chemical systems, the chemist has been constructing molecular assemblies and supramolecular arrays that possess switching functions. See, for example, a) R. A. Bissell, A. P. de Silva, H. Q. M. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187; b) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; c) S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1011; d) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. García, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657; e) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345; f) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483; g) S. H. Kawai, S. L. Gilat, R. Poniset, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275; h) S. H. Kawai, S. L. Gilat, J.-M. Lehn, ibid. 1995, 1, 284.
94. The concept of molecular switches has been around for three decades, since the Nobel Laureate R. P. Feynman (Sat. Rev. 1960, 43, 45) proposed storing information in molecules. While K. E. Drexler (Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992) has proposed many molecular devices based on chemical systems, the chemist has been constructing molecular assemblies and supramolecular arrays that possess switching functions. See, for example, a) R. A. Bissell, A. P. de Silva, H. Q. M. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187; b) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; c) S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1011; d) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. García, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657; e) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345; f) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483; g) S. H. Kawai, S. L. Gilat, R. Poniset, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275; h) S. H. Kawai, S. L. Gilat, J.-M. Lehn, ibid. 1995, 1, 284.
95. The concept of molecular switches has been around for three decades, since the Nobel Laureate R. P. Feynman (Sat. Rev. 1960, 43, 45) proposed storing information in molecules. While K. E. Drexler (Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992) has proposed many molecular devices based on chemical systems, the chemist has been constructing molecular assemblies and supramolecular arrays that possess switching functions. See, for example, a) R. A. Bissell, A. P. de Silva, H. Q. M. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187; b) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; c) S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1011; d) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. García, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657; e) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345; f) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483; g) S. H. Kawai, S. L. Gilat, R. Poniset, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275; h) S. H. Kawai, S. L. Gilat, J.-M. Lehn, ibid. 1995, 1, 284.
96. The concept of molecular switches has been around for three decades, since the Nobel Laureate R. P. Feynman (Sat. Rev. 1960, 43, 45) proposed storing information in molecules. While K. E. Drexler (Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992) has proposed many molecular devices based on chemical systems, the chemist has been constructing molecular assemblies and supramolecular arrays that possess switching functions. See, for example, a) R. A. Bissell, A. P. de Silva, H. Q. M. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187; b) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; c) S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1011; d) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. García, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657; e) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345; f) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483; g) S. H. Kawai, S. L. Gilat, R. Poniset, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275; h) S. H. Kawai, S. L. Gilat, J.-M. Lehn, ibid. 1995, 1, 284.
97. The concept of molecular switches has been around for three decades, since the Nobel Laureate R. P. Feynman (Sat. Rev. 1960, 43, 45) proposed storing information in molecules. While K. E. Drexler (Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992) has proposed many molecular devices based on chemical systems, the chemist has been constructing molecular assemblies and supramolecular arrays that possess switching functions. See, for example, a) R. A. Bissell, A. P. de Silva, H. Q. M. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187; b) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; c) S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1011; d) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. García, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657; e) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345; f) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483; g) S. H. Kawai, S. L. Gilat, R. Poniset, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275; h) S. H. Kawai, S. L. Gilat, J.-M. Lehn, ibid. 1995, 1, 284.
98. The concept of molecular switches has been around for three decades, since the Nobel Laureate R. P. Feynman (Sat. Rev. 1960, 43, 45) proposed storing information in molecules. While K. E. Drexler (Nanosystems: Molecular Machinery, Manufacturing and Computation, Wiley, New York, 1992) has proposed many molecular devices based on chemical systems, the chemist has been constructing molecular assemblies and supramolecular arrays that possess switching functions. See, for example, a) R. A. Bissell, A. P. de Silva, H. Q. M. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, K. R. A. S. Sandanayake, Chem. Soc. Rev. 1992, 21, 187; b) B. L. Feringa, W. F. Jager, B. de Lange, Tetrahedron 1993, 49, 8267; c) S. H. Kawai, S. L. Gilat, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 1011; d) T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. García, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657; e) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345; f) T. D. James, S. Shinkai, J. Chem. Soc. Chem. Commun. 1995, 1483; g) S. H. Kawai, S. L. Gilat, R. Poniset, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275; h) S. H. Kawai, S. L. Gilat, J.-M. Lehn, ibid. 1995, 1, 284.
99. P. R. Ashton, M. Blower, D. Philp, N. Spencer, J. F. Stoddart, M. S. Tolley, R. Ballardini, M. Ciano, V. Balzani, M. T. Gandolfi, L. Prodi, C. H. McLean, New J. Chem. 1993, 17, 689.
100. R. Ballardini, V. Balzani, M. T. Gandolfi, L. Prodi, M. Venturi, D. Philp, H. G. Ricketts, J. F. Stoddart, Angew. Chem. Int. Ed. Engl. 1993, 31, 1301.
101. A. C. Benniston, A. Harriman, V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275.
102. a) R. A. Bissell, J. F. Stoddart, Computations for the Nanoscale, Kluwer Academic, 1993, Dordrecht, p. 141;
103. b) R. A. Bissell, E. Córdova, A. E. Kaifer, J. F. Stoddart, Nature 1994, 369, 133.
104. a) P. R. Ashton, R. Ballardini, V. Balzani, M. T. Gandolfi, D. J.-F. Marquis, L. Pérez-Garcia, L. Prodi, J. F. Stoddart, M. Venturi, J. Chem. Soc. Chem. Commun. 1994, 177;
105. b) P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. Menzer, L. Pérez-García, L. Prodi, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1995, 117, 11171.
106. R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. J. Langford, S. Menzer, L. Prodi, J. F. Stoddart, M. Venturi, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1996, 35, 978.
107. A. Livoreil, C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1994, 116, 9399.
108. M. Bauer, W. M. Müller, U. Müller, K. Rissanen, F. Vögtle, Liebigs Ann. 1995, 649.
109. a) A. Ueno, I. Suzuki, T. Osa, J. Am. Chem. Soc. 1989, 111, 6391;
110. b) A. Ueno, I. Suzuki, M. Fukushima, M. Okhubo, T. Osa, F. Hamada, K. Murai, Chem. Lett. 1990, 605;
111. c) S. Minato, T. Osa, A. Ueno. J. Chem. Soc. Chem. Commun. 1991, 107;
112. d) K. Hamasaki, A. Ueno, F. Toda, T. Osa, Bull. Chem. Soc. Jpn. 1994, 67, 516;
113. e) M. Nakamura, A. Ikeda, N. Ise, T. Ikeda, H. Ikeda, F. Toda, A. Ueno, J. Chem. Soc. Chem. Commun. 1995, 721;
114. f) R. Corradini, A. Dossena, R. Marchelli, A. Panagia, G. Sartor, M. Saviano, A. Lombardi, V. Pavone, Chem. Eur. J. 1996, 2, 373.
115. S. Shinkai, M. Ishihara, K. Ueada, O. Manabe, J. Chem. Soc. Perkin Trans. II. 1985, 511.
116. I. K. Lednev, M. V. Alfimov, Supramolecular Science 1994, 1, 55.
117. a) H. L. Anderson, J. K. M. Sanders, Angew. Chem. Int. Ed. Engl. 1990, 102, 1400;
118. b) S. D. Erickson, J. A. Simon, W. C. Still, J. Org. Chem. 1993, 58, 1305;
119. c) S. S. Yoon, W. C. Still, Angew. Chem. Int. Ed. Engl. 1994, 33, 2458.
120. C. J. Brown, D. Philp, N. Spencer, J. F. Stoddart, Isr. J. Chem. 1992, 32, 61.
121. A. C. Benniston, A. Harriman, Synlett. 1993, 223.
122. M. Hartmann, M. Racthe, Z. Chem. 1979, 19, 373.
123. C. L. Brown, D. Philp, J. F. Stoddart, Synlett 1991, 462.
124. 4O axis of the hydroquinone ring is inclined by 48° to the mean plane of the cyclophane.
125. Accompanying this coplanar relationship between the ester function and the para-xylyl residue is an intramolecular [C-H ⋯ O] hydrogen bond between one of the methylene groups of the cyclophane and the carbonyl oxygen atom of the ester: the [H ⋯ O] distance is 2.3 Å.
126. P. R. Ashton, C. L. Brown, J. R. Chapman, R. T. Gallagher, J. F. Stoddart, Tetrahedron Lett. 1992, 33, 7771.
127. P. R. Ashton, E. J. T. Chrystal, T. T. Goodnow, A. E. Kaifer, K. P. Parry, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Chem. Soc. Chem. Commun. 1991, 634.
128. E. L. Eliel, S. H. Wielen, L. W. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994.
129. I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Compounds, Academic Press, London, 1965.
130. -5 M has an efficiency lower than 0.5%.
131. N. J. Turro, Modern Molecular Photochemistry, Benjamin, Menlo Park, 1978.
132. a) P. R. Ashton, D. Philp, N. Spencer, J. F. Stoddart, J. Chem. Soc. Chem. Commun. 1991, 1677;
133. b) P. R. Ashton, C. L. Brown, E. J. T. Chrystal T. T. Goodnow, A. E. Kaifer, K. P. Parry, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. Int. Ed. Engl. 1991, 30, 1039.
134. V. Balzani, F. Barigelletti, L. De Cola, Top. Curr. Chem. 1990, 158, 31.
135. G. J. Kavarnos, Photoinduced Electron Transfer, VCH, New York, 1993.
136. O. Johansen, A. W. H. Mau, W. H. F. Sasse, Chem. Phys. Lett. 1983, 94, 107.
137. T. Watanabe, K. Honda, J. Phys. Chem. 1982, 86, 2617.
138. 4+.
139. 4+, was not available in a sufficient amount for electrochemical investigations.
140. G. M. Sheldrick, SHELTXL PC Rev. 5.03, 1994, Siemens Analytical X-Ray Instruments, Madison, WI.