Azo-Dye Rotaxanes

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 12, 1997, Pages 1310-1313

  Anderson, Sally ^a   Claridge, Tim D W ^a   Anderson, Harry L ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Azo compounds; Cyclodextrins; Cyclophanes; Rotaxanes; Supramolecular chemistry

Indexed keywords

EID: 0030793332     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199713101     Document Type: Article

References (32)

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8. Cram et al. and Gokel et al. unsuccessfully attempted to prepare azo-dye rotaxanes from crown ether/diazonium salt complexes: G. W. Gokel, D. J. Cram, J. Chem. Soc. Chem. Commun. 1973, 481-482; J. R. Beadle, D. M. Dishong, R. K. Khanna, G. W. Gokel, Tetrahedron 1984, 40, 3935-3944.
9. Cram et al. and Gokel et al. unsuccessfully attempted to prepare azo-dye rotaxanes from crown ether/diazonium salt complexes: G. W. Gokel, D. J. Cram, J. Chem. Soc. Chem. Commun. 1973, 481-482; J. R. Beadle, D. M. Dishong, R. K. Khanna, G. W. Gokel, Tetrahedron 1984, 40, 3935-3944.
10. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
11. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
12. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
13. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
14. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
15. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
16. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
17. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
18. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
19. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
20. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
21. Hydrophobic binding has been used to prepare rotaxanes: a) S. Anderson, H. L. Anderson, Angew. Chem. 1996, 108, 2075-2078; Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959; b) G. Wenz, ibid. 1994, 106, 851-870 and 1994, 33, 803-822; c) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; d) M. Kunitake, K. Kotoo, O. Manabe, T. Muramatsu, N. Nakashima, Chem. Lett. 1993, 1033-1036; e) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; f) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; g) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190; h) H. Ogino, ibid. 1981, 103, 1303-1304.
22. Negative-ion ESI-MS measurements were carried out on a VG-Bio Q instrument. We are grateful to Dr R. T. Aplin for recording these mass spectra.
23. -1. Mixing times of up to 200 ms were used, and all observed NOEs were negative.
24. -1. Mixing times of up to 200 ms were used, and all observed NOEs were negative.
25. Cyclophane 3c was synthesized according to Diederich et al.: S. B. Ferguson, E. M. Sanford, E. M. Seward, F. Diederich, J. Am. Chem. Soc. 1991, 113, 5410-5419.
26. -5M.
27. Several photochemically interesting rotaxanes have been investigated: a) D. B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Fréchet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1996, 118, 12012-12020; b) N. Solladié, J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1996, 108, 957-960; Angew. Chem. Int. Ed. Engl. 1996, 35, 906-909; c) A. C. Benniston, A. Harriman, V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; d) J.-C. Chambron, A. Harriman, V. Heitz, J.-P. Sauvage, ibid. 1993, 115, 6109-6114; 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, ibid. 1992, 114, 193-218.
28. Several photochemically interesting rotaxanes have been investigated: a) D. B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Fréchet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1996, 118, 12012-12020; b) N. Solladié, J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1996, 108, 957-960; Angew. Chem. Int. Ed. Engl. 1996, 35, 906-909; c) A. C. Benniston, A. Harriman, V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; d) J.-C. Chambron, A. Harriman, V. Heitz, J.-P. Sauvage, ibid. 1993, 115, 6109-6114; 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, ibid. 1992, 114, 193-218.
29. Several photochemically interesting rotaxanes have been investigated: a) D. B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Fréchet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1996, 118, 12012-12020; b) N. Solladié, J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1996, 108, 957-960; Angew. Chem. Int. Ed. Engl. 1996, 35, 906-909; c) A. C. Benniston, A. Harriman, V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; d) J.-C. Chambron, A. Harriman, V. Heitz, J.-P. Sauvage, ibid. 1993, 115, 6109-6114; 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, ibid. 1992, 114, 193-218.
30. Several photochemically interesting rotaxanes have been investigated: a) D. B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Fréchet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1996, 118, 12012-12020; b) N. Solladié, J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1996, 108, 957-960; Angew. Chem. Int. Ed. Engl. 1996, 35, 906-909; c) A. C. Benniston, A. Harriman, V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; d) J.-C. Chambron, A. Harriman, V. Heitz, J.-P. Sauvage, ibid. 1993, 115, 6109-6114; 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, ibid. 1992, 114, 193-218.
31. Several photochemically interesting rotaxanes have been investigated: a) D. B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Fréchet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1996, 118, 12012-12020; b) N. Solladié, J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1996, 108, 957-960; Angew. Chem. Int. Ed. Engl. 1996, 35, 906-909; c) A. C. Benniston, A. Harriman, V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; d) J.-C. Chambron, A. Harriman, V. Heitz, J.-P. Sauvage, ibid. 1993, 115, 6109-6114; 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, ibid. 1992, 114, 193-218.
32. Several photochemically interesting rotaxanes have been investigated: a) D. B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Fréchet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc. 1996, 118, 12012-12020; b) N. Solladié, J.-C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1996, 108, 957-960; Angew. Chem. Int. Ed. Engl. 1996, 35, 906-909; c) A. C. Benniston, A. Harriman, V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; d) J.-C. Chambron, A. Harriman, V. Heitz, J.-P. Sauvage, ibid. 1993, 115, 6109-6114; 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, ibid. 1992, 114, 193-218.