Synthesis of a water-soluble conjugated [3]rotaxane

Angewandte Chemie (International Edition in English)

Volumn 35, Issue 17, 1996, Pages 1956-1959

  Anderson, Sally ^a   Anderson, Harry L ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Alkynes; Cyclophanes; Luminescence; Molecular wires; Supramolecular chemistry

Indexed keywords

EID: 0029959270     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199619561     Document Type: Article

References (21)

1. J. L. Brédas, Adv. Mater. 1995, 7, 263-274; N. C. Greenham, S. C. Moratti, D. D. C. Bradley, R. H. Friend, A. B. Holmes, Nature 1993, 365, 628-630; U. Scherf, K. Müllen. Synthesis 1992, 23-38; Conjugated Polymers (Eds.: J. L. Brédas, R. Silbey), Kluwer Academic, Dordrecht, 1991; O.A. Patil, A. J. Heeger, F. Wudl, Chem. Rev. 1988, 88, 183-200.
2. J. L. Brédas, Adv. Mater. 1995, 7, 263-274; N. C. Greenham, S. C. Moratti, D. D. C. Bradley, R. H. Friend, A. B. Holmes, Nature 1993, 365, 628-630; U. Scherf, K. Müllen. Synthesis 1992, 23-38; Conjugated Polymers (Eds.: J. L. Brédas, R. Silbey), Kluwer Academic, Dordrecht, 1991; O.A. Patil, A. J. Heeger, F. Wudl, Chem. Rev. 1988, 88, 183-200.
3. J. L. Brédas, Adv. Mater. 1995, 7, 263-274; N. C. Greenham, S. C. Moratti, D. D. C. Bradley, R. H. Friend, A. B. Holmes, Nature 1993, 365, 628-630; U. Scherf, K. Müllen. Synthesis 1992, 23-38; Conjugated Polymers (Eds.: J. L. Brédas, R. Silbey), Kluwer Academic, Dordrecht, 1991; O.A. Patil, A. J. Heeger, F. Wudl, Chem. Rev. 1988, 88, 183-200.
4. J. L. Brédas, Adv. Mater. 1995, 7, 263-274; N. C. Greenham, S. C. Moratti, D. D. C. Bradley, R. H. Friend, A. B. Holmes, Nature 1993, 365, 628-630; U. Scherf, K. Müllen. Synthesis 1992, 23-38; Conjugated Polymers (Eds.: J. L. Brédas, R. Silbey), Kluwer Academic, Dordrecht, 1991; O.A. Patil, A. J. Heeger, F. Wudl, Chem. Rev. 1988, 88, 183-200.
5. J. L. Brédas, Adv. Mater. 1995, 7, 263-274; N. C. Greenham, S. C. Moratti, D. D. C. Bradley, R. H. Friend, A. B. Holmes, Nature 1993, 365, 628-630; U. Scherf, K. Müllen. Synthesis 1992, 23-38; Conjugated Polymers (Eds.: J. L. Brédas, R. Silbey), Kluwer Academic, Dordrecht, 1991; O.A. Patil, A. J. Heeger, F. Wudl, Chem. Rev. 1988, 88, 183-200.
6. Rotaxanes were first prepared by solid-phase synthesis (I. T. Harrison, S. Harrison, J. Am. Chem. Soc. 1967, 89, 5723-5724) and by directed synthesis (G. Schill, H. Zollenkopf, Liebigs Ann. Chem. 1969, 721, 53-7-4). For an early use of the hydrophobic effect to direct rotaxane synthesis see H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304.
7. Rotaxanes were first prepared by solid-phase synthesis (I. T. Harrison, S. Harrison, J. Am. Chem. Soc. 1967, 89, 5723-5724) and by directed synthesis (G. Schill, H. Zollenkopf, Liebigs Ann. Chem. 1969, 721, 53-7-4). For an early use of the hydrophobic effect to direct rotaxane synthesis see H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304.
8. Rotaxanes were first prepared by solid-phase synthesis (I. T. Harrison, S. Harrison, J. Am. Chem. Soc. 1967, 89, 5723-5724) and by directed synthesis (G. Schill, H. Zollenkopf, Liebigs Ann. Chem. 1969, 721, 53-7-4). For an early use of the hydrophobic effect to direct rotaxane synthesis see H. Ogino, J. Am. Chem. Soc. 1981, 103, 1303-1304.
9. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
10. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
11. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
12. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
13. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
14. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
15. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
16. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
17. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
18. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
19. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
20. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.
21. For some recent rotaxanes see: a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828; b) H. W. Gibson, S. Liu, P. Lecavalier, C. Wu, Y. X. Shen, J. Am. Chem. Soc. 1995, 117, 852-874; c) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782; d) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott, T. Schmidt, Liebigs Ann. 1995, 739-743; e) A. C. Benniston, A. Harriman. V. M. Lynch, J. Am. Chem. Soc. 1995, 117, 5275-5291; f) G. Wenz, Angew. Chem. 1994, 106, 851-870; Angew. Chem. Int. Ed. Engl. 1994, 33, 803-822; g) A. Harada, J. Li, M. Kamachi, J. Am. Chem. Soc. 1994, 116, 3192-3196; Nature 1992, 356, 325-327; h) G. Wenz, B. Keller, Angew. Chem. 1992, 104, 201-204; Angew. Chem. Int. Ed. Engl. 1992, 31, 197-199; i) R. S. Wylie, D. H. Macartney, J. Am. Chem. Soc. 1992, 114, 3136-3138; j) R. Isnin, A. E. Kaifer, ibid. 1991, 113, 8188-8190.