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Volumn 65, Issue 7, 2000, Pages 1924-1936

Switching of pseudorotaxanes and catenanes incorporating a tetrathiafulvalene unit by redox and chemical inputs

Author keywords

[No Author keywords available]

Indexed keywords

CATENANE; MACROCYCLIC COMPOUND; POLYETHER; TAXANE DERIVATIVE; TETRATHIAFULVALENE DERIVATIVE;

EID: 0034616406     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991781t     Document Type: Article
Times cited : (251)

References (84)
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    • For reviews, see: (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood, Chichester, 1991. (b) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (c) Balzani, V. Tetrahedron 1992, 48, 10443-10514. (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. (e) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595-597. (f) De Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 992-996. (g) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202. (h) Benniston, A. C. Chem. Soc. Rev. 1996, 25, 427-435. (i) Shinkai, S. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, pp 671-700. (j) 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. (k) Ward, M. D. Chem. Ind. 1997, 640-645. (l) Modular Chemistry; Michl, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1997. (m) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80. (n) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207. (o) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247. (p) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414. (q) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619. (r) Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 42-52. (s) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. (t) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
    • (1997) Chem. Ind. , pp. 640-645
    • Ward, M.D.1
  • 17
    • 0004171539 scopus 로고    scopus 로고
    • Kluwer Academic Publishers: Dordrecht
    • For reviews, see: (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood, Chichester, 1991. (b) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (c) Balzani, V. Tetrahedron 1992, 48, 10443-10514. (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. (e) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595-597. (f) De Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 992-996. (g) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202. (h) Benniston, A. C. Chem. Soc. Rev. 1996, 25, 427-435. (i) Shinkai, S. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, pp 671-700. (j) 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. (k) Ward, M. D. Chem. Ind. 1997, 640-645. (l) Modular Chemistry; Michl, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1997. (m) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80. (n) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207. (o) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247. (p) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414. (q) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619. (r) Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 42-52. (s) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. (t) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
    • (1997) Modular Chemistry
    • Michl, J.1
  • 18
    • 0002036125 scopus 로고    scopus 로고
    • For reviews, see: (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood, Chichester, 1991. (b) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (c) Balzani, V. Tetrahedron 1992, 48, 10443-10514. (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. (e) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595-597. (f) De Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 992-996. (g) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202. (h) Benniston, A. C. Chem. Soc. Rev. 1996, 25, 427-435. (i) Shinkai, S. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, pp 671-700. (j) 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. (k) Ward, M. D. Chem. Ind. 1997, 640-645. (l) Modular Chemistry; Michl, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1997. (m) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80. (n) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207. (o) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247. (p) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414. (q) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619. (r) Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 42-52. (s) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. (t) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 71-80
    • Beer, P.D.1
  • 19
    • 0542397763 scopus 로고    scopus 로고
    • For reviews, see: (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood, Chichester, 1991. (b) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (c) Balzani, V. Tetrahedron 1992, 48, 10443-10514. (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. (e) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595-597. (f) De Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 992-996. (g) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202. (h) Benniston, A. C. Chem. Soc. Rev. 1996, 25, 427-435. (i) Shinkai, S. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, pp 671-700. (j) 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. (k) Ward, M. D. Chem. Ind. 1997, 640-645. (l) Modular Chemistry; Michl, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1997. (m) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80. (n) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207. (o) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247. (p) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414. (q) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619. (r) Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 42-52. (s) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. (t) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 201-207
    • Swager, T.M.1
  • 20
    • 0032536556 scopus 로고    scopus 로고
    • For reviews, see: (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood, Chichester, 1991. (b) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (c) Balzani, V. Tetrahedron 1992, 48, 10443-10514. (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. (e) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595-597. (f) De Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 992-996. (g) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202. (h) Benniston, A. C. Chem. Soc. Rev. 1996, 25, 427-435. (i) Shinkai, S. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, pp 671-700. (j) 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. (k) Ward, M. D. Chem. Ind. 1997, 640-645. (l) Modular Chemistry; Michl, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1997. (m) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80. (n) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207. (o) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247. (p) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414. (q) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619. (r) Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 42-52. (s) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. (t) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 216-247
    • Boulas, P.L.1    Gómez-Kaifer, M.2    Echegoyen, L.3
  • 21
    • 0542373936 scopus 로고    scopus 로고
    • For reviews, see: (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood, Chichester, 1991. (b) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (c) Balzani, V. Tetrahedron 1992, 48, 10443-10514. (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. (e) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595-597. (f) De Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 992-996. (g) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202. (h) Benniston, A. C. Chem. Soc. Rev. 1996, 25, 427-435. (i) Shinkai, S. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, pp 671-700. (j) 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. (k) Ward, M. D. Chem. Ind. 1997, 640-645. (l) Modular Chemistry; Michl, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1997. (m) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80. (n) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207. (o) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247. (p) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414. (q) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619. (r) Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 42-52. (s) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. (t) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 405-414
    • Balzani, V.1    Gómez-López, M.2    Stoddart, J.F.3
  • 22
    • 0001261605 scopus 로고    scopus 로고
    • For reviews, see: (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood, Chichester, 1991. (b) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (c) Balzani, V. Tetrahedron 1992, 48, 10443-10514. (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. (e) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595-597. (f) De Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 992-996. (g) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202. (h) Benniston, A. C. Chem. Soc. Rev. 1996, 25, 427-435. (i) Shinkai, S. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, pp 671-700. (j) 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. (k) Ward, M. D. Chem. Ind. 1997, 640-645. (l) Modular Chemistry; Michl, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1997. (m) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80. (n) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207. (o) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247. (p) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414. (q) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619. (r) Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 42-52. (s) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. (t) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 611-619
    • Sauvage, J.-P.1
  • 23
    • 0002170921 scopus 로고    scopus 로고
    • For reviews, see: (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood, Chichester, 1991. (b) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (c) Balzani, V. Tetrahedron 1992, 48, 10443-10514. (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. (e) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595-597. (f) De Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 992-996. (g) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202. (h) Benniston, A. C. Chem. Soc. Rev. 1996, 25, 427-435. (i) Shinkai, S. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, pp 671-700. (j) 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. (k) Ward, M. D. Chem. Ind. 1997, 640-645. (l) Modular Chemistry; Michl, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1997. (m) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80. (n) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207. (o) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247. (p) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414. (q) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619. (r) Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 42-52. (s) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. (t) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 42-52
    • Niemz, A.1    Rotello, V.M.2
  • 24
    • 0032964012 scopus 로고    scopus 로고
    • For reviews, see: (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood, Chichester, 1991. (b) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (c) Balzani, V. Tetrahedron 1992, 48, 10443-10514. (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. (e) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595-597. (f) De Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 992-996. (g) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202. (h) Benniston, A. C. Chem. Soc. Rev. 1996, 25, 427-435. (i) Shinkai, S. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, pp 671-700. (j) 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. (k) Ward, M. D. Chem. Ind. 1997, 640-645. (l) Modular Chemistry; Michl, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1997. (m) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80. (n) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207. (o) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247. (p) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414. (q) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619. (r) Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 42-52. (s) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. (t) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 62-71
    • Kaifer, A.E.1
  • 25
    • 0033410470 scopus 로고    scopus 로고
    • For reviews, see: (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood, Chichester, 1991. (b) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (c) Balzani, V. Tetrahedron 1992, 48, 10443-10514. (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. (e) Swager, T. M.; Marsella, M. J. Adv. Mater. 1994, 6, 595-597. (f) De Silva, A. P.; McCoy, C. P. Chem. Ind. 1994, 992-996. (g) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202. (h) Benniston, A. C. Chem. Soc. Rev. 1996, 25, 427-435. (i) Shinkai, S. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, pp 671-700. (j) 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. (k) Ward, M. D. Chem. Ind. 1997, 640-645. (l) Modular Chemistry; Michl, J., Ed.; Kluwer Academic Publishers: Dordrecht, 1997. (m) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80. (n) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207. (o) Boulas, P. L.; Gómez-Kaifer, M.; Echegoyen, L. Angew. Chem., Int. Ed. 1998, 37, 216-247. (p) Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414. (q) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619. (r) Niemz, A.; Rotello, V. M. Acc. Chem. Res. 1999, 32, 42-52. (s) Kaifer, A. E. Acc. Chem. Res. 1999, 32, 62-71. (t) Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 143-150
    • Piotrowiak, P.1
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    • For recent papers, see: (a) Willner, I.; Willner, B. Adv. Mater. 1997, 9, 351-355. (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. (c) Deans, R.; Niemz, A.; Breinlinger, E. C.; Rotello, V. M. J. Am. Chem. Soc. 1997, 119, 10863-10864. (d) Livoreil, A.; Sauvage, J.-P.; Armaroli, N.; Balzani, V.; Flamigni, L.; Ventura, B. J. Am. Chem. Soc. 1997, 119, 12114-12124. (e) Wang, Y.; Alvarez, J.; Kaifer, A. E. Chem. Commun. 1998, 1457-1458. (f) Takashita, M.; Irie, M. J. Org. Chem. 1998, 63, 6643-6649. (g) Archut, A.; Azzellini, G. C.; Balzani, V.; De Cola, L.; Vögtle, F. J. Am. Chem. Soc. 1998, 120, 12187-12191. (h) Steinberg-Yfrach, G.; Rigaud, J.-L.; Durantini, E. N.; Moore, A. L.; Gust, D.; Moore, T. A. Nature 1998, 392, 479-482. (i) de Silva, A. P.; Dixon, I. M.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Maxwell, P. R. S.; Rice, T. E. J. Am. Chem. Soc. 1999, 121, 1393- 1394. (j) Fabbrizzi, L.; Gatti, F.; Pallavicini, P.; Zambarbieri, E. Chem. Eur. J. 1999, 5, 682-690. (k) Asakawa, M.; Ashton, P. R.; Balzani, V.; Brown, C. L.; Credi, A.; Menzer, S.; Newton, S. P.; Raymo, F. M.; Shipway, A. N.; Spencer, N.; Quick, A.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Chem. Eur. J. 1999, 5, 860-875. (l) Ishow, E.; Credi, A.; Balzani, V.; Spadola, F.; Mandolini, L. Chem. Eur. J. 1999, 5, 984- 989.
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    • Asakawa, M.1    Ashton, P.R.2    Balzani, V.3    Brown, C.L.4    Credi, A.5    Menzer, S.6    Newton, S.P.7    Raymo, F.M.8    Shipway, A.N.9    Spencer, N.10    Quick, A.11    Stoddart, J.F.12    White, A.J.P.13    Williams, D.J.14
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    • (1999) Chem. Eur. J. , vol.5 , pp. 984-989
    • Ishow, E.1    Credi, A.2    Balzani, V.3    Spadola, F.4    Mandolini, L.5
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    • For related pseudorotaxanes, rotaxanes, and catenanes containing TTF units, see: (a) Jørgensen, T.; Becher, J.; Chambron, J.-C.; Sauvage, J.-P. Tetrahedron Lett. 1994, 35, 4339-4342. (b) Li, Z. T.; Stein, P. C.; Svenstrup, N.; Lund, K. H.; Becher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2524-2528. (c) Li, Z. T.; Becher, J. Chem. Commun. 1996, 639-640. (d) Li, Z. T.; Stein, P. C.; Becher, J.; Jensen, D.; Mørk, P.; Svenstrup, N. Chem. Eur. J. 1996, 2, 624-633. (e) Devonport, M.; Blower, M. A.; Bryce, M. R.; Goldenberg, L. M. J. Org. Chem. 1997, 62, 885-887. (f) Becher, J.; Li, Z. T.; Blanchard, P.; Svenstrup, N.; Lau, J.; Nielsen, M. B.; Leriche, P. Pure Appl. Chem. 1997, 69, 465-470. (g) Li, Z. T.; Becher, J. Synlett 1997, 557-560. (h) Nielsen, M. B.; Thorup, N.; Becher, J. J. Chem. Soc., Perkin Trans. 1 1998, 1305-1308.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4339-4342
    • Jørgensen, T.1    Becher, J.2    Chambron, J.-C.3    Sauvage, J.-P.4
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    • For related pseudorotaxanes, rotaxanes, and catenanes containing TTF units, see: (a) Jørgensen, T.; Becher, J.; Chambron, J.-C.; Sauvage, J.-P. Tetrahedron Lett. 1994, 35, 4339-4342. (b) Li, Z. T.; Stein, P. C.; Svenstrup, N.; Lund, K. H.; Becher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2524-2528. (c) Li, Z. T.; Becher, J. Chem. Commun. 1996, 639-640. (d) Li, Z. T.; Stein, P. C.; Becher, J.; Jensen, D.; Mørk, P.; Svenstrup, N. Chem. Eur. J. 1996, 2, 624-633. (e) Devonport, M.; Blower, M. A.; Bryce, M. R.; Goldenberg, L. M. J. Org. Chem. 1997, 62, 885-887. (f) Becher, J.; Li, Z. T.; Blanchard, P.; Svenstrup, N.; Lau, J.; Nielsen, M. B.; Leriche, P. Pure Appl. Chem. 1997, 69, 465-470. (g) Li, Z. T.; Becher, J. Synlett 1997, 557-560. (h) Nielsen, M. B.; Thorup, N.; Becher, J. J. Chem. Soc., Perkin Trans. 1 1998, 1305-1308.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 2524-2528
    • Li, Z.T.1    Stein, P.C.2    Svenstrup, N.3    Lund, K.H.4    Becher, J.5
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    • For related pseudorotaxanes, rotaxanes, and catenanes containing TTF units, see: (a) Jørgensen, T.; Becher, J.; Chambron, J.-C.; Sauvage, J.-P. Tetrahedron Lett. 1994, 35, 4339-4342. (b) Li, Z. T.; Stein, P. C.; Svenstrup, N.; Lund, K. H.; Becher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2524-2528. (c) Li, Z. T.; Becher, J. Chem. Commun. 1996, 639-640. (d) Li, Z. T.; Stein, P. C.; Becher, J.; Jensen, D.; Mørk, P.; Svenstrup, N. Chem. Eur. J. 1996, 2, 624-633. (e) Devonport, M.; Blower, M. A.; Bryce, M. R.; Goldenberg, L. M. J. Org. Chem. 1997, 62, 885-887. (f) Becher, J.; Li, Z. T.; Blanchard, P.; Svenstrup, N.; Lau, J.; Nielsen, M. B.; Leriche, P. Pure Appl. Chem. 1997, 69, 465-470. (g) Li, Z. T.; Becher, J. Synlett 1997, 557-560. (h) Nielsen, M. B.; Thorup, N.; Becher, J. J. Chem. Soc., Perkin Trans. 1 1998, 1305-1308.
    • (1996) Chem. Commun. , pp. 639-640
    • Li, Z.T.1    Becher, J.2
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    • For related pseudorotaxanes, rotaxanes, and catenanes containing TTF units, see: (a) Jørgensen, T.; Becher, J.; Chambron, J.-C.; Sauvage, J.-P. Tetrahedron Lett. 1994, 35, 4339-4342. (b) Li, Z. T.; Stein, P. C.; Svenstrup, N.; Lund, K. H.; Becher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2524-2528. (c) Li, Z. T.; Becher, J. Chem. Commun. 1996, 639-640. (d) Li, Z. T.; Stein, P. C.; Becher, J.; Jensen, D.; Mørk, P.; Svenstrup, N. Chem. Eur. J. 1996, 2, 624-633. (e) Devonport, M.; Blower, M. A.; Bryce, M. R.; Goldenberg, L. M. J. Org. Chem. 1997, 62, 885-887. (f) Becher, J.; Li, Z. T.; Blanchard, P.; Svenstrup, N.; Lau, J.; Nielsen, M. B.; Leriche, P. Pure Appl. Chem. 1997, 69, 465-470. (g) Li, Z. T.; Becher, J. Synlett 1997, 557-560. (h) Nielsen, M. B.; Thorup, N.; Becher, J. J. Chem. Soc., Perkin Trans. 1 1998, 1305-1308.
    • (1996) Chem. Eur. J. , vol.2 , pp. 624-633
    • Li, Z.T.1    Stein, P.C.2    Becher, J.3    Jensen, D.4    Mørk, P.5    Svenstrup, N.6
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    • For related pseudorotaxanes, rotaxanes, and catenanes containing TTF units, see: (a) Jørgensen, T.; Becher, J.; Chambron, J.-C.; Sauvage, J.-P. Tetrahedron Lett. 1994, 35, 4339-4342. (b) Li, Z. T.; Stein, P. C.; Svenstrup, N.; Lund, K. H.; Becher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2524-2528. (c) Li, Z. T.; Becher, J. Chem. Commun. 1996, 639-640. (d) Li, Z. T.; Stein, P. C.; Becher, J.; Jensen, D.; Mørk, P.; Svenstrup, N. Chem. Eur. J. 1996, 2, 624-633. (e) Devonport, M.; Blower, M. A.; Bryce, M. R.; Goldenberg, L. M. J. Org. Chem. 1997, 62, 885-887. (f) Becher, J.; Li, Z. T.; Blanchard, P.; Svenstrup, N.; Lau, J.; Nielsen, M. B.; Leriche, P. Pure Appl. Chem. 1997, 69, 465-470. (g) Li, Z. T.; Becher, J. Synlett 1997, 557-560. (h) Nielsen, M. B.; Thorup, N.; Becher, J. J. Chem. Soc., Perkin Trans. 1 1998, 1305-1308.
    • (1997) J. Org. Chem. , vol.62 , pp. 885-887
    • Devonport, M.1    Blower, M.A.2    Bryce, M.R.3    Goldenberg, L.M.4
  • 50
    • 0001523842 scopus 로고    scopus 로고
    • For related pseudorotaxanes, rotaxanes, and catenanes containing TTF units, see: (a) Jørgensen, T.; Becher, J.; Chambron, J.-C.; Sauvage, J.-P. Tetrahedron Lett. 1994, 35, 4339-4342. (b) Li, Z. T.; Stein, P. C.; Svenstrup, N.; Lund, K. H.; Becher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2524-2528. (c) Li, Z. T.; Becher, J. Chem. Commun. 1996, 639-640. (d) Li, Z. T.; Stein, P. C.; Becher, J.; Jensen, D.; Mørk, P.; Svenstrup, N. Chem. Eur. J. 1996, 2, 624-633. (e) Devonport, M.; Blower, M. A.; Bryce, M. R.; Goldenberg, L. M. J. Org. Chem. 1997, 62, 885-887. (f) Becher, J.; Li, Z. T.; Blanchard, P.; Svenstrup, N.; Lau, J.; Nielsen, M. B.; Leriche, P. Pure Appl. Chem. 1997, 69, 465-470. (g) Li, Z. T.; Becher, J. Synlett 1997, 557-560. (h) Nielsen, M. B.; Thorup, N.; Becher, J. J. Chem. Soc., Perkin Trans. 1 1998, 1305-1308.
    • (1997) Pure Appl. Chem. , vol.69 , pp. 465-470
    • Becher, J.1    Li, Z.T.2    Blanchard, P.3    Svenstrup, N.4    Lau, J.5    Nielsen, M.B.6    Leriche, P.7
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    • For related pseudorotaxanes, rotaxanes, and catenanes containing TTF units, see: (a) Jørgensen, T.; Becher, J.; Chambron, J.-C.; Sauvage, J.-P. Tetrahedron Lett. 1994, 35, 4339-4342. (b) Li, Z. T.; Stein, P. C.; Svenstrup, N.; Lund, K. H.; Becher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2524-2528. (c) Li, Z. T.; Becher, J. Chem. Commun. 1996, 639-640. (d) Li, Z. T.; Stein, P. C.; Becher, J.; Jensen, D.; Mørk, P.; Svenstrup, N. Chem. Eur. J. 1996, 2, 624-633. (e) Devonport, M.; Blower, M. A.; Bryce, M. R.; Goldenberg, L. M. J. Org. Chem. 1997, 62, 885-887. (f) Becher, J.; Li, Z. T.; Blanchard, P.; Svenstrup, N.; Lau, J.; Nielsen, M. B.; Leriche, P. Pure Appl. Chem. 1997, 69, 465-470. (g) Li, Z. T.; Becher, J. Synlett 1997, 557-560. (h) Nielsen, M. B.; Thorup, N.; Becher, J. J. Chem. Soc., Perkin Trans. 1 1998, 1305-1308.
    • (1997) Synlett , pp. 557-560
    • Li, Z.T.1    Becher, J.2
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    • For related pseudorotaxanes, rotaxanes, and catenanes containing TTF units, see: (a) Jørgensen, T.; Becher, J.; Chambron, J.-C.; Sauvage, J.-P. Tetrahedron Lett. 1994, 35, 4339-4342. (b) Li, Z. T.; Stein, P. C.; Svenstrup, N.; Lund, K. H.; Becher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2524-2528. (c) Li, Z. T.; Becher, J. Chem. Commun. 1996, 639-640. (d) Li, Z. T.; Stein, P. C.; Becher, J.; Jensen, D.; Mørk, P.; Svenstrup, N. Chem. Eur. J. 1996, 2, 624-633. (e) Devonport, M.; Blower, M. A.; Bryce, M. R.; Goldenberg, L. M. J. Org. Chem. 1997, 62, 885-887. (f) Becher, J.; Li, Z. T.; Blanchard, P.; Svenstrup, N.; Lau, J.; Nielsen, M. B.; Leriche, P. Pure Appl. Chem. 1997, 69, 465-470. (g) Li, Z. T.; Becher, J. Synlett 1997, 557-560. (h) Nielsen, M. B.; Thorup, N.; Becher, J. J. Chem. Soc., Perkin Trans. 1 1998, 1305-1308.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 1305-1308
    • Nielsen, M.B.1    Thorup, N.2    Becher, J.3
  • 53
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    • note
    • The [2]pseudorotaxanes and the [2]catenanes are labeled with the numbers of their two components separated by the symbols "·" and "/", respectively.
  • 54
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    • 4 were also obtained as mixtures of their cis- and trans-isomers. All attempts to separate the two isomers of these compounds were unsuccessful. For the synthesis of 4, see: Andreu, R.; Garin, J.; Orduna, J.; Saviron, M.; Cousseau, J.; Gorgues, A.; Morrisson, V.; Nozdryn, T.; Becher, J.; Clausen, R. P.; Bryce, M. R.; Skabara, P. J.; Dehaen, W. Tetrahedron Lett. 1994, 35, 9243-9246.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9243-9246
    • Andreu, R.1    Garin, J.2    Orduna, J.3    Saviron, M.4    Cousseau, J.5    Gorgues, A.6    Morrisson7
  • 58
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    • note
    • ex = 350 nm).
  • 64
    • 0342787552 scopus 로고    scopus 로고
    • note
    • -1.
  • 65
    • 0343222154 scopus 로고    scopus 로고
    • note
    • 4+.
  • 66
    • 4243285540 scopus 로고    scopus 로고
    • Work in progress
    • 4+ is very fast and can be considered instantaneous on the time scale of the present experiment (Hammarström, L.; Balzani, V.; Stoddart, J. F. Work in progress).
    • Hammarström, L.1    Balzani, V.2    Stoddart, J.F.3
  • 69
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    • note
    • None of these process can be attributed to 1,5-dioxynaphthalene-type impurities since (i) the potential values are different from that of the model compound, and (ii) the presence of such impurities would have been clearly evidenced by luminescence measurements.
  • 70
    • 0342352673 scopus 로고    scopus 로고
    • note
    • The alternative explanation, based on lack of reversibility of the electrode process on account of restricted access to the "inside" TTF unit, can be ruled out on the basis of the behavior observed for all other catenanes and rotaxanes previously investigated. See, for example, refs 10 and 16a.
  • 71
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    • 4+ and a phenylenediamine-based dumbbell takes place at different potentials. They rationalized this result to "communication" of the two units through the interposed electron donor moiety, see: Córdova, E.; Bissell, R. A.; Kaifer, A. E. J. Org. Chem. 1995, 60, 1033-1038.
    • (1995) J. Org. Chem. , vol.60 , pp. 1033-1038
    • Córdova, E.1    Bissell, R.A.2    Kaifer, A.E.3
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    • For a report on an adduct formed between TTF and p-chloroanil, see: Mayerle, J. J.; Crowley, J. I. Acta Crystallogr. 1979, B35, 2988-2995.
    • (1979) Acta Crystallogr. , vol.B35 , pp. 2988-2995
    • Mayerle, J.J.1    Crowley, J.I.2
  • 73
    • 0342352672 scopus 로고    scopus 로고
    • note
    • + results from an adduct formation between the TTF unit and o-chloroanil.
  • 74
    • 0343657800 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy.
  • 75
    • 0343657799 scopus 로고    scopus 로고
    • note
    • b′.
  • 77
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    • For examples of the reversible chemically controlled switching of [2]pseudorotaxanes as a result of the competitive formation of adducts, see: (a) Ballardini, R.; Balzani, V.; Credi, A.; Gandolfi, M. T.; Langford, S. J.; Menzer, S.; Prodi, L.; Stoddart, J. F.; Venturi, M.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 978-981. (b) Credi, A.; Balzani, V.; Langford, S. J.; Stoddart, J. F. J. Am. Chem. Soc. 1997, 119, 2679-2681.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2679-2681
    • Credi, A.1    Balzani, V.2    Langford, S.J.3    Stoddart, J.F.4
  • 78
    • 0343657798 scopus 로고    scopus 로고
    • note
    • 4+ resonate (see ref 14) in the region of δ = 3.0-3.5.
  • 80
    • 0343657795 scopus 로고    scopus 로고
    • note
    • The location of the TTF unit inside the cavity of the tetracationic cyclophane was confirmed by the cross-peaks between the protons of the methylene groups attached to this unit and both the α-bipyridinium and the p-phenylene protons observed in a 2D ROESY spectrum.


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