Quantitative and spontaneous formation of a doubly interlocking [2]catenane using copper(I) and palladium(II) as templating and assembling centers [7]

Journal of the American Chemical Society

Volumn 121, Issue 47, 1999, Pages 11014-11015

  Ibukuro, Fumiaki ^a,b   Fujita, Makoto ^a,c   Yamaguchi, Kentaro ^d   Sauvage, Jean Pierre ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b GRADUATE UNIVERSITY FOR ADVANCED STUDIES   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; PALLADIUM;

CHEMICAL INTERACTION; CHEMICAL STRUCTURE; LETTER; MOLECULAR DYNAMICS; PHYSICAL CHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033485731     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992391r     Document Type: Letter

References (24)

1. Sauvage, J.-P.; Hosseini, W., volume Eds. In Comprehensive Supramolecular Chemistry; Lehn, J.-M., Ed.; Pergamon Press: Oxford, UK., 1996; Vol. 9 and references therein.
2. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451- 460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
3. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451- 460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
4. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451- 460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
5. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451- 460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
6. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451- 460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
7. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451- 460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
8. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451-460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
9. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451- 460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
10. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451- 460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
11. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451- 460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
12. For leading references in the field of catenanes, see: (a) Schill, G. In Catenanes, Rotaxanes, and Knots; Academic Press: New York, 1971. (b) Frisch, H. L.; Wasserman, E. J. Am. Chem. Soc. 1961, 83, 3789-3795. (c) Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Rev. 1987, 759-810. (d) Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P. Top. Curr. Chem. 1993, 165, 131-162. (e) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828. (f) Hunter, C. A. J. Am. Chem. Soc. 1992, 114, 5303-5311. (g) Vögtle, F.; Dünnwald, T.; Schmidt, T. Acc. Chem. Res. 1996, 29, 451- 460. (h) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458-6467. (i) Hamilton, D. G.; Davis, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608-620. (j) Fujita, M. Acc. Chem. Res. 1999, 32, 53. (k) Sauvage, J.-P.; Dietrich-Buchecker, C. O. In Catenanes, Rotaxanes, and Kots; Wiley-VCH: Weinhein, New York, Eds. 1999.
13. Dietrich-Buchecker, C. O.; Sauvage, J.-P. Chem. Commun., 1999, 615.
14. Dietrich-Buchecker, C. O.; Sauvage, J.-P.; Kintzinger, J.-P. Tetrahedron Lett. 1983, 24, 5098.
15. Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Nature 1994, 367, 720-723.
16. Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582.
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18. Cárdenas, D. J.; Sauvage, J.-P. Inorg. Chem. 1997, 36, 2777-2783.
19. Batten, S. R.; Robson, R. Angew. Chem., Int. Ed. 1998, 37, 1460-1494 and references therein.
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22. 10+: also see Supporting Information.
23. 5+.
24. 13C NMR, Elemental Analysis, etc.): see Supporting Information.