Borromean rings: A one-pot synthesis

Angewandte Chemie - International Edition

Volumn 43, Issue 34, 2004, Pages 4399-4401

  Schalley, Christoph A ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Self assembly; Structure elucidation; Template synthesis; Topochemistry

Indexed keywords

CHEMICAL BONDS; POSITIVE IONS; SELF ASSEMBLY;

COVALENT BONDS; METAL IONS; MOLECULAR BORROMEAN RINGS;

SYNTHESIS (CHEMICAL);

METAL ION;

CHEMICAL STRUCTURE; COVALENT BOND; ENERGY; SHORT SURVEY; SYNTHESIS;

EID: 4644221524     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460583     Document Type: Short Survey

References (47)

1. a) G. Schill, Catenanes, Rotaxanes and Knots, Academic Press, New York, 1971;
2. b) Molecular Catenanes, Rotaxanes, and Knots (Eds.: J.-P. Sauvage, C. Dietrich-Buchecker), Wiley-VCH, Weinheim, 1999.
3. a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484; Angew. Chem. Int. Ed. 2000, 39, 3348;
4. a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484; Angew. Chem. Int. Ed. 2000, 39, 3348;
5. b) C. A. Schalley, A. Lützen, M. Albrecht, Chem. Eur. J. 2004, 10, 1072.
6. Pictures of the knots were generated with the shareware program Knotplot by Rob Scharein: http://www.cs.ubc.ca/ nest/imager/contributions/scharein/ KnotPlot.html.
7. a) C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1989, 101, 192; Angew. Chem. Int. Ed. Engl. 1989, 28, 189;
8. a) C. O. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1989, 101, 192; Angew. Chem. Int. Ed. Engl. 1989, 28, 189;
9. b) R. F. Carlina, C. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1996, 118, 9110;
10. c) P. R. Ashton, O. A. Matthews, S. Menzer, F. M. Raymo, N. Spenzer, J. F. Stoddart, D. J. Williams, Liebigs Ann. 1997, 2485;
11. d) G. Rapenne, C. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1999, 121, 994;
12. e) S. C. J. Meskers, H. P. J. M. Dekkers, G. Rapenne, J.-P. Sauvage, Chem. Eur. J. 2000, 6, 2129;
13. f) O. Safarowsky, M. Nieger, R. Fröhlich, F. Vögtle, Angew. Chem. 2000, 112, 1699; Angew. Chem. Int. Ed. 2000, 39, 1616;
14. f) O. Safarowsky, M. Nieger, R. Fröhlich, F. Vögtle, Angew. Chem. 2000, 112, 1699; Angew. Chem. Int. Ed. 2000, 39, 1616;
15. g) H. Adams, E. Ashworth, G. A. Breault, J. Guo, C. A. Hunter, P. C. Mayers, Nature 2001, 411, 763;
16. h) C. R. Woods, M. Benaglia, S. Toyota, K. Hardcastle, J. S. Siegel, Angew. Chem. 2001, 113, 771; Angew. Chem. Int. Ed. 2001, 40, 749;
17. h) C. R. Woods, M. Benaglia, S. Toyota, K. Hardcastle, J. S. Siegel, Angew. Chem. 2001, 113, 771; Angew. Chem. Int. Ed. 2001, 40, 749;
18. i) F. Vögtle, A. Hünten, E. Vogel, S. Buschbeck, O. Safarowsky, J. Recker, A. H. Parham, M. Knott, W. M. Müller, U. Müller, Y. Okamoto, T. Kubota, W. Lindner, E. Francotte, S. Grimme, Angew. Chem. 2001, 113, 2534; Angew. Chem. Int. Ed. 2001, 40, 2468;
19. i) F. Vögtle, A. Hünten, E. Vogel, S. Buschbeck, O. Safarowsky, J. Recker, A. H. Parham, M. Knott, W. M. Müller, U. Müller, Y. Okamoto, T. Kubota, W. Lindner, E. Francotte, S. Grimme, Angew. Chem. 2001, 113, 2534; Angew. Chem. Int. Ed. 2001, 40, 2468;
20. j) O. Lukin, W. M. Müller, U. Müller, A. Kaufmann, C. Schmidt, J. Leszczynski, F. Vögtle, Chem. Eur. J. 2003, 9, 3507.
21. Metallic microknots and Borromean Rings have been generated on a micro- to millimeter scale by chemical means. Their fabrication relies on the electrodeposition of a metal on two suitably patterned cylinders, and finally producing a junction between the two cylinders at the right parts of their surfaces. Removing the cylinders finally yields the desired microknots: H. Wu, S. Brittain, J. Anderson, B. Grzybowski, S. Whitesides, G. M. Whitesides, J. Am. Chem. Soc. 2000, 122, 12691.
22. a) C. Mao, W. Sun, N. C. Seeman, Nature, 1997, 386, 137;
23. the synthesis of trefoil and figure-eight knots based on DNA and RNA have also been reported: b) S. M. Du, B. D. Stollar, N. C. Seeman, J. Am. Chem. Soc. 1995, 117, 1194;
24. c) H. Wang, R. J. Di Gate, N. C. Seeman, Proc. Natl. Acad. Sci. USA 1996, 93, 9477.
25. K. S. Chichak, S. J. Cantrill, A. R. Pease, S.-H. Chiu, G. W. V. Cave, J. L. Atwood, J. F. Stoddart, Science 2004, 304, 1308; for a report on this publication, see J. S. Siegel, Science, 2004, 304, 1256.
26. K. S. Chichak, S. J. Cantrill, A. R. Pease, S.-H. Chiu, G. W. V. Cave, J. L. Atwood, J. F. Stoddart, Science 2004, 304, 1308; for a report on this publication, see J. S. Siegel, Science, 2004, 304, 1256.
27. P. R. Cromwell, E. Beltrami, M. Rampichini, Mathematical Intelligencer 1998, 20, 53.
28. a) T. J. Hubin, A. G. Kolchinski, A. L. Vance, D. H. Busch, Adv. Supramol. Chem. 1999, 5, 237;
29. b) Templated Organic Synthesis (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim 2000;
30. c) T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200-202, 5;
31. d) M. Kogej, P. Ghosh, C. A. Schalley, How to thread a string into the eye of a molecular needle: Template-directed synthesis of mechanically interlocked molecules in Strategies and Tactics in Organic Synthesis, Vol. 4 (Ed.: M. Harmata), Elsevier, Amsterdam, 2004, p. 171.
32. Precursors for the synthesis of Borromean rings have been reported previously: J. C. Loren, M. Yoshizawa, R. F. Haldimann, A. Linden, J. S. Siegel, Angew. Chem. 2003, 115, 5880; Angew. Chem. Int. Ed. 2003, 42, 5702.
33. Precursors for the synthesis of Borromean rings have been reported previously: J. C. Loren, M. Yoshizawa, R. F. Haldimann, A. Linden, J. S. Siegel, Angew. Chem. 2003, 115, 5880; Angew. Chem. Int. Ed. 2003, 42, 5702.
34. a) M. Schmittel, A. Ganz, D. Fenske, Org. Lett. 2002, 4, 2289;
35. b) S.-H. Chiu, A. R. Pease, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2002, 114, 280; Angew. Chem. Int. Ed. 2002, 41, 270.
36. b) S.-H. Chiu, A. R. Pease, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2002, 114, 280; Angew. Chem. Int. Ed. 2002, 41, 270.
37. a) G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312;
38. b) D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154;
39. b) D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154;
40. c) J.-M. Lehn, Chem. Eur. J. 2000, 6, 2097;
41. d) M. Albrecht, Chem. Rev. 2001, 101, 3457.
42. a) S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938; Angew. Chem. Int. Ed. 2002, 41, 898;
43. a) S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938; Angew. Chem. Int. Ed. 2002, 41, 898;
44. reviews: b) P. A. Brady, J. K. M. Sanders, Chem. Soc. Rev. 1997, 26, 327;
45. c) J.-M. Lehn, Chem. Eur. J. 1999, 5, 2455.
46. For MS studies aimed at the structural characterization of topologically interesting molecules, see also a) C. A. Schalley, Int. J. Mass Spectrom., 2000, 194, 11;
47. b) C. A. Schalley, Mass Spectrom. Rev. 2001, 20, 253.