Ligand self-recognition in the self-assembly of a [{Cu(L)}2]2+ complex: The role of chirality

Angewandte Chemie - International Edition

Volumn 37, Issue 7, 1998, Pages 928-932

  Masood, M Athar ^a   Enemark, Eric J ^a   Stack, T Daniel P ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

Chirality; Copper; N ligands; Self assembly; Supramolecular chemistry

Indexed keywords

EID: 0031971605     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980420)37:7<928::AID-ANIE928>3.0.CO;2-T     Document Type: Article

References (48)

1. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995.
2. R. C. Scarrow, D. L. White, K. N. Raymond, J. Am. Chem. Soc. 1985, 107, 6540-6546.
3. J.-M. Lehn, A. Rigault, J. Siegel, J. Harrowfield, B. Chevrier, D. Moras, Proc. Natl. Acad. Sci. USA 1987, 84, 2565-2569.
4. W. Zarges, J. Hall, J.-M. Lehn, C. Bolm, Helv. Chim. Acta 1991, 74, 1843-1852.
5. R. Krämer, J.-M. Lehn, A. De Cian, J. Fischer, Angew. Chem. 1993, 105, 764-768; Angew. Chem. Int. Ed. Engl. 1993, 32, 703-706.
6. R. Krämer, J.-M. Lehn, A. De Cian, J. Fischer, Angew. Chem. 1993, 105, 764-768; Angew. Chem. Int. Ed. Engl. 1993, 32, 703-706.
7. E. J. Enemark, T. D. P. Stack, Angew. Chem. 1995, 107, 1082-1084; Angew. Chem. Int. Ed. Engl. 1995, 34, 996-998.
8. E. J. Enemark, T. D. P. Stack, Angew. Chem. 1995, 107, 1082-1084; Angew. Chem. Int. Ed. Engl. 1995, 34, 996-998.
9. M. Albrecht, S. Kotila, Angew. Chem. 1995, 107, 2285-2287; Angew. Chem. Int. Ed. Engl. 1995, 34, 2134-2136.
10. M. Albrecht, S. Kotila, Angew. Chem. 1995, 107, 2285-2287; Angew. Chem. Int. Ed. Engl. 1995, 34, 2134-2136.
11. E. J. Enemark, T. D. P. Stack, Inorg. Chem. 1996, 35, 2719-2720.
12. G. S. Hanan, C. R. Arana, J.-M. Lehn, D. Fenske, Angew. Chem. 1995, 107, 1191-1193; Angew. Chem. Im. Ed. Engl. 1995, 34, 1122-1124.
13. G. S. Hanan, C. R. Arana, J.-M. Lehn, D. Fenske, Angew. Chem. 1995, 107, 1191-1193; Angew. Chem. Im. Ed. Engl. 1995, 34, 1122-1124.
14. C. O. Dietrich-Buchecker, J.-P. Sauvage, J. Am. Chem. Soc. 1984, 106, 3043-3046.
15. C. O. Dietrich-Buchecker, J.-P. Sauvage, N. Armaroli, P. Ceroni, V. Balzani, Angew. Chem. 1996, 108, 1190-1193; Angew. Chem. Int. Ed. Engl. 1996, 35, 1119-1121.
16. C. O. Dietrich-Buchecker, J.-P. Sauvage, N. Armaroli, P. Ceroni, V. Balzani, Angew. Chem. 1996, 108, 1190-1193; Angew. Chem. Int. Ed. Engl. 1996, 35, 1119-1121.
17. P. Baxter, J.-M. Lehn, A. De Cian, J. Fischer, Angew. Chem. 1993, 105, 92-95; Angew. Chem. Int. Ed. Engl. 1993, 32, 69-72.
18. P. Baxter, J.-M. Lehn, A. De Cian, J. Fischer, Angew. Chem. 1993, 105, 92-95; Angew. Chem. Int. Ed. Engl. 1993, 32, 69-72.
19. R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, Angew. Chem. 1994, 106, 1697-1699; Angew. Chem. Int. Ed. Engl. 1994, 33, 1621-1623.
20. R. W. Saalfrank, R. Burak, A. Breit, D. Stalke, R. Herbst-Irmer, J. Daub, M. Porsch, E. Bill, M. Müther, A. X. Trautwein, Angew. Chem. 1994, 106, 1697-1699; Angew. Chem. Int. Ed. Engl. 1994, 33, 1621-1623.
21. T. Beissel, R. E. Powers, K. N. Raymond, Angew. Chem. 1996, 108, 1166-1168; Angew. Chem. Int. Ed. Engl. 1996, 35, 1084-1086.
22. T. Beissel, R. E. Powers, K. N. Raymond, Angew. Chem. 1996, 108, 1166-1168; Angew. Chem. Int. Ed. Engl. 1996, 35, 1084-1086.
23. B. Hasenknopf, J.-M. Lehn, B. O. Kneisel, G. Baum, D. Fenske, Angew. Chem. 1996, 108, 1987-1990; Angew. Chem. Int. Ed. Engl. 1996, 35, 1838-1840.
24. B. Hasenknopf, J.-M. Lehn, B. O. Kneisel, G. Baum, D. Fenske, Angew. Chem. 1996, 108, 1987-1990; Angew. Chem. Int. Ed. Engl. 1996, 35, 1838-1840.
25. D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229-2260.
26. J. P. Schneider, J. W. Kelly, Chem. Rev. 1995, 95, 2169-2187.
27. R. Ziessel, M.-T. Youinou, Angew. Chem. 1993, 105, 929-932; Angew. Chem. Int. Ed. Engl. 1993, 32, 877-880.
28. R. Ziessel, M.-T. Youinou, Angew. Chem. 1993, 105, 929-932; Angew. Chem. Int. Ed. Engl. 1993, 32, 877-880.
29. E. C. Constable, A. M. W. C. Thompson, P. Harveson, L. Macko, M. Zehnder, Chem. Eur. J. 1995, 1, 360-367.
30. Homochirality refers to a metal complex in which all ligand stereo-centers are of identical chirality. Stereospecificity refers to the generation of metal configurations that correlate with the chirality of the associated ligand.
31. C. R. Woods, M. Benaglia, F. Cozzi, J. S. Siegel, Angew. Chem. 1996, 108, 1985-1987; Angew. Chem. Int. Ed. Engl. 1996, 35, 1830-1833.
32. C. R. Woods, M. Benaglia, F. Cozzi, J. S. Siegel, Angew. Chem. 1996, 108, 1985-1987; Angew. Chem. Int. Ed. Engl. 1996, 35, 1830-1833.
33. R. Krämer, J.-M. Lehn, A. Marquis-Rigault, Proc. Natl. Acad. Sci. USA 1993, 90, 5394-5398.
34. D. L. Caulder, K. N. Raymond, Angew. Chem. 1997, 109, 1508-1510; Angew. Chem. Int. Ed. Engl. 1997, 36, 1439-1442.
35. D. L. Caulder, K. N. Raymond, Angew. Chem. 1997, 109, 1508-1510; Angew. Chem. Int. Ed. Engl. 1997, 36, 1439-1442.
36. T. A. Whitney, J. Org. Chem. 1980, 45, 4214-4216.
37. J. E. Parks, B. E. Wagner, R. H. Holm, J. Organomet. Chem. 1973, 56, 53-66.
38. See experimental section for details.
39. G. C. van Stein, G. van Koten, K. Vrieze, C. Brevard, A. L. Spek, J. Am. Chem. Soc. 1984, 106, 4486-4492.
40. G. C. van Stein, G. van Koten, K. Vrieze, C. Brevard, Inorg. Chem. 1984, 23, 4269-4278.
41. 1H NMR shows an approximately 3:1 mixture of two products, one the racemic mixture of homochiral complexes and the other a single heterochiral complex. Comparison of the chemical shifts with those from studies with the enantiopure ligand indicates that the major product is the homochiral species.
42. The minimum root-mean-square difference for all non-hydrogen atoms is 0.24 Å.
43. G. Bidan, B. Divisia-Blohorn, M. Lapkowski, J.-M. Kern, J.-P. Sauvage, J. Am. Chem. Soc. 1992, 114, 5986-5994.
44. IUPAC, IUPAC Nomenclature of Inorganic Chemistry, Butterworths, London, 1970.
45. R. E. Ernst, M. J. O'Connor, R. H. Holm, J. Am. Chem. Soc. 1967, 89, 6104-6113.
46. The molecular dynamics calculations (in vacuum at 297 K) were performed on a CACHE Scientific Workstation. While the parameters of the copper center for these calculations are certainly approximate, the calculations provide a way to visualize this facile interconversion.
47. 4 symmetry is cut into two homochiral halves. In the case presented here, the assembly of two homochiral objects is still a chiral object.
48. 2·MeOH).