Assembly of a nanoscale chiral ball through supramolecular aggregation of bowl-shaped triangular helicates

Angewandte Chemie - International Edition

Volumn 41, Issue 22, 2002, Pages 4244-4247

  Childs, Laura J ^a   Alcock, Nathaniel W ^a   Hannon, Michael J ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

Copper; Helical structures; Nanostructures; Self assembly; Supramolecular chemistry

Indexed keywords

AGGLOMERATION; MOLECULAR STRUCTURE; STEREOCHEMISTRY;

LIGANDS;

COPPER COMPOUNDS;

COPPER ION; LIGAND; METAL;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; COVALENT BOND; LIGAND BINDING; MACROMOLECULE; MOLECULAR INTERACTION; MOLECULAR MIMICRY; NANOTECHNOLOGY; PROTEIN AGGREGATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037112647     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021115)41:22<4244::AID-ANIE4244>3.0.CO;2-5     Document Type: Article

References (56)

1. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1155-1196.
2. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1155-1196.
3. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995; D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1155-1196.
4. M. Fujita, Acc. Chem. Res. 1999, 32, 53-61; S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853-907; R. W. Saalfrank, I. Bernt, Curr. Opin. Solid State Mater. Sci. 1998, 3, 407-413; D. L. Calder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975-982; C. Piguet, J. Inclusion Phenom. Macrocyclic Chem. 1999, 34, 361-391; E.C. Constable, Prog. Inorg. Chem. 1994, 42, 67-138; A. F. Williams, Pure Appl. Chem. 1996, 68, 1285-1289; M. Albrecht, J. Inclusion Phenom. Macrocyclic Chem. 2000, 36, 127-151.
5. M. Fujita, Acc. Chem. Res. 1999, 32, 53-61; S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853-907; R. W. Saalfrank, I. Bernt, Curr. Opin. Solid State Mater. Sci. 1998, 3, 407-413; D. L. Calder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975-982; C. Piguet, J. Inclusion Phenom. Macrocyclic Chem. 1999, 34, 361-391; E.C. Constable, Prog. Inorg. Chem. 1994, 42, 67-138; A. F. Williams, Pure Appl. Chem. 1996, 68, 1285-1289; M. Albrecht, J. Inclusion Phenom. Macrocyclic Chem. 2000, 36, 127-151.
6. M. Fujita, Acc. Chem. Res. 1999, 32, 53-61; S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853-907; R. W. Saalfrank, I. Bernt, Curr. Opin. Solid State Mater. Sci. 1998, 3, 407-413; D. L. Calder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975-982; C. Piguet, J. Inclusion Phenom. Macrocyclic Chem. 1999, 34, 361-391; E.C. Constable, Prog. Inorg. Chem. 1994, 42, 67-138; A. F. Williams, Pure Appl. Chem. 1996, 68, 1285-1289; M. Albrecht, J. Inclusion Phenom. Macrocyclic Chem. 2000, 36, 127-151.
7. M. Fujita, Acc. Chem. Res. 1999, 32, 53-61; S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853-907; R. W. Saalfrank, I. Bernt, Curr. Opin. Solid State Mater. Sci. 1998, 3, 407-413; D. L. Calder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975-982; C. Piguet, J. Inclusion Phenom. Macrocyclic Chem. 1999, 34, 361-391; E.C. Constable, Prog. Inorg. Chem. 1994, 42, 67-138; A. F. Williams, Pure Appl. Chem. 1996, 68, 1285-1289; M. Albrecht, J. Inclusion Phenom. Macrocyclic Chem. 2000, 36, 127-151.
8. M. Fujita, Acc. Chem. Res. 1999, 32, 53-61; S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853-907; R. W. Saalfrank, I. Bernt, Curr. Opin. Solid State Mater. Sci. 1998, 3, 407-413; D. L. Calder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975-982; C. Piguet, J. Inclusion Phenom. Macrocyclic Chem. 1999, 34, 361-391; E.C. Constable, Prog. Inorg. Chem. 1994, 42, 67-138; A. F. Williams, Pure Appl. Chem. 1996, 68, 1285-1289; M. Albrecht, J. Inclusion Phenom. Macrocyclic Chem. 2000, 36, 127-151.
9. M. Fujita, Acc. Chem. Res. 1999, 32, 53-61; S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853-907; R. W. Saalfrank, I. Bernt, Curr. Opin. Solid State Mater. Sci. 1998, 3, 407-413; D. L. Calder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975-982; C. Piguet, J. Inclusion Phenom. Macrocyclic Chem. 1999, 34, 361-391; E.C. Constable, Prog. Inorg. Chem. 1994, 42, 67-138; A. F. Williams, Pure Appl. Chem. 1996, 68, 1285-1289; M. Albrecht, J. Inclusion Phenom. Macrocyclic Chem. 2000, 36, 127-151.
10. M. Fujita, Acc. Chem. Res. 1999, 32, 53-61; S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853-907; R. W. Saalfrank, I. Bernt, Curr. Opin. Solid State Mater. Sci. 1998, 3, 407-413; D. L. Calder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975-982; C. Piguet, J. Inclusion Phenom. Macrocyclic Chem. 1999, 34, 361-391; E.C. Constable, Prog. Inorg. Chem. 1994, 42, 67-138; A. F. Williams, Pure Appl. Chem. 1996, 68, 1285-1289; M. Albrecht, J. Inclusion Phenom. Macrocyclic Chem. 2000, 36, 127-151.
11. M. Fujita, Acc. Chem. Res. 1999, 32, 53-61; S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853-907; R. W. Saalfrank, I. Bernt, Curr. Opin. Solid State Mater. Sci. 1998, 3, 407-413; D. L. Calder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975-982; C. Piguet, J. Inclusion Phenom. Macrocyclic Chem. 1999, 34, 361-391; E.C. Constable, Prog. Inorg. Chem. 1994, 42, 67-138; A. F. Williams, Pure Appl. Chem. 1996, 68, 1285-1289; M. Albrecht, J. Inclusion Phenom. Macrocyclic Chem. 2000, 36, 127-151.
12. R. F. Carina, G. Bernardinelli, A. F. Williams, Angew. Chem. 1993, 105, 1483-1485; Angew. Chem. Int. Ed. Engl. 1993, 32, 1461-1463.
13. R. F. Carina, G. Bernardinelli, A. F. Williams, Angew. Chem. 1993, 105, 1483-1485; Angew. Chem. Int. Ed. Engl. 1993, 32, 1461-1463.
14. L. J. Childs, N. W. Alcock, M. J. Hannon, Angew. Chem. 2001, 113, 1113-1115; Angew. Chem. Int. Ed. 2001, 40, 1079-1081.
15. L. J. Childs, N. W. Alcock, M. J. Hannon, Angew. Chem. 2001, 113, 1113-1115; Angew. Chem. Int. Ed. 2001, 40, 1079-1081.
16. M. J. Hannon, C. L. Painting, W. Errington, Chem. Commun. 1997, 1805-1806; N. W. Alcock, P. R. Barker, J. M. Haider, M. J. Hannon, C. L. Painting, Z. Pikramenou, E. A. Plummer, K. Rissanen, P. Saarenketo, J. Chem. Soc. Dalton Trans. 2000, 1447-1461.
17. M. J. Hannon, C. L. Painting, W. Errington, Chem. Commun. 1997, 1805-1806; N. W. Alcock, P. R. Barker, J. M. Haider, M. J. Hannon, C. L. Painting, Z. Pikramenou, E. A. Plummer, K. Rissanen, P. Saarenketo, J. Chem. Soc. Dalton Trans. 2000, 1447-1461.
18. See for example: S.-Y. Yu. T. Kusukawa, K. Biradha, M. Fujita, J. Am. Chem. Soc. 2000, 122, 2665-2666; R.W. Saalffank, I. Bernt, F. Hampel, Chem. Eur. J. 2001, 7, 2770-2774.
19. See for example: S.-Y. Yu. T. Kusukawa, K. Biradha, M. Fujita, J. Am. Chem. Soc. 2000, 122, 2665-2666; R.W. Saalffank, I. Bernt, F. Hampel, Chem. Eur. J. 2001, 7, 2770-2774.
20. M. J. Hannon, C. L. Painting, A. Jackson, J. Hamblin, W. Errington, Chem. Commun. 1997, 1807-1808; M. J. Hannon, C. L. Painting, N. W. Alcock, Chem. Commun. 1999, 2023-2024.
21. M. J. Hannon, C. L. Painting, A. Jackson, J. Hamblin, W. Errington, Chem. Commun. 1997, 1807-1808; M. J. Hannon, C. L. Painting, N. W. Alcock, Chem. Commun. 1999, 2023-2024.
22. The Ph rings are approximately coplanar with the pyridylimine units in the meso isomers of other compounds that we have crystallo-graphically characterized, whereas in the rac isomers of similar supramolecular structures there is twisting about the interannular bonds, see ref. 7.
23. For recent examples of solvent-free reactions see, for metal complexes A. Orita, L. Jiang, T. Nakano, N. Ma, J. Otera, Chem. Commun. 2002, 1362-1363; for ligands G. W. V. Cave, C. L. Raston, J. Chem. Soc. Perkin Trans. 1 2001, 24, 3258-3264.
24. For recent examples of solvent-free reactions see, for metal complexes A. Orita, L. Jiang, T. Nakano, N. Ma, J. Otera, Chem. Commun. 2002, 1362-1363; for ligands G. W. V. Cave, C. L. Raston, J. Chem. Soc. Perkin Trans. 1 2001, 24, 3258-3264.
25. At low temperature, the NMR spectrum in acetonitrile also shows signals arising from two species and is analogous to the room-temperature NMR spectrum in dichloromethane.
26. -3. Refinement used SHELXL 97 (G. M. Sheldrick,1997);
27. b) CCDC-187879 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+ 44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
28. B. Hasenknopf, J. M. Lehn, N. Boumediene, A. DupontGervais, A. VanDorsselaer, B. O. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956-10962; 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, 1838-1846; O. Mamula, A. von Zelewsky, G. Bernardinelli, Angew. Chem. 1998, 110, 301-305; Angew. Chem. Int. Ed. 1998, 37, 290-293; P. L. Jones. K. J. Byrom, J. C. Jeffery, J. A. McCleverty, M.D. Ward. Chem. Commun. 1997, 1361-1362; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft, T. Kulke, Chem. Commun. 1999, 195-196; C. Provent, E. Rivara-Minten, S. Hewage, G. Brunner, A. F. Williams, Chem. Eur. J. 1999, 5, 3487-3494.
29. B. Hasenknopf, J. M. Lehn, N. Boumediene, A. DupontGervais, A. VanDorsselaer, B. O. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956-10962; 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, 1838-1846; O. Mamula, A. von Zelewsky, G. Bernardinelli, Angew. Chem. 1998, 110, 301-305; Angew. Chem. Int. Ed. 1998, 37, 290-293; P. L. Jones. K. J. Byrom, J. C. Jeffery, J. A. McCleverty, M.D. Ward. Chem. Commun. 1997, 1361-1362; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft, T. Kulke, Chem. Commun. 1999, 195-196; C. Provent, E. Rivara-Minten, S. Hewage, G. Brunner, A. F. Williams, Chem. Eur. J. 1999, 5, 3487-3494.
30. B. Hasenknopf, J. M. Lehn, N. Boumediene, A. DupontGervais, A. VanDorsselaer, B. O. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956-10962; 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, 1838-1846; O. Mamula, A. von Zelewsky, G. Bernardinelli, Angew. Chem. 1998, 110, 301-305; Angew. Chem. Int. Ed. 1998, 37, 290-293; P. L. Jones. K. J. Byrom, J. C. Jeffery, J. A. McCleverty, M.D. Ward. Chem. Commun. 1997, 1361-1362; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft, T. Kulke, Chem. Commun. 1999, 195-196; C. Provent, E. Rivara-Minten, S. Hewage, G. Brunner, A. F. Williams, Chem. Eur. J. 1999, 5, 3487-3494.
31. B. Hasenknopf, J. M. Lehn, N. Boumediene, A. DupontGervais, A. VanDorsselaer, B. O. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956-10962; 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, 1838-1846; O. Mamula, A. von Zelewsky, G. Bernardinelli, Angew. Chem. 1998, 110, 301-305; Angew. Chem. Int. Ed. 1998, 37, 290-293; P. L. Jones. K. J. Byrom, J. C. Jeffery, J. A. McCleverty, M.D. Ward. Chem. Commun. 1997, 1361-1362; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft, T. Kulke, Chem. Commun. 1999, 195-196; C. Provent, E. Rivara-Minten, S. Hewage, G. Brunner, A. F. Williams, Chem. Eur. J. 1999, 5, 3487-3494.
32. B. Hasenknopf, J. M. Lehn, N. Boumediene, A. DupontGervais, A. VanDorsselaer, B. O. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956-10962; 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, 1838-1846; O. Mamula, A. von Zelewsky, G. Bernardinelli, Angew. Chem. 1998, 110, 301-305; Angew. Chem. Int. Ed. 1998, 37, 290-293; P. L. Jones. K. J. Byrom, J. C. Jeffery, J. A. McCleverty, M.D. Ward. Chem. Commun. 1997, 1361-1362; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft, T. Kulke, Chem. Commun. 1999, 195-196; C. Provent, E. Rivara-Minten, S. Hewage, G. Brunner, A. F. Williams, Chem. Eur. J. 1999, 5, 3487-3494.
33. B. Hasenknopf, J. M. Lehn, N. Boumediene, A. DupontGervais, A. VanDorsselaer, B. O. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956-10962; 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, 1838-1846; O. Mamula, A. von Zelewsky, G. Bernardinelli, Angew. Chem. 1998, 110, 301-305; Angew. Chem. Int. Ed. 1998, 37, 290-293; P. L. Jones. K. J. Byrom, J. C. Jeffery, J. A. McCleverty, M.D. Ward. Chem. Commun. 1997, 1361-1362; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft, T. Kulke, Chem. Commun. 1999, 195-196; C. Provent, E. Rivara-Minten, S. Hewage, G. Brunner, A. F. Williams, Chem. Eur. J. 1999, 5, 3487-3494.
34. B. Hasenknopf, J. M. Lehn, N. Boumediene, A. DupontGervais, A. VanDorsselaer, B. O. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956-10962; 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, 1838-1846; O. Mamula, A. von Zelewsky, G. Bernardinelli, Angew. Chem. 1998, 110, 301-305; Angew. Chem. Int. Ed. 1998, 37, 290-293; P. L. Jones. K. J. Byrom, J. C. Jeffery, J. A. McCleverty, M.D. Ward. Chem. Commun. 1997, 1361-1362; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft, T. Kulke, Chem. Commun. 1999, 195-196; C. Provent, E. Rivara-Minten, S. Hewage, G. Brunner, A. F. Williams, Chem. Eur. J. 1999, 5, 3487-3494.
35. B. Hasenknopf, J. M. Lehn, N. Boumediene, A. DupontGervais, A. VanDorsselaer, B. O. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956-10962; 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, 1838-1846; O. Mamula, A. von Zelewsky, G. Bernardinelli, Angew. Chem. 1998, 110, 301-305; Angew. Chem. Int. Ed. 1998, 37, 290-293; P. L. Jones. K. J. Byrom, J. C. Jeffery, J. A. McCleverty, M.D. Ward. Chem. Commun. 1997, 1361-1362; G. Baum, E. C. Constable, D. Fenske, C. E. Housecroft, T. Kulke, Chem. Commun. 1999, 195-196; C. Provent, E. Rivara-Minten, S. Hewage, G. Brunner, A. F. Williams, Chem. Eur. J. 1999, 5, 3487-3494.
36. Supramolecular triangles (assembled using square-planar Pd/Pt chemistry) which stack linearly through the faces were reported and give infinite tubes or discrete dimers: R. -D. Schnebeck, E. Freisinger, B. Lippert, Chem. Commun. 1999, 675-676; M. C. Jennings, R. J. Puddephatt, Chem. Commun. 2001, 2676-2677, and references therein. Metal-ligand interactions have been used to assemble planar triangular ligands into a tetrahedral array: I. M. Müller, R. Robson, F. Separovic, Angew. Chem. 2001, 113, 4519-4520; Angew. Chem. Int. Ed. 2001, 40, 4385-4386.
37. Supramolecular triangles (assembled using square-planar Pd/Pt chemistry) which stack linearly through the faces were reported and give infinite tubes or discrete dimers: R. -D. Schnebeck, E. Freisinger, B. Lippert, Chem. Commun. 1999, 675-676; M. C. Jennings, R. J. Puddephatt, Chem. Commun. 2001, 2676-2677, and references therein. Metal-ligand interactions have been used to assemble planar triangular ligands into a tetrahedral array: I. M. Müller, R. Robson, F. Separovic, Angew. Chem. 2001, 113, 4519-4520; Angew. Chem. Int. Ed. 2001, 40, 4385-4386.
38. Supramolecular triangles (assembled using square-planar Pd/Pt chemistry) which stack linearly through the faces were reported and give infinite tubes or discrete dimers: R. -D. Schnebeck, E. Freisinger, B. Lippert, Chem. Commun. 1999, 675-676; M. C. Jennings, R. J. Puddephatt, Chem. Commun. 2001, 2676-2677, and references therein. Metal-ligand interactions have been used to assemble planar triangular ligands into a tetrahedral array: I. M. Müller, R. Robson, F. Separovic, Angew. Chem. 2001, 113, 4519-4520; Angew. Chem. Int. Ed. 2001, 40, 4385-4386.
39. Supramolecular triangles (assembled using square-planar Pd/Pt chemistry) which stack linearly through the faces were reported and give infinite tubes or discrete dimers: R. -D. Schnebeck, E. Freisinger, B. Lippert, Chem. Commun. 1999, 675-676; M. C. Jennings, R. J. Puddephatt, Chem. Commun. 2001, 2676-2677, and references therein. Metal-ligand interactions have been used to assemble planar triangular ligands into a tetrahedral array: I. M. Müller, R. Robson, F. Separovic, Angew. Chem. 2001, 113, 4519-4520; Angew. Chem. Int. Ed. 2001, 40, 4385-4386.
40. 2 over the range 15.5-0.5 mM revealed no change in the positions of the resonance signals corresponding to either trimer or dimer implying no further aggregation of the triangle (or dimer) into a higher-order species occurs at these concentrations. The ratio of the two species varies over the concentration ratios as expected.
41. The crystals resolve spontaneously and all the balls in the crystal are of the same chirality.
42. For discussions of C-H···X bonds see for example: T. Steiner, Chem. Commun. 1997, 727-734; T. Steiner, Chem. Commun. 1999, 313-314; G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296; G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449; For short contacts to anions see for example: M. L. Tong, H. K. Lee, X. M. Chen, R. B. Huang, T. C. W. Mak, J. Chem. Soc. Dalton Trans. 1999, 3657-3659; C. V. K. Sharma, S. T. Griffin, R. D. Rogers, Chem. Commun. 1998, 215-216, and references therein; M. J. Hannon, C. L. Painting, E. A. Plummer, L. J. Childs, N. W. Alcock, Chem. Eur. J. 2002, 8, 2226-2238.
43. For discussions of C-H···X bonds see for example: T. Steiner, Chem. Commun. 1997, 727-734; T. Steiner, Chem. Commun. 1999, 313-314; G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296; G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449; For short contacts to anions see for example: M. L. Tong, H. K. Lee, X. M. Chen, R. B. Huang, T. C. W. Mak, J. Chem. Soc. Dalton Trans. 1999, 3657-3659; C. V. K. Sharma, S. T. Griffin, R. D. Rogers, Chem. Commun. 1998, 215-216, and references therein; M. J. Hannon, C. L. Painting, E. A. Plummer, L. J. Childs, N. W. Alcock, Chem. Eur. J. 2002, 8, 2226-2238.
44. For discussions of C-H···X bonds see for example: T. Steiner, Chem. Commun. 1997, 727-734; T. Steiner, Chem. Commun. 1999, 313-314; G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296; G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449; For short contacts to anions see for example: M. L. Tong, H. K. Lee, X. M. Chen, R. B. Huang, T. C. W. Mak, J. Chem. Soc. Dalton Trans. 1999, 3657-3659; C. V. K. Sharma, S. T. Griffin, R. D. Rogers, Chem. Commun. 1998, 215-216, and references therein; M. J. Hannon, C. L. Painting, E. A. Plummer, L. J. Childs, N. W. Alcock, Chem. Eur. J. 2002, 8, 2226-2238.
45. For discussions of C-H···X bonds see for example: T. Steiner, Chem. Commun. 1997, 727-734; T. Steiner, Chem. Commun. 1999, 313-314; G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296; G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449; For short contacts to anions see for example: M. L. Tong, H. K. Lee, X. M. Chen, R. B. Huang, T. C. W. Mak, J. Chem. Soc. Dalton Trans. 1999, 3657-3659; C. V. K. Sharma, S. T. Griffin, R. D. Rogers, Chem. Commun. 1998, 215-216, and references therein; M. J. Hannon, C. L. Painting, E. A. Plummer, L. J. Childs, N. W. Alcock, Chem. Eur. J. 2002, 8, 2226-2238.
46. For discussions of C-H···X bonds see for example: T. Steiner, Chem. Commun. 1997, 727-734; T. Steiner, Chem. Commun. 1999, 313-314; G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296; G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449; For short contacts to anions see for example: M. L. Tong, H. K. Lee, X. M. Chen, R. B. Huang, T. C. W. Mak, J. Chem. Soc. Dalton Trans. 1999, 3657-3659; C. V. K. Sharma, S. T. Griffin, R. D. Rogers, Chem. Commun. 1998, 215-216, and references therein; M. J. Hannon, C. L. Painting, E. A. Plummer, L. J. Childs, N. W. Alcock, Chem. Eur. J. 2002, 8, 2226-2238.
47. For discussions of C-H···X bonds see for example: T. Steiner, Chem. Commun. 1997, 727-734; T. Steiner, Chem. Commun. 1999, 313-314; G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296; G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449; For short contacts to anions see for example: M. L. Tong, H. K. Lee, X. M. Chen, R. B. Huang, T. C. W. Mak, J. Chem. Soc. Dalton Trans. 1999, 3657-3659; C. V. K. Sharma, S. T. Griffin, R. D. Rogers, Chem. Commun. 1998, 215-216, and references therein; M. J. Hannon, C. L. Painting, E. A. Plummer, L. J. Childs, N. W. Alcock, Chem. Eur. J. 2002, 8, 2226-2238.
48. For discussions of C-H···X bonds see for example: T. Steiner, Chem. Commun. 1997, 727-734; T. Steiner, Chem. Commun. 1999, 313-314; G. R. Desiraju, Acc. Chem. Res. 1991, 24, 290-296; G. R. Desiraju, Acc. Chem. Res. 1996, 29, 441-449; For short contacts to anions see for example: M. L. Tong, H. K. Lee, X. M. Chen, R. B. Huang, T. C. W. Mak, J. Chem. Soc. Dalton Trans. 1999, 3657-3659; C. V. K. Sharma, S. T. Griffin, R. D. Rogers, Chem. Commun. 1998, 215-216, and references therein; M. J. Hannon, C. L. Painting, E. A. Plummer, L. J. Childs, N. W. Alcock, Chem. Eur. J. 2002, 8, 2226-2238.
49. Recent work has demonstrated that nanoscale capsules may also be assembled from poly-monodentate ligands and suitable metal ions. See for example: B. F. Abrahams, S. J. Egan, R. Robson, J. Am. Chem. Soc. 1999, 121, 3535-3536; N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796; B. Olenyuk, J. A. Whiteford, A. Fechtenkötter, P. J. Stang, Nature 1999, 398, 796-799; Poly-didentate ligands with octahedral metal centers can also give capsules: D. L. Caulder, K. N. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200; Z. R. Bell, J. C. Jeffery, J. A. McCleverty, M. D. Ward, Angew. Chem. 2002, 114, 2625-2628; Angew. Chem. Int. Ed. 2002, 41, 2515-2518; R. W. Saalfrank, E. Uller, B. Demleitner, I. Bernt. Struct. Bonding 2000, 96, 149-175; R. W. Saalfrank, N. Löw, B. Demleitner, D. Stalke, M. Teichert, Chem. Eur. J. 1998, 4, 1305-1311.
50. Recent work has demonstrated that nanoscale capsules may also be assembled from poly-monodentate ligands and suitable metal ions. See for example: B. F. Abrahams, S. J. Egan, R. Robson, J. Am. Chem. Soc. 1999, 121, 3535-3536; N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796; B. Olenyuk, J. A. Whiteford, A. Fechtenkötter, P. J. Stang, Nature 1999, 398, 796-799; Poly-didentate ligands with octahedral metal centers can also give capsules: D. L. Caulder, K. N. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200; Z. R. Bell, J. C. Jeffery, J. A. McCleverty, M. D. Ward, Angew. Chem. 2002, 114, 2625-2628; Angew. Chem. Int. Ed. 2002, 41, 2515-2518; R. W. Saalfrank, E. Uller, B. Demleitner, I. Bernt. Struct. Bonding 2000, 96, 149-175; R. W. Saalfrank, N. Löw, B. Demleitner, D. Stalke, M. Teichert, Chem. Eur. J. 1998, 4, 1305-1311.
51. Recent work has demonstrated that nanoscale capsules may also be assembled from poly-monodentate ligands and suitable metal ions. See for example: B. F. Abrahams, S. J. Egan, R. Robson, J. Am. Chem. Soc. 1999, 121, 3535-3536; N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796; B. Olenyuk, J. A. Whiteford, A. Fechtenkötter, P. J. Stang, Nature 1999, 398, 796-799; Poly-didentate ligands with octahedral metal centers can also give capsules: D. L. Caulder, K. N. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200; Z. R. Bell, J. C. Jeffery, J. A. McCleverty, M. D. Ward, Angew. Chem. 2002, 114, 2625-2628; Angew. Chem. Int. Ed. 2002, 41, 2515-2518; R. W. Saalfrank, E. Uller, B. Demleitner, I. Bernt. Struct. Bonding 2000, 96, 149-175; R. W. Saalfrank, N. Löw, B. Demleitner, D. Stalke, M. Teichert, Chem. Eur. J. 1998, 4, 1305-1311.
52. Recent work has demonstrated that nanoscale capsules may also be assembled from poly-monodentate ligands and suitable metal ions. See for example: B. F. Abrahams, S. J. Egan, R. Robson, J. Am. Chem. Soc. 1999, 121, 3535-3536; N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796; B. Olenyuk, J. A. Whiteford, A. Fechtenkötter, P. J. Stang, Nature 1999, 398, 796-799; Poly-didentate ligands with octahedral metal centers can also give capsules: D. L. Caulder, K. N. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200; Z. R. Bell, J. C. Jeffery, J. A. McCleverty, M. D. Ward, Angew. Chem. 2002, 114, 2625-2628; Angew. Chem. Int. Ed. 2002, 41, 2515-2518; R. W. Saalfrank, E. Uller, B. Demleitner, I. Bernt. Struct. Bonding 2000, 96, 149-175; R. W. Saalfrank, N. Löw, B. Demleitner, D. Stalke, M. Teichert, Chem. Eur. J. 1998, 4, 1305-1311.
53. Recent work has demonstrated that nanoscale capsules may also be assembled from poly-monodentate ligands and suitable metal ions. See for example: B. F. Abrahams, S. J. Egan, R. Robson, J. Am. Chem. Soc. 1999, 121, 3535-3536; N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796; B. Olenyuk, J. A. Whiteford, A. Fechtenkötter, P. J. Stang, Nature 1999, 398, 796-799; Poly-didentate ligands with octahedral metal centers can also give capsules: D. L. Caulder, K. N. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200; Z. R. Bell, J. C. Jeffery, J. A. McCleverty, M. D. Ward, Angew. Chem. 2002, 114, 2625-2628; Angew. Chem. Int. Ed. 2002, 41, 2515-2518; R. W. Saalfrank, E. Uller, B. Demleitner, I. Bernt. Struct. Bonding 2000, 96, 149-175; R. W. Saalfrank, N. Löw, B. Demleitner, D. Stalke, M. Teichert, Chem. Eur. J. 1998, 4, 1305-1311.
54. Recent work has demonstrated that nanoscale capsules may also be assembled from poly-monodentate ligands and suitable metal ions. See for example: B. F. Abrahams, S. J. Egan, R. Robson, J. Am. Chem. Soc. 1999, 121, 3535-3536; N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796; B. Olenyuk, J. A. Whiteford, A. Fechtenkötter, P. J. Stang, Nature 1999, 398, 796-799; Poly-didentate ligands with octahedral metal centers can also give capsules: D. L. Caulder, K. N. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200; Z. R. Bell, J. C. Jeffery, J. A. McCleverty, M. D. Ward, Angew. Chem. 2002, 114, 2625-2628; Angew. Chem. Int. Ed. 2002, 41, 2515-2518; R. W. Saalfrank, E. Uller, B. Demleitner, I. Bernt. Struct. Bonding 2000, 96, 149-175; R. W. Saalfrank, N. Löw, B. Demleitner, D. Stalke, M. Teichert, Chem. Eur. J. 1998, 4, 1305-1311.
55. Recent work has demonstrated that nanoscale capsules may also be assembled from poly-monodentate ligands and suitable metal ions. See for example: B. F. Abrahams, S. J. Egan, R. Robson, J. Am. Chem. Soc. 1999, 121, 3535-3536; N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796; B. Olenyuk, J. A. Whiteford, A. Fechtenkötter, P. J. Stang, Nature 1999, 398, 796-799; Poly-didentate ligands with octahedral metal centers can also give capsules: D. L. Caulder, K. N. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200; Z. R. Bell, J. C. Jeffery, J. A. McCleverty, M. D. Ward, Angew. Chem. 2002, 114, 2625-2628; Angew. Chem. Int. Ed. 2002, 41, 2515-2518; R. W. Saalfrank, E. Uller, B. Demleitner, I. Bernt. Struct. Bonding 2000, 96, 149-175; R. W. Saalfrank, N. Löw, B. Demleitner, D. Stalke, M. Teichert, Chem. Eur. J. 1998, 4, 1305-1311.
56. Recent work has demonstrated that nanoscale capsules may also be assembled from poly-monodentate ligands and suitable metal ions. See for example: B. F. Abrahams, S. J. Egan, R. Robson, J. Am. Chem. Soc. 1999, 121, 3535-3536; N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796; B. Olenyuk, J. A. Whiteford, A. Fechtenkötter, P. J. Stang, Nature 1999, 398, 796-799; Poly-didentate ligands with octahedral metal centers can also give capsules: D. L. Caulder, K. N. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200; Z. R. Bell, J. C. Jeffery, J. A. McCleverty, M. D. Ward, Angew. Chem. 2002, 114, 2625-2628; Angew. Chem. Int. Ed. 2002, 41, 2515-2518; R. W. Saalfrank, E. Uller, B. Demleitner, I. Bernt. Struct. Bonding 2000, 96, 149-175; R. W. Saalfrank, N. Löw, B. Demleitner, D. Stalke, M. Teichert, Chem. Eur. J. 1998, 4, 1305-1311.