PdII-directed dynamic assembly of a dodecapyridine ligand into end-capped and open tubes: The importance of kinetic control in self-assembly

Angewandte Chemie - International Edition

Volumn 42, Issue 28, 2003, Pages 3267-3270

  Tashiro, Shohei ^a   Tominaga, Masahide ^a   Kusukawa, Takahiro ^a   Kawano, Masaki ^a   Sakamoto, Shigeru ^b   Yamaguchi, Kentaro ^b   Fujita, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

Coordination modes; Molecular recognition; Nanotubes; Palladium; Self assembly

Indexed keywords

CHEMICAL BONDS; CRYSTALLIZATION; SELF ASSEMBLY;

LIGANDS;

PALLADIUM;

DODECAPYRIDINE; LIGAND; PALLADIUM; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLIZATION; KINETICS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0042267230     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351397     Document Type: Article

References (36)

1. For reviews: a) I. Huc, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 1997, 94, 2106-2110;
2. b) J.-M. Lehn, Chem. Eur J. 1999, 5, 2455-2463;
3. c) G. R. L. Cousins, S.-A. Poulsen, J. K. M. Sanders, Curr. Opin. Chem. Biol. 2000, 4, 270-279;
4. d) S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938-993; Angew. Chem. Int. Ed. 2002, 41, 898-952.
5. d) S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938-993; Angew. Chem. Int. Ed. 2002, 41, 898-952.
6. a) M. Fujita, S. Nagao, K. Ogura, J. Am. Chem. Soc. 1995, 117, 1649-1650;
7. b) B. Hasenknopf, J.-M. Lehn, N. Boumediene, A. Dupont-Gervais, A. V. Dorsselaer, B. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956-10962;
8. c) B. Klekota, M. H. Hammond, B. L. Miller, Tetrahedron Lett. 1997, 38, 8639-8642;
9. d) M. Scherer, D. L. Caulder, D. W. Johnson, K. N. Raymond, Angew. Chem. 1999, 111, 1690-1694; Angew. Chem. Int. Ed. 1999, 38, 1588-1592;
10. d) M. Scherer, D. L. Caulder, D. W. Johnson, K. N. Raymond, Angew. Chem. 1999, 111, 1690-1694; Angew. Chem. Int. Ed. 1999, 38, 1588-1592;
11. e) M. Albrecht, O. Blau, R. Fröhlich, Chem. Eur. J. 1999, 5, 48-56;
12. f) S. Hiraoka, M. Fujita, J. Am. Chem. Soc. 1999, 121, 10239-10240;
13. g) Y. Kubota, S. Sakamoto, K. Yamaguchi, M. Fujita, Proc. Natl. Acad. Sci. USA 2002, 99, 4854-4856;
14. h) S. Otto, R. L. E. Furlan, J. K. M. Sanders, Science 2002, 297, 590-593.
15. a) G. W. Orr, L. J. Barbour, J. L. Atwood, Science 1999, 285, 1049-1052;
16. b) M. Ziegler, J. J. Miranda, U. N. Andersen, D. W. Johnson, J. A. Leary, K. N. Raymond, Angew. Chem. 2001, 113, 755-758; Angew. Chem. Int. Ed. 2001, 40, 733-736;
17. b) M. Ziegler, J. J. Miranda, U. N. Andersen, D. W. Johnson, J. A. Leary, K. N. Raymond, Angew. Chem. 2001, 113, 755-758; Angew. Chem. Int. Ed. 2001, 40, 733-736;
18. c) S. Hiraoka, T. Yi, M. Shiro, M. Shionoya, J. Am. Chem. Soc. 2002, 124, 14510-14511;
19. d) C.-Y. Su, Y.-P. Cai, C.-L. Chen, F. Lissner, B.-S. Kang, W. Kaim, Angew. Chem. 2002, 114, 3519-3523; Angew. Chem. Int. Ed. 2002, 41, 3371-3375.
20. d) C.-Y. Su, Y.-P. Cai, C.-L. Chen, F. Lissner, B.-S. Kang, W. Kaim, Angew. Chem. 2002, 114, 3519-3523; Angew. Chem. Int. Ed. 2002, 41, 3371-3375.
21. 4] (10 mol%), toluene, reflux) to give 2 in 13% yield.
22. a) M. Aoyagi, K. Biradha, M. Fujita, J. Am. Chem. Soc. 1999, 121, 7457-7458;
23. b) M. Aoyagi, S. Tashiro, M. Tominaga, K. Biradha, M. Fujita, Chem. Commun. 2002, 2036-2037;
24. c) M. Tominaga, S. Tashiro, M. Aoyagi, M. Fujita, Chem. Commun. 2002, 2038-2039.
25. a) I. Tabushi, K. Shimokawa, N. Shimizu, H. Shirakata, K. Fujita, J. Am. Chem. Soc. 1976, 98, 7855-7856;
26. b) S. Zhao, J. H. T. Luong, J. Chem. Soc. Chem. Commun. 1995, 663-664;
27. c) D. Whang, J. Heo, J. H. Park, K. Kim, Angew. Chem. 1998, 110, 83-85; Angew. Chem. Int. Ed. 1998, 37, 78-80;
28. c) D. Whang, J. Heo, J. H. Park, K. Kim, Angew. Chem. 1998, 110, 83-85; Angew. Chem. Int. Ed. 1998, 37, 78-80;
29. d) T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Nature 1998, 394, 764-766;
30. e) S. Saito, C. Nuckolls, J. Rebek, Jr., J. Am. Chem. Soc. 2000, 122, 9628-9630.
31. 24+, see the Supporting Information.
32. a) S. Sakamoto, M. Fujita, K. Kim, K. Yamaguchi, Tetrahedron 2000, 56, 955-964;
33. b) Y. Yamanoi, Y. Sakamoto, T. Kusukawa, M. Fujita, S. Sakamoto, K. Yamaguchi, J. Am. Chem. Soc. 2001, 123, 980-981.
34. n+ peaks were observed. See Supporting Information.
35. At 80°C, broad methyl signals were observed indicating that the coalescence temperature was being approached (see the Supporting Information).
36. -3. Several water molecules, nitrate molecules, and 1,2-ethanediamine ligands are disordered. Guest molecules sit on two positions (1:1 ratio) in the cavity of a host molecule. The thermal temperature factors of some disordered groups were constrained. The bond lengths of severely disordered molecules were chemically restrained. CCDC-204999 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 CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).