Self-assembled M6L4-type coordination nanocage with 2,2′-bipyridine ancillary ligands. Facile crystallization and x-ray analysis of shape-selective enclathration of neutral guests in the cage

Journal of the American Chemical Society

Volumn 124, Issue 45, 2002, Pages 13576-13582

  Kusukawa, Takahiro ^a   Fujita, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AQUEOUS PHASE;

COMPLEXATION; CRYSTALLIZATION; NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

ORGANIC COMPOUNDS;

2,2' BIPYRIDINE; BIPYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTALLIZATION; GEOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITION; STRUCTURE ANALYSIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0037073162     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020712k     Document Type: Article

References (31)

1. Cram D. J.; Cram J. M. Container Molecules and Their Guests; RSC: Cambridge, United Kingdom, 1994.
2. Stabilization and activation of molecules enclathrated in the cavity: (a) Cram, D. J.; Tanner, M. E.; Thomas, R Angew. Chem., Int. Ed. Engl. 1991, 30, 1024. (b) Warmuth, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347. (c) Warmuth, R. J. Chem. Soc. Chem. Commun. 1998, 59. (d) Warmuth, R.; Marvel, M. A. Angew. Chem., Int. Ed. Engl. 2000, 39, 1117. (e) Kang, J.; Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. (f) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (g) Kang, J.; Hilmersson, G.; Santamarfa, J.; Rebek, J., Jr. J. Am. Chem. Soc, 1998, 120, 3650. (h) Ziegler, M.; Brumaghim, J. L.; Raymond, K. N.; Angew. Chem., Int. Ed. Engl. 2000, 39, 4119.
3. Stabilization and activation of molecules enclathrated in the cavity: (a) Cram, D. J.; Tanner, M. E.; Thomas, R Angew. Chem., Int. Ed. Engl. 1991, 30, 1024. (b) Warmuth, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347. (c) Warmuth, R. J. Chem. Soc. Chem. Commun. 1998, 59. (d) Warmuth, R.; Marvel, M. A. Angew. Chem., Int. Ed. Engl. 2000, 39, 1117. (e) Kang, J.; Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. (f) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (g) Kang, J.; Hilmersson, G.; Santamarfa, J.; Rebek, J., Jr. J. Am. Chem. Soc, 1998, 120, 3650. (h) Ziegler, M.; Brumaghim, J. L.; Raymond, K. N.; Angew. Chem., Int. Ed. Engl. 2000, 39, 4119.
4. Stabilization and activation of molecules enclathrated in the cavity: (a) Cram, D. J.; Tanner, M. E.; Thomas, R Angew. Chem., Int. Ed. Engl. 1991, 30, 1024. (b) Warmuth, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347. (c) Warmuth, R. J. Chem. Soc. Chem. Commun. 1998, 59. (d) Warmuth, R.; Marvel, M. A. Angew. Chem., Int. Ed. Engl. 2000, 39, 1117. (e) Kang, J.; Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. (f) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (g) Kang, J.; Hilmersson, G.; Santamarfa, J.; Rebek, J., Jr. J. Am. Chem. Soc, 1998, 120, 3650. (h) Ziegler, M.; Brumaghim, J. L.; Raymond, K. N.; Angew. Chem., Int. Ed. Engl. 2000, 39, 4119.
5. Stabilization and activation of molecules enclathrated in the cavity: (a) Cram, D. J.; Tanner, M. E.; Thomas, R Angew. Chem., Int. Ed. Engl. 1991, 30, 1024. (b) Warmuth, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347. (c) Warmuth, R. J. Chem. Soc. Chem. Commun. 1998, 59. (d) Warmuth, R.; Marvel, M. A. Angew. Chem., Int. Ed. Engl. 2000, 39, 1117. (e) Kang, J.; Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. (f) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (g) Kang, J.; Hilmersson, G.; Santamarfa, J.; Rebek, J., Jr. J. Am. Chem. Soc, 1998, 120, 3650. (h) Ziegler, M.; Brumaghim, J. L.; Raymond, K. N.; Angew. Chem., Int. Ed. Engl. 2000, 39, 4119.
6. Stabilization and activation of molecules enclathrated in the cavity: (a) Cram, D. J.; Tanner, M. E.; Thomas, R Angew. Chem., Int. Ed. Engl. 1991, 30, 1024. (b) Warmuth, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347. (c) Warmuth, R. J. Chem. Soc. Chem. Commun. 1998, 59. (d) Warmuth, R.; Marvel, M. A. Angew. Chem., Int. Ed. Engl. 2000, 39, 1117. (e) Kang, J.; Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. (f) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (g) Kang, J.; Hilmersson, G.; Santamarfa, J.; Rebek, J., Jr. J. Am. Chem. Soc, 1998, 120, 3650. (h) Ziegler, M.; Brumaghim, J. L.; Raymond, K. N.; Angew. Chem., Int. Ed. Engl. 2000, 39, 4119.
7. Stabilization and activation of molecules enclathrated in the cavity: (a) Cram, D. J.; Tanner, M. E.; Thomas, R Angew. Chem., Int. Ed. Engl. 1991, 30, 1024. (b) Warmuth, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347. (c) Warmuth, R. J. Chem. Soc. Chem. Commun. 1998, 59. (d) Warmuth, R.; Marvel, M. A. Angew. Chem., Int. Ed. Engl. 2000, 39, 1117. (e) Kang, J.; Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. (f) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (g) Kang, J.; Hilmersson, G.; Santamarfa, J.; Rebek, J., Jr. J. Am. Chem. Soc, 1998, 120, 3650. (h) Ziegler, M.; Brumaghim, J. L.; Raymond, K. N.; Angew. Chem., Int. Ed. Engl. 2000, 39, 4119.
8. Stabilization and activation of molecules enclathrated in the cavity: (a) Cram, D. J.; Tanner, M. E.; Thomas, R Angew. Chem., Int. Ed. Engl. 1991, 30, 1024. (b) Warmuth, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347. (c) Warmuth, R. J. Chem. Soc. Chem. Commun. 1998, 59. (d) Warmuth, R.; Marvel, M. A. Angew. Chem., Int. Ed. Engl. 2000, 39, 1117. (e) Kang, J.; Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. (f) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (g) Kang, J.; Hilmersson, G.; Santamarfa, J.; Rebek, J., Jr. J. Am. Chem. Soc, 1998, 120, 3650. (h) Ziegler, M.; Brumaghim, J. L.; Raymond, K. N.; Angew. Chem., Int. Ed. Engl. 2000, 39, 4119.
9. Stabilization and activation of molecules enclathrated in the cavity: (a) Cram, D. J.; Tanner, M. E.; Thomas, R Angew. Chem., Int. Ed. Engl. 1991, 30, 1024. (b) Warmuth, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1347. (c) Warmuth, R. J. Chem. Soc. Chem. Commun. 1998, 59. (d) Warmuth, R.; Marvel, M. A. Angew. Chem., Int. Ed. Engl. 2000, 39, 1117. (e) Kang, J.; Santamaría, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. (f) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (g) Kang, J.; Hilmersson, G.; Santamarfa, J.; Rebek, J., Jr. J. Am. Chem. Soc, 1998, 120, 3650. (h) Ziegler, M.; Brumaghim, J. L.; Raymond, K. N.; Angew. Chem., Int. Ed. Engl. 2000, 39, 4119.
10. (a) Timmerman, P.; Verboom, W.; van Veggel, F. C. J. M.; van Duynhoven, J. P. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1994, 33, 2345.
11. (b) van Wageningen, A. M. A.; Timmerman, P.; van Duynhoven, J. P. M.; Verboom, W.; van Veggel, F. C. M.; Reinhoudt, D. N. Chem. Eur. J. 1997, 3, 639.
12. (c) Fraser, J. R.; Borecka, B.; Trotter, J.; Sherman, J. C. J. Org. Chem. 1995, 60, 1207.
13. (d) Sherman, J. C.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2194.
14. (e) Chapman, R. G.; Sherman, J. C. J. Org. Chem. 2000. 65, 513.
15. (f) Naumann, C.; Place, S.; Sherman, J. C. J. Am. Chem. Soc. 2002, 124, 16.
16. (a) Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Nature 1998. 394, 764.
17. (b) Heinz, T., Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 1136.
18. (c) Ma, S.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. 1999, 38, 2600.
19. (d) Tucci, F. C.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 4928.
20. (a) Fujita, M.; Oguro, D.; Miyazawa, M.; Oka, H.; Yamaguchi, K.; Ogura, K. Nature 1995, 378, 469.
21. (b) Kusukawa, T.; Fujita, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3144.
22. (c) Kusukawa, T.; Fujita, M J. Am. Chem. Soc. 1999, 121, 1397.
23. Preliminary results were communicated in: Kusukawa. T.; Yoshizawa. M.; Fujita, M. Angew. Chem. Int. Ed. 2001, 40, 1879.
24. 2, part A is inequivalent with A′, Note that the carbonyl of A is pointed toward A′, whereas that of A′ is toward B. Hence two molecules are inequivalent.
25. Preliminary results for la were communicated in ref 5b.
26. (a) Ito, H.; Kusukawa, T.; Fujita, M. Chem. Lett. 2000, 598.
27. (b) Yoshizawa, M.; Kusukawa, T.; Fujita, M.; Yamaguchi, K. J. Am. Chem. Soc. 2000, 122, 6311.
28. (c) Yoshizawa, M.; Kusukawa, T.; Fujita, M.; Sakamoto, S.; Yamaguchi, K. J. Am. Chem. Soc. 2001, 123 10454.
29. (d) Yoshizawa, M.; Takeyama, Y.; Kusukawa, T.; Fujita, M. Angew. Chem., Int. Ed. 2002, 41, 1347.
30. Wimmer, S.; Castan, P.; Wimmer, F. L.; Johnson, N. P. J. Chem. Soc., Dalton Trans. 1989, 403.
31. Anderson, L. H.; Anderson, S.; Sanders, M. K. J. Chem. Soc., Perkin Trans. J. Chem. Soc., Perkin Trans. I. 1995, 2231.