Bis-capsules: Cooperative reversible encapsulation of two molecules in adjacent separate chambers

Angewandte Chemie - International Edition

Volumn 39, Issue 1, 2000, Pages 194-196

  Chopra, Naveen ^a   Naumann, Christoph ^a   Sherman, John C ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

Calixarenes; Cavitands; Host guest chemistry; Molecular recognition; Noncovalent interactions

Indexed keywords

BISCARCEPLEX; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENCAPSULATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034598542     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. a) D. J. Cram, S. Karbach, Y. H. Kim, L. Baczynskyj, G. W. Kalleymeyn, J. Am. Chem. Soc. 1985, 107, 2575-2576; see also: D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020;
2. a) D. J. Cram, S. Karbach, Y. H. Kim, L. Baczynskyj, G. W. Kalleymeyn, J. Am. Chem. Soc. 1985, 107, 2575-2576; see also: D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020;
3. a) D. J. Cram, S. Karbach, Y. H. Kim, L. Baczynskyj, G. W. Kalleymeyn, J. Am. Chem. Soc. 1985, 107, 2575-2576; see also: D. J. Cram, Angew. Chem. 1988, 100, 1041-1052; Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020;
4. b) D. J. Cram, J. M. Cram, Container Compounds and Their Guests, Royal Society of Chemistry, Cambridge, 1994;
5. c) J. C. Sherman, Tetrahedron 1995, 51, 3395-3422;
6. d) A. Jasat, J. C. Sherman, Chem. Rev. 1999, 99, 931-967.
7. M. E. Tanner, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1990, 112, 1659-1660.
8. a) R. Wyler, J. de Mendoza, J. Rebek, Jr., Angew. Chem. 1993, 105, 1820; Angew. Chem. Int. Ed. Engl. 1993, 32, 1699-1701;
9. a) R. Wyler, J. de Mendoza, J. Rebek, Jr., Angew. Chem. 1993, 105, 1820; Angew. Chem. Int. Ed. Engl. 1993, 32, 1699-1701;
10. b) M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1688, and references therein;
11. c) for intriguing polymeric capsules linked tail-to-tail rather than side-to-side, see R. K. Castellano, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 3657-3663;
12. d) J. Yoon, D. J. Cram, Chem. Commun. 1997, 2065-2066.
13. N. Chopra, J. C. Sherman, Angew. Chem. 1997, 109, 1828-1830; Angew. Chem. Int. Ed. Engl. 1997, 36, 1727-1729.
14. N. Chopra, J. C. Sherman, Angew. Chem. 1997, 109, 1828-1830; Angew. Chem. Int. Ed. Engl. 1997, 36, 1727-1729.
15. J. C. Sherman, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 2194-2204.
16. a) R. G. Chapman, J. C. Sherman, J. Am. Chem. Soc. 1995, 117, 9081-9082;
17. b) R. G. Chapman, G. Olovsson, J. Trotter, J. C. Sherman, J. Am. Chem. Soc. 1998, 120, 6252-6260.
18. 3 in 3 · 2MeOAc).
19. For encapsulation of two or more guest molecules in a single large chamber, see a) F. C. Tucci, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 4928-4929;
20. b) R. Meissner, X. Garcias, S. Mecozzi, J. Rebek, Jr., J. Am. Chem. Soc. 1997, 119, 77-85;
21. c) T. Heinz, D. Rudkevich, J. Rebek, Jr., Nature 1998, 394, 764-766;
22. d) J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52;
23. e) J. Kang, J. Santamaria, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 7389-7390;
24. f) N. Chopra, J. C. Sherman, Angew. Chem. 1999. 111, 2109-2111; Angew. Chem. Int. Ed. 1999, 38, 1955-1957.
25. f) N. Chopra, J. C. Sherman, Angew. Chem. 1999. 111, 2109-2111; Angew. Chem. Int. Ed. 1999, 38, 1955-1957.
26. a) R. G. Chapman, N. Chopra, E. D. Cochien, J. C. Sherman, J. Am. Chem. Soc. 1994, 116, 369-370;
27. b) R. G. Chapman, J. C. Sherman, J. Org. Chem. 1998, 63, 4103-4110.
28. initial.
29. 3 · MeOAc] + 2[3 · 2MeOAc). See the Supporting Information for the derivation of this equation.
30. R. G. Chapman, J. C. Sherman, J. Am. Chem. Soc. 1998, 120, 9818-9826.
31. R. G. Chapman, J. C. Sherman, J. Am. Chem. Soc. 1999, 121, 1962-1963.