A self-assembled cylindrical capsule: New supramolecular phenomena through encapsulation

Chemistry - A European Journal

Volumn 6, Issue 1, 2000, Pages 187-195

  Körner, Steffi K ^a   Tucci, Fabio C ^a   Rudkevich, Dmitry M ^a   Heinz, Thomas ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Encapsulation; Hydrogen bonding; Molecular recognition; Self assembly; Supramolecular chemistry

Indexed keywords

BENZENE DERIVATIVE; BENZOYL PEROXIDE; DIPHENYLCARBAZIDE; MESITYLENE; MESYLIC ACID DERIVATIVE; N,N DIMETHYLFORMAMIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ENCAPSULATION; HYDROGEN BOND; MACROMOLECULE; MICROCAPSULE; MOLECULAR DYNAMICS; MOLECULAR RECOGNITION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE;

BENZENE DERIVATIVES; BENZOYL PEROXIDE; DIMETHYLFORMAMIDE; HYDROGEN BONDING; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 0033981072     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000103)6:1<187::AID-CHEM187>3.0.CO;2-I     Document Type: Article

References (37)

1. J.-M. Lehn, Angew. Chem. 1988, 100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89-112.
2. J.-M. Lehn, Angew. Chem. 1988, 100, 91; Angew. Chem. Int. Ed. Engl. 1988, 27, 89-112.
3. a) D. J. Cram, J. M. Cram, Container Molecules and their Guests, Royal Society of Chemistry, Cambridge, 1994, pp. 131-216;
4. b) A. Jasat, J. C. Sherman, Chem. Rev. 1999, 99, 931-967;
5. c) A. Collet, J.-P. Dutasta, B. Lozach, J. Canceill, Top. Curr. Chem. 1993, 165, 103-129.
6. a) M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668;
7. b) J. de Mendoza, Chem. Eur. J. 1998, 4, 1373-1377.
8. T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Nature 1998, 394, 764-766.
9. F. C. Tucci, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 4928-4929.
10. a) J. R. Moran, J. L. Ericson, E. Dalcanale, J. A. Bryant, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 5707-5714;
11. b) D. J. Cram, H.-J. Choi, J. A. Bryant, C. B. Knobler, J. Am. Chem. Soc. 1992, 114, 7748-7765.
12. L. M. Tunstad, J. A. Tucker, E. Dalcanale, J. Weiser, J. A. Bryant, J. C. Sherman, R. C. Helgeson, C. B. Knobler, D. J. Cram, J. Org. Chem. 1989, 54, 1305-1312.
13. a) D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 12216-12225;
14. b) F. C. Tucci, D. M. Rudkevich, J. Rebek, Jr., J. Org. Chem. 1999, 64, 4555-4559.
15. Other examples of larger self-assembled cavities: a) L. R. MacGillivray, J. L. Atwood, Nature 1997, 389, 469-472;
16. b) S. Ma, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 4977-4981; review on deeper cavities: D. M. Rudkevich, J. Rebek, Jr., Eur. J. Org. Chem. 1999, 1991-2005.
17. b) S. Ma, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 4977-4981; review on deeper cavities: D. M. Rudkevich, J. Rebek, Jr., Eur. J. Org. Chem. 1999, 1991-2005.
18. a) A. Nicholls, K. A. Sharp, B. Honig, Proteins 1991, 11, 281-296;
19. b) S. Mecozzi, J. Rebek, Jr., Chem. Eur. J. 1998, 4, 1016-1022.
20. K. T. Chapman, W. C. Still, J. Am. Chem. Soc. 1989, 111, 3075-3077.
21. F. Mohamadi, N. G. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
22. T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 1206-1209; Angew. Chem. Int. Ed. 1999, 38, 1136-1139.
23. T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 1206-1209; Angew. Chem. Int. Ed. 1999, 38, 1136-1139.
24. C. N. Eid, D. J. Cram, J. Chem. Ed. 1993, 70, 349-351. For a computational approach see: B. C. Hamman, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1328-1330; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1330.
25. C. N. Eid, D. J. Cram, J. Chem. Ed. 1993, 70, 349-351. For a computational approach see: B. C. Hamman, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1328-1330; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1330.
26. C. N. Eid, D. J. Cram, J. Chem. Ed. 1993, 70, 349-351. For a computational approach see: B. C. Hamman, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1328-1330; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1330.
27. a) O. Mogck, M. Pons, V. Böhmer, W. Vogt, J. Am. Chem. Soc. 1997, 119, 5706-5712;
28. b) T. Szabo, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 6193-6194.
29. Cyclobutadiene in covalently assembled carcerands: D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027. Benzyne: R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 109, 1406-1409; Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350; R. Warmuth, Chem. Commun. 1998, 59-60; for a Diels-Alder in a self-assembled capsule: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
30. Cyclobutadiene in covalently assembled carcerands: D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027. Benzyne: R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 109, 1406-1409; Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350; R. Warmuth, Chem. Commun. 1998, 59-60; for a Diels-Alder in a self-assembled capsule: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
31. Cyclobutadiene in covalently assembled carcerands: D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027. Benzyne: R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 109, 1406-1409; Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350; R. Warmuth, Chem. Commun. 1998, 59-60; for a Diels-Alder in a self-assembled capsule: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
32. Cyclobutadiene in covalently assembled carcerands: D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027. Benzyne: R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 109, 1406-1409; Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350; R. Warmuth, Chem. Commun. 1998, 59-60; for a Diels-Alder in a self-assembled capsule: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
33. Cyclobutadiene in covalently assembled carcerands: D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027. Benzyne: R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 109, 1406-1409; Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350; R. Warmuth, Chem. Commun. 1998, 59-60; for a Diels-Alder in a self-assembled capsule: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
34. Cyclobutadiene in covalently assembled carcerands: D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027. Benzyne: R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 109, 1406-1409; Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350; R. Warmuth, Chem. Commun. 1998, 59-60; for a Diels-Alder in a self-assembled capsule: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
35. Organic Peroxides, Vol. II, (Ed.: D. Swern), Wiley-Interscience, New York, 1971, pp. 620-621, 799-929.
36. Analogously, amides 5a, b were prepared and fully characterized; they are also commercially available.
37. See also: T. J. Broxton, N. W. Duddy, Aust. J. Chem. 1979, 32, 1717-1726.