Assembly of resorcinarene capsules in wet solvents

Journal of the American Chemical Society

Volumn 125, Issue 12, 2003, Pages 3432-3433

  Shivanyuk, Alexander ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CADMIUM CHLORIDE; CHLOROFORM; PHENOL DERIVATIVE; RESORCINARENE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CRYSTAL STRUCTURE; ENCAPSULATION; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; SOLVATION; STOICHIOMETRY;

EID: 0037467371     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027982n     Document Type: Article

References (35)

1. MacGillivray, L. R.; Atwood, J. L. Nature 1997, 389, 469-472.
2. For a related structure, see: Gerkensmeier, T.; Iwanek, W.; Agena, C.; Froelich, R.; Kotila, S.; Naether, C.; Mattay, J. Eur. J. Org. Chem. 1999, 2257-2262.
3. Atwood, J. L.; Barbour, L. J.; Jerga, A. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4837-4841.
4. Shivanyuk, A.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 7662-7665. Philip, I. E.; Kaifer, A. E. J. Am. Chem. Soc. 2002, 124, 12678-12679.
5. Shivanyuk, A.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 7662-7665. Philip, I. E.; Kaifer, A. E. J. Am. Chem. Soc. 2002, 124, 12678-12679.
6. Supramolecular assembly has also been determined through pulsed gradient spin-echo NMR techniques: (a) Frish, L.; Vysotsky, M. O.; Matthews, S. E.; Böehmer, V.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2002, 2, 88-93. (b) Frish, L.; Matthews, S. E.; Böhmer, V.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2 1999, 669-672. (c) Timmerman, P.; Weidmann, J. L.; Jolliffe, K. A.; Prins. L. J.; Reinhoudt, D. N.; Shinkai, S.; Frish, L.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2 2000, 2077-2089.
7. Supramolecular assembly has also been determined through pulsed gradient spin-echo NMR techniques: (a) Frish, L.; Vysotsky, M. O.; Matthews, S. E.; Böehmer, V.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2002, 2, 88-93. (b) Frish, L.; Matthews, S. E.; Böhmer, V.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2 1999, 669-672. (c) Timmerman, P.; Weidmann, J. L.; Jolliffe, K. A.; Prins. L. J.; Reinhoudt, D. N.; Shinkai, S.; Frish, L.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2 2000, 2077-2089.
8. Supramolecular assembly has also been determined through pulsed gradient spin-echo NMR techniques: (a) Frish, L.; Vysotsky, M. O.; Matthews, S. E.; Böehmer, V.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2002, 2, 88-93. (b) Frish, L.; Matthews, S. E.; Böhmer, V.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2 1999, 669-672. (c) Timmerman, P.; Weidmann, J. L.; Jolliffe, K. A.; Prins. L. J.; Reinhoudt, D. N.; Shinkai, S.; Frish, L.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2 2000, 2077-2089.
9. Neuhaus, D.; Williamson, W. The Nuclear Overhauser Effect In Structural and Conformational Analysis; VCH Publishers Inc.: New York, 1989.
10. For the use of dynamic NOE experiments to determine assembly sizes, see: Vreekamp R. H.; van Duynhoven, J. P. M.; Hubert, M.; Verboom, W.; Reinhoudt. D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1215-1218.
11. Shivanyuk, A.; Rebek, J., Jr. J. Chem. Commun. 2001, 2424-2425.
12. Hayashida, O.; Shivanyuk, A.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2002, 41, 3423-3426.
13. Aoyama, Y.; Tanaka, Y.; Toi, H.; Ogoshi, H. J. Am. Chem. Soc. 1988, 110, 634-635. Aoyama, Y.; Tanaka, Y.; Sugahara, S. J. J. Am. Chem. Soc. 1989, 111, 5397-5404.
14. Aoyama, Y.; Tanaka, Y.; Toi, H.; Ogoshi, H. J. Am. Chem. Soc. 1988, 110, 634-635. Aoyama, Y.; Tanaka, Y.; Sugahara, S. J. J. Am. Chem. Soc. 1989, 111, 5397-5404.
15. Wilson, C. F.; Eastman, M. P.; Hartzell, C. J. J. Phys. Chem. B 1997, 101, 9309-9313.
16. Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239-241.
17. Mecozzi, A. S.; Rebek, J., Jr. Chem.-Eur. J. 1998, 4, 1016-1022.
18. Moran, J. R.; Karbach, S.; Cram. D. J. J. Am. Chem. Soc. 1982, 104, 5826-5828.
19. Sherman, J. C.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2194-2204. Cram, D. J.; Cram, J. M. Container Molecules and their Guests; Royal Society of Chemistry: Cambridge, 1994.
20. Sherman, J. C.; Knobler, C. B.; Cram, D. J. J. Am. Chem. Soc. 1991, 113, 2194-2204. Cram, D. J.; Cram, J. M. Container Molecules and their Guests; Royal Society of Chemistry: Cambridge, 1994.
21. Sherman, J. C. Tetrahedron 1995, 51, 3395-3422. Shivanyuk, A.; Paulus, E. F.; Böhmer, V. Angew. Chem., Int. Ed. 1999, 38, 2906-2909.
22. Sherman, J. C. Tetrahedron 1995, 51, 3395-3422. Shivanyuk, A.; Paulus, E. F.; Böhmer, V. Angew. Chem., Int. Ed. 1999, 38, 2906-2909.
23. Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Nature 1998, 394, 764-766.
24. Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668. Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Nature 1998, 394, 764-766.
25. Kobayashi, K.; Asakawa, Y.; Kikuchi, Y.; Toi, H.; Aoyama, Y. J. Am. Chem. Soc. 1993, 115, 2648-2654.
26. Murayama, K.; Aoki, K. Chem. Commun. 1998, 607-608.
27. Shivanyuk, A.; Rissanen, K.; Kolehmainen, E. Chem. Commun. 2000, 1107-1108. See also: Rose, K. N.; Barbour, L. J.; Orr, G. W.; Atwood, J. L. Chem. Commun. 1998, 407-408.
28. Shivanyuk, A.; Rissanen, K.; Kolehmainen, E. Chem. Commun. 2000, 1107-1108. See also: Rose, K. N.; Barbour, L. J.; Orr, G. W.; Atwood, J. L. Chem. Commun. 1998, 407-408.
29. Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 6, 509-519. Fochi, F.; Jacopozzi, P.; Wegelius, E.; Rissanen, K.; Cozzini, P.; Marastoni, E.; Fisicaro, E.; Manini, P.; Fokkens, R.; Dalcanale, E. J. Am. Chem. Soc. 2001, 123, 7539-7552. Beissel, T.; Powers, R. E.; Parac, T. N.; Raymond, K. N. J. Am Chem. Soc. 1999, 121, 4200-4206.
30. Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 6, 509-519. Fochi, F.; Jacopozzi, P.; Wegelius, E.; Rissanen, K.; Cozzini, P.; Marastoni, E.; Fisicaro, E.; Manini, P.; Fokkens, R.; Dalcanale, E. J. Am. Chem. Soc. 2001, 123, 7539-7552. Beissel, T.; Powers, R. E.; Parac, T. N.; Raymond, K. N. J. Am Chem. Soc. 1999, 121, 4200-4206.
31. Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. Chem. Commun. 2001, 6, 509-519. Fochi, F.; Jacopozzi, P.; Wegelius, E.; Rissanen, K.; Cozzini, P.; Marastoni, E.; Fisicaro, E.; Manini, P.; Fokkens, R.; Dalcanale, E. J. Am. Chem. Soc. 2001, 123, 7539-7552. Beissel, T.; Powers, R. E.; Parac, T. N.; Raymond, K. N. J. Am Chem. Soc. 1999, 121, 4200-4206.
32. Böhmer, V.; Vysotsky M. O. Aust. J. Chem. 2001, 54, 671-677. Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Intl. Ed. 2002, 41, 1488-1508.
33. Böhmer, V.; Vysotsky M. O. Aust. J. Chem. 2001, 54, 671-677. Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J., Jr. Angew. Chem., Intl. Ed. 2002, 41, 1488-1508.
34. For parallel results from other laboratories, see: Avram, L.; Cohen, Y. J. Am. Chem. Soc. 2002, 124, 15148-15149. Avram, L.; Cohen, Y. Org. Lett. 2002, 4, 4365-4368.
35. For parallel results from other laboratories, see: Avram, L.; Cohen, Y. J. Am. Chem. Soc. 2002, 124, 15148-15149. Avram, L.; Cohen, Y. Org. Lett. 2002, 4, 4365-4368.