Molecular recognition and assembly

Acta Chemica Scandinavica

Volumn 50, Issue 8, 1996, Pages 707-716

  Rebek Jr , Julius ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; HYDROGEN BOND; MACROMOLECULE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HYDROGEN BONDING; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SOLVENTS;

EID: 0030211067     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.50-0707     Document Type: Review

References (39)

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3. For selected examples of three-dimensional supramolecular aggregates, see: (a) Seto, C. and Whitesides, G. M. J. Am. Chem. Soc. 13 (1991) 712 (b) Simard, M., Su, D. and Wuest, J. D. J. Am. Chem. Soc. 113 (1991) 4696 (c) Baxter, P., Lehn, J.-M., DeCian, A. and Fischer, J. Angew. Chem., Int. Ed. Engl. 32 (1993) 69 (d) Bonar-Law, R. P. and Sanders, J. K. M. Tetrahedron Lett. 34 (1993) 1677 (e) Ghadiri, M. R., Granja, J. R., Milligan, R. A., McRee, D. E. and Khazanovich, N. Nature (London) 366 (1993) 324 (f) Yang, J., Fan, E., Geib, S. and Hamilton, A. D. J. Am. Chem. Soc. 115 (1993) 5314; (g) Ghadiri, M. R., Kobayshi, K., Granja, J. R., Chadha, R. K. and McRhee, D. E. Angew. Chem., Int. Ed. Engl. 34 (1995) 93 (h) Mathias, J. P., Seto, C. T., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 1725 (i) Mathias, J. P., Simanek, E. E., Zerkowski, J. A., Seto, C. T. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4316 (j) Mathias, J. P., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4326.
4. For selected examples of three-dimensional supramolecular aggregates, see: (a) Seto, C. and Whitesides, G. M. J. Am. Chem. Soc. 13 (1991) 712 (b) Simard, M., Su, D. and Wuest, J. D. J. Am. Chem. Soc. 113 (1991) 4696 (c) Baxter, P., Lehn, J.-M., DeCian, A. and Fischer, J. Angew. Chem., Int. Ed. Engl. 32 (1993) 69 (d) Bonar-Law, R. P. and Sanders, J. K. M. Tetrahedron Lett. 34 (1993) 1677 (e) Ghadiri, M. R., Granja, J. R., Milligan, R. A., McRee, D. E. and Khazanovich, N. Nature (London) 366 (1993) 324 (f) Yang, J., Fan, E., Geib, S. and Hamilton, A. D. J. Am. Chem. Soc. 115 (1993) 5314; (g) Ghadiri, M. R., Kobayshi, K., Granja, J. R., Chadha, R. K. and McRhee, D. E. Angew. Chem., Int. Ed. Engl. 34 (1995) 93 (h) Mathias, J. P., Seto, C. T., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 1725 (i) Mathias, J. P., Simanek, E. E., Zerkowski, J. A., Seto, C. T. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4316 (j) Mathias, J. P., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4326.
5. For selected examples of three-dimensional supramolecular aggregates, see: (a) Seto, C. and Whitesides, G. M. J. Am. Chem. Soc. 13 (1991) 712 (b) Simard, M., Su, D. and Wuest, J. D. J. Am. Chem. Soc. 113 (1991) 4696 (c) Baxter, P., Lehn, J.-M., DeCian, A. and Fischer, J. Angew. Chem., Int. Ed. Engl. 32 (1993) 69 (d) Bonar-Law, R. P. and Sanders, J. K. M. Tetrahedron Lett. 34 (1993) 1677 (e) Ghadiri, M. R., Granja, J. R., Milligan, R. A., McRee, D. E. and Khazanovich, N. Nature (London) 366 (1993) 324 (f) Yang, J., Fan, E., Geib, S. and Hamilton, A. D. J. Am. Chem. Soc. 115 (1993) 5314; (g) Ghadiri, M. R., Kobayshi, K., Granja, J. R., Chadha, R. K. and McRhee, D. E. Angew. Chem., Int. Ed. Engl. 34 (1995) 93 (h) Mathias, J. P., Seto, C. T., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 1725 (i) Mathias, J. P., Simanek, E. E., Zerkowski, J. A., Seto, C. T. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4316 (j) Mathias, J. P., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4326.
6. For selected examples of three-dimensional supramolecular aggregates, see: (a) Seto, C. and Whitesides, G. M. J. Am. Chem. Soc. 13 (1991) 712 (b) Simard, M., Su, D. and Wuest, J. D. J. Am. Chem. Soc. 113 (1991) 4696 (c) Baxter, P., Lehn, J.-M., DeCian, A. and Fischer, J. Angew. Chem., Int. Ed. Engl. 32 (1993) 69 (d) Bonar-Law, R. P. and Sanders, J. K. M. Tetrahedron Lett. 34 (1993) 1677 (e) Ghadiri, M. R., Granja, J. R., Milligan, R. A., McRee, D. E. and Khazanovich, N. Nature (London) 366 (1993) 324 (f) Yang, J., Fan, E., Geib, S. and Hamilton, A. D. J. Am. Chem. Soc. 115 (1993) 5314; (g) Ghadiri, M. R., Kobayshi, K., Granja, J. R., Chadha, R. K. and McRhee, D. E. Angew. Chem., Int. Ed. Engl. 34 (1995) 93 (h) Mathias, J. P., Seto, C. T., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 1725 (i) Mathias, J. P., Simanek, E. E., Zerkowski, J. A., Seto, C. T. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4316 (j) Mathias, J. P., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4326.
7. For selected examples of three-dimensional supramolecular aggregates, see: (a) Seto, C. and Whitesides, G. M. J. Am. Chem. Soc. 13 (1991) 712 (b) Simard, M., Su, D. and Wuest, J. D. J. Am. Chem. Soc. 113 (1991) 4696 (c) Baxter, P., Lehn, J.-M., DeCian, A. and Fischer, J. Angew. Chem., Int. Ed. Engl. 32 (1993) 69 (d) Bonar-Law, R. P. and Sanders, J. K. M. Tetrahedron Lett. 34 (1993) 1677 (e) Ghadiri, M. R., Granja, J. R., Milligan, R. A., McRee, D. E. and Khazanovich, N. Nature (London) 366 (1993) 324 (f) Yang, J., Fan, E., Geib, S. and Hamilton, A. D. J. Am. Chem. Soc. 115 (1993) 5314; (g) Ghadiri, M. R., Kobayshi, K., Granja, J. R., Chadha, R. K. and McRhee, D. E. Angew. Chem., Int. Ed. Engl. 34 (1995) 93 (h) Mathias, J. P., Seto, C. T., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 1725 (i) Mathias, J. P., Simanek, E. E., Zerkowski, J. A., Seto, C. T. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4316 (j) Mathias, J. P., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4326.
8. For selected examples of three-dimensional supramolecular aggregates, see: (a) Seto, C. and Whitesides, G. M. J. Am. Chem. Soc. 13 (1991) 712 (b) Simard, M., Su, D. and Wuest, J. D. J. Am. Chem. Soc. 113 (1991) 4696 (c) Baxter, P., Lehn, J.-M., DeCian, A. and Fischer, J. Angew. Chem., Int. Ed. Engl. 32 (1993) 69 (d) Bonar-Law, R. P. and Sanders, J. K. M. Tetrahedron Lett. 34 (1993) 1677 (e) Ghadiri, M. R., Granja, J. R., Milligan, R. A., McRee, D. E. and Khazanovich, N. Nature (London) 366 (1993) 324 (f) Yang, J., Fan, E., Geib, S. and Hamilton, A. D. J. Am. Chem. Soc. 115 (1993) 5314; (g) Ghadiri, M. R., Kobayshi, K., Granja, J. R., Chadha, R. K. and McRhee, D. E. Angew. Chem., Int. Ed. Engl. 34 (1995) 93 (h) Mathias, J. P., Seto, C. T., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 1725 (i) Mathias, J. P., Simanek, E. E., Zerkowski, J. A., Seto, C. T. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4316 (j) Mathias, J. P., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4326.
9. For selected examples of three-dimensional supramolecular aggregates, see: (a) Seto, C. and Whitesides, G. M. J. Am. Chem. Soc. 13 (1991) 712 (b) Simard, M., Su, D. and Wuest, J. D. J. Am. Chem. Soc. 113 (1991) 4696 (c) Baxter, P., Lehn, J.-M., DeCian, A. and Fischer, J. Angew. Chem., Int. Ed. Engl. 32 (1993) 69 (d) Bonar-Law, R. P. and Sanders, J. K. M. Tetrahedron Lett. 34 (1993) 1677 (e) Ghadiri, M. R., Granja, J. R., Milligan, R. A., McRee, D. E. and Khazanovich, N. Nature (London) 366 (1993) 324 (f) Yang, J., Fan, E., Geib, S. and Hamilton, A. D. J. Am. Chem. Soc. 115 (1993) 5314; (g) Ghadiri, M. R., Kobayshi, K., Granja, J. R., Chadha, R. K. and McRhee, D. E. Angew. Chem., Int. Ed. Engl. 34 (1995) 93 (h) Mathias, J. P., Seto, C. T., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 1725 (i) Mathias, J. P., Simanek, E. E., Zerkowski, J. A., Seto, C. T. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4316 (j) Mathias, J. P., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4326.
10. For selected examples of three-dimensional supramolecular aggregates, see: (a) Seto, C. and Whitesides, G. M. J. Am. Chem. Soc. 13 (1991) 712 (b) Simard, M., Su, D. and Wuest, J. D. J. Am. Chem. Soc. 113 (1991) 4696 (c) Baxter, P., Lehn, J.-M., DeCian, A. and Fischer, J. Angew. Chem., Int. Ed. Engl. 32 (1993) 69 (d) Bonar-Law, R. P. and Sanders, J. K. M. Tetrahedron Lett. 34 (1993) 1677 (e) Ghadiri, M. R., Granja, J. R., Milligan, R. A., McRee, D. E. and Khazanovich, N. Nature (London) 366 (1993) 324 (f) Yang, J., Fan, E., Geib, S. and Hamilton, A. D. J. Am. Chem. Soc. 115 (1993) 5314; (g) Ghadiri, M. R., Kobayshi, K., Granja, J. R., Chadha, R. K. and McRhee, D. E. Angew. Chem., Int. Ed. Engl. 34 (1995) 93 (h) Mathias, J. P., Seto, C. T., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 1725 (i) Mathias, J. P., Simanek, E. E., Zerkowski, J. A., Seto, C. T. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4316 (j) Mathias, J. P., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4326.
11. For selected examples of three-dimensional supramolecular aggregates, see: (a) Seto, C. and Whitesides, G. M. J. Am. Chem. Soc. 13 (1991) 712 (b) Simard, M., Su, D. and Wuest, J. D. J. Am. Chem. Soc. 113 (1991) 4696 (c) Baxter, P., Lehn, J.-M., DeCian, A. and Fischer, J. Angew. Chem., Int. Ed. Engl. 32 (1993) 69 (d) Bonar-Law, R. P. and Sanders, J. K. M. Tetrahedron Lett. 34 (1993) 1677 (e) Ghadiri, M. R., Granja, J. R., Milligan, R. A., McRee, D. E. and Khazanovich, N. Nature (London) 366 (1993) 324 (f) Yang, J., Fan, E., Geib, S. and Hamilton, A. D. J. Am. Chem. Soc. 115 (1993) 5314; (g) Ghadiri, M. R., Kobayshi, K., Granja, J. R., Chadha, R. K. and McRhee, D. E. Angew. Chem., Int. Ed. Engl. 34 (1995) 93 (h) Mathias, J. P., Seto, C. T., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 1725 (i) Mathias, J. P., Simanek, E. E., Zerkowski, J. A., Seto, C. T. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4316 (j) Mathias, J. P., Simanek, E. E. and Whitesides, G. M. J. Am. Chem. Soc. 116 (1994) 4326.
12. Wyler, R., de Mendoza, J. and Rebek, J. Jr. Angew. Chem., Int. Ed. Engl. 32 (1993) 1699.
13. Branda, N., Wyler, R. and Rebek, J. Jr. Science 263 (1994) 1267.
14. Branda, N., Grotzfeld, R. M., Valdés, C. and Rebek, J., Jr. J. Am. Chem. Soc. 117 (1995) 85.
15. Meissner, R., de Mendoza, J. and Rebek, J. Jr. Science 270 (1995) 1485.
16. Garcias, X., Toledo, L. and Rebek, J. Jr. Tetrahedron Lett. (1995) 8535.
17. Valdés, C., Spitz, U. P., Kubik, S. and Rebek, J. Jr. Angew. Chem., Int. Ed. Engl. 35 (1995) 1885.
18. Valdés, C., Spitz, U. P., Toledo, L., Kubik, S. and Rebek, J. Jr. J. Am. Chem. Soc. 117 (1995) 12733.
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23. Chapman, R.G. and Sherman, J. C. J. Am. Chem. Soc. 117 (1995) 9081.
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25. For recent reviews see: (a) Böhmer, V. Angew. Chem., Int. Ed. Engl. 34 (1995) 713 (b) Linnane, P. and Shinkai, S. Chem. Ind. (1994) 811 (c) Gutsche, C. D. Aldrichim. Acta 28 (1995) 3 (d) Shinkai, S. Tetrahedron 49 (1993) 8933.
26. For recent reviews see: (a) Böhmer, V. Angew. Chem., Int. Ed. Engl. 34 (1995) 713 (b) Linnane, P. and Shinkai, S. Chem. Ind. (1994) 811 (c) Gutsche, C. D. Aldrichim. Acta 28 (1995) 3 (d) Shinkai, S. Tetrahedron 49 (1993) 8933.
27. For recent reviews see: (a) Böhmer, V. Angew. Chem., Int. Ed. Engl. 34 (1995) 713 (b) Linnane, P. and Shinkai, S. Chem. Ind. (1994) 811 (c) Gutsche, C. D. Aldrichim. Acta 28 (1995) 3 (d) Shinkai, S. Tetrahedron 49 (1993) 8933.
28. For recent reviews see: (a) Böhmer, V. Angew. Chem., Int. Ed. Engl. 34 (1995) 713 (b) Linnane, P. and Shinkai, S. Chem. Ind. (1994) 811 (c) Gutsche, C. D. Aldrichim. Acta 28 (1995) 3 (d) Shinkai, S. Tetrahedron 49 (1993) 8933.
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35. For examples of covalently linked hemispheres see: Robbins, T. A., Knobler, C. B., Bellow, D. R. and Cram, D. J. J. Am. Chem. Soc. 116 (1994) 111; Ikeda, A. and Shinkai, S. J. Chem. Soc., Perkin Trans. 1 (1993) 2671; Garel, L., Dutasta, J. P. and Collet, A. Angew. Chem., Int. Ed. Engl. 32 (1993) 1169; Canceill, J., Lacombe, L. and Collet, A. J. Am. Chem. Soc. 108 (1986) 4230 and references therein. For a review of molecules with large interior cavities see: Seel, C. and Vögtle, F. Angew. Chem., Int. Ed. Engl. 31 (1992) 528.
36. For examples of covalently linked hemispheres see: Robbins, T. A., Knobler, C. B., Bellow, D. R. and Cram, D. J. J. Am. Chem. Soc. 116 (1994) 111; Ikeda, A. and Shinkai, S. J. Chem. Soc., Perkin Trans. 1 (1993) 2671; Garel, L., Dutasta, J. P. and Collet, A. Angew. Chem., Int. Ed. Engl. 32 (1993) 1169; Canceill, J., Lacombe, L. and Collet, A. J. Am. Chem. Soc. 108 (1986) 4230 and references therein. For a review of molecules with large interior cavities see: Seel, C. and Vögtle, F. Angew. Chem., Int. Ed. Engl. 31 (1992) 528.
37. For examples of covalently linked hemispheres see: Robbins, T. A., Knobler, C. B., Bellow, D. R. and Cram, D. J. J. Am. Chem. Soc. 116 (1994) 111; Ikeda, A. and Shinkai, S. J. Chem. Soc., Perkin Trans. 1 (1993) 2671; Garel, L., Dutasta, J. P. and Collet, A. Angew. Chem., Int. Ed. Engl. 32 (1993) 1169; Canceill, J., Lacombe, L. and Collet, A. J. Am. Chem. Soc. 108 (1986) 4230 and references therein. For a review of molecules with large interior cavities see: Seel, C. and Vögtle, F. Angew. Chem., Int. Ed. Engl. 31 (1992) 528.
38. For examples of covalently linked hemispheres see: Robbins, T. A., Knobler, C. B., Bellow, D. R. and Cram, D. J. J. Am. Chem. Soc. 116 (1994) 111; Ikeda, A. and Shinkai, S. J. Chem. Soc., Perkin Trans. 1 (1993) 2671; Garel, L., Dutasta, J. P. and Collet, A. Angew. Chem., Int. Ed. Engl. 32 (1993) 1169; Canceill, J., Lacombe, L. and Collet, A. J. Am. Chem. Soc. 108 (1986) 4230 and references therein. For a review of molecules with large interior cavities see: Seel, C. and Vögtle, F. Angew. Chem., Int. Ed. Engl. 31 (1992) 528.
39. For examples of covalently linked hemispheres see: Robbins, T. A., Knobler, C. B., Bellow, D. R. and Cram, D. J. J. Am. Chem. Soc. 116 (1994) 111; Ikeda, A. and Shinkai, S. J. Chem. Soc., Perkin Trans. 1 (1993) 2671; Garel, L., Dutasta, J. P. and Collet, A. Angew. Chem., Int. Ed. Engl. 32 (1993) 1169; Canceill, J., Lacombe, L. and Collet, A. J. Am. Chem. Soc. 108 (1986) 4230 and references therein. For a review of molecules with large interior cavities see: Seel, C. and Vögtle, F. Angew. Chem., Int. Ed. Engl. 31 (1992) 528.