Reversible encapsulation and its consequences in solution

Accounts of Chemical Research

Volumn 32, Issue 4, 1999, Pages 278-286

  Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE; AROMATIC COMPOUND; BENZENE DERIVATIVE; CALIXARENE; CYCLOHEXANE; CYCLOHEXANE DERIVATIVE; DIMER; GLYCOL; METHANE; OLIGOMER; SOLVENT;

CHEMICAL STRUCTURE; CRYSTAL; ENCAPSULATION; HYDROGEN BOND; MACROMOLECULE; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; REVIEW;

EID: 0032956037     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar970201g     Document Type: Review

References (49)

1. Rebek, J., Jr. Assembly and Encapsulation with Self-Complementary Molecules. Chem. Soc. Rev. 1996, 255-264. For a broader coverage, see: Conn, M. M.; Rebek, J., Jr. Self-Assembling Capsules. Chem. Rev. 1997, 97, 1647-1668.
2. Rebek, J., Jr. Assembly and Encapsulation with Self-Complementary Molecules. Chem. Soc. Rev. 1996, 255-264. For a broader coverage, see: Conn, M. M.; Rebek, J., Jr. Self-Assembling Capsules. Chem. Rev. 1997, 97, 1647-1668.
3. Kemp, D. S.; Petrakis, K. S. Synthesis and Conformational Analysis of cis,cis-1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylic Acid. J. Org. Chem. 1981, 46, 5140-5143. Other uses: Rebek, J., Jr. Molecular Recognition with Model Systems. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Kemp's Triacid Scaffolding for Synthesis of Combinatorial Nonpeptide Uncoded Libraries. Tetrahedron Lett. 1995, 36, 6623-6626.
4. Kemp, D. S.; Petrakis, K. S. Synthesis and Conformational Analysis of cis,cis-1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylic Acid. J. Org. Chem. 1981, 46, 5140-5143. Other uses: Rebek, J., Jr. Molecular Recognition with Model Systems. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Kemp's Triacid Scaffolding for Synthesis of Combinatorial Nonpeptide Uncoded Libraries. Tetrahedron Lett. 1995, 36, 6623-6626.
5. Kemp, D. S.; Petrakis, K. S. Synthesis and Conformational Analysis of cis,cis-1,3,5-Trimethylcyclohexane-1,3,5-tricarboxylic Acid. J. Org. Chem. 1981, 46, 5140-5143. Other uses: Rebek, J., Jr. Molecular Recognition with Model Systems. Angew. Chem., Int. Ed. Engl. 1990, 29, 245-255. Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Kemp's Triacid Scaffolding for Synthesis of Combinatorial Nonpeptide Uncoded Libraries. Tetrahedron Lett. 1995, 36, 6623-6626.
6. 4]-metacyclophan-3,5,10,12,17,19,24,26-octols. J. Am. Chem. Soc. 1980, 102, 6046-50. Other uses: Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, U.K., 1994. Sherman, J. C. Carceplexes and Hemicarceplexes: Molecular Encapsulation-From Hours to Forever. Tetrahedron 1995, 51, 3395-3422.
7. 4]-metacyclophan-3,5,10,12,17,19,24,26-octols. J. Am. Chem. Soc. 1980, 102, 6046-50. Other uses: Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, U.K., 1994. Sherman, J. C. Carceplexes and Hemicarceplexes: Molecular Encapsulation-From Hours to Forever. Tetrahedron 1995, 51, 3395-3422.
8. 4]-metacyclophan-3,5,10,12,17,19,24,26-octols. J. Am. Chem. Soc. 1980, 102, 6046-50. Other uses: Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, U.K., 1994. Sherman, J. C. Carceplexes and Hemicarceplexes: Molecular Encapsulation-From Hours to Forever. Tetrahedron 1995, 51, 3395-3422.
9. Gutsche, C. D.; Muthukrishnan, R. Association Phenomena. 5. Synthesis and Properties of 1,4-Dipolar Substituted Cyclohexenes. J. Org. Chem. 1978, 43, 4069-4075. Other uses: Böhmer, V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilities. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745. Shinkai, S. Calixarenes-The Third Generation of Supramolecules. Tetrahedron 1993, 49, 8933-8968.
10. Gutsche, C. D.; Muthukrishnan, R. Association Phenomena. 5. Synthesis and Properties of 1,4-Dipolar Substituted Cyclohexenes. J. Org. Chem. 1978, 43, 4069-4075. Other uses: Böhmer, V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilities. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745. Shinkai, S. Calixarenes-The Third Generation of Supramolecules. Tetrahedron 1993, 49, 8933-8968.
11. Gutsche, C. D.; Muthukrishnan, R. Association Phenomena. 5. Synthesis and Properties of 1,4-Dipolar Substituted Cyclohexenes. J. Org. Chem. 1978, 43, 4069-4075. Other uses: Böhmer, V. Calixarenes, Macrocycles with (Almost) Unlimited Possibilities. Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745. Shinkai, S. Calixarenes-The Third Generation of Supramolecules. Tetrahedron 1993, 49, 8933-8968.
12. Wyler, R.; de Mendoza, J.; Rebek, J., Jr. A Synthetic Cavity Assembles Through Self-Complementary Hydrogen Bonds. Angew. Chem., Int. Ed. Engl. 1993, 32, 1699-1701.
13. Valdés, C.; Spitz, U. P.; Toledo, L.; Kubik, S.; Rebek, J., Jr. Synthesis and Self-Assembly of Pseudo-Spherical Homo- and Heterodimeric Capsules. J. Am. Chem. Soc. 1995, 117, 12733-12745.
14. Branda, N.; Wyler, R.; Rebek, J., Jr. Encapsulation of Methane and Other Small Molecules in a Self-Assembling Superstructure. Science 1994, 263, 1267-1268. For methane complexation inside a cryptophane: Garel, L.; Dutasta, J.-P.; Collet, A. Complexation of Methane and Chlorofluorohydrocarbons with Cryptophan A in Organic Solution. Angew. Chem., Int. Ed. Engl. 1993, 32, 1169.
15. Branda, N.; Wyler, R.; Rebek, J., Jr. Encapsulation of Methane and Other Small Molecules in a Self-Assembling Superstructure. Science 1994, 263, 1267-1268. For methane complexation inside a cryptophane: Garel, L.; Dutasta, J.-P.; Collet, A. Complexation of Methane and Chlorofluorohydrocarbons with Cryptophan A in Organic Solution. Angew. Chem., Int. Ed. Engl. 1993, 32, 1169.
16. Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Reversible Encapsulation of Disc-Shaped Guests by a Synthetic, Self-Assembled Host. Science 1996, 271, 487-489.
17. O'Leary, B. M.; Grotzfeld, R. M.; Rebek, J., Jr. Ring Inversion Dynamics of Encapsulated Cyclohexane. J. Am. Chem. Soc. 1997, 119, 11701-11702.
18. Paliwal, S.; Geib, S.; Wilcox, C. S. Molecular Torsion Balance for Weak Molecular Recognition Forces. Effects of "Tilted-T" Edge-to-Face Aromatic Interactions on Conformational Selection and Solid-State Structure. J. Am. Chem. Soc. 1994, 116, 4497-4498.
19. Timmerman, P.; Verboom, W.; Veggel, F. C. J. M.; Duynhoven, J. P. M.; Reinhoudt, D. N. A Novel Type of Stereoisomerism in Calix[4]arene-Based Carceplexes. Angew. Chem., Int. Ed. Engl. 1994, 34, 2345-2348.
20. Helgeson, R. C.; Paek, K.; Knobler, C. B.; Maverick, E. B.; Cram, D. J. Guest-Assisted and Guest-Inhibited Shell Closures Provide Differently Shaped Carceplexes and Hemicarceplexes. J. Am. Chem. Soc. 1996, 118, 5590-5604.
21. van Wageningen, A. M. A.; Timmerman, P.; Verboom, W.; van Veggel, F. C. J. M.; van Duynhoven, J. P. M.; Reinhoudt, D. N. Calix[4]arene-based (Hemi)carcerands and Carceplexes: Synthesis, Functionalization and Molecular Modeling Study. Chem.-Eur. J. 1997, 3, 639-654.
22. Chapman, R. G.; Sherman, J. C. Study of Templation and Molecular Encapsulation Using Highly Stable and Guest-Selective Self-Assembling Structures. J. Am. Chem. Soc. 1995, 117, 9081-9082.
23. Cram, D. J. Lecture at the C. David Gutsche Symposium, Washington University, St. Louis, MO, May 5, 1990.
24. Cram, D. J.; Karbach, S.; Kim, Y. H. Shell Closure of Two Cavitands Forms Carcerand Complexes with Components of the Medium as Permanent Guests. J. Am. Chem. Soc. 1985, 107, 2575-2576.
25. Collet, A.; Dutasta, J. P.; Lozach, B.; Canceill, J. In Chemistry I-Directed Synthesis and Molecular Recognition; Weber, E., Ed.; Topics in Current Chemistry, Vol. 165; Springer-Verlag: Berlin, 1993; pp 104-129.
26. Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Reversible Encapsulation of Guest Molecules in a Calixarene Dimer. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326-1329.
27. Mogck, O.; Paulus, E. F.; Böhmer, V.; Thondorf, I.; Vogt, W. J. Hydrogen-bonded Dimers of Tetraurea Calix[4]arenes: Unambiguous Proof by Single-Crystal X-ray Analysis. J. Chem. Soc., Chem. Commun. 1996, 2533-2534.
28. Castellano, R K.; Rudkevich, D. M.; Rebek, J., Jr. Polycaps: Reversibly Formed Polymeric Capsules. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 7132-7137.
29. We are grateful to Professor A. Hamilton and Abdullah Zafar for these measurements.
30. Castellano, R. K.; Rebek, J., Jr. Formation of Discrete, Functional Assemblies and Informational Polymers through Hydrogen Bonding Preferences of Calixarene Aryl and Sulfonyl Tetraureas. J. Am. Chem. Soc. 1998, 120, 3657-3663.
31. Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Self-Assembling Dendrimers. Science 1996, 271, 1095-1098.
32. Cram, D. J.; Choi, H.-J.; Bryant, J. A.; Knobler, C. B. Solvophobic and Entropic Driving Forces for Forming Velcraplexes, Which are Four-Fold, Lock-Key Dimers in Organic Media. J. Am. Chem. Soc. 1992, 114, 7748-7765. Moran, J. R.; Ericson, J. L.; Dalcanale, E.; Bryant, J. A.; Knobler, C. B.; Cram, D. J. Vases and Kites as Cavitands. J. Am. Chem. Soc. 1991, 113, 5707-5714.
33. Cram, D. J.; Choi, H.-J.; Bryant, J. A.; Knobler, C. B. Solvophobic and Entropic Driving Forces for Forming Velcraplexes, Which are Four-Fold, Lock-Key Dimers in Organic Media. J. Am. Chem. Soc. 1992, 114, 7748-7765. Moran, J. R.; Ericson, J. L.; Dalcanale, E.; Bryant, J. A.; Knobler, C. B.; Cram, D. J. Vases and Kites as Cavitands. J. Am. Chem. Soc. 1991, 113, 5707-5714.
34. Rudkevich, D. M.; Hilmersson, G.; Rebek, J., Jr. Intramolecular Hydrogen Bonding Controls the Exchange Rates of Guests in a Cavitand. J. Am. Chem. Soc. 1997, 41, 9911-9912.
35. Meissner, R.; de Mendoza, J.; Rebek, J., Jr. Autoencapsulation Through Intermolecular Forces: A Synthetic Self-Assembling Spherical Complex. Science 1995, 270, 1485-1488.
36. Meissner, R.; Gardas, X.; Mecozzi, S.; Rebek, J., Jr. Synthesis and Assembly of New Molecular Hosts: Solvation and the Energetics of Encapsulation. J. Am. Chem. Soc. 1997, 119, 77-85.
37. Mecozzi, S.; Rebek, J., Jr. The 55% Solution: A Formula for Molecular Recognition in the Liquid State. Chem.-Eur J. 1998, 4, 1016-1022.
38. Kang, J.; Rebek, J., Jr. Entropically-Driven Binding in a Self-Assembling Molecular Capsule. Nature 1996, 382, 239-241.
39. Rivera-Ortiz, J.; Martin, T.; Rebek, J., Jr. Chiral Spaces: Dissymmetric Capsules Through Self-Assembly. Science 1998, 279, 1021-1023.
40. Kang, J.; Rebek, J., Jr. Acceleration of a Diels-Alder Reaction by a Self-Assembled Molecular Capsule. Nature 1997, 385, 50-52.
41. Kang, J.; Hilmersson, G.; Santamaría, J.; Rebek, J., Jr. Diels-Alder Reactions through Reversible Encapsulation. J. Am. Chem. Soc. 1998, 120, 3650-3656.
42. Kang, J.; Santamaria, J.; Hilmersson, G.; Rebek, J., Jr. Self-Assembled Molecular Capsule Catalyzes a Diels-Alder Reaction. J. Am. Chem. Soc. 1998, 120, 7389-7390.
43. Easton, C. J.; Lincoln, S. F. Chiral Discrimination by Modified Cyclodextrins. Chem. Soc. Rev. 1996, 25, 163-170.
44. Castellano, R.; Kim, B. H.; Rebek, J., Jr. Chiral Capsules: Asymmetric Binding in Calixarene-Based Dimers. J. Am. Chem. Soc. 1997, 119, 12671-12672.
45. Tokunaga, Y.; Rebek, J., Jr. Chiral Capsules: Softballs with Asymmetric Surfaces Bind Camphor Derivatives. J. Am. Chem. Soc. 1998, 120, 66-69.
46. Szabo, T.; Hilmersson, G.; Rebek, J., Jr. Dynamics of Assembly and Guest Exchange in the Tennis Ball. J. Am. Chem. Soc. 1998, 120, 6193-6194.
47. Philp, D.; Stoddart, J. F. Sell-Assembly in Natural and Unnatural Systems. Angew. Chem., Int. Ed. Engl. 1996, 35, 1155-1196.
48. Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Molecular Self-Assembly and Nanochemistry: A Chemical Strategy for the Synthesis of Nanostructures. Science 1991, 254, 1312-1319.
49. Vreekamp, R. H.; van Duynhoven, J. P. M.; Hubert, M.; Verboom, W.; Reinhoudt, D. M. Molecular Boxes Based on Calix[4]arene Double Rosettes. Angew. Chem., Int. Ed. Engl. 1996, 35, 1215-1218.