Self-assembly and anion encapsulation properties of cavitand-based coordination cages

Journal of the American Chemical Society

Volumn 123, Issue 31, 2001, Pages 7539-7552

  Fochi, F ^a   Jacopozzi, P ^a   Wegelius, E ^b   Rissanen, K ^b   Cozzini, P ^a   Marastoni, E ^a   Fisicaro, E ^a   Manini, P ^a   Fokkens, R ^c   Dalcanale, E ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

^c UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; ENTHALPY; ENTROPY; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; SOLVENTS;

COORDINATION CAGES;

ENCAPSULATION;

ANION; COORDINATION COMPOUND; LIGAND; OLIGOMER; PALLADIUM; PLATINUM;

ARTICLE; CALORIMETRY; CHELATION; CRYSTAL STRUCTURE; ENCAPSULATION; ENTHALPY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034807023     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0103492     Document Type: Article

References (70)

1. Cram, D. J.; Cram, J. M. Container Molecules and their Guests, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, 1994; Vol. 4.
2. Sherman, J. C. Tetrahedron 1995, 51, 3395-3422.
3. Rebek, J., Jr. Chem. Soc. ReV. 1996, 255-264.
4. Warmuth, R. J. Inclusion Phenom. Mol. Recognit. Chem. 2000, 37, 1-38.
5. Kang, J.; Hilmersson, G.; Santamaría, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650-3656.
6. van Wageningen, A. M. A.; Timmerman, P.; van Duynhoven, J. P. M.; Verboom, W.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Chem. Eur. J. 1997, 3, 639-654.
7. Conn, M. M.; Rebek, J., Jr. Chem. ReV. 1997, 97, 1647-1668.
8. MacGillivray, L. R.; Atwood, J. L. Angew. Chem., Int. Ed. 1999, 38, 1018-1033.
9. Jasat, A.; Sherman, J. C. Chem. ReV. 1999, 99, 931-967.
10. For recent reviews on this topic, see: (a) Lehn, J.-M. Supramolecular Chemistry: Concepts and PerspectiVes; VCH: Weinheim, Germany, 1995; pp 144-160.
11. Baxter, P. N. W. In ComprehensiVe Supramolecular Chemistry; Lehn, J.-M., Chair Ed.; Atwood, J. L., Davis, J. E. D., MacNicol, D. D., Vogtle, F., Executive Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 9, Chapter 5, pp 165-211.
12. Fujita, M. In ComprehensiVe Supramolecular Chemistry; Lehn, J.-M., Chair Ed.; Atwood, J. L., Davis, J. E. D., MacNicol, D. D., Vogtle, F., Executive Eds.; Pergamon Press: Oxford, U.K., 1996; Vol. 9, Chapter 7, pp 253-282.
13. Fujita, M. Chem. Soc. ReV. 1999, 27, 417-425.
14. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975-982.
15. Saalfrank, R. W.; Demleitner, B. In Transition Metals in Supramolecular Chemistry; PerspectiVes in Supramolecular Chemistry; Sauvage, J. P., Ed.; Wiley-VCH: Weinheim, 1999, Vol. 5, pp 1-51.
16. Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. ReV. 2000, 100, 853-908.
17. For recent examples of molecular containers assembled using multidentate pyridine ligands, see: (a) Takeda, N.; Umemoto, K.; Yamaguchi, K.; Fujita, M. Nature 1999, 398, 794-796.
18. Olenyuk, B.; Whiteford, J. A.; Fechtenkötter, A.; Stang, P. J. Nature 1999, 398, 796-799.
19. Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 1397-1398.
20. Ikeda, A.; Yoshima, M.; Udzu, H.; Fukuhara, C.; Shinkai, S. J. Am. Chem. Soc. 1999, 121, 4296-4297.
21. Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239-10240.
22. Olenyuk, B.; Levin, M. D.; Whiteford, J. A.; Shield, J. E.; Stang, P. J. J. Am. Chem. Soc. 1999, 121, 10434-10435.
23. For molecular containers assembled using multidentate cathecolate ligands, see ref 5e.
24. For miscellaneous ligands, see: (a) Saalfrank, R. W.; Burak, R.; Breit, A.; Stalke, D.; Herbst-Irmer, R.; Daub, J.; Porsch, M.; Bill, E.; Müther, M.; Trautwein, A. X. Angew. Chem., Int. Ed. Engl. 1994, 33, 1621-1623.
25. Mann, S.; Huttner, G.; Zsolnai, L.; Heinze, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 2808-2809.
26. Saalfrank, R. W.; Bernt, I.; Uller, E.; Hampel, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 2482-2485.
27. Hartshorn, C. M.; Steel, P. J. Chem. Commun. 1997, 541-542.
28. Lee, S. B.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 4317-4320.
29. Abrahams, B. F.; Egan, S. J.; Robson, R. J. Am. Chem. Soc. 1999, 121, 3535-3536.
30. Jacopozzi, P.; Dalcanale, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 613-615.
31. Fox, D. O.; Dalley, N. K.; Harrison, R. G. J. Am. Chem. Soc. 1998, 120, 7111-7112.
32. Fox, O. D.; Drew, M. G. B.; Beer, P. D. Angew. Chem., Int. Ed. 2000, 39, 136-140.
33. Cuminetti, N.; Ebbing, M. H. K.; Prados, P.; de Mendoza, J.; Dalcanale, E. Tetrahedron Lett. 2001, 42, 527-530.
34. Cram, D. J.; Karbach, S.; Kim, H.-E.; Knobler, C. B.; Maverick, E. F.; Ericson, J. L.; Helgeson, R. C. J. Am. Chem. Soc. 1988, 110, 2229-2237.
35. Ligand abbreviations: dppm) bis(diphenylphosphino)methane; dppe) 1,2-bis(diphenylphosphino)ethane; dppp) 1,3-bis(diphenylphos-phino)propane; dppb) 1,4-bis(diphenylphosphino)butane.
36. Lawrence, G. A. Chem. ReV. 1986, 86, 17-33.
37. For studies of noncovalent aggregation by ES-MS, see: (a) Marquis-Rigault, A.; Dupont-Gervais, A.; Van Dorsselaer, A.; Lehn, J.-M. Chem. Eur. J. 1996, 2, 1395-1398.
38. Hirsch, K. A.; Wilson, S. R.; Moore, J. S. J. Am. Chem. Soc. 1997, 119, 10401-10412.
39. Schalley, C. A.; Martín, T.; Obst, U.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 2133-2138.
40. Van Hecke, G. R.; DeW. Horrocks, W., Jr. Inorg. Chem. 1966, 5, 1968-1974.
41. The complete set of X-ray crystal structures is available only for the M(dppx)Cl2 series (see Steffen, W. L.; Palenik, G. J. Inorg. Chem. 1976, 15, 2432-2438 and reference cited therein). The reported P-M-P angles have been obtained through the Cambridge Data Bank.
42. In ref 10 several crystal structures of cavitands are reported, from which is possible to estimate the average C4-aromatic ring R angle of 29° for methylene-bridged cavitands and 41° for ethylene-bridged cavitands. A close average C4-aromatic ring R angle of 31° [range 30.1(3)° < R < 31.4(3)°] has been derived for methylene-bridged cavitand 1b from the crystal structure of 7d.
43. Cage 8b at 298 K is in equilibrium with many oligomeric species; therefore it is not possible to separate the various contributions to the overall heat of reaction.
44. For the thermodynamics of self-assembly, see: (a) Chi, X.; Guerin, A. J.; Haycock, R. A.; Hunter, C. A.; Sarson, L. D. J. Chem. Soc., Chem. Commun. 1995, 2563-2565.
45. Ercolani, G. J. Phys. Chem. B 1998, 102, 5699-5703.
46. Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239-241.
47. Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77-85.
48. Parac, T. N.; Caulder, D. L.; Raymond, K. N. J. Am. Chem. Soc. 1998, 120, 8003-8004.
49. Parac, T. N.; Scherer, M.; Raymond, K. N. Angew. Chem., Int. Ed. 2000, 39, 1239-1242.
50. For an example of entropy-driven anion complexation, see: Berger, M.; Schmidtchen, F. P. Angew. Chem., Int. Ed. 1998, 37, 2694-2696.
51. For a detailed NMR study of the exchange process in hydrogen-bonded cali[4]arenes capsules, see: Mogck, O.; Pons, M.; Böhmer, V.; Vogt, W. J. Am. Chem. Soc. 1997, 119, 5706-5712.
52. Moore, W. J. In Physical Chemistry, 5th ed.; Longman Group Limited: London, 1976; p 430.
53. Marcus, Y. In Ion SolVation; Wiley & Sons: Chichester, 1985.
54. m, solv also for nonspherical ones.
55. Schalley, C. A.; Castellano, R. K.; Brody, M. S.; Rudkevich, D. M.; Siuzdak, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 4568-4579.
56. Nicholls, A.; Sharp, K.; Honig, B. Proteins 1991, 11, 281-296.
57. Mecozzi, S.; Rebek, J., Jr. Chem. Eur. J. 1998, 6, 1016-1022.
58. The 1.7 Å probe is the smallest one which does not fall out of the lateral portals of the cage.
59. The occupancy factor of a guest molecule in the cavity of a host is defined as the ratio of the van der Waals molecular volume of the guest to the volume of the cavity calculated on the van der Waals interior surface of the host (ref 19b).
60. The possibility of encapsulating two anions in one cage has been excluded due to electrostatic repulsion.
61. Levi, S.; Guatteri, P.; van Veggel, F. C. J. M.; Vancso, J.; Dalcanale, E.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2001, 40, 1892-1896.
62. Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J. C.; Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305-1312.
63. Román, E.; Peinador, C.; Mendoza, S.; Kaifer, A. E. J. Org. Chem. 1999, 64, 2577-2578.
64. Fallis, S.; Anderson, G. K.; Rath, N. P. Organometallics 1991, 10, 3180-3184.
65. Stang, P. J.; Cao, D. H.; Saito, S.; Arif, A. M. J. Am. Chem. Soc. 1995, 117, 6273-6283.
66. Otwinowski, Z.; Minor, W. Methods in Enzymology; Carter, C. W., Jr., Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276, Macromolecular Crystallography, part A, pp 307-326.
67. Sheldrick, G. M. SHELXS97 - A Program for Automatic Solution of Crystal Structures; University of Göttingen: Germany, 1997.
68. Sheldrick, G. M. SHELXL97 - A Program for Crystal Structure Refinement; University of Göttingen: Germany, 1997.
69. Karas, M.; Bachmann, D.; Bahr, U.; Hillenkamp, F. Int. J. Mass Spectrom. Ion Process. 1987, 78, 53-68.
70. Vestal, M. L.; Juhasz, P.; Martin, S. A. Rapid Commun. Mass Spectrom. 1995, 9, 1044-1050.