Guest encapsulation and self-assembly of a cavitand-based coordination capsule

Chemistry - A European Journal

Volumn 12, Issue 12, 2006, Pages 3310-3319

  Haino, Takeharu ^a   Kobayashi, Mutsumi ^a   Fukazawa, Yoshimasa ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

Cavitands; Metal co ordination; Molecular recognition; Self assembly; Supramolecular chemistry

Indexed keywords

BORON COMPOUNDS; DIMERS; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL); THERMODYNAMICS;

CAVITAND-BASED COORDINATION CAPSULE; METAL CO-ORDINATION; MOLECULAR RECOGNITION;

SELF ASSEMBLY;

EID: 33646066280     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500976     Document Type: Article

References (105)

1. For reviews on large cavities, see: a) D. M. Rudkevich, J. Rebek, Jr., Eur. J. Org. Chem. 1999, 1991-2005;
2. b) D. M. Rudkevich, Chem. Eur. J. 2000, 6, 2679-2689;
3. c) D. J. Cram, Science 1983, 219, 1177-1183;
4. d) C. D. Gutsche, Calixarenes Revisited, The Royal Society of Chemistry, Cambridge, 1998;
5. e) D. M. Rudkevich in Functional Synthetic Receptors (Eds.: T. Schrader, A. D. Hamilton), Wiley, Weinheim, 2005, pp. 257-298.
6. For reviews on carceplexes and hemicarceplexes, see: a) E. Maverick, D. J. Cram, Compr. Supramol. Chem. 1996, 2, 367-418;
7. b) D. J. Cram, Nature 1992, 356, 29-36;
8. c) J. C. Sherman, Tetrahedron 1995, 51, 3395-3422;
9. d) R. G. Chapman, J. C. Sherman, Tetrahedron 1997, 53, 15911-15945;
10. e) A. Jasat, J. C. Sherman, Chem. Rev. 1999, 99, 931-967;
11. f) H.-J. Choi, D. J. Cram, C. B. Knobler, E. F. Marverick, Pure Appl. Chem. 1993, 65, 539-543.
12. For reviews on self-assembling capsules and cages, see: a) J. Rebek, Jr., Angew. Chem. 2005, 11, 2104-2115;
13. Angew. Chem. Int. Ed. 2005, 44, 2068-2078;
14. b) J. Rebek, Jr., Chem. Soc. Rev. 1996, 255-264;
15. c) M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668;
16. d) F. Hof, J. Rebek, Jr., Proc. Natl. Acad. Sci. USA 2002, 99, 4775-4777;
17. e) F. Hof, S. L. Craig, C. Nuckolls, J. Rebek, Jr., Angew. Chem. 2002, 114, 1556-1578;
18. Angew. Chem. Int. Ed. 2002, 41, 1488-1508;
19. f) L. J. Prins, D. N. Reinhoudt, P. Timmerman, Angew. Chem. 2001, 113, 2446-2492;
20. Angew. Chem. Int. Ed. 2001, 40, 2382-2426.
21. a) T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Nature 1999, 37, 3410-3413;
22. b) F. C. Tucci, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 4928-4929;
23. c) R. S. Meissner, J. Rebek, Jr., J. D. Mendoza, Science 1995, 270, 1485-1488;
24. d) K. D. Shimizu, J. Rebek, Jr., Proc. Natl. Acad. Sci. USA 1995, 92, 12403-12407;
25. e) B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425-1427;
26. Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1329;
27. f) R. K. Castellano, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 1996, 118, 10002-10003;
28. g) N. Branda, R. M. Grotzfeld, C. Valdés, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 85-88;
29. h) B. M. O'Leary, R. M. Grotzfeld, J. Rebek, Jr., J. Am. Chem. Soc. 1997, 119, 11 701-11702;
30. J. M. Rivera, T. Martín, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 819-820;
31. j) B. M. O'Leary, T. Szabo, N. Svenstrup, C. A. Schalley, A. Lützen, M. Schäfer, J. Rebek, Jr., J. Am. Chem. Soc. 2001, 123, 11 519-11 533;
32. k) D. W. Johnson, F. Hof, P. M. Iovine, C. Nuckolls, J. Rebek, Jr., Angew. Chem. 2002, 114, 3947-3950;
33. Angew. Chem. Int. Ed. 2002, 41, 3793-3796;
34. l) L. R. MacGillivray, J. L. Atwood, Nature 1997, 389, 469-472;
35. A. Shivanyuk, J. Rebek, Jr., Proc. Natl. Acad. Sci. USA 2001, 98, 7662-7665;
36. n) R. E. Brewster, S. B. Shuker, J. Am. Chem. Soc. 2002, 124, 7902-7903;
37. o) L. R. MacGillivray, P. R. Diamente, J. L. Reid, J. A. Ripmeester, Chem. Commun. 2000, 359-360;
38. p) C. M. Drain, R. Fischer, E. G. Nolen, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1993, 243-245;
39. q) K. Kobayashi, T. Shirasaka, K. Yamaguchi, S. Sakamoto, E. Horn, N. Furukawa, Chem. Commun. 2000, 41-42;
40. r) K. Kobayashi, K. Ishii, S. Sakamoto, T. Shirasaka, K. Yamaguchi, J. Am. Chem. Soc. 2003, 125, 10615-10624.
41. a) S. R. Seidel, P. J. Stang, Acc. Chem. Res. 2002, 35, 972-983;
42. b) Y. K. Kryschenko, S. R. Seidel, D. C. Muddiman, A. I. Nepomuceno, P. J. Stang, J. Am. Chem. Soc. 2003, 125, 9647-9652;
43. c) K.-W. Chi, C. Addicott, Y. K. Kryschenko, P. J. Stang, J. Org. Chem. 2004, 69, 964-966;
44. d) P. S. Mukherjee, N. Das, P. J. Stang, J. Org. Chem. 2004, 69, 3526-3529;
45. e) D. L. Caulder, C. Brückner, R. E. Powers, S. König, T. N. Parac, J. A. Leary, K. E. Raymond, J. Am. Chem. Soc. 2001, 123, 8923-8938;
46. f) M. Scherer, D. L. Caulder, D. W. Johnson, K. E. Raymond, Angew. Chem. 1999, 111, 1689-1694;
47. Angew. Chem. Int. Ed. 1999, 38, 1588-1592;
48. g) D. L. Caulder, R. E. Powers, T. N. Parac, K. E. Raymond, Angew. Chem. 1998, 110, 1940-1943;
49. Angew. Chem. Int. Ed. 1998, 37, 1840-1843;
50. h) T. N. Parac, D. L. Caulder, K. E. Raymond, J. Am. Chem. Soc. 1998, 120, 8003-8004;
51. D. W. Johnson, J. Xu, R. W. Saalfrank, K. E. Raymond, Angew. Chem. 1999, 111, 3058-3061;
52. Angew. Chem. Int. Ed. 1999, 38, 2882-2885;
53. j) D. L. Caulder, K. E. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200;
54. k) D. K. Chand, K. Biradha, M. Fujita, Chem. Commun. 2001, 1652-1653;
55. N. Takeda, K. Umemoto, K. Yamaguchi, M. Fujita, Nature 1999, 398, 794-796;
56. T. Kusukawa, M. Fujita, Angew. Chem. 1998, 110, 3327-3329;
57. Angew. Chem. Int. Ed. 1998, 37, 3142-3144;
58. n) T. Kusukawa, M. Fujita, J. Am. Chem. Soc. 1999, 121, 1397-1398;
59. o) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, Nature 1995, 378, 469-471;
60. p) P. Baxter, J.-M. Lehn, A. DeCian, J. Fisher, Angew. Chem. 1993, 105, 92-95;
61. Angew. Chem. Int. Ed. Engl. 1993, 32, 69;
62. q) E. Leiz, A. V. Dorsselaer, R. Krämer, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1993, 990;
63. r) H. Sleiman, P. N. W. Baxter, J.-M. Lehn, K. Rissanen, J. Chem. Soc. Chem. Commun. 1995, 715-716;
64. s) G. S. Hanan, C. R. Arana, J.-M. Lehn, D. Fenske, Angew. Chem. 1995, 107, 1191;
65. Angew. Chem. Int. Ed. Engl. 1995, 34, 1122-1124;
66. t) A. Ikeda, Y. Yoshimura, H. Udzu, C. Fukuhara, S. Shinkai, J. Am. Chem. Soc. 1999, 121, 4296-4297.
67. a) P. Jacopozzi, E. Dalcanale, Angew. Chem. 1997, 109, 665-667:
68. Angew. Chem. Int. Ed. Engl. 1997, 36, 613-615;
69. b) B. Bibal, B. Tinant, J.-P. Declercq, J.-P. Dutasta, Chem. Commun. 2002, 432-433;
70. c) S. J. Park, J.-I. Hong, Chem. Commun. 2001, 1554-1555;
71. d) K. Kobayashi, Y. Yamada, M. Yamanaka, Y. Sei, K. Yamaguchi, J. Am. Chem. Soc. 2004, 126, 13896-13897;
72. e) O. D. Fox, J. F.-Y. Leung, J. M. Hunter, N. K. Dalley, R. G. Harrison. Inorg. Chem. 2000, 39, 783-790;
73. f) O. D. Fox, E. J. S. Wilkinson, P. D. Beer, M. G. B. Drew, Chem. Commun. 2000, 391-392.
74. T. Haino, M. Kobayashi, M. Chikaraishi, Y. Fukazawa, Chem. Commun. 2005, 2321-2323.
75. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
76. A. Nicholls, K. A. Sharp, B. Honig, Proteins 1991, 11, 281.
77. F. M. Romero, R. Ziessel, Tetrahedron Lett. 1995, 36, 6471-6474.
78. M. H. Todd, S. Balasubramanian, C. Abell, Tetrahedron Lett. 1997, 38, 6781-6784.
79. P. Timmerman, H. Boerrigter, W. Verboom, G. J. Van Hummel, S. Harkema, D. N. Reinhoudt, J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 19, 167-191.
80. L. Sebo, F. Diederich, V. Gramlich, Helv. Chim. Acta 2000, 83, 93-113.
81. D. C. Teller, E. Swanson, C. DeHaen, Methods in Enzymology Vol. 61, Academic Press, New York, 1979, pp. 103-124.
82. Y. Cohen, L. Avram, L. Frish, Angew. Chem. 2005, 117, 524-560;
83. Angew. Chem. Int. Ed. 2005, 44, 520-554.
84. a) M. S. Kaucher, Y.-F. Lam, S. Pieraccini, G. Bottarelli, J. T. Davis, Chem. Eur. J. 2005, 11, 164-173;
85. b) L. Avram, Y. Cohen, Org. Lett. 2003, 5, 1099-1102.
86. E. O. Stejskal, J. E. Tanner, J. Chem. Phys. 1965, 42, 288-292.
87. a) A. S. Altieri, D. P. Hinton, R. A. Byrd, J. Am. Chem. Soc. 1995, 117, 7566-7567;
88. b) V. V. Krishnan, J. Magn. Reson. 1997, 124, 468-473.
89. a) L. C. Palmer, J. Rebek, Jr., Org. Biomol. Chem. 2004, 2, 3051-3059;
90. b) C. L. Perrin, T. J. Dwyer, Chem. Rev. 1990, 90, 935-967.
91. T. Haino, H. Araki, Y. Yamanaka, Y. Fukazawa, Tetrahedron Lett. 2001, 42, 3203-3206.
92. a) K. Kobayashi, Y. Asakawa, Y. Kikuchi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1993, 115, 2648-2654;
93. b) D. Falábu, A. Shivanyuk, M. Nissinen, K. Rissanen, Org. Lett. 2002, 4, 3019-3022.
94. A. Scarso, L. Trembleau, J. Rebek, Jr., J. Am. Chem. Soc. 2004, 126, 13512-13518.
95. a) J. Kang, J. Rebek, Jr., Nature 1996, 382, 239-241;
96. b) R. M. Grotz-feld, N. Branda, J. Rebek, Jr., Science 1996, 271, 487-489.
97. a) Y. Inoue, T. Hakushi, J. Chem. Soc. Perkin Trans. 2 1985, 935-946;
98. b) Y. Inoue, F. Amano, N. Okada, H. Inada, M. Ouchi, A. Tai, T. Hakushi, Y. Lu, L.-H. Tong, J. Chem. Soc. Perkin Trans. 2 1990, 1239-1246;
99. c) D. B. Smithrud, T. B. Wyman, F. Diederich, J. Am. Chem. Soc. 1991, 113, 5420-5426.
100. Benzoic acids and methylpyridone formed homodimers in the self-assembled cylindrical capsule. See: T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 1206-1209;
101. Angew. Chem. Int. Ed. 1999, 38, 1136-1139.
102. a) J. M. Rivera, T. Martín, J. Rebek, Jr., Science 1998, 279, 1021-1023;
103. b) J. M. Rivera, T. Martín, J. Rebek, Jr., J. Am. Chem. Soc. 2001, 123, 5213-5220;
104. c) R. K. Castellano, B. H. Kim, J. Rebek, Jr., J. Am. Chem. Soc. 1997, 119, 12671-12672;
105. d) R. K. Castellano, C. Nuckolls, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 11 156-11 163.