Three-dimensional supermolecules assembled from a tris(Zn2+-cyclen) complex and di- and trianionic cyanuric acid in aqueous solution (cyclen = 1,4,7,10-tetraazacyclododecane)

Journal of the American Chemical Society

Volumn 122, Issue 4, 2000, Pages 576-584

  Aoki, Shin ^a   Shiro, Motoo ^b   Koike, Tohru ^a   Kimura, Eiichi ^a  

^a HIROSHIMA UNIV SCHOOL OF MEDICINE   (Japan)

^b RIGAKU CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYANURIC ACID; DODECANE; ZINC DERIVATIVE;

ACID BASE BALANCE; AQUEOUS SOLUTION; ARTICLE; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CRYSTAL STRUCTURE; MOLECULAR STABILITY; SOLUBILITY;

EID: 0033980052     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993352i     Document Type: Article

References (87)

1. Ingber, D. E. Sci. Am. 1997, June, 30-39.
2. (a) Balzani, V.; De Cola, L. Supramolecular Chemistry; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992.
3. (b) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, Germany, 1995.
4. (a) Philip, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1155-1196.
5. (b) Linton, B.; Hamilton, A. D. Chem. Rev. 1997, 97, 1669-1680.
6. (c) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005-2062
7. (d) Sauvage, J.-P. Acc. Chem. Res. 1998, 31, 611-619.
8. (e) Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 1643-1663.
9. Feibush, B.; Figueroa, A.; Charles, R.; Onan, K. D.; Feibush, P.; Karger, B. L. J. Am. Chem. Soc. 1986, 108, 3310-3318.
10. (a) Chang, S. K.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 1318-1319.
11. (b) Chang, S. K.; Engen, D. V.; Fan, E.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 7640-7645.
12. Rudkevich, D. M.; Huck, W. T. S.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Transition Metals in Supramolecular Chemistry; Fabbrizzi, L., Poggi, A., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1994.
13. (a) Meissner, R. S.; Rebek, J., Jr.; de Mendoza, J. Science 1995, 270, 1485-1488.
14. (b) Shimizu, K. D.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12403-12407.
15. (c) Kang, J.; Rebek, J., Jr. Nature 1997, 382, 239-241.
16. (d) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50-52.
17. (e) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668.
18. (f) Heinz, T.; Rudkevich, D. M.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1999, 38, 1136-11139.
19. (g) Rebek, J., Jr. Acc. Chem. Res. 1999, 278-286.
20. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37-44.
21. For reviews, see: (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319. (b) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37-44.
22. (a) Huck, W. T. S.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1215-1218.
23. (b) Klok, H. A.; Jolliffe, K. A.; Scharuer, C. L.; Prins, L. J.; Spatz, J. P.; Möller, M.; Timmerman, P.; Reinhoudt, D. N. J. Am. Chem. Soc. 1999, 121, 7154-7155.
24. (a) Russell, V. A.; Ward, M. D. Chem. Mater. 1996, 8, 1654-1666.
25. (b) Kim, H. S.; Hartgerink, J. S.; Ghadiri, M. R. J. Am. Chem. Soc. 1998, 120, 4417-4424 and references therein.
26. (a) Baxter, P. N. W.; Lehn, J.-M.; Fishcher, J.; Youinou, M.-T. Angew. Chem., Int. Ed. Engl. 1994, 33, 2284-2287.
27. (b) Hasenknopf, B.; Lehn, J.-M.; Kneisel, B. O.; Baum, G.; Fenske, D. Angew. Chem., Int. Ed. Engl. 1996, 35, 1838-1840.
28. (c) Hasenknopf, B.; Lehn, J.-M.; Boumedien, N.; Dupont-Gervais, A.; Van Dorsselaer, A.; Kneisel, B. O.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956-10962.
29. (a) MacGillivray, L. R.; L. Atwood, J. Nature 1997, 389, 469-472.
30. (b) Orr, W. G.; Barbour, L. J.; Atwood, J. L. Science 1999, 285, 1049-1052.
31. (a) Maverick, A. W.; Buchkinghum, S. C.; Yao, Q.; Bradbury, J. R.; Stanley, G. G. J. Am. Chem. Soc. 1986, 108, 7430-7431.
32. (b) Maverick, A. W.; Ivie, M. L.; Waggenspack, J. H.; Fronczek, F. R. Inorg. Chem. 1990, 29, 2403-2409.
33. (a) Fujita, M.; Oguro, D.; Miyazawa, M.; Oka, H.; Yamaguchi, K.; Ogura, K. Nature 1995, 378, 469-471.
34. (b) Fujita, M. J. Synth. Org. Chem., Jpn. 1996, 54, 953-963.
35. (c) Fujita, M.; Ibukuro, F.; Seki, H.; Kamo, O.; Imanari, M.; Ogura, K. J. Am. Chem. Soc. 1996, 118, 899-900.
36. (d) Fujita, M. Chem. Soc. Rev. 1998, 27, 417-425.
37. (e) Takeda, N.; Umemoto, K.; Yamaguchi, K.; Fujita, M. Nature 1999, 398, 794-796.
38. (a) Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502-518.
39. (b) Olenyuk, B.; Whiteford, J. A.; Fechtenkötter, A.; Stang, P. J. Nature 1999, 398, 796-799.
40. (c) Olenyuk, P. J.; Fechtenkötter, A.; Stang, P. J. J. Chem. Soc., Dalton Trans. 1998, 1707-1728 and references therein.
41. (a) Schwabacher, A. W.; Lee, J.; Lei, H. J. Am. Chem. Soc. 1992, 114, 7597-7598.
42. (b) Lee, J.; Schwabacher, A. W. J. Am. Chem. Soc. 1994, 116, 8382-8383.
43. Barbour, L. J.; Orr, G. W.; Atwood, J. L. Nature 1998, 393, 671-673.
44. (a) Brückner, C.; Powers, R. E.; Raymond, Angew. Chem., Int. Ed. Engl. 1998, 37, 1837-1839.
45. (b) Caulder, D. L.; Powers, R. E.; Parac, T. N.; Raymond, K. N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1840-1843.
46. (c) Caulder, D. L.; Raymond, K. N. J. Chem. Soc., Dalton Trans. 1999, 1185-1200.
47. For other examples in aqueous system, see: (a) Scrimin, P.; Tecilla, P.; Tonellato, U.; Vignaga, N. J. Chem. Soc., Chem. Commun. 1991, 449-451. (b) Saalfrank, R. W.; Hörner, B.; Stalke, D.; Salbeck, J.; Angew. Chem., Int. Ed. Engl. 1993, 32, 1179-1182. (c) Liu, F.-Q.; Harder, G.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 3271-3272. (d) Whang, D.; Park, K.-M.; Heo, J.; Ashton, P.; Kim, K. J. Am. Chem. Soc. 1998, 120, 4899-4900.
48. For other examples in aqueous system, see: (a) Scrimin, P.; Tecilla, P.; Tonellato, U.; Vignaga, N. J. Chem. Soc., Chem. Commun. 1991, 449- 451. (b) Saalfrank, R. W.; Hörner, B.; Stalke, D.; Salbeck, J.; Angew. Chem., Int. Ed. Engl. 1993, 32, 1179-1182. (c) Liu, F.-Q.; Harder, G.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 3271-3272. (d) Whang, D.; Park, K.-M.; Heo, J.; Ashton, P.; Kim, K. J. Am. Chem. Soc. 1998, 120, 4899-4900.
49. For other examples in aqueous system, see: (a) Scrimin, P.; Tecilla, P.; Tonellato, U.; Vignaga, N. J. Chem. Soc., Chem. Commun. 1991, 449- 451. (b) Saalfrank, R. W.; Hörner, B.; Stalke, D.; Salbeck, J.; Angew. Chem., Int. Ed. Engl. 1993, 32, 1179-1182. (c) Liu, F.-Q.; Harder, G.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 3271-3272. (d) Whang, D.; Park, K.-M.; Heo, J.; Ashton, P.; Kim, K. J. Am. Chem. Soc. 1998, 120, 4899-4900.
50. For other examples in aqueous system, see: (a) Scrimin, P.; Tecilla, P.; Tonellato, U.; Vignaga, N. J. Chem. Soc., Chem. Commun. 1991, 449- 451. (b) Saalfrank, R. W.; Hörner, B.; Stalke, D.; Salbeck, J.; Angew. Chem., Int. Ed. Engl. 1993, 32, 1179-1182. (c) Liu, F.-Q.; Harder, G.; Tilley, T. D. J. Am. Chem. Soc. 1998, 120, 3271-3272. (d) Whang, D.; Park, K.-M.; Heo, J.; Ashton, P.; Kim, K. J. Am. Chem. Soc. 1998, 120, 4899-4900.
51. For reviews, see: (a) Kimura, E. Tetrahedron 1992, 48, 6175-6217. (b) Kimura, E. In Progress in Inorganic Chemistry; Karlin, K. D., Ed.; John Wiley & Sons: New York, 1994; Vol. 41, pp 443-491. (c) Kimura, E.; Shionoya, M. In Metal Ions In Biological Systems; Sigel, A., Sigel, H., Eds., Marcel Dekker: New York, 1996; Vol. 33, pp 29-52. (d) Kimura, E.; Koike, T.; Shionoya, M. Structure and Bonding: Metal Site in Proteins and Models; Sadler, P. J., Ed.; Springer: Berlin, 1997; Vol. 89, pp 1-28. (e) Kimura, E.; Koike, T.; Aoki, S. J. Synth. Org. Chem., Jpn. 1997, 55, 130-139. (f) Kimura, E.; Koike, T. J. Chem. Soc., Chem. Commun. 1999, 1495-1500.
52. For reviews, see: (a) Kimura, E. Tetrahedron 1992, 48, 6175- 6217. (b) Kimura, E. In Progress in Inorganic Chemistry; Karlin, K. D., Ed.; John Wiley & Sons: New York, 1994; Vol. 41, pp 443-491. (c) Kimura, E.; Shionoya, M. In Metal Ions In Biological Systems; Sigel, A., Sigel, H., Eds., Marcel Dekker: New York, 1996; Vol. 33, pp 29-52. (d) Kimura, E.; Koike, T.; Shionoya, M. Structure and Bonding: Metal Site in Proteins and Models; Sadler, P. J., Ed.; Springer: Berlin, 1997; Vol. 89, pp 1-28. (e) Kimura, E.; Koike, T.; Aoki, S. J. Synth. Org. Chem., Jpn. 1997, 55, 130-139. (f) Kimura, E.; Koike, T. J. Chem. Soc., Chem. Commun. 1999, 1495-1500.
53. For reviews, see: (a) Kimura, E. Tetrahedron 1992, 48, 6175- 6217. (b) Kimura, E. In Progress in Inorganic Chemistry; Karlin, K. D., Ed.; John Wiley & Sons: New York, 1994; Vol. 41, pp 443-491. (c) Kimura, E.; Shionoya, M. In Metal Ions In Biological Systems; Sigel, A., Sigel, H., Eds., Marcel Dekker: New York, 1996; Vol. 33, pp 29-52. (d) Kimura, E.; Koike, T.; Shionoya, M. Structure and Bonding: Metal Site in Proteins and Models; Sadler, P. J., Ed.; Springer: Berlin, 1997; Vol. 89, pp 1-28. (e) Kimura, E.; Koike, T.; Aoki, S. J. Synth. Org. Chem., Jpn. 1997, 55, 130-139. (f) Kimura, E.; Koike, T. J. Chem. Soc., Chem. Commun. 1999, 1495-1500.
54. For reviews, see: (a) Kimura, E. Tetrahedron 1992, 48, 6175- 6217. (b) Kimura, E. In Progress in Inorganic Chemistry; Karlin, K. D., Ed.; John Wiley & Sons: New York, 1994; Vol. 41, pp 443-491. (c) Kimura, E.; Shionoya, M. In Metal Ions In Biological Systems; Sigel, A., Sigel, H., Eds., Marcel Dekker: New York, 1996; Vol. 33, pp 29-52. (d) Kimura, E.; Koike, T.; Shionoya, M. Structure and Bonding: Metal Site in Proteins and Models; Sadler, P. J., Ed.; Springer: Berlin, 1997; Vol. 89, pp 1-28. (e) Kimura, E.; Koike, T.; Aoki, S. J. Synth. Org. Chem., Jpn. 1997, 55, 130-139. (f) Kimura, E.; Koike, T. J. Chem. Soc., Chem. Commun. 1999, 1495-1500.
55. For reviews, see: (a) Kimura, E. Tetrahedron 1992, 48, 6175- 6217. (b) Kimura, E. In Progress in Inorganic Chemistry; Karlin, K. D., Ed.; John Wiley & Sons: New York, 1994; Vol. 41, pp 443-491. (c) Kimura, E.; Shionoya, M. In Metal Ions In Biological Systems; Sigel, A., Sigel, H., Eds., Marcel Dekker: New York, 1996; Vol. 33, pp 29-52. (d) Kimura, E.; Koike, T.; Shionoya, M. Structure and Bonding: Metal Site in Proteins and Models; Sadler, P. J., Ed.; Springer: Berlin, 1997; Vol. 89, pp 1-28. (e) Kimura, E.; Koike, T.; Aoki, S. J. Synth. Org. Chem., Jpn. 1997, 55, 130-139. (f) Kimura, E.; Koike, T. J. Chem. Soc., Chem. Commun. 1999, 1495-1500.
56. For reviews, see: (a) Kimura, E. Tetrahedron 1992, 48, 6175- 6217. (b) Kimura, E. In Progress in Inorganic Chemistry; Karlin, K. D., Ed.; John Wiley & Sons: New York, 1994; Vol. 41, pp 443-491. (c) Kimura, E.; Shionoya, M. In Metal Ions In Biological Systems; Sigel, A., Sigel, H., Eds., Marcel Dekker: New York, 1996; Vol. 33, pp 29-52. (d) Kimura, E.; Koike, T.; Shionoya, M. Structure and Bonding: Metal Site in Proteins and Models; Sadler, P. J., Ed.; Springer: Berlin, 1997; Vol. 89, pp 1-28. (e) Kimura, E.; Koike, T.; Aoki, S. J. Synth. Org. Chem., Jpn. 1997, 55, 130-139. (f) Kimura, E.; Koike, T. J. Chem. Soc., Chem. Commun. 1999, 1495-1500.
57. (a) Shionoya, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1993, 115, 6730-6737.
58. (b) Shionoya, M.; Kimura, E.; Hayashida, H.; Petho, G.; Marzilli, L. G. Supramol. Chem. 1993, 2, 173-176.
59. (c) Shionoya, M.; Sugiyama, M.; Kimura, E. J. Chem. Soc., Chem. Commun. 1994, 1747-1748.
60. (d) Shionoya, M.; Ikeda, T.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 3848-3859.
61. (e) Koike, T.; Goto, T.; Aoki, S.; Kimura, E.; Shiro, M. Inorg. Chim. Acta 1998, 270, 424-432.
62. (f) Aoki, S.; Honda, Y.; Kimura, E. J. Am. Chem. Soc. 1998, 120, 10018-10026.
63. (g) Aoki, S.; Sugimura, C.; Kimura, E. J. Am. Chem. Soc. 1998, 120, 10094-10102.
64. (h) Kimura, E.; Kikuchi, M.; Kitamura, H.; Koike, T. Chem. Eur. J. 1999, 5, 3113-3123.
65. (a) Kimura, E.; Ikeda, T.; Shionoya, M. Pure Appl. Chem. 1997, 69, 2187-2195.
66. (b) Kimura, E.; Ikeda, T.; Aoki, S.; Shionoya, M. J. Biol. Inorg. Chem. 1998, 3, 259-267.
67. (c) Kikuta, E.; Murata, M.; Katsube, N.; Koike, T.; Kimura, E. J. Am. Chem. Soc. 1999, 121, 5126-5436.
68. (d) Kikuta, E.; Katsube, N.; Kimura, E. J. Biol. Inorg. Chem. 1999, 4, 431-440.
69. (a) Koike, T.; M. Takashige, E. Kimura, H. Fujioka, M. Shiro, Chem. Eur. J. 1996, 2, 617-623.
70. (b) Fujioka, H.; Koike, T.; Yamada, N.; Kimura, E. Heterocycles 1996, 42, 775-787.
71. Kimura, E.; Aoki, S. Koike, T.; Shiro, M. J. Am. Chem. Soc. 1997, 119, 3068-3076.
72. Kimura, E.; Ikeda, T.; Shionoya, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 663-664.
73. 3 = 14.6).
74. - (2.14 Å): Falvello, L. R.; Pascual, I.; Tomás, M. Inorg. Chim. Acta 1995, 229, 135-142.
75. -1)) on addition of 1.5 equiv of CA with an isosbestic point at 274 nm, possibly by a hypochromic effect due to π-π stacking between the two benzene rings.
76. For the Crystal Information Files (CIFs) for the X-ray crystal structure analysis of 10 and 15, see Supporting Information.
77. (a) Martell, A. E.; Motekaitis, R. J. Determination and Use of Stability Constants, 2nd ed.; VCH: New York, 1992.
78. (b) Martell, A. E.; Hancock, R. D. Metal Complexes in Aqueous Solutions.; Plenum Press: New York, 1996.
79. 23
80. 2O exhibited complicated peaks with small upfield shifts, implying that the dimeric zinc(II) complex may also assemble with CA, but without distinct structures.
81. 1H NMR spectra of 10 showed negligible pD dependency at pD 6.0-11.0 and negligible temperature dependency in the range of 25-85°C.
82. The distance between amine atoms on MA and oxygen atoms on CA in 5 is 2.94 Å, and the distance between amine atoms on 1,3,5-triazine ring of MA and imide nitrogens of CA is 2.86 Å: Wang, B., Y.; Wei, B.; Wang, Q. J. Crystallogr. Spectrosc. Res. 1990, 20, 79-84.
83. We could not observe mass peaks or fragmentations corresponding to 10 and 15 in electron ionization (EI), fast atom bombardment (FAB), electron spray ionization (ESI), and time-of-flight (TOF) mass spectrometric experiments.
84. 3- were found in the inner cavity of 15. (37) The theoretical ratio of [9], [9 in 10], and [9 in 17 (see following discussion in the text)] should be 0.25:0.5:0.25, if 15 is equally degraded into 9, 10, and 17, which almost fit to the observed NMR results.
85. 6 showed three peaks corresponding to 9, 10, and 17.
86. a value of the third imide proton of CA in supercomplexes.
87. app of 2.2 under the same condition.