Calix[6]arenes and zinc: Biomimetic receptors for neutral molecules

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6183-6189

  Sénèque, Olivier ^a   Rager, Marie Noëlle ^a   Giorgi, Michel ^b   Reinaud, Olivia ^a  

^a CNRS   (France)

^b Inst Mediterraneen d'Ecologie P   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; RECEPTOR; ZINC;

ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; ENZYME SUBSTRATE COMPLEX; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING; X RAY DIFFRACTION;

EID: 0038633748     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000185+     Document Type: Article

References (56)

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17. 2+ center appears extremely difficult to control.
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24. Both enantiomers were included in the unit cell. In solution, these were in conformational exchange. However, the exchange process was slow on the NMR time scale. A detailed spectroscopic study showed that the coordinating guest molecule experienced a chiral environment. This will be published elsewhere.
25. The relative conformation of the phenolic units is different from what was previously observed in the calixarene-based copper(I) complex, 9 the reasons of which are under investigation.
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27. 2], d(Zn-N) = 2.046(3) Å [Bel'sky, V. K.; Streltsova, N. R.; Bulychev, B. M.; Storozhenko, P. A.; Ivankina, L. V.; Gorbunov, A. I. Inorg. Chem. Acta 1989, 164, 211-220]; for a 5-coordinated dicationic Zn complex, d(Zn-N) = 2.059(4) Å [Matthews, C. J.; Clegg, W.; Heath, S. L.; Martin, N. C.; Stuart Hill, M. N.; Lockhart, J. C. Inorg. Chem. 1998, 37, 199-207]; for 5-coordinated neutral complexes: d(Zn-N) = 2.114(4) Å [Castro, J. A.; Romero, J.; Garcia-Vasquez, J. A.; Macias, A.; Souza, A.; Englert, U. Polyhedron 1993, 12, 1391-1397] and d(Zn-N) = 2.087(4) Å [Becker, B.; Radacki, K.; Wojnowski, W. J. Organomet. Chem. 1996, 521, 39-49].
28. 2], d(Zn-N) = 2.046(3) Å [Bel'sky, V. K.; Streltsova, N. R.; Bulychev, B. M.; Storozhenko, P. A.; Ivankina, L. V.; Gorbunov, A. I. Inorg. Chem. Acta 1989, 164, 211-220]; for a 5-coordinated dicationic Zn complex, d(Zn-N) = 2.059(4) Å [Matthews, C. J.; Clegg, W.; Heath, S. L.; Martin, N. C.; Stuart Hill, M. N.; Lockhart, J. C. Inorg. Chem. 1998, 37, 199-207]; for 5-coordinated neutral complexes: d(Zn-N) = 2.114(4) Å [Castro, J. A.; Romero, J.; Garcia-Vasquez, J. A.; Macias, A.; Souza, A.; Englert, U. Polyhedron 1993, 12, 1391-1397] and d(Zn-N) = 2.087(4) Å [Becker, B.; Radacki, K.; Wojnowski, W. J. Organomet. Chem. 1996, 521, 39-49].
29. 2], d(Zn-N) = 2.046(3) Å [Bel'sky, V. K.; Streltsova, N. R.; Bulychev, B. M.; Storozhenko, P. A.; Ivankina, L. V.; Gorbunov, A. I. Inorg. Chem. Acta 1989, 164, 211-220]; for a 5-coordinated dicationic Zn complex, d(Zn-N) = 2.059(4) Å [Matthews, C. J.; Clegg, W.; Heath, S. L.; Martin, N. C.; Stuart Hill, M. N.; Lockhart, J. C. Inorg. Chem. 1998, 37, 199-207]; for 5-coordinated neutral complexes: d(Zn-N) = 2.114(4) Å [Castro, J. A.; Romero, J.; Garcia-Vasquez, J. A.; Macias, A.; Souza, A.; Englert, U. Polyhedron 1993, 12, 1391-1397] and d(Zn-N) = 2.087(4) Å [Becker, B.; Radacki, K.; Wojnowski, W. J. Organomet. Chem. 1996, 521, 39-49].
30. 2], d(Zn-N) = 2.046(3) Å [Bel'sky, V. K.; Streltsova, N. R.; Bulychev, B. M.; Storozhenko, P. A.; Ivankina, L. V.; Gorbunov, A. I. Inorg. Chem. Acta 1989, 164, 211-220]; for a 5-coordinated dicationic Zn complex, d(Zn-N) = 2.059(4) Å [Matthews, C. J.; Clegg, W.; Heath, S. L.; Martin, N. C.; Stuart Hill, M. N.; Lockhart, J. C. Inorg. Chem. 1998, 37, 199-207]; for 5-coordinated neutral complexes: d(Zn-N) = 2.114(4) Å [Castro, J. A.; Romero, J.; Garcia-Vasquez, J. A.; Macias, A.; Souza, A.; Englert, U. Polyhedron 1993, 12, 1391-1397] and d(Zn-N) = 2.087(4) Å [Becker, B.; Radacki, K.; Wojnowski, W. J. Organomet. Chem. 1996, 521, 39-49].
31. Representative examples of Zn-based supramolecular receptors for neutral molecules: (a) Bonar-Law, R. P.; Sanders, J K. M. J. Chem. Soc., Chem. Commun. 1991, 574-577. (b) Imai, H.; Uemori, Y. J. Chem. Soc., Perkin Trans. 2 1994, 1793-1797. (c) Imai, H.; Kyuno, E. Inorg. Chem. 1990, 29, 2416-2422. (d) Haskard, C. A.; Easton, C. J.; May, B. L.; Lincoln, S. F. Inorg. Chem. 1996, 35, 1059-1064. (e) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron. Lett. 1996, 37, 5369-5372. (f) Froidevaux, J.; Ochsenbein, P.; Bonin, M.; Schenk, K.; Maltese, P.; Gisselbrecht, J.-P.; Weiss, J. J. Am. Chem. Soc. 1997, 119, 12362-12363. (g) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (h) For a rare example of carbohydrate recognition, see: Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
32. Representative examples of Zn-based supramolecular receptors for neutral molecules: (a) Bonar-Law, R. P.; Sanders, J K. M. J. Chem. Soc., Chem. Commun. 1991, 574-577. (b) Imai, H.; Uemori, Y. J. Chem. Soc., Perkin Trans. 2 1994, 1793-1797. (c) Imai, H.; Kyuno, E. Inorg. Chem. 1990, 29, 2416-2422. (d) Haskard, C. A.; Easton, C. J.; May, B. L.; Lincoln, S. F. Inorg. Chem. 1996, 35, 1059-1064. (e) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron. Lett. 1996, 37, 5369-5372. (f) Froidevaux, J.; Ochsenbein, P.; Bonin, M.; Schenk, K.; Maltese, P.; Gisselbrecht, J.-P.; Weiss, J. J. Am. Chem. Soc. 1997, 119, 12362-12363. (g) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (h) For a rare example of carbohydrate recognition, see: Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
33. Representative examples of Zn-based supramolecular receptors for neutral molecules: (a) Bonar-Law, R. P.; Sanders, J K. M. J. Chem. Soc., Chem. Commun. 1991, 574-577. (b) Imai, H.; Uemori, Y. J. Chem. Soc., Perkin Trans. 2 1994, 1793-1797. (c) Imai, H.; Kyuno, E. Inorg. Chem. 1990, 29, 2416-2422. (d) Haskard, C. A.; Easton, C. J.; May, B. L.; Lincoln, S. F. Inorg. Chem. 1996, 35, 1059-1064. (e) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron. Lett. 1996, 37, 5369-5372. (f) Froidevaux, J.; Ochsenbein, P.; Bonin, M.; Schenk, K.; Maltese, P.; Gisselbrecht, J.-P.; Weiss, J. J. Am. Chem. Soc. 1997, 119, 12362-12363. (g) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (h) For a rare example of carbohydrate recognition, see: Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
34. Representative examples of Zn-based supramolecular receptors for neutral molecules: (a) Bonar-Law, R. P.; Sanders, J K. M. J. Chem. Soc., Chem. Commun. 1991, 574-577. (b) Imai, H.; Uemori, Y. J. Chem. Soc., Perkin Trans. 2 1994, 1793-1797. (c) Imai, H.; Kyuno, E. Inorg. Chem. 1990, 29, 2416-2422. (d) Haskard, C. A.; Easton, C. J.; May, B. L.; Lincoln, S. F. Inorg. Chem. 1996, 35, 1059-1064. (e) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron. Lett. 1996, 37, 5369-5372. (f) Froidevaux, J.; Ochsenbein, P.; Bonin, M.; Schenk, K.; Maltese, P.; Gisselbrecht, J.-P.; Weiss, J. J. Am. Chem. Soc. 1997, 119, 12362-12363. (g) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (h) For a rare example of carbohydrate recognition, see: Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
35. Representative examples of Zn-based supramolecular receptors for neutral molecules: (a) Bonar-Law, R. P.; Sanders, J K. M. J. Chem. Soc., Chem. Commun. 1991, 574-577. (b) Imai, H.; Uemori, Y. J. Chem. Soc., Perkin Trans. 2 1994, 1793-1797. (c) Imai, H.; Kyuno, E. Inorg. Chem. 1990, 29, 2416-2422. (d) Haskard, C. A.; Easton, C. J.; May, B. L.; Lincoln, S. F. Inorg. Chem. 1996, 35, 1059-1064. (e) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron. Lett. 1996, 37, 5369-5372. (f) Froidevaux, J.; Ochsenbein, P.; Bonin, M.; Schenk, K.; Maltese, P.; Gisselbrecht, J.-P.; Weiss, J. J. Am. Chem. Soc. 1997, 119, 12362-12363. (g) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (h) For a rare example of carbohydrate recognition, see: Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
36. Representative examples of Zn-based supramolecular receptors for neutral molecules: (a) Bonar-Law, R. P.; Sanders, J K. M. J. Chem. Soc., Chem. Commun. 1991, 574-577. (b) Imai, H.; Uemori, Y. J. Chem. Soc., Perkin Trans. 2 1994, 1793-1797. (c) Imai, H.; Kyuno, E. Inorg. Chem. 1990, 29, 2416-2422. (d) Haskard, C. A.; Easton, C. J.; May, B. L.; Lincoln, S. F. Inorg. Chem. 1996, 35, 1059-1064. (e) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron. Lett. 1996, 37, 5369-5372. (f) Froidevaux, J.; Ochsenbein, P.; Bonin, M.; Schenk, K.; Maltese, P.; Gisselbrecht, J.-P.; Weiss, J. J. Am. Chem. Soc. 1997, 119, 12362-12363. (g) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (h) For a rare example of carbohydrate recognition, see: Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
37. Representative examples of Zn-based supramolecular receptors for neutral molecules: (a) Bonar-Law, R. P.; Sanders, J K. M. J. Chem. Soc., Chem. Commun. 1991, 574-577. (b) Imai, H.; Uemori, Y. J. Chem. Soc., Perkin Trans. 2 1994, 1793-1797. (c) Imai, H.; Kyuno, E. Inorg. Chem. 1990, 29, 2416-2422. (d) Haskard, C. A.; Easton, C. J.; May, B. L.; Lincoln, S. F. Inorg. Chem. 1996, 35, 1059-1064. (e) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron. Lett. 1996, 37, 5369-5372. (f) Froidevaux, J.; Ochsenbein, P.; Bonin, M.; Schenk, K.; Maltese, P.; Gisselbrecht, J.-P.; Weiss, J. J. Am. Chem. Soc. 1997, 119, 12362-12363. (g) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (h) For a rare example of carbohydrate recognition, see: Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
38. Representative examples of Zn-based supramolecular receptors for neutral molecules: (a) Bonar-Law, R. P.; Sanders, J K. M. J. Chem. Soc., Chem. Commun. 1991, 574-577. (b) Imai, H.; Uemori, Y. J. Chem. Soc., Perkin Trans. 2 1994, 1793-1797. (c) Imai, H.; Kyuno, E. Inorg. Chem. 1990, 29, 2416-2422. (d) Haskard, C. A.; Easton, C. J.; May, B. L.; Lincoln, S. F. Inorg. Chem. 1996, 35, 1059-1064. (e) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron. Lett. 1996, 37, 5369-5372. (f) Froidevaux, J.; Ochsenbein, P.; Bonin, M.; Schenk, K.; Maltese, P.; Gisselbrecht, J.-P.; Weiss, J. J. Am. Chem. Soc. 1997, 119, 12362-12363. (g) Huang, X.; Rickman, B. H.; Borhan, B.; Berova, N.; Nakanishi, K. J. Am. Chem. Soc. 1998, 120, 6185-6186. (h) For a rare example of carbohydrate recognition, see: Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi, N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991-9001.
39. Bergquist, C.; Parkin, G. J. Am. Chem. Soc. 1999, 121, 6322-6323.
40. Christianson, D. W.; Fierke, C. A. Acc. Chem. Res. 1996, 29, 331-339, and references therein.
41. Recently, a tetrahedral alcohol complex has been described, using the anionic tris(2-mercapto-1-arylimidazolyl)hydroborato ligand: Kimblin, C.; Bridgewater, B. M.; Churchill, D. G.; Parkin, G. J. Chem. Soc., Chem. Commun. 1999, 2301-2302.
42. Due to the high flexibility of the calix[6]arene macrocycle, the capacity of its aromatic cavity to act as a molecular host has been scarcely used. Most previous studies concerned the complexation with ammonium and tetra(alkyl)-ammonium cations: (a) Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217-218. (b) Chang, S.-K., Jang, M. J.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937-1940. (c) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett., 1993, 205-208. (d) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644. (e) Odashima, K.; Yagi, K.; Tohda, K.; Umezawa, Y. Anal. Chem. 1993, 65, 1074-1083. (f) Han, S.-Y.; Kang, M-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835-839. (g) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032-4034. (h) Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J. W. Chem. Lett. 1995, 297-298. (i) Magrans, J. O.; Ortiz, A. R.; Molins, M. A.; Lebouille, P. H. P.; Sànchez-Quesada, J.; Prados, P.; Pons, M.; Gago, F.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1712-1715.
43. Due to the high flexibility of the calix[6]arene macrocycle, the capacity of its aromatic cavity to act as a molecular host has been scarcely used. Most previous studies concerned the complexation with ammonium and tetra(alkyl)-ammonium cations: (a) Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217-218. (b) Chang, S.-K., Jang, M. J.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937-1940. (c) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett., 1993, 205-208. (d) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644. (e) Odashima, K.; Yagi, K.; Tohda, K.; Umezawa, Y. Anal. Chem. 1993, 65, 1074-1083. (f) Han, S.-Y.; Kang, M-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835-839. (g) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032-4034. (h) Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J. W. Chem. Lett. 1995, 297-298. (i) Magrans, J. O.; Ortiz, A. R.; Molins, M. A.; Lebouille, P. H. P.; Sànchez-Quesada, J.; Prados, P.; Pons, M.; Gago, F.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1712-1715.
44. Due to the high flexibility of the calix[6]arene macrocycle, the capacity of its aromatic cavity to act as a molecular host has been scarcely used. Most previous studies concerned the complexation with ammonium and tetra(alkyl)-ammonium cations: (a) Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217-218. (b) Chang, S.-K., Jang, M. J.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937-1940. (c) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett., 1993, 205-208. (d) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644. (e) Odashima, K.; Yagi, K.; Tohda, K.; Umezawa, Y. Anal. Chem. 1993, 65, 1074-1083. (f) Han, S.-Y.; Kang, M-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835-839. (g) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032-4034. (h) Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J. W. Chem. Lett. 1995, 297-298. (i) Magrans, J. O.; Ortiz, A. R.; Molins, M. A.; Lebouille, P. H. P.; Sànchez-Quesada, J.; Prados, P.; Pons, M.; Gago, F.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1712-1715.
45. Due to the high flexibility of the calix[6]arene macrocycle, the capacity of its aromatic cavity to act as a molecular host has been scarcely used. Most previous studies concerned the complexation with ammonium and tetra(alkyl)-ammonium cations: (a) Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217-218. (b) Chang, S.-K., Jang, M. J.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937-1940. (c) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett., 1993, 205-208. (d) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644. (e) Odashima, K.; Yagi, K.; Tohda, K.; Umezawa, Y. Anal. Chem. 1993, 65, 1074-1083. (f) Han, S.-Y.; Kang, M-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835-839. (g) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032-4034. (h) Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J. W. Chem. Lett. 1995, 297-298. (i) Magrans, J. O.; Ortiz, A. R.; Molins, M. A.; Lebouille, P. H. P.; Sànchez-Quesada, J.; Prados, P.; Pons, M.; Gago, F.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1712-1715.
46. Due to the high flexibility of the calix[6]arene macrocycle, the capacity of its aromatic cavity to act as a molecular host has been scarcely used. Most previous studies concerned the complexation with ammonium and tetra(alkyl)-ammonium cations: (a) Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217-218. (b) Chang, S.-K., Jang, M. J.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937-1940. (c) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett., 1993, 205-208. (d) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644. (e) Odashima, K.; Yagi, K.; Tohda, K.; Umezawa, Y. Anal. Chem. 1993, 65, 1074-1083. (f) Han, S.-Y.; Kang, M-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835-839. (g) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032-4034. (h) Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J. W. Chem. Lett. 1995, 297-298. (i) Magrans, J. O.; Ortiz, A. R.; Molins, M. A.; Lebouille, P. H. P.; Sànchez-Quesada, J.; Prados, P.; Pons, M.; Gago, F.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1712-1715.
47. Due to the high flexibility of the calix[6]arene macrocycle, the capacity of its aromatic cavity to act as a molecular host has been scarcely used. Most previous studies concerned the complexation with ammonium and tetra(alkyl)-ammonium cations: (a) Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217-218. (b) Chang, S.-K., Jang, M. J.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937-1940. (c) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett., 1993, 205-208. (d) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644. (e) Odashima, K.; Yagi, K.; Tohda, K.; Umezawa, Y. Anal. Chem. 1993, 65, 1074-1083. (f) Han, S.-Y.; Kang, M-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835-839. (g) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032-4034. (h) Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J. W. Chem. Lett. 1995, 297-298. (i) Magrans, J. O.; Ortiz, A. R.; Molins, M. A.; Lebouille, P. H. P.; Sànchez-Quesada, J.; Prados, P.; Pons, M.; Gago, F.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1712-1715.
48. Due to the high flexibility of the calix[6]arene macrocycle, the capacity of its aromatic cavity to act as a molecular host has been scarcely used. Most previous studies concerned the complexation with ammonium and tetra(alkyl)-ammonium cations: (a) Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217-218. (b) Chang, S.-K., Jang, M. J.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937-1940. (c) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett., 1993, 205-208. (d) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644. (e) Odashima, K.; Yagi, K.; Tohda, K.; Umezawa, Y. Anal. Chem. 1993, 65, 1074-1083. (f) Han, S.-Y.; Kang, M-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835-839. (g) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032-4034. (h) Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J. W. Chem. Lett. 1995, 297-298. (i) Magrans, J. O.; Ortiz, A. R.; Molins, M. A.; Lebouille, P. H. P.; Sànchez-Quesada, J.; Prados, P.; Pons, M.; Gago, F.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1712-1715.
49. Due to the high flexibility of the calix[6]arene macrocycle, the capacity of its aromatic cavity to act as a molecular host has been scarcely used. Most previous studies concerned the complexation with ammonium and tetra(alkyl)-ammonium cations: (a) Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217-218. (b) Chang, S.-K., Jang, M. J.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937-1940. (c) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett., 1993, 205-208. (d) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644. (e) Odashima, K.; Yagi, K.; Tohda, K.; Umezawa, Y. Anal. Chem. 1993, 65, 1074-1083. (f) Han, S.-Y.; Kang, M-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835-839. (g) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032-4034. (h) Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J. W. Chem. Lett. 1995, 297-298. (i) Magrans, J. O.; Ortiz, A. R.; Molins, M. A.; Lebouille, P. H. P.; Sànchez-Quesada, J.; Prados, P.; Pons, M.; Gago, F.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1712-1715.
50. Due to the high flexibility of the calix[6]arene macrocycle, the capacity of its aromatic cavity to act as a molecular host has been scarcely used. Most previous studies concerned the complexation with ammonium and tetra(alkyl)-ammonium cations: (a) Chang, S.-K.; Hwang, H.-S.; Son, H.; Youk, J.; Kang, Y. S. J. Chem. Soc., Chem. Commun. 1991, 217-218. (b) Chang, S.-K., Jang, M. J.; Han, S. Y.; Lee, J. H.; Kang, M. H.; No, K. T. Chem. Lett. 1992, 1937-1940. (c) Araki, K.; Shimizu, H.; Shinkai, S. Chem. Lett., 1993, 205-208. (d) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644. (e) Odashima, K.; Yagi, K.; Tohda, K.; Umezawa, Y. Anal. Chem. 1993, 65, 1074-1083. (f) Han, S.-Y.; Kang, M-H.; Jung, Y. E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835-839. (g) Takeshita, M.; Nishio, S.; Shinkai, S. J. Org. Chem. 1994, 59, 4032-4034. (h) Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J. W. Chem. Lett. 1995, 297-298. (i) Magrans, J. O.; Ortiz, A. R.; Molins, M. A.; Lebouille, P. H. P.; Sànchez-Quesada, J.; Prados, P.; Pons, M.; Gago, F.; de Mendoza, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1712-1715.
51. Recent reviews on calixarenes: (a) Gutsche, C. D. Calixarenes Revisited, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry; Cambridge, UK, 1998. (b) Wieser, C.; Dieleman, C. B.; Matt, D. Coord. Chem. Rev. 1997, 109, 93-161. (c) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734. (d) Böhmer, V. Angew. Chem., Int. Ed Engl. 1995, 34, 713-745.
52. Recent reviews on calixarenes: (a) Gutsche, C. D. Calixarenes Revisited, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry; Cambridge, UK, 1998. (b) Wieser, C.; Dieleman, C. B.; Matt, D. Coord. Chem. Rev. 1997, 109, 93-161. (c) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734. (d) Böhmer, V. Angew. Chem., Int. Ed Engl. 1995, 34, 713-745.
53. Recent reviews on calixarenes: (a) Gutsche, C. D. Calixarenes Revisited, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry; Cambridge, UK, 1998. (b) Wieser, C.; Dieleman, C. B.; Matt, D. Coord. Chem. Rev. 1997, 109, 93-161. (c) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734. (d) Böhmer, V. Angew. Chem., Int. Ed Engl. 1995, 34, 713-745.
54. Recent reviews on calixarenes: (a) Gutsche, C. D. Calixarenes Revisited, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry; Cambridge, UK, 1998. (b) Wieser, C.; Dieleman, C. B.; Matt, D. Coord. Chem. Rev. 1997, 109, 93-161. (c) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734. (d) Böhmer, V. Angew. Chem., Int. Ed Engl. 1995, 34, 713-745.
55. Reese, C. B.; Pei-Zhuo, Z. J. Chem. Soc., Perkin Trans. 1 1993, 19, 2291-2302.
56. Mackay, S.; Gilmore, C. J.; Edwards, C.; Tremayne, M.; Stewart, N.; Shackland, K. « maXus: a computer program for the solution and refinement of crystal structures from diffraction data », University of Glasgow, Scotland, UK; Nonius BV, Delft, The Netherlands; and Mac-Science Co. Ltd., Yokohama, Japan, 1998.