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Facile synthesis of cucurbit[n]uril derivatives via direct functionalization: Expanding utilization of cucurbit[n]uril
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Vesicle formed by amphiphilc cucurbit[6]uril: Versatile, noncovalent modification of the vesicle surface, and multivalent binding of sugar-decorated vesicles to lectin
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Lee, H.-K.; Park, K. M.; Jeon, Y. J.; Kim, D.; Oh, D. H.; Kim, H. S.; Park, C. K.; Kim, K. Vesicle formed by amphiphilc cucurbit[6]uril: Versatile, noncovalent modification of the vesicle surface, and multivalent binding of sugar-decorated vesicles to lectin J. Am. Chem. Soc. 2005, 127, 5006-5007.
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Synthesis of disubstituted cucurbit[6]uril and its rotaxane derivative
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Zhao, Y.-J.; Xue, S. -F.; Zhu, Q. -J.; Tao, Z.; Zhang, J. -X.; Wei, Z. -B.; Long, L. -S.; Hu, M.-L.; Xiao, H. -P.; Day, A. I. Synthesis of a symmetrical tetrasubstituted cucurbit[6]uril and its host-guest compound with 2,2′-bipyridine. Chin. Sci. Bull. 2004, 49, 1111-1116.
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Gerasko, O. A.; Sokolov, M. N.; Fedin, V. P. Mono- and polynuclear aqua complexes and cucurbit[6]uril: versatile building blocks for supramolecular chemistry. Pure Appl. Chem., 2004, 76, 1633-1646.
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We have found that the symmetry of fully methyl-substituted Q[5] (DEMeQ[5]) is higher than that of the partially methyl-substituted Q[5]; the corresponding dipole (0.0393 Debye) is quite smaller than that of dimethyl-substituted Q[5], (0.7444 Debye), or hexamethyl-substituted Q[5] (1.2115 Debye). The normal Q[5] has the smallest dipole, 0.0216 Debye, due to its high symmetry. On the other hand, among the four Q[5]s, HMeQ[5] has the best water solubility (up to 17 g/100 g water); while the Q[5] has the least water solubility (only 0.03 g/100 g water). The order of dipoles of the four Q[5]s is qualitatively consistent with that of the solubility of these Q[5]s, that is HMeQ[5] > DMeQ[5] > DEMeQ[5] > Q[5].
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We have found that the symmetry of fully methyl-substituted Q[5] (DEMeQ[5]) is higher than that of the partially methyl-substituted Q[5]; the corresponding dipole (0.0393 Debye) is quite smaller than that of dimethyl-substituted Q[5], (0.7444 Debye), or hexamethyl-substituted Q[5] (1.2115 Debye). The normal Q[5] has the smallest dipole, 0.0216 Debye, due to its high symmetry. On the other hand, among the four Q[5]s, HMeQ[5] has the best water solubility (up to 17 g/100 g water); while the Q[5] has the least water solubility (only 0.03 g/100 g water). The order of dipoles of the four Q[5]s is qualitatively consistent with that of the solubility of these Q[5]s, that is HMeQ[5] > DMeQ[5] > DEMeQ[5] > Q[5].
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Ma, P.-H.; Dong, J.; Xiang, S.-C.; Xue, S.i-F.; Zhu, Q.-J.; Tao, Z.; Zhang J.-X.; Zhou, X. Interaction of host-guest complexes of cucurbit[n]urilswith double probe guests. Sci. China Ser. B. 2004, 47, 301-310.
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Fu, H.-Y.; Xue, S.-F.; Zhu, Q.-J.; Tao, Z.; Zhang, J.-X.; Day A. I. Investigation of host-guest compounds of cucurbit[n = 5-8]uril with some ortho pyridiniumammonium Ions J. Incl. Phenom. Macro. 2005, 52, 101-107.
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