Probing the interactions of calix[4]arene-based amphiphiles and cyclodextrins in water

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Michels, Jasper J. and Huskens, Jurriaan and Engbersen, Johan F.J. and Reinhoudt, David N. (2000) Probing the interactions of calix[4]arene-based amphiphiles and cyclodextrins in water. Langmuir, 16 (11). pp. 4864-4870. ISSN 0743-7463

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Abstract:The surfactant behavior of the water-soluble calix[4]arene 1, which has carboxylate groups at the upper rim and two phenyl groups at the lower rim, and its complexation to -cyclodextrin were studied. The critical micelle concentration (cmc) of 1 and of tetrapropoxycalix[4]arenetetracarboxylate 2 are 35 and 650 M, respectively. The stabilities of the 1:1 inclusion complexes of -cyclodextrin with 1 and 2 are 1.3 × 104 and 1.5 × 103 M-1, respectively. The stability of the former complex was derived from a calorimetric titration under conditions where 1 is largely micellized. A minimization routine is described for determining the heat contributions of demicellization and complexation. The association of 1 to -cyclodextrin is enthalpy-driven, which, together with the high K value and the 1:1 binding stoichiometry, indicates that both pendant phenyl rings of 1 are included in the y-cyclodextrin cavity.
Item Type:Article
Copyright:© 2000 American Chemical Society
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/11656
Official URL:http://dx.doi.org/10.1021/la991438j
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Metis ID: 106272