Water-soluble calixarenes—self-aggregation and complexation of noncharged aromatic guests in buffered aqueous solution |
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Authors: | Marion Rehm Jürgen Schatz |
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Institution: | a Division of Organic Chemistry I, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany b Organic Chemistry 1, Friedrich-Alexander-University Erlangen-Nuremberg, Henkestr. 42, D-91054 Erlangen, Germany |
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Abstract: | Water-soluble calix4]arenes are useful receptors for hydrophobic substrates in aqueous buffered solution. The inclusion of 22 aromatic guests as well as the self-aggregation behavior of amphiphilic hosts was studied by 1H NMR spectroscopy. The association constants obtained range from 10 to 1000 L mol−1. In all cases, the aromatic moiety is included into the hydrophobic pocket of the calixarenes maximizing hydrophobic contacts. Additionally, substituents such as methyl or chlorine exhibit a preference for inclusion in the pocket of the macrocycles owing to CH/π or Cl/π interactions. In case self-aggregation is observed, millimolar CMC values are to be found. |
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Keywords: | Supramolecular chemistry Calix[4]arenes Host-guest interaction NMR titration Aqueous solution |
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