Abstract
The dynamic stereochemistry of amphiphilic derivatives of α-, β-, and γ-cyclodextrins ( 1– 3) has been investigated by means of variable temperature 1H and 13C NMR spectroscopy in DMF-d 7 solutions. The most significant spectral changes were detected for the smallest hexakis(6-thiophenyl-6-deoxy)-α-cyclodextrin ( 1) and they decrease with the increase of the macrocycle size. On the basis of ROESY measurements, these changes reflecting restricted movements of thiophenyl groups upon the temperature decrease were interpreted in terms of self-inclusion of at least one thiophenyl group. Molecular modeling of these compounds is consistent with these findings.
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