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Macromolecular Recognition of Cyclodextrin: Inversion of Selectivity of β ‐Cyclodextrin toward Adamantyl Groups Induced by Macromolecular Chains
Author(s) -
Taura Daisuke,
Taniguchi Yosuke,
Hashidzume Akihito,
Harada Akira
Publication year - 2009
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.200900283
Subject(s) - isothermal titration calorimetry , cyclodextrin , macromolecule , circular dichroism , chemistry , polymer , polymer chemistry , copolymer , proton nmr , crystallography , stereochemistry , organic chemistry , biochemistry
Interaction of β ‐cyclodextrin ( β ‐CD) with alternating copolymers (pAdMA and pAdPhMA) of sodium maleate with adamantyl (Ad) and with adamantylphenyl (AdPh) vinyl ether has been investigated by several NMR techniques. Comparing the apparent association constants ( K ) for the polymers with the K for the model compounds, which are determined by the analysis of 1 H NMR and isothermal titration calorimetry data, respectively, the selectivities of β ‐CD toward Ad and AdPh moieties are contrasting for the model and polymer systems. This phenomenon is described by circular dichroism and 2D NMR as follows; the most stable inclusion complex for the β ‐CD/AdPh model system is extremely destabilized for the corresponding polymer system because of competition with hydrophobic interaction between neighboring AdPh moieties.