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Published on: February 7, 2017
Adaptive binding of a shape-shifting bullvalene within β-cyclodextrin
Qiyuan Tao1, André P Birvé1, Jack D Evans1
1School of Physics Chemistry and Earth Sciences, Adelaide University, Adelaide, South Australia 5005, Australia. thomas.fallon@adelaide.edu.au.
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Herein, we report adaptive host-guest binding between an amphiphilic dicationic bis-pyridinium bullvalene and cyclodextrins. Isothermal titration calorimetry identifies β-cyclodextrin as the strongest 1:1 host, while low-temperature NMR spectroscopy shows that complexation drives the guest ensemble toward the β,γ' isomer through inclusion of the hydrophobic bullvalene core. Computational modelling supports this shape-selective binding mode and predicts supramolecular dynamic deracemization in favour of the (Rα)-β,γ' enantiomer.
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