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β-Cyclodextrin PAMAM Dendrimer: How to Overcome the Tumbling Process for Getting Fully Available Host Cavities

The synthesis of a G0 polyamidoamide (PAMAM) dendrimer end-capped with four β-cyclodextrin (β-CD) units, named as Tetra-CD was performed by using copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC). This new platform presents a considerable high water-solubility in comparison to native β-CD. Tumbling process involving half of the CD cavities in D2O was evidenced by 1H NMR spectroscopy. Interaction of adamantane with Tetra-CD has been fully investigated by 1D/2D NMR techniques and mass spectrometry besides a joint study on new β-CD monomers (named as A and B) and on a dimer (Di-CD) and a trimer (Tri-CD). The obtained results demonstrate that the tumbling effect can be shifted in the presence of an appropriate hydrophobic guest resulting in the full host-ability of the CD units in water for that guest.