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Article Dans Une Revue European Journal of Organic Chemistry Année : 2020

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

Résumé

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.
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Dates et versions

hal-02501116 , version 1 (23-10-2020)

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Israel González-Méndez, Aurélien Hameau, Regis Laurent, Christian Bijani, Valérie Bourdon, et al.. β-Cyclodextrin PAMAM Dendrimer: How to Overcome the Tumbling Process for Getting Fully Available Host Cavities. European Journal of Organic Chemistry, 2020, 2020 (9), pp.1114-1121. ⟨10.1002/ejoc.201901823⟩. ⟨hal-02501116⟩
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