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β‐Cyclodextrin PAMAM Dendrimer: How to Overcome the Tumbling Process for Getting Fully Available Host Cavities
Author(s) -
GonzálezMéndez Israel,
Hameau Aurélien,
Laurent Régis,
Bijani Christian,
Bourdon Valérie,
Caminade AnneMarie,
Rivera Ernesto,
MoineauChane Ching Kathleen I.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901823
Subject(s) - dendrimer , trimer , cyclodextrin , adamantane , chemistry , dimer , monomer , tetra , circular dichroism , solubility , alkyne , nuclear magnetic resonance spectroscopy , cycloaddition , polymer , polymer chemistry , combinatorial chemistry , crystallography , stereochemistry , organic chemistry , catalysis , medicinal chemistry
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 D 2 O was evidenced by 1 H 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.