Anion Exchange Renders Hydrophobic Capsules and Cargoes Water‐Soluble

Control over the solubility properties of container molecules is a central challenge in host–guest chemistry. Herein we present a simple anion‐exchange protocol that allows the dissolution in water of various hydrophobic metal–organic container molecules prepared by iron(II)‐templated subcomponent s...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-07, Vol.56 (31), p.9136-9140
Main Authors: Percástegui, Edmundo G., Mosquera, Jesús, Nitschke, Jonathan R.
Format: Article
Language:English
Subjects:
Anion exchange
Anion exchanging
Anions
Aromatic compounds
Cages
Containers
Dismantling
Dissolution
Drugs
host–guest systems
Hydrophobicity
Iron
Ligands
Self-assembly
Sulfates
supramolecular chemistry
Supramolecular compounds
water-soluble capsules
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Summary:Control over the solubility properties of container molecules is a central challenge in host–guest chemistry. Herein we present a simple anion‐exchange protocol that allows the dissolution in water of various hydrophobic metal–organic container molecules prepared by iron(II)‐templated subcomponent self‐assembly. Our process involved the exchange of less hydrophilic trifluoromethanesulfonate anions for hydrophilic sulfate; the resulting water‐soluble cages could be rendered water‐insoluble through reverse anion exchange. Notably, this strategy allowed cargoes within capsules, including polycyclic aromatic compounds and complex organic drugs, to be brought into water. Hydrophobic effects appeared to enhance binding, as many of these cargoes were not bound in non‐aqueous media. Studies of the scope of this method revealed that cages containing tetratopic and tritopic ligands were more stable in water, whereas cages with ditopic ligands disassembled. Let's jump in the water: Anion exchange enabled a variety of large and hydrophobic self‐assembled capsules to be dissolved in water, where they encapsulated a wide range of guests that may not be bound in acetonitrile. The resulting water‐soluble cages could be rendered water‐insoluble through reverse anion exchange (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201705093