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Anion Exchange Renders Hydrophobic Capsules and Cargoes Water‐Soluble
Author(s) -
Percástegui Edmundo G.,
Mosquera Jesús,
Nitschke Jonathan R.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201705093
Subject(s) - chemistry , dissolution , trifluoromethanesulfonate , aqueous solution , ion exchange , hydrophobic effect , solubility , solvent , molecule , water soluble , salt (chemistry) , metal ions in aqueous solution , sulfation , sulfate , combinatorial chemistry , inorganic chemistry , metal , organic chemistry , ion , catalysis , biochemistry
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.