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Metal‐Coordination‐Assisted Folding and Guest Binding in Helical Aromatic Oligoamide Molecular Capsules
Author(s) -
Horeau Maxime,
Lautrette Guillaume,
Wicher Barbara,
Blot Virginie,
Lebreton Jacques,
Pipelier Muriel,
Dubreuil Didier,
Ferrand Yann,
Huc Ivan
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.201701693
Subject(s) - foldamer , pyridazine , chemistry , monomer , helix (gastropod) , pyridine , crystallography , folding (dsp implementation) , coordination sphere , metal ions in aqueous solution , metal , stereochemistry , combinatorial chemistry , crystal structure , organic chemistry , polymer , ecology , snail , electrical engineering , biology , engineering
The development of foldamer‐based receptors is driven by the design of monomers with specific properties. Herein, we introduce a pyridazine‐pyridine‐pyridazine diacid monomer and its incorporation into helical aromatic oligoamide foldamer containers. This monomer codes for a wide helix diameter and can sequester metal ions on the inner wall of the helix cavity. Crystallographic studies and NMR titrations show that part of the metal coordination sphere remains available and may then promote the binding of a guest within the cavity. In addition to metal coordination, binding of the guest is assisted by cooperative interactions with the helix host, thereby resulting in significant enhancements depending on the foldamer sequence, and in slow guest capture and release on the NMR time scale. In the absence of metal ions, the pyridazine‐pyridine‐pyridazine monomer promotes an extended conformation of the foldamer that results in aggregation, including the formation of an intertwined duplex.