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Interplay between a Foldamer Helix and a Macrocycle in a Foldarotaxane Architecture
Author(s) -
Gauthier Maxime,
Koehler Victor,
Clavel Caroline,
Kauffmann Brice,
Huc Ivan,
Ferrand Yann,
Coutrot Frédéric
Publication year - 2021
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.202100349
Subject(s) - foldamer , rotaxane , axle , steric effects , helix (gastropod) , supramolecular chemistry , crystallography , chemistry , stereochemistry , crystal structure , engineering , snail , mechanical engineering , ecology , biology
The design and synthesis of a novel rotaxane/foldaxane hybrid architecture is reported. The winding of an aromatic oligoamide helix host around a dumbbell‐shaped thread‐like guest, or axle, already surrounded by a macrocycle was evidenced by NMR spectroscopy and X‐ray crystallography. The process proved to depend on the position of the macrocycle along the axle and the associated steric hindrance. The macrocycle thus behaves as a switchable shield that modulates the affinity of the helix for the axle. Reciprocally, the foldamer helix acts as a supramolecular auxiliary that compartmentalizes the axle. In some cases, the macrocycle is forced to move along the axle to allow the foldamer to reach its best recognition site.