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Small‐Molecule Recognition for Controlling Molecular Motion in Hydrogen‐Bond‐Assembled Rotaxanes
Author(s) -
MartinezCuezva Alberto,
Berna Jose,
Orenes RaulAngel,
Pastor Aurelia,
Alajarin Mateo
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201402962
Subject(s) - chemistry , amide , hydrogen bond , molecule , pyridine , nitrogen atom , molecular recognition , solid state , catenane , ring (chemistry) , rotaxane , stereochemistry , polymer chemistry , crystallography , supramolecular chemistry , medicinal chemistry , organic chemistry
Di(acylamino)pyridines successfully template the formation of hydrogen‐bonded rotaxanes through five‐component clipping reactions. A solid‐state study showed the participation of the pyridine nitrogen atom in the stabilization of the mechanical bond between the thread and the benzylic amide macrocycle. The addition of external complementary binders to a series of interlocked bis(2,6‐di(acylamino)pyridines) promoted restraint of the back and forward ring motion. The original translation can be restored through a competitive recognition event by the addition of a preorganized bis(di(acylamino)pyridine) that forms stronger ADA–DAD complexes with the external binders.