Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 26, Pages 6762-6767Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402962
Keywords
Brownian motion; competitive binding; hydrogen-bond arrays; rotaxanes; template synthesis
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Funding
- MINECO [CTQ2009-12216/BQU, CTQ2013-46651]
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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.
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