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Org Lett. 2011 Jan 7;13(1):30-3. doi: 10.1021/ol102422h. Epub 2010 Dec 6.

Switching around two axles: controlling the configuration and conformation of a hydrazone-based switch.

Author information

1
Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, United States.

Abstract

A hydrazone-based rotary switch, having a quinolinyl stator and a pyridine ring as part of the rotor, can be induced using pH to undergo a four-step switching sequence. This process yields three stable isomers and a fourth "metastable" one that can all be addressed separately based on the sequence of acid and base added. The switching process proceeds via conformational and/or configurational changes, allowing the molecule to rotate around two different axles.

PMID:
21133395
DOI:
10.1021/ol102422h

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