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Royal Society of Chemistry, Chemical Science, 6(3), p. 1851, 2012

DOI: 10.1039/c2sc20072d

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Tightening or Loosening a pH-Sensitive Double-Lasso Molecular Machine Readily Synthesized from an Ends-Activated [c2]Daisy Chain

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The ready synthesis of a new double-lasso molecular machine from an ends-activated [c2]daisy chain has been achieved. This original architecture consists of a unique double-lasso structure, where the two macrocycles can slide along the threaded pseudo-macrocycle upon variation of pH. The interlocked structure allows for two very different conformations: at low pH, it has a loose conformation with a big cavity. The interlocked molecule thus behaves like a controllable ''jump rope''. After deprotonation, the molecule adopts a helical-type tightened conformation with a shrunken cavity. In this conformation, no jump rope movement is possible due to the tightened lasso.