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Issue 94, 2016
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A high-yield synthesis and acid–base response of phosphate-templated [3]rotaxanes

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Abstract

Anion-templated rotaxanes are a rare class of functional organic molecules capable of novel switching and mechanical behaviors. Yet, investigations of these properties are limited by existing synthetic strategies. We show a high-yielding synthesis (80%) of [3]rotaxanes using shape-persistent macrocycles, cyanostars, and anionic organo-phosphate templates catalyzed by low steric-demand click chemistry. The reaction yields correlate with the template's binding affinities. Use of longer linkers relieves steric congestion to enable a reversible acid–base response, opening the way to molecular switching.

Graphical abstract: A high-yield synthesis and acid–base response of phosphate-templated [3]rotaxanes

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Supplementary files

Article information


Submitted
07 Oct 2016
Accepted
24 Oct 2016
First published
24 Oct 2016

Chem. Commun., 2016,52, 13675-13678
Article type
Communication

A high-yield synthesis and acid–base response of phosphate-templated [3]rotaxanes

B. Qiao, Y. Liu, S. Lee, M. Pink and A. H. Flood, Chem. Commun., 2016, 52, 13675
DOI: 10.1039/C6CC08113D

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