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Issue 9, 2019
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Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane

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Abstract

The rate at which the macrocyclic cyclobis(paraquat-p-phenylene) ring of a bistable [2]rotaxane moves from a tetrathiafulvalene station to an oxyphenylene station upon oxidation of the tetrathiafulvalene station is found to be increased in the presence of added salts. Compared to the salt-free case, 0.1 M solutions of a series of tetraalkylammonium hexafluorophosphate salts (R4N·PF6, R = H, Me, Et or n-Bu) and of tetrabutylammonium perchlorate (n-Bu4N·ClO4) all afford an increased switching rate, which is largest in the case of n-Bu4N·ClO4 with smaller anions. Variation in the size of the ammonium cation has no significant effect. These results indicate that the addition of excess ions can be used as an accelerator to speed up shuttling processes in rotaxanes and catenanes based on the mobile cyclobis(paraquat-p-phenylene) ring, and that the choice of anion offers a convenient means of controlling the extent of this effect.

Graphical abstract: Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane

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Article information


Submitted
13 Jan 2019
Accepted
05 Feb 2019
First published
05 Feb 2019

Org. Biomol. Chem., 2019,17, 2432-2441
Article type
Paper
Author version available

Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) [2]rotaxane

S. S. Andersen, A. W. Saad, R. Kristensen, T. S. Pedersen, L. J. O'Driscoll, A. H. Flood and J. O. Jeppesen, Org. Biomol. Chem., 2019, 17, 2432
DOI: 10.1039/C9OB00085B

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