Issue 1, 2018

Variations in the fuel structure control the rate of the back and forth motions of a chemically fuelled molecular switch

Abstract

This work deals with the use of 2-cyano-2-arylpropanoic acids as chemical fuels for an acid–base operated molecular switch that consists of a Sauvage-type catenand composed of two identical macrocycles incorporating a phenanthroline unit. When used as a base promoter of the decarboxylation of propanoic acid derivatives, the switch undergoes large amplitude motion from the neutral catenand to a protonated catenate and back again to the neutral state. The rate of back proton transfer, which determines the rate of the overall process, was markedly affected by para-substituents in the order Cl > H > CH3 > OCH3 (ρ = +5.2). Thus, the time required to complete a full cycle was almost two days for the OCH3 derivative and dropped to a few minutes for the Cl derivative. These results show for the first time that the rate of operation of a molecular switch can be regulated by variations in the fuel structure.

Graphical abstract: Variations in the fuel structure control the rate of the back and forth motions of a chemically fuelled molecular switch

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Sep 2017
Accepted
18 Oct 2017
First published
18 Oct 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 181-188

Variations in the fuel structure control the rate of the back and forth motions of a chemically fuelled molecular switch

C. Biagini, S. Albano, R. Caruso, L. Mandolini, J. A. Berrocal and S. Di Stefano, Chem. Sci., 2018, 9, 181 DOI: 10.1039/C7SC04123C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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