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

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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

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Publication details

The article was received on 20 Sep 2017, accepted on 18 Oct 2017 and first published on 18 Oct 2017


Article type: Edge Article
DOI: 10.1039/C7SC04123C
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    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, Advance Article , DOI: 10.1039/C7SC04123C

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