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

Chiara Biagini, Simone Albano, Rachele Caruso, Luigi Mandolini, José Augusto Berrocal, Stefano Di Stefano

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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.

Original languageEnglish
Pages (from-to)181-188
Number of pages8
JournalChemical Science
Volume9
Issue number1
DOIs
Publication statusPublished - 1 Jul 2018

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Switches
Derivatives
Acids
Proton transfer
Phenanthrolines
Propionates
Decarboxylation

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Biagini, Chiara ; Albano, Simone ; Caruso, Rachele ; Mandolini, Luigi ; Berrocal, José Augusto ; Di Stefano, Stefano. / Variations in the fuel structure control the rate of the back and forth motions of a chemically fuelled molecular switch. In: Chemical Science. 2018 ; Vol. 9, No. 1. pp. 181-188.
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Biagini, C, Albano, S, Caruso, R, Mandolini, L, Berrocal, JA & Di Stefano, S 2018, 'Variations in the fuel structure control the rate of the back and forth motions of a chemically fuelled molecular switch', Chemical Science, vol. 9, no. 1, pp. 181-188. https://doi.org/10.1039/c7sc04123c

Variations in the fuel structure control the rate of the back and forth motions of a chemically fuelled molecular switch. / Biagini, Chiara; Albano, Simone; Caruso, Rachele; Mandolini, Luigi; Berrocal, José Augusto; Di Stefano, Stefano.

In: Chemical Science, Vol. 9, No. 1, 01.07.2018, p. 181-188.

Research output: Contribution to journalArticleAcademicpeer-review

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