The back and forth motions of a crown-ether based wheel along the axis of a bistable rotaxane are triggered by the decarboxylation of 2-cyano-2-phenylpropanoic acid and detected by the oscillation of the EPR nitrogen splitting of a dialkyl nitroxide function mounted within the macrocyclic ring. When the p-Cl derivative of the acid is used, back and forth motions are accelerated. Conversely, with p-CH3 and p-OCH3 derivatives, the back motion is strongly inhibited by the insurgence of collateral radical reactions.
2-Cyano-2-phenylpropanoic acid triggers the back and forth motions of an acid-base-operated paramagnetic molecular switch / Franchi, P.; Poderi, C.; Mezzina, E.; Biagini, C.; Di Stefano, Stefano; Lucarini, M.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 84:14(2019), pp. 9364-9368. [10.1021/acs.joc.9b01164]
2-Cyano-2-phenylpropanoic acid triggers the back and forth motions of an acid-base-operated paramagnetic molecular switch
Biagini C.;Di Stefano S.
;
2019
Abstract
The back and forth motions of a crown-ether based wheel along the axis of a bistable rotaxane are triggered by the decarboxylation of 2-cyano-2-phenylpropanoic acid and detected by the oscillation of the EPR nitrogen splitting of a dialkyl nitroxide function mounted within the macrocyclic ring. When the p-Cl derivative of the acid is used, back and forth motions are accelerated. Conversely, with p-CH3 and p-OCH3 derivatives, the back motion is strongly inhibited by the insurgence of collateral radical reactions.| File | Dimensione | Formato | |
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Franchi_2-Cyano_2019.pdf
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