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.
2019
molecular machine; molecular motion; chemical fuel; catenane
01 Pubblicazione su rivista::01a Articolo in rivista
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]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1305586
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