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 S.; Lucarini M.. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 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
Franchi P.;Poderi C.;Mezzina E.;Lucarini M.
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
