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.
Franchi P., Poderi C., Mezzina E., Biagini C., Di Stefano S., Lucarini M. (2019). 2-Cyano-2-phenylpropanoic Acid Triggers the Back and Forth Motions of an Acid-Base-Operated Paramagnetic Molecular Switch. JOURNAL OF ORGANIC CHEMISTRY, 84(14), 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.| File | Dimensione | Formato | |
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