In this work, we report that 2-cyano-2-phenylpropanoic acid and itsp-Cl,p-CH(3)andp-OCH(3)derivatives can be used as chemical fuels to control the geometry of the calix[4]arene scaffold in its cone conformation. It is shown that, under the action of the fuel, the cone calix[4]arene platform assumes a "locked" shape with two opposite aromatic rings strongly convergent and the other two strongly divergent ("pinched cone" conformation). Only when the fuel is exhausted, the cone calix[4]arene scaffold returns to its resting, "unlocked" shape. Remarkably, the duration of the "locked" state can be controlled at will by varying the fuel structure or amount. A kinetic study of the process shows that the consume of the fuel is catalyzed by the "unlocked" calixarene that behaves as an autocatalyst for its own production. A mechanism is proposed for the reaction of fuel consumption.
Del Giudice, D., Spatola, E., Cacciapaglia, R., Casnati, A., Baldini, L., Ercolani, G., et al. (2020). Time programmable locking/unlocking of the Calix[4]arene scaffold by means of chemical fuels. CHEMISTRY-A EUROPEAN JOURNAL, 26(65), 14954-14962 [10.1002/chem.202002574].
Time programmable locking/unlocking of the Calix[4]arene scaffold by means of chemical fuels
Ercolani, Gianfranco
;
2020-08-05
Abstract
In this work, we report that 2-cyano-2-phenylpropanoic acid and itsp-Cl,p-CH(3)andp-OCH(3)derivatives can be used as chemical fuels to control the geometry of the calix[4]arene scaffold in its cone conformation. It is shown that, under the action of the fuel, the cone calix[4]arene platform assumes a "locked" shape with two opposite aromatic rings strongly convergent and the other two strongly divergent ("pinched cone" conformation). Only when the fuel is exhausted, the cone calix[4]arene scaffold returns to its resting, "unlocked" shape. Remarkably, the duration of the "locked" state can be controlled at will by varying the fuel structure or amount. A kinetic study of the process shows that the consume of the fuel is catalyzed by the "unlocked" calixarene that behaves as an autocatalyst for its own production. A mechanism is proposed for the reaction of fuel consumption.File | Dimensione | Formato | |
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