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.
5-ago-2020
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/06 - CHIMICA ORGANICA
English
calixarene
chemical fuel
conformational control
molecular machine
molecular motions
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].
Del Giudice, D; Spatola, E; Cacciapaglia, R; Casnati, A; Baldini, L; Ercolani, G; Di Stefano, S
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/258587
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