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.
Pubblicato
Rilevanza internazionale
Articolo
Esperti anonimi
Settore CHIM/06
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
Articolo su rivista
File in questo prodotto:
File Dimensione Formato  
099-Chemistry(2020)-26-14954.pdf

accesso solo dalla rete interna

Tipologia: Versione Editoriale (PDF)
Licenza: Copyright dell'editore
Dimensione 616.4 kB
Formato Adobe PDF
616.4 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/258587
Citazioni
  • ???jsp.display-item.citation.pmc??? 6
  • Scopus 9
  • ???jsp.display-item.citation.isi??? 12
social impact