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Thinking outside the “Blue Box”: from molecular to supramolecular pH-responsiveness

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http://hdl.handle.net/2183/24551
Atribución-NoComercial 3.0 España
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Title
Thinking outside the “Blue Box”: from molecular to supramolecular pH-responsiveness
Author(s)
Blanco-Gómez, Arturo
Neira, Iago
Barriada, José Luis
Melle-Franco, Manuel
Peinador, Carlos
García, Marcos D.
Date
2019-10-23
Citation
A. Blanco-Gómez, I. Neira, J. L. Barriada, M. Melle-Franco, C. Peinador and M. D. García, Chem. Sci., 2019, 10, 10680–10686.
Abstract
[Abstract] We present herein the development of a new polycationic cyclophane: the “red box”, second in a series of hydrazone-based analogues of the well-known organic receptor cyclobis(paraquat-p-phenylene)cyclophane (“blue box”). The macrocycle has been prepared in an excellent yield in aqueous media, and shows both a remarkable pH-responsiveness and unusual hydrolytic stability of the two hydrazone C[double bond, length as m-dash]N bonds, associated with charge delocalization of the amine lone pair. Whilst in aqueous media the “red box” is able to complex a variety of aromatic substrates, both in its acidic and basic form, in organic media the cyclophane is only able to capture those in the acidic form, resulting in supramolecular pH-responsiveness.
Keywords
Supramolecular chemistry
Host-guest chemistry
Molecular switches
Supramolecular switches
Cyclophanes
 
Editor version
https://doi.org/10.1039/C9SC04489B
Rights
Atribución-NoComercial 3.0 España
ISSN
2041-6539

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