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Thinking outside the "Blue Box": from molecular to supramolecular pH-responsiveness.


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.

SUBMITTER: Blanco-Gomez A 

PROVIDER: S-EPMC7069232 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Thinking outside the "Blue Box": from molecular to supramolecular pH-responsiveness.

Blanco-Gómez Arturo A   Neira Iago I   Barriada José L JL   Melle-Franco Manuel M   Peinador Carlos C   García Marcos D MD  

Chemical science 20191023 46


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-<i>p</i>-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 pa  ...[more]

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