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Issue 46, 2019
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Thinking outside the “Blue Box”: from molecular to supramolecular pH-responsiveness

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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.

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

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Publication details

The article was received on 05 Sep 2019, accepted on 22 Oct 2019 and first published on 23 Oct 2019


Article type: Edge Article
DOI: 10.1039/C9SC04489B
Chem. Sci., 2019,10, 10680-10686
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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

    A. Blanco-Gómez, I. Neira, J. L. Barriada, M. Melle-Franco, C. Peinador and M. D. García, Chem. Sci., 2019, 10, 10680
    DOI: 10.1039/C9SC04489B

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