Issue 46, 2019

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
05 Sep 2019
Accepted
22 Oct 2019
First published
23 Oct 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 10680-10686

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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