Thinking outside the Blue Box: from molecular to supramolecular pH-responsiveness
authors Blanco-Gomez, A; Neira, I; Barriada, JL; Melle-Franco, M; Peinador, C; Garcia, MD
nationality International
journal CHEMICAL SCIENCE
keywords ASSEMBLED PD-II; SWITCHES; COMPLEXATION; ROTAXANES; CATENANE; DRIVEN
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=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 pHresponsiveness.
publisher ROYAL SOC CHEMISTRY
issn 2041-6520
isbn 2041-6539
year published 2019
volume 10
issue 46
beginning page 10680
ending page 10686
digital object identifier (doi) 10.1039/c9sc04489b
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000499471800018
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journal analysis (jcr 2019):
journal impact factor 9.346
5 year journal impact factor 8.945
category normalized journal impact factor percentile 88.418
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