The Red Cage: Implementation of pH-Responsiveness Within a Macrobicyclic Pyridinium-Based Molecular Host
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TitleThe Red Cage: Implementation of pH-Responsiveness Within a Macrobicyclic Pyridinium-Based Molecular Host
P. Cortón, H. Wang, I. Neira, A. Blanco-Gómez, E. Pazos, C. Peinador, H. Li and M. D. García, “The red cage”: implementation of pH-responsiveness within a macrobicyclic pyridinium-based molecular host, Org. Chem. Front., 2021, 9, 81–87. https://doi.org/10.1039/D1QO01331A
[Abstract] We present herein the implementation of pH-responsiveness into a new polycationic macrobicyclic structure, namely what we have termed the “red cage”. The hydrolytically-stable cryptand-like compound has been prepared in a relatively high yield in aqueous media by a kinetically-controlled hydrazone-exchange reaction, promoted by the unusual high stability of the new hydrazone C[double bond, length as m-dash]N bonds formed. In organic media the macrobicycle was found not able to complex model aromatic substrates. In buffered aqueous solutions, as a comparison, the “red cage” was found able to recognize them, but the binding was observed to be more efficient in acidic form of the cyclophane compared with its conjugate base.