Naphthocage: A Flexible yet Extremely Strong Binder for Singly Charged Organic Cations

We
report a quite flexible naphthol-based cage (so-called “naphthocage”)
which adopts a self-inclusion conformation in its free state and is
able to bind singly charged organic cations extremely strongly (Ka > 107 M–1).
Ion-selective
electrodes prepared with this naphthocage show a super-Nernstian response
to acetylcholine. In addition, the highly stable complex (1010 M–1) between ferrocenium and the naphthocage can
be switched electrochemically, which lays a basis for its application
in stimuli-responsive materials.