The redox and cation binding properties of a series of four quinone-functionalized calix[4]arenes have been studied in acetonitrile. Di-, tri-, and tetraquinone calixarenes exhibit successive (separate) first electron transfers into each of the quinone units. Comparison with linear analogues cited in the literature suggests that the behavior is similar for both linear and cyclic systems. All four compounds when reduced to the monoanion state demonstrate interactions with Na+ and Ag+ to varying degrees. The neutral calix[4]arenemonoquinone binds Na+ and shows a binding enhancement on the order of 10(6) when reduced to its monoanion state.