Synthesis of a Highly Electron-Deficient, Water-Stable, Large Ionic Box: Multielectron Accumulation and Proton Conductivity.

π-acidic boxes exhibiting electron reservoir and proton conduction are unprecedented because of their instability in water. We present the synthesis of one of the strongest electron-deficient ionic boxes showing e uptake as well as proton conductivity. Two large anions fit in the box to form anion-π interactions and form infinite anion-solvent wires. The box with NO···water wires confers high proton conductivity and presents the first example that manifests redox and ionic functionality in an organic electron-deficient macrocycle.