Phenazine-1,6-dicarboxamides: Redox-Responsive Molecular Switches

We introduce phenazine-1,6-dicarboxamides as redox-responsive molecular switches. The reduction of their phenazine core transforms them from hydrogen-bond acceptors into hydrogen-bond donors and thus forces the secondary amide substituents to turn around. The resulting conformational changes are envisioned to form the basis for butterfly coil foldamers undergoing reversible extension and contraction in response to changing their oxidation state.