One-step synthesis and cation-dependent redox properties of new ‘quinonoid macrocycles’ bearing ion-binding polyether moieties

Abstract

A one-step synthesis of novel macrocyclic quinonoid compounds bearing ion-binding polyether moieties, ‘quinonoid macrocycles,’ has been developed. By using an oxidative C–C coupling reaction as the ring-closure step, acyclic polyether precursors bearing hydroquinone dimethyl ether groups on both terminals were readily converted into new quinonoid macrocycles. The macrocycles obtained show characteristic cation-dependent redox properties very different from those of common quinonoid compounds. Since electrochemically reduced quinonoid macrocycles bind Li⁺ and other alkali metal cations more strongly than their neutral forms, their redox properties were effectively modified by adding these metal cations.