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A series of redox-active conjugation-extended ring assemblies involving one or more central five-membered or related heterocycles has been synthesized and characterized. These compounds, in contrast to the corresponding open-chain polyene- or phenylene-bridged systems, maintain an enhanced conjugative interaction among the bridging and terminal rings, and a rigid and coplanar conformation throughout the redox process, generating thermodynamically stable radical ions as well as doubly ionized species, which are quite favorable as redox reagents. Consequently, valuable experimental results to clarify the mechanisms of redox reactions of conjugation- extended systems have been revealed. Moreover, currently interesting properties such as a novel amphoteric three-stage or four-stage redox reaction, a relatively high conductivity for the complexes of extended 'ITF derivatives, a strong fluorescence emission for doubly ionized species, and a unique electrochromism for extended viologens have been observed and these are discussed in detail.

Conjugation-extended ring assemblies with central heterocycles. New multistage redox systems