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The reductive electron transfer behaviour of 2,5-disubstituted furans with the general formula A is investigated. A comparison with related dicyanovinyl substituted benzene derivatives, a monosubstituted furan, thiophenes and pyrrols is given. Radical anions, dianions and trianions are characterized by cyclic voltammetry and UV/VIS/NIRspectroelectrochemistry. Electronic spectra are reported. The reduction of A to their dianions depends sensitively on the length of the ^-conjugated side chains and can be shifted from a stepwise process with two clearly separated waves to an electron transfer mechanism with a single "two-electron" transfer wave in the cyclic voltammogram. The compounds A with higher conjugated side groups tend to the "merging wave" behaviour. A structural evaluation of these findings is discussed. The furans A and the thiophenes exhibit electrochemichromic behaviour. Applications of A in material science chemistry arc shortly adressed.

zeitschrift für physikalische chemie

Structural Effects Determining the Reductive Electron Transfer Chemistry of 2.5-Disubstituted Furans — One and “Two-electron” Transfer Behaviour Investigated by Cyclic Voltammetry and UV/VIS/NIR-Spectroelectrochemistry