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N , N' -Diphenyl-3,7-diazacyclooctane and structurally related N , N' -diphenylbispidine derivatives react with silver(I) ions in a high-yielding C-C coupling reaction to produce dication-diradical species, with the silver ions serving a double function both as template and as an oxidant. The resulting bis(benzidino)phane derivatives are persistent organic radicals, stable for several months in solution as well as in the solid state, at room temperature and above, as well as being exposed to the atmosphere. The molecular structure features a double-decker cyclophane motif, stabilized by intramolecular π-dimerization of two delocalized benzidinium radical segments. Intermolecular π-dimers are formed in the solid state.

Formation of persistent organic diradicals from N,N′-diphenyl-3,7-diazacyclooctanes