Stable N,N'-Diarylated Dihydrodiazaacene Radical Cations.

Three stable N,N' -diarylated dihydroazaacene radical cations were prepared by oxidation of neutral N,N' -diarylated dihydroazaacenes synthesized via palladium-catalyzed Buchwald-Hartwig aminations of aryl iodides with N,N' -dihydroazaacenes. Both neutral as well as oxidized species were investigated via UV-vis spectroscopy, single crystal analysis, and DFT calculations. All the radical cations are surprisingly stable - their absorption spectra in dichloromethane remain unchanged in ambient conditions for at least 24 hours.