Cyclic voltammetry and ESR studies reveal the nature of the cation radicals of some 1, 3, 5- tris (diarylamino) benzenes. Results show effectively delocalized radical cations with long solution lifetimes in cold media but with much less kinetic stability at ambient temperature than their monomeric triarylaminium cation radical counterparts. Intramolecular ortho coupling, perhaps via disproportionation, is a postulated cation radical decay mode.