One and two electron oxidation of N,N',N '',N'''-tetramethyl-1,5,12,16-tetraaza[5,5]paracyclophane (Me3C), a bis-trimethylene bridged bis-p-phenylene diamine (PD), and its ethyl and isopropyl analogues are discussed. The monocation and dication are both stable, as demonstrated by optical studies that show they are in equilibrium in solution with an especially small difference in first and second oxidation potentials for Me3C in MeCN (+23 to -20 mV, measured by simulation of the optical spectrum and of the cyclic voltammogram, respectively).