The reduction of nine symmetric dicyanoaromatic radical anions by sodium amalgam in the presence of cryptand[2.2.2] was studied using cyclic voltammetry and using optical and electron paramagnetic resonance (EPR) spectroscopies in two aprotic solvents. All radicals are charge-delocalized (Class III) mixed valence species, as shown by the weak solvatochromism of their low-energy optical bands and by the vibrational structure exhibited by most of the bands. The maximum of the low-energy optical transition decreases logarithmically with the number of bonds (n) between cyano groups in a series of p-phenylene-bridged radicals, from p-phenyl (n = 5) to p-quaterphenyl (n = 17), although the energy of the latter lies higher than the value predicted by the linear regression. The energy of this band decreases linearly with the cos 2 value of the torsion angle between phenyl rings in the spectra of biphenyl-4,4′-dicarbonitrile radical anion and their methyl-substituted derivatives. The fact that charge delocalization is maintained in radicals with non-Kekulé bridges, with unusually large bridges and with bridges with highly twisted biphenyl systems suggests that cyano charge-bearing units have small reorganization energies and induce high electronic couplings through the bridges.