Since highly condensed symmetric hydrocarbons like corannulene, hexabenzocoronene, [60]fullerene etc. tend to undergo symmetry reduction upon charging by Jahn-Teller distortion, we tested to use bridged triphenylenes to obtain higher spin states. In another approach a new access towards directly connected delocalized radicals and radical ions was predicted as basis towards high spin ground states. Towards easier reducable pi-units extended oligo-semiquinone-methides have been prepared enabling charging to high spin ground states.