indicating only minor generation of aromaticity noting that the charge is distributed over both rings. To explain this behavior, it is worth noting that the triplet dianion can be seen as being formed from two independent PCT rings that are both doublet monoanions exhibiting slight global aromaticity. In contrast, the singlet dianion is more closely related to the combination of a dianion PCT with a neutral PCT, and its slightly higher energy can be related to the repulsion of the two electrons within the LUMO of one PCT unit. More pronounced shielding components are seen for the trianion (-16.9 / -21.7 ppm) and singlet tetraanion (-34.1 / -36.4 ppm). The latter values closely resemble the shielding of -38.7 ppm observed for the dianion of isolated PCT, highlighting the minimal influence of the thiophene and second PCT on the electronic structure. Within Figure , it is the triplet tetraanion that clearly sticks out. This state is formed as a combination of a singlet and a triplet dianion, where the former is Hückel aromatic and the latter is Baird antiaromatic. Consequently, the triplet tetraanion possesses one strongly aromatic and one strongly antiaromatic ring. The antiaromaticity is also reflected by its more unfavorable redox potential of -2.81 V. Analogous results on PCT-2T-PCT are presented in the Supporting Information section 10. These results are very similar to those obtained for PCT-T-PCT, highlighting the minimal influence of the second thiophene unit.