To achieve a planar octaphyrin-based macrobicyclic species, the DTT bridge was replaced by a shorter butadiyne bridge and the two pyrrole rings adjacent to the bridgehead C atoms were linked pairwise via methylene bridges. This leads to the D2h symmetric molecule 7, a compound that displays only a perimetric ring current with current densities in the range 23 -33 nAT -1 (Figure ). To achieve a differentiation between the two 22-electron macromonocycles in a near-planar macrobicycle, we replaced two CH moieties on one side by two SiH moieties, leading to 8. According to ACID, two clockwise ring-currents can be detected for this species; one over the perimeter and one over one of the 22-electron cycles (Figure ). As seen visually, the 22-electron cycle with the stronger ring current is the ring with CH units. The NICS-XY scans also show that the aromatic character of one of the two macromonocycles decreases when going from 7 to 8. Hence, there is an imperfect cancellation of the two 22-electron ring-currents in the butadiyne-bridge of 8, analogous to the situation in 6 (Figure ). GIMIC reveals current strengths of 11.7 -14.4 nAT -1 at this bridge. Interestingly, EDDB reveals that the extent of delocalization in the two macromonocycles of 8 are, respectively, larger and smaller than in the two equivalent macromonocycles of 7 (Figure ). Furthermore, Kim and co-workers argued that the triplet state of the dication of 2