Nonplanar dithiopheno-bridged octaphyrins as expanded naphthalenes: The fact that naphthalene exhibits two circuits with six -electrons and one with ten becomes apparent through electronic aromaticity indices. EDDB reveals delocalization through both the perimeter and the central CC bond (4, Figure ), and as the electronic structure is a superposition of the -dectet and the two -sextet resonance forms, the EDDB-based percentage effectiveness of cyclic delocalization of -electrons in each cycle is similar. In contrast, and as noted above, magnetic indices give an obscured picture since the induced ring currents from the two hexagons circuits of 4 cancel each other perfectly in the central CC bond (Figure ). This is also clear from the current densities obtained with GIMIC as the average current strength in the perimeter bonds is ~13 nAT -1 (diatropic) while the current strength in the central CC bond is nil (for a definition of the strengths of the integrated current densities see ref. 86). Yet, when gradually distorting one of the hexagons leading to a puckered Cs symmetric structure (5, Figure ) the ring current in the puckered hexagon is attenuated whereby the two 6-electron ring currents do not cancel anymore and a current density in the inter-ring CC bond emerges (for current densities of gradually more distorted naphthalenes see Tables and). One can also see that the -electron delocalization is very attenuated in the puckered hexagon while it is enhanced in the planar hexagon (Figure ). Yet, it is also possible to achieve a differentiation in the 6-electron currents, and a current density in the inter-ring CC bond, by going to the nearly planar benzocyclooctatetraene dication (6, Figure ). For 6, a NICS-XY scan shows that the local 6-electron aromaticity in the hexagon dominates over that in the octagon (Figure ), whereby the resulting current density in the central CC bond is 4.7 nAT -1 . Clearly, a structural differentiation between the two 6-electron cycles, achieved either by distortion or altered ring size, provides for a differentiation in the ring currents of the two cycles, leading to an imperfect cancellation of the currents in the inter-ring CC bond. In 2 and 3, the dissimilarities between the two 26-electron cycles come about because of the orientation of the dithienothiophene (DTT) bridge which leads to a better -conjugation with one half of the octaphyrin than with the other half, reflected in C-C-C-C dihedral angles to the DTT bridge which are 7 and 33º, respectively. This provides a better electron delocalization in one 26-electron cycle than in the other (41.7 vs. 35.6%), although the best delocalization is along the perimeter (42.5%).