Computational analysis: Here we use quantum chemical calculations to probe the conceptual theories described above. We start by examining the electronic structure and aromaticity of naphthalene (4), puckered naphthalene (5), and the benzocyclooctatetraene dication (6) as 10-electron bicyclic molecules, and connect these to the nonplanar dithiophenobridged octaphyrins 2 and 3 which have one short and two long bridges. Subsequently, we study bicyclic macrocycles with three bridges of (approximately) equal lengths whereby these compounds adopt cage-type structures. We especially analyze compounds that allow us to contest the presumption that 1 and 1 6+ are 3D-aromatics that follow the 6n + 2 and 2(n + 1) 2 rules. At the end, we explore tetrahedral and cubic -conjugated compounds (Figure ) with potentials to be 3D-aromatics.