Helicenes do not fulfill the 6n + 2 electron count and the supramolecular scaffold with isolated aromatic compounds (by taking a large distance between them) would also show no delocalization between the individual compounds. From Figures and it is apparent that a variety of compound types have been labelled as 3D-aromatic throughout time, yet, is the term meaningful if used that broadly? In our view, there is a high need for a strict definition, and we build on what is known for the closo-boranes, labelled by Aihara as 3D aromatic. We further relate to what is generally accepted for 2D aromaticity (Figure ). Hence, the four necessary conditions for true 3D-aromaticity that all must be fulfilled are (i) (at least) triply degenerate MOs or a closely related orbital topology which exists for tetrahedral or higher symmetry molecules, (ii) a closed-shell electronic structure, which leads to a 6n + 2 electron count for tetrahedral or octahedral molecules (or molecules that are nearly so), (iii) extensive electron delocalization involving the complete molecule leading to a resonance stabilization, and (iv) similar (electronic and magnetic) properties in the three xyz directions. None of these conditions by itself is a sufficient condition. Notably, a definition requiring the fulfilment of all of these conditions is in line with Aihara's original observations for closo-boranes as 3D-aromatics. Now, how do 1 -3 and 1 6+ comply with the essential features and the established definitions for 3D-aromaticity and bicycloaromaticity? As the D3 point group in 1 does not induce triply or higher-order orbital degeneracies, is the aromaticity in 1 -3 and 1 6+ instead related to the Hückel-aromaticity of two-dimensional polycyclic aromatic hydrocarbons (PAHs)? Compounds 1 -3 and 1 6+ are unusual and intriguing, yet, even though their aromatic character is apparent from both experimental and computational observations, the cause of this aromaticity has not been analyzed in depth. In particular, there has been no search for macrocycles that potentially disprove the hypothesis that 1 and its hexacation comply with the 6n + 2 rule for 3D-aromaticity and Hirsch's 2(n + 1) 2 rule for spherical aromaticity. In this work we present a deeper theoretical analysis of 1 -3 and related compounds, along with a computational analysis to establish the precise nature of the aromaticity of these compounds.