Polyhedral Phenylacetylenes: The Interplay of Aromaticity and Antiaromaticity in Convex Graphyne Substructures

We have studied a series of bridged phenylacetylene macrocycles with topologies based on Platonic and Archimedean polyhedra, using density functional calculations to determine both their molecular structure and their electronic response to external magnetic fields (NICS maps). We are able to elucidate the interplay of aromaticity and anti-aromaticity as a function of structural parameters, in particular the symmetry properties of the intramolecular bond connectivities, in these compounds.