First experimental evidence of 3-D aromaticity in stacked antiaromatic compounds

Aromatic molecules consist of planar carbon-based rings with alternating single and double (π) bonds. These molecules contain 4n+2 (n = 0, 1, 2 …) π electrons—π electrons are those involved in π bonds—which results in high stability because the π electrons delocalize over the ring structure. Aromatic molecules can interact through offset π-π stacking, and the overlap of π orbitals in aromatic structures with π-π stacking can facilitate electron conduction, making such materials attractive for use in electronics. The overlap between π orbitals would be increased if π-π stacking was face-to-face rather than offset. However, face-to-face stacking is energetically unfavorable in aromatic molecules because of the repulsion of π electrons.