The electronic properties of a hexaphyrin was finetuned via core-modification leading to the formation of a Hückel aromatic 30π hexaphyrin which incorporates two pyrrole and four furan rings in the π-conjugated pathway. This Hückel aromatic hexaphyrin modified its conformation upon two-electron ring oxidation either with triflic acid or Meerwein salt [Et 3 O] + [SbCl 6 ] À to yield 28π Möbius aromatic dication species. Reversible aromatic transition was established by spectroscopic techniques and further supported by quantum chemical calculations.

We describe a simple strategy to synthesize structurally diverse 38π diradicaloid expanded isophlorinoids with eigth heterocyclic rings.