The electronic properties of a hexaphyrin was fine-tuned 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 [Et3 O]+ [SbCl6 ]- to yield 28π Möbius aromatic dication species. Reversible aromatic transition was established by spectroscopic techniques and further supported by quantum chemical calculations.
Keywords: Annulenes; Aromaticity; Heterocycles; Porphyrinoids; Spectroelectrochemistry.
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