Naphthyl-Separated Stone–Wales Defect-Type Nanographene via Scholl Cyclization of Tetra(1-naphthyl)naphthalene

The Scholl-type oxidative cyclodehydrogenation of tetra(1-naphthyl)naphthalene furnishes a defect nanographene containing two formal azulene subunits formed via a 1,2'-naphthyl rearrangement. X-ray crystallography reveals a negatively curved polycyclic framework that forms a columnar packing motif in the solid state. Electrochemical analysis shows two reversible oxidations and three reductions, highlighting the redox amphoteric character of the compound. Spectroscopic and computational studies suggest that the formal azulene subunits behave like electronically isolated pentagonal and heptagonal rings.