Synthesis of a π-extended azacoronene composed of naphthalene and acenaphtho[1,2-c]pyrrole toward a chiral curved π structure

Abstract

[Formula: see text]-Extended azacoronene has been synthesized via an S[Formula: see text]Ar reaction using acenaphthopyrrole and octafluoronaphthalene utilizing successive Scholl reactions. Although the chiral conformers could not be isolated, the new azacoronene analog exhibited longer-wavelength absorption and reversible oxidation properties, which are characteristic of pyrrole-fused azacoronenes. When combined with the results of our DFT calculations, the experimental results indicate weaker global aromaticity than that of previously reported azacoronenes.