Pyrrole-Fused Azacoronene Analog with Sulfur Embedded in the Outer Periphery.

The synthesis of sulfur-embedded hexapyrrolohexaazacoronene (HPHAC) analog and its corresponding desulfurized and rearranged compounds was achieved from tetrafluoroisothianaphthene. Structures of all the new π-skeletons were determined by X-ray crystallography. Comparison of the electronic spectrum of with those of its derivatives revealed less involvement of the sulfur atom in π-conjugation. Similar to the reference HPHAC (), compound and its derivatives exhibited reversible oxidation behavior. The aromaticity of both neutral and dication states has been investigated through DFT calculations.