Radially π-Extended Pyrrole-Fused Azacoronene: A Series of Crystal Structures of HPHAC with Various Oxidation States

Radially pi-extended hexapyrrolohexaazacoronene (HPHAC 2) was synthesized in two steps with 2,5-di-tert-butyl-acenaphtho[1,2-c]pyrrole and hexafluorobenzene. Like its parent HPHAC 1a, 2 exhibited reversible oxidation behavior. Crystal structures of not only the neutral and dicationic compounds but also the radical cation were all revealed. While analyzing its peculiar structure, the formation of a 1:1 complex with C-60 was observed in solution by NMR and absorption analyses. The spectroscopic analyses of 2 and la were performed based on magnetic circular dichroism and theoretical calculations.

Automated summary

A new compound HPHAC 2 was synthesized, exhibiting reversible oxidation behavior, and its crystal structures and formation of a complex with C-60 were revealed. Spectroscopic analyses were performed based on magnetic circular dichroism and theoretical calculations.