[2 + 2 + 2] cyclotrimerisation as a convenient route to 6N-doped nanographenes: A synthetic introduction to hexaazasuperbenzenes

Abstract

6N-containing polyphenylene precursors were generated via [2 + 2 + 2] cyclotrimerisation. On methoxy substitution complete ring-closure can be achieved (via FeCl3-mediated oxidative cyclodehydrogenation) to give asymmetric and C3v symmetric hexaazasuperbenzenes. Investigations using DDQ/H+ mediated conditions reveal this to be a promising alternative and selective route to partial cyclodehydrogenation.