Synthesis and structure of a twisted, colossal quinone

A very large quinone was prepared by the double Diels–Alder reaction of 2,5,9,12-tetra(t-butyl)diacenaphtho[1,2-b:1′,2′-d]thiophene and benzoquinone. The crystal structure of the polycyclic product shows that the central anthraquinone ring system is quite twisted (50°), and the overall structure possesses approximate D2 symmetry.