Two chiral fluoranthene-based polyaromatics were isolated from a Diels-Alder cycloaddition between two molecules of 7,9-diphenylcyclopenta[a] acenapthylene-8-one. The two highly coloured, novel compounds were characterized by a combination of spectroscopic techniques and single crystal X-ray diffraction. Structural differences between the unexpected products included the nature of their conjugated fluoranthene portions and the position, strain and handedness of their chiral centres. This journal is