Intriguing Diels–Alder products: chiral centres with an added twist

Abstract

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.