Optical resolution of pseudo-para-disubstituted [2.2]paracyclophane: a chiral building block for optically active helicene-stacked molecules emitting circularly polarized luminescence

Abstract

Optical resolution of pseudo-para-disubstituted [2.2]paracyclophane was achieved using the diastereomer method. Optically active π-stacked molecules consisting of phenanthrene and benzo[c]phenanthrene were synthesized using the enantiopure pseudo-para-disubstituted [2.2]paracyclophanes as chiral building blocks. Helicity was induced on the stacked phenanthrene and benzo[c]phenanthrene moieties by the planar chiral [2.2]paracyclophane, and the molecule formed an optically active S-shaped structure. The S-shaped molecule emitted circularly polarized luminescence, which was compared with that of the corresponding optically active U-shaped molecule prepared from pseudo-meta-disubstituted [2.2]paracyclophane.