Construction of helical structures with planar chiral [2.2]paracyclophane: fusing helical and planar chiralities

Abstract

Optically active conjugated molecules bearing one-handed helical structures, in which two [4]helicenes or two phenanthrenes are stacked at terminal benzene moieties, were prepared using enantiopure [2.2]paracyclophane as a chiral scaffold. The obtained molecules exhibited excellent chiroptical properties such as circularly polarized luminescence with high disymmetry factors. Planar chiral pseudo-meta-disubstituted [2.2]paracyclophane was also optically resolved on the sub-gram-scale.