Synthesis and characterization of one-handed helical oligo( o -phenylene)s: control of axial chirality by planar chiral [2.2]paracyclophane.

Optically active oligo( o -phenylene)-layered molecules were synthesized from planar chiral enantiopure [2.2]paracyclophane. Their structures and optical properties were characterized by experimental and theoretical approaches. The axial chiralities between phenylene rings of the oligo( o -phenylene)s were controlled by the planar chirality to form one-handed helical structures. The o -quinquephenyl-layered molecule was emissive, and circularly polarized luminescence was observed with a high anisotropy factor (| g lum | value) of 0.012.