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

Abstract

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 (|glum| value) of 0.012.