Synthesis of optically active folded cyclic dimers and trimers

Optically active higher-ordered structures, such as one-handed helical and propeller-shaped structures, can be constructed by folding the π-conjugated system using [2.2]paracyclophane as the chiral crossing unit, leading to circularly polarized luminescence (CPL) properties. Chiral cyclic dimers and trimers were synthesized using planar chiral [2.2]paracyclophane-containing enantiopure ribbon-shaped compounds as the chiral monomers. Unicursal π-conjugated systems were folded at the [2.2]paracyclophane units, and exhibited good photoluminescence quantum efficiencies and CPL anisotropy factors. Opposite chiroptical properties were observed between the dimer and trimer, despite the same absolute configuration of the planar chiral [2.2]paracyclophane units, which was reproduced by theoretical studies.