Synthesis of optically active π-stacked compounds based on planar chiral tetrasubstituted [2.2]paracyclophane

Abstract

Optically active X-shaped compounds based on planar chiral [2.2]paracyclophane were synthesized. These compounds composed of two different π-electron systems stacked at central aromatic rings through chemoselective Sonogashira–Hagihara coupling. The optical and chiroptical properties of the obtained compounds were investigated, which exhibited large molar absorption coefficients, good photoluminescence quantum efficiency, and intense circularly polarized luminescence (CPL) with large dissymmetry factors on the order of 10⁻³, indicating that the compounds are excellent CPL emitters.