New types of planar chiral (R-p)- and (S-p)-4,7,12,15-tetrasubstituted [2.2]paracyclophanes were synthesized from racemic 4,12-dihydroxy[2.2]paracyclophane as the starting compound. Regioselective dibromination and transformation afforded a series of planar chiral (R-p)and (S-p)-4,7,12,15-tetrasubstituted [2.2]paracyclophanes, which can be used as chiral building blocks. In this study, left-and right-handed double helical structures were constructed via chemoselective Sonogashira-Hagihara coupling. The double helical compounds were excellent circularly polarized luminescence (CPL) emitters with large molar extinction coefficients, good photoluminescence quantum efficiencies, and large CPL dissymmetry factors.