Planar Chiral [2.2]Paracyclophanes: Optical Resolution and Transformation to Optically Active π-Stacked Molecules

In this article, our recent results from practical optical resolution methods of disubstituted and tetrasubstituted [2.2]paracyclophane compounds and their transformations are described. The obtained enantiopure [2.2]paracyclophane compounds have been used as chiral building blocks to prepare optically active π-stacked molecules. π-Stacked molecules construct optically active second-ordered structures, such as V-, N-, M-, X-, triangle-shaped, and one-handed double helical structures, due to the orientation of stacked π-electron systems. They emit circularly polarized luminescence (CPL) by photo-excitation. [2.2]Paracyclophane-based chiral π-stacked molecules in this article emit brightly owing to good photoluminescence (PL) quantum efficiencies as well as large molar extinction coefficients. In particular, emission is of course CPL with a large disymmetry factor (glum value). It is basically difficult to achieve CPL with high brightness, high PL efficiency, and large glum value by using other chiral scaffolds; therefore, planar chiral [2.2]paracyclophane is an ideal scaffold to be an excellent CPL emitters.