Pillar[5]arene-Based Dual Chiral Organoboranes with Allowed Host–Guest Chemistry and Circularly Polarized Luminescence

We first describe two examples of highly luminescent organoboranes (NP5BN1 and NP5BN2) with dual chirality that were achieved by molecular functionalization of planar chiral pillar[5]arenes with naphthyls. Sufficiently strong steric effects are imposed by triarylamine (Ar3N) and triarylborane (Ar3B) moieties and further enhanced by the proximity of the chiral building blocks, leading to the isolation of multiple enantiomers via chiral high-performance liquid chromatography. The intramolecular charge transfer from N-donor to B-acceptor across both chiral subunits enabled the circularly polarized luminescence and thermally robust colorimetric responses in their emissions. Furthermore, their remarkable host–guest chemistry was allowed at no expense in the pursuit of advanced chiroptical properties using pillar[5]arene-based supramolecular scaffolds.