Applying the B/N Lewis Pair Approach to Access Fusion-Expanded Binaphthyl-Based Chiral Analogues.

We herein describe the synthesis of two axially chiral systems ( HBN and BBN ) by the incorporation of B centers into binaphthyl derivatives ( HPy and BPy ). Heteroatom-doped chiral polycyclic aromatic hydrocarbons were thus formed by fusion of the azaboroles to binaphthyls with the formation of B-N dative bonds. The resulting B-N Lewis pairs that serve as attractive fluorophores enabled modulation of the chiroptical properties both in solution and in the solid state.