B,N-Embedded Helical Nanographenes Showing an Ion-Triggered Chiroptical Switching Function

Intramolecular oxidative aromatic coupling of 3,6-bis(m-terphenyl-2'-yl)carbazole provided a bis(m-terphenyl)-fused carbazole, while that of 3,6-bis(m-terphenyl-2'-yl)-1,8-diphenylcarbazole afforded a bis(quaterphenyl)-fused carbazole. Borylation of the latter furnished a B,N-embedded helical nanographene binding a fluoride anion via a structural change from the three-coordinate boron to the four-coordinate boron. The anionic charge derived from the fluoride anion is stabilized over the expanded π-framework, which leads to the high binding constant (K_a) of 1×10⁵ M^-1. The four-coordinate boron species was converted back to the parent three-coordinate boron species with Ag⁺, and the chiroptical switch between the three-coordinate boron and four-coordinate boron species has been achieved via the ion recognition with the change in the color and g_lum values.