Synthesis, Structure, and Properties of a Nitrogen–Boron–Nitrogen-Embedded Polycyclic π-System Containing a Pleiaheptalene Framework

A novel polycyclic π-system (1) featuring both a pleiaheptalene framework (a three-fused heptagon system) and nitrogen–boron–nitrogen (NBN) unit was constructed by electrophilic borylation. A combined experimental and computational study demonstrated that 1 has a highly twisted π-backbone with approximate C2 symmetry, which can undergo conformational isomerization at room temperature in contrast to pleiaheptalene. It was also found that 1 can bind the fluoride ion in the solution, which induces changes in the absorption and emission spectra.