Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates

We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF3K and B(Mes)(2). Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.

Automated summary

Two synthetic strategies were developed to synthesize triptycene-derived bulky boranes, boronates, and boron ate-complexes with various boron substituents. The study showed the quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds through single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements.