Two synthetic strategies towards bulky boranes, boronates and boron ate‐complexes derived from triptycenes have been developed. These approaches started from borylated or brominated anthracenes and involved a Br/Li exchange and [4+2] cycloaddition reaction with in‐situ generated benzyne to produce a series of triptycene boronates and borates substituted in positions 1 or 9 with various boron substituents such as BPin, Bneo, BF 3 K and B(Mes) 2 . X‐ray diffraction crystallographic analysis and UV‐Vis/fluorimetric measurements provided quantitative information on the effect of the triptycene scaffold on their structure and their photophysical and electronic properties.
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