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.