Rational building strategies and appropriate synthons have been developed for the use of triptycene as a rigid presenting scaffold. Palladium catalyzed cross-coupling reactions such as, Sonogashira and Suzuki couplings were used to install a variety of different synthetic handles around the triptycene periphery in a high yielding and controlled manner. These triptycene molecular handles were investigated for their potential in the construction of molecular arrays with defined spatial orientation e.g., for host-guest interactions or drug delivery systems. Such molecular synthons afforded expansion from the triptycene core employing arm extension increasing the internal free volume characteristic of triptycene scaffolds for such applications. In addition a range of mesogenic and glycosyl triptycene derivatives were achieved as a synthetic proof of concept for future work on potential drug delivery systems.