Central-ring functionalization and application of the rigid, aromatic, and H-shaped pentiptycene scaffold.

The progress of pentiptycene chemistry is reviewed. Pentiptycene belongs to the iptycene family and possesses a rigid, aromatic, and H-shaped scaffold. An important feature for pentiptycene vs. triptycene is the presence of a 'sterically shielded' central benzene ring. Such a feature has led to the use of pentiptycene as a conformational regulator and in the formation of functional molecules, including fluorescent chemosensors, molecular machines, low dielectric constant materials, and porous solids. The synthesis of these materials relies on central-ring prefunctionalized pentiptycene building blocks. A useful approach toward the preparation of these building blocks is the derivatization of pentiptycene quinone.