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

• Published in: Chemical communications (Cambridge, England) no. 13; pp. 1501 - 1512
• Main Authors: Yang, Jye-Shane, Yan, Jyu-Lun
• Format: Journal Article
• Language: English
• Published: England 01.01.2008
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/b713428m

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.