Synthesis of Substituted Iptycenes

Abstract

Iptycenes are a class of aromatic compounds that contain several arene units fused to a bicyclo[2.2.2]octatriene bridgehead system. This unique, rigid, three-dimensional molecular structure provides several open electron-rich cavities with an abundance of reactive positions, and makes them useful for a wide range of applications. There is no doubt that the synthesis and reactions of iptycene derivatives with different functional groups form the fundamental basis of iptycene development. In this account, the synthesis of substituted iptycenes is described. In particular, the different synthetic strategies toward substituted triptycenes and pentiptycenes are the main focus. 1 Introduction 2 Synthesis of Substituted Triptycenes 2.1 Direct Diels–Alder Addition Reactions 2.2 Selective Substitution of the Triptycene Skeleton 2.2.1 Acetylation 2.2.2 Nitration 2.2.3 Halogenation 3 Synthesis of Substituted Pentiptycenes 4 Synthesis of Other Substituted Iptycenes 5 Conclusion and Outlook