Introduction and Background

Abstract

Iptycenes are a class of aromatic compounds with arene units fused to bicyclo[2.2.2]octatriene bridgehead system. The first and simplest member of this family, triptycene was obtained by Bartlett et al. (J Am Chem Soc 64:2649–2653, 1942) in 1942. In the next 40 years, iptycene chemistry had not attracted much attention, and the studies almost focused on the synthesis and reactions of triptycene and its derivatives. In 1981, Hart et al. [J Org Chem 46(22):4427–4432, 1981] first proposed the concept “iptycene” based on triptycene, denoting the number of arene planes separated by a bridgehead system. Since then, the door of iptycene chemistry has truly been opened, and the potential applications of iptycenes and their derivatives with unique three-dimensional rigid structures have been gradually developed. In recent years, iptycenes and their derivatives, especially triptycenes [3–10] and pentiptycenes [4, 5, 11, 12] have drawn much attention, and more and more applications in molecular machines, supramolecular chemistry, material science, coordination chemistry, sensor applications, and many other research areas have been discovered. It can be believed that iptycene chemistry is winning more and more chemists’ attentions, and walking into its golden age with great opportunities and challenges. In addition, this year also marks the 70^th anniversary for the development of iptycene chemistry (1942–2012).