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• Invited Article •

Advances on Synthesis and Applications of Iptycenes and Their Derivatives

Cao Jing, Jiang Yi, Chen Chuan-Feng   

  1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
  • Received: Online: Published:
  • Contact: Chen Chuan-Feng E-mail:cchen@iccas.ac.cn
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Iptycenes and their derivatives are a class of structurally unique compounds consisting of more than three arene units fused together through a bicyclooctatriene framework. Iptycene is also extended triptycene, and it can be named after the number of arene planes separated by a bridgehead system. Pentiptycenes with five arene units are the most common members of iptycenes, and pentiptycene quinones are the most studied iptycene derivatives. Since they possess a rigid, aromatic, and three dimensional scaffold, iptycenes and their derivatives have been found more and more specific applications in supramolecular chemistry, material chemistry, molecular machines, etc. In this review, the synthesis of iptycenes, iptycene quinones and their derivatives is first highlighted, and then the recent progress in the applications of iptycene derivatives in conjugated polymeric materials, organic porous and low dielectric constant materials, chemical sensors, monolayer assemblied structures, molecular machinery, and supramolecular chemistry based on novel synthetic hosts are introduced.

Contents
1 Introduction
2 Synthesis of iptycenes and their derivatives
2.1 Synthesis of iptycenes
2.2 Synthesis of iptycene quinones
2.3 Derivatization of iptycene quinones
3 Applications of iptycenes and their derivatives
3.1 Conjugated polymeric materials
3.2 Organic porous and low dielectric constant materials
3.3 Chemical sensors
3.4 Monolayer assemblied structures
3.5 Molecular machinery
3.6 Supramolecular chemistry based on novel synthetic hosts
4 Conclusions and outlook

Key words: iptycene, synthesis, application, host, supramolecular chemistry

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