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Triptycene-Derived Macrocyclic Arenes

From Calixarenes to Helicarenes
  • Ying Han
  • Chuan-Feng ChenEmail author
Living reference work entry

Abstract

With unique structural features, easy functionalization, and wide applications, macrocyclic arenes, including calixarenes, resorcinarene, cyclotriveratrylene, pillararenes, and their analogues, have attracted much attention and also become one of the most important and studied synthetic macrocyclic hosts during the last decades. Triptycene has been proved to be useful building block for the development of new synthetic hosts with specific structures and properties. Consequently, a series of triptycene-derived calixarenes, heteracalixarenes, tetralactam macrocycles, and their analogues have conveniently been synthesized with satisfactory yields by one-pot method or two-step fragment-coupling reactions. Moreover, the triptycene-derived macrocyclic hosts had large enough cavities and showed fixed conformation in solution. These structural features made them exhibit not only well molecular recognition properties toward small organic molecules, fullerenes, and organic dyes but also wide potential applications in self-assemblies. Especially, we have recently developed a new kind of chiral macrocyclic arenes named as helicarenes based on chiral 2,6-dihydroxyl-substituted triptycene subunits bridged by methylene groups. It was found that the helicarenes exhibited convenient synthesis, high stability, good solubility, fixed conformation, easy functionalization, and wide complexation with different kinds of chiral and achiral organic guests. In particular, the switchable complexation based on these macrocycles could be efficiently controlled by multi-stimuli including acid-base, redox, anion, or light stimulus in the presence of photoacid. Moreover, the helicarenes could also show potential applications in molecular assembly and molecular machines.

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Copyright information

© Springer Nature Singapore Pte Ltd. 2019

Authors and Affiliations

  1. 1.Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and FunctionInstitute of Chemistry, Chinese Academy of SciencesBeijingChina
  2. 2.University of Chinese Academy of SciencesBeijingChina

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