Synthesis and study of calix[4]arenes bearing azo moieties at the meta position

Martin Tlustý, Petr Slavík, Hana Dvořáková, Václav Eigner, Pavel Lhoták*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Direct mercuration and subsequent transformation of organomercurial intermediates into the corresponding nitroso derivatives enabled the construction of calix[4]arenes bearing azo moieties at the meta position (to the alkoxy groups). These compounds, representing a unique substitution pattern in calixarene chemistry, showed very unusual dynamic behaviour in solution. Temperature dependent1H NMR spectra confirmed that the introduction of two bulky moieties (or even just one) into the meta position of calix[4]arene led to the rigidification of the molecule as demonstrated by complete arrest of the typical pinched cone – pinched cone interconversion in solution. The rigidified molecules can be used as ligands capable of cation−π interactions with N-methylpyridinium salts.

Original languageEnglish
Pages (from-to)1230-1237
Number of pages8
Issue number9
Early online date12 Jan 2017
Publication statusPublished - 2 Mar 2017


  • Azocompounds
  • Calixarene
  • Conformational behaviour
  • DynamicH NMR
  • Mercuration
  • meta-Substitution

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