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

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Published copy (DOI)

Author(s)

  • Martin Tlustý
  • Petr Slavík
  • Hana Dvořáková
  • Václav Eigner
  • Pavel Lhoták

Department/unit(s)

Publication details

JournalTetrahedron
DateAccepted/In press - 9 Jan 2017
DateE-pub ahead of print - 12 Jan 2017
DatePublished (current) - 2 Mar 2017
Issue number9
Volume73
Number of pages8
Pages (from-to)1230-1237
Early online date12/01/17
Original languageEnglish

Abstract

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.

    Research areas

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

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