New oxacalix[4]arene carboxylate detects viologen in protic media

Anna Peterson, Mari Liis Ludvig, Jevgenija Martõnova, Sandra Kaabel, Paul Kerner, Merle Uudsemaa, Aleksander Trummal, Maria Fomitšenko, Tõnis Pehk, Riina Aav, Jasper Adamson*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

3 Citations (Scopus)

Abstract

We demonstrate that Ullman fragment-coupling can be used to synthesise an oxacalix[4]arene monocarboxylic acid, which provides easy access to its water-soluble carboxylato derivatives. Crystallographic and computational data suggest that the new carboxyl-substituted oxacalix[4]arene adopts a 1,3-alternate conformation both in the solid-state and in methanol solution. Its water-soluble tetrabutylammonium derivate can detect the herbicide paraquat at neutral pH in aqueous media (K a = 111 ± 3 M–1) and in methanol (K a = 2020 ± 70 M–1).

Original languageEnglish
Pages (from-to)313-319
Number of pages7
JournalSupramolecular Chemistry
Volume32
Issue number5
DOIs
Publication statusPublished - 3 May 2020
MoE publication typeA1 Journal article-refereed

Keywords

  • 1,3-alternate conformation
  • herbicide sensing
  • Oxacalix[4]arene carboxylate

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