A Fluoroponytailed NHC–Silver Complex Formed from Vinyl-imidazolium/AgNO3 under Aqueous– Ammoniacal Conditions

Gabriel Partl, Marcus Rauter, Lukas Fliri, Thomas Gelbrich, Christoph Kreutz, Thomas Müller, Volker Kahlenberg, Sven Nerdinger*, Herwig Schottenberger*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

2 Citations (Scopus)
83 Downloads (Pure)

Abstract

3-(1H,1H,2H,2H-Perfluorooctyl)-1-vinylimidazolium chloride [2126844–17–3], a strong fluorosurfactant with remarkably high solubility in water, was expediently converted into the respective doubly NHC-complexed silver salt with nitrate as counter ion in quantitative yield. Due to its vinyl substituents, [bis(3-(1H,1H,2H,2H-perfluorooctyl)-1-vinylimidazol-2-ylidene)silver(I)] nitrate, Ag(FNHC)2NO3, represents a polymerizable N-heterocyclic carbene transfer reagent, thus potentially offering simple and robust access to coordination polymers with crosslinking metal bridges. The compound was characterized by infrared and NMR spectroscopy, mass spectrometry as well as elemental analysis, and supplemented by X-ray single-crystal structure determination. It crystallizes in the monoclinic crystal system in the space group P21/c. With 173.3, the geometry of the Ag-carbene bridge deviates slightly from linearity. The disordered perfluoroalkyl side chains exhibit a helical conformation.

Original languageEnglish
Article number4137
JournalMolecules
Volume27
Issue number13
Early online date28 Jun 2022
DOIs
Publication statusPublished - 1 Jul 2022
MoE publication typeA1 Journal article-refereed

Keywords

  • cationic fluorosurfactant
  • crosslinker
  • fluoroponytail
  • N-heterocyclic carbene
  • silver

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