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

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A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Date

2022-07-01

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en

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Molecules, Volume 27, issue 13

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.

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Publisher Copyright: © 2022 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

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

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Citation

Partl, G, Rauter, M, Fliri, L, Gelbrich, T, Kreutz, C, Müller, T, Kahlenberg, V, Nerdinger, S & Schottenberger, H 2022, ' A Fluoroponytailed NHC–Silver Complex Formed from Vinyl-imidazolium/AgNO 3 under Aqueous– Ammoniacal Conditions ', Molecules, vol. 27, no. 13, 4137 . https://doi.org/10.3390/molecules27134137