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

doi:10.3390/molecules27134137

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

University of Innsbruck
Infineon Technologies Austria AG
Novartis

Research output: Contribution to journal › Article › Scientific › peer-review

2 Citations (Scopus)

135 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 language	English
Article number	4137
Journal	Molecules
Volume	27
Issue number	13
Early online date	28 Jun 2022
DOIs	https://doi.org/10.3390/molecules27134137
Publication status	Published - 1 Jul 2022
MoE publication type	A1 Journal article-refereed

Funding

Funding: This work was supported by the the Austrian Research Promotion Agency FFG (West Austrian BioNMR, 858017 to C.K.) and funded by Sandoz GmbH under academic cooperation project P7240-013-0033 “Crystal Engineering”.

Keywords

cationic fluorosurfactant
crosslinker
fluoroponytail
N-heterocyclic carbene
silver

Access to Document

10.3390/molecules27134137Licence: CC BY

CHEM_Partl_et_al_A_Fluoroponytailed_NHC-Silver_Complex_2022_MoleculesFinal published version, 888 KBLicence: CC BY

Cite this

@article{99a25996d9ee4f208fbc1bf81de6420d,

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

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.",

keywords = "cationic fluorosurfactant, crosslinker, fluoroponytail, N-heterocyclic carbene, silver",

author = "Gabriel Partl and Marcus Rauter and Lukas Fliri and Thomas Gelbrich and Christoph Kreutz and Thomas M{\"u}ller and Volker Kahlenberg and Sven Nerdinger and Herwig Schottenberger",

note = "Publisher Copyright: {\textcopyright} 2022 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2022",

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doi = "10.3390/molecules27134137",

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TY - JOUR

T1 - A Fluoroponytailed NHC–Silver Complex Formed from Vinyl-imidazolium/AgNO3 under Aqueous– Ammoniacal Conditions

AU - Partl, Gabriel

AU - Rauter, Marcus

AU - Fliri, Lukas

AU - Gelbrich, Thomas

AU - Kreutz, Christoph

AU - Müller, Thomas

AU - Kahlenberg, Volker

AU - Nerdinger, Sven

AU - Schottenberger, Herwig

PY - 2022/7/1

Y1 - 2022/7/1

N2 - 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.

AB - 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.

KW - cationic fluorosurfactant

KW - crosslinker

KW - fluoroponytail

KW - N-heterocyclic carbene

KW - silver

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