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
N1 - Publisher Copyright:
© 2022 by the authors. Licensee MDPI, Basel, Switzerland.
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
UR - http://www.scopus.com/inward/record.url?scp=85133465422&partnerID=8YFLogxK
U2 - 10.3390/molecules27134137
DO - 10.3390/molecules27134137
M3 - Article
AN - SCOPUS:85133465422
SN - 1420-3049
VL - 27
JO - Molecules
JF - Molecules
IS - 13
M1 - 4137
ER -