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Synthesis of 1-[1H,1H,2H,2H-perfluooctyl]-3-[2-(oxiran-2-yl)ethyl]imidazolium 4-[(2-oxiran-2-yl)ethoxy]benzenesulfonate as a New Perfluorinated Ionic Monomer

1
Laboratoire de Chimie Moléculaire et Thio-Organique (LCMT), Normandie Université, ENSICAEN, UNICAEN, UMR CNRS 6507, 6 Boulevard Maréchal Juin, 14050 Caen, France
2
Université de Lyon, CNRS, Université Claude Bernard Lyon 1, INSA Lyon, Université Jean Monnet, UMR 5223, Ingénierie des Matériaux Polymères, CEDEX 04, 69621 Villeurbanne, France
*
Authors to whom correspondence should be addressed.
Academic Editor: Fawaz Aldabbagh
Molbank 2022, 2022(3), M1409; https://doi.org/10.3390/M1409
Received: 18 June 2022 / Revised: 11 July 2022 / Accepted: 13 July 2022 / Published: 15 July 2022
(This article belongs to the Section Organic Synthesis)
Access to perfluorinated compounds represents a growing challenge in the academic and industrial fields to achieve target compounds with specific physico-chemical properties. Especially, the insertion of a perfluorinated chain within an ionic liquid can provide improvements not just in terms of hydrophobicity and lipophobicity, but also viscosity, density as well as thermal stability. In this research area, we have recently developed new access points to several epoxy imidazolium salts combined with fluorinated anions such as bistriflimide (NTf2), hexafluorophosphate (PF6) or tetrafluoroborate (BF4). Here, we reported the synthesis of a perfluorinated imidazolium cation associated with a sulfonate anion as a new functionalized partner. This sequence required four steps from imidazole (cationic part) and three steps from sodium 4-hydroxybenzenesulfonate (anionic part), respectively. This perfluorinated ionic liquid was fully characterized by nuclear magnetic resonance with 1H-NMR, 19F-NMR, 13C-NMR, DEPT, COSY, HSQC, HMBC and IR spectroscopy. The two parts of the salt were confirmed by high-resolution mass spectrometry (HRMS), and we combined thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) to determine the thermal properties of this new compound. View Full-Text
Keywords: perfluorinated imidazolium; sulfonate; epoxides; ionic liquid perfluorinated imidazolium; sulfonate; epoxides; ionic liquid
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MDPI and ACS Style

Kui, T.; Livi, S.; Baudoux, J. Synthesis of 1-[1H,1H,2H,2H-perfluooctyl]-3-[2-(oxiran-2-yl)ethyl]imidazolium 4-[(2-oxiran-2-yl)ethoxy]benzenesulfonate as a New Perfluorinated Ionic Monomer. Molbank 2022, 2022, M1409. https://doi.org/10.3390/M1409

AMA Style

Kui T, Livi S, Baudoux J. Synthesis of 1-[1H,1H,2H,2H-perfluooctyl]-3-[2-(oxiran-2-yl)ethyl]imidazolium 4-[(2-oxiran-2-yl)ethoxy]benzenesulfonate as a New Perfluorinated Ionic Monomer. Molbank. 2022; 2022(3):M1409. https://doi.org/10.3390/M1409

Chicago/Turabian Style

Kui, Tony, Sébastien Livi, and Jérôme Baudoux. 2022. "Synthesis of 1-[1H,1H,2H,2H-perfluooctyl]-3-[2-(oxiran-2-yl)ethyl]imidazolium 4-[(2-oxiran-2-yl)ethoxy]benzenesulfonate as a New Perfluorinated Ionic Monomer" Molbank 2022, no. 3: M1409. https://doi.org/10.3390/M1409

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