New aryl-containing fluorinated sulfonic acids and their ammonium salts, useful as electrolytes for fuel cells or ionic liquids

Arvai, Roman; Toulgoat, Fabien; Médebielle, Maurice; Langlois, Bernard R.; Alloin, Fannie; Iojoiu, Cristina; Sanchez, Jean‐Yves

doi:10.1016/j.jfluchem.2008.06.009

Cited by 28 publications

(11 citation statements)

References 17 publications

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“…[171] Alkaline hydrolysis into the corresponding sulfonic acids was also reported for benzyl sulfonyl fluoride, [172] danzyl fluoride, [173] and other perfluoroalkyl-substituted derivatives. [174] Intramolecular SuFEx reaction is especially interesting since it provides an access to pharmaceutically relevant sultams. Thus, saturated aminoheterocycles 19 bearing a sulfonyl fluoride group easily underwent cyclization to bridged bicyclic sultams 20 (Scheme 15, B).…”

Section: Applications In Synthetic and Medicinal Chemistrymentioning

confidence: 99%

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

2021

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Current medicinal chemistry relies heavily on the quality of building blocks, i. e. reagents used to introduce chemical diversity into the target molecules. The last decade witnessed an emergence of many novel (or well-overlooked old) chemotypes for drug discovery, which is related to adapting new synthetic methodologies, designing new sp 3 -enriched bioisosteres, paying attention to previously underrated (or even unwanted) structural motifs, or combination thereof. In this review with 532 references, a survey of selected chemotypes that emerged recently in medicinal chemistry is provided, with a focus on the synthesis of the corresponding building blocks. Thus, saturated (hetero)aliphatic boronates, sulfonyl fluorides, sulfinates, non-classical sp 3 -enriched benzene isosteres, bicyclic morpholine/piperidine/piperazine analogs, as well as gemdifluorinated cycloalkanes (as an example of emerging fluorinated motifs) are discussed.

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Section: Applications In Synthetic and Medicinal Chemistrymentioning

confidence: 99%

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

2021

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“…19,20,22 These exceptional properties also enable their application as new alternative cleaner compounds substituting the usually harmful perfluorinated surfactants used in a wide range of industrial applications. 19,20,22 Several fluorinated ionic liquids have been explored for other applications as in electrochemistry, where they are mostly used as electrolyte components in the production of energy storage devices, 23,24 metal batteries as lithium, 25,26 fuel, 27 and solar cells. 28 These compounds can be also useful in catalysis of several reactions.…”

Section: ■ Introductionmentioning

confidence: 99%

Influence of Nanosegregation on the Phase Behavior of Fluorinated Ionic Liquids

et al. 2017

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Fluorinated ionic liquids (FILs) have received increasing attention due to their physicochemical properties. They allow us to enlarge the tuneability power of traditional ionic liquids. With the aim to understand the thermodynamic behavior of these compounds, a study of solid−fluid transitions using differential scanning calorimetry, thermogravimetric analysis, rheology, and molecular dynamics simulation has been performed. A comparison between different cations, anions, and hydrogenated alkyl chains was carried out using ionic liquids with fluorinated alkyl chain lengths equal to or longer than four carbon atoms. In this work, we provide evidence of the fluorinated domain influence on the thermodynamic behavior of these compounds. Moreover, the results suggest that the nanosegregation of the fluorous domains might be an interesting structural feature that modifies and/or enhances the rich phase behavior of the FILs, increasing the probability of these compounds to adopt different conformations. This information is crucial to design the best FIL and can increase their potential on a wide range of applications.

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“…Literature related to FILs has mainly focused on their synthesis and their application as reaction media 4–8. Other reports have mentioned their outperforming application in electrolytes for fuel and solar cells,9 in lithium batteries,10 as well as catalysts11 or liquid crystals for optoelectronic applications 12…”

Section: Introductionmentioning

confidence: 99%

Influence of Nanosegregation on the Surface Tension of Fluorinated Ionic Liquids

et al. 2016

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We have investigated, both theoretically and experimentally, the balance between the presence of alkyl and perfluoroalkyl side chains on the surface organization and surface tension of fluorinated ionic liquids (FILs). A series of ILs composed of 1-alkyl-3-methylimidazolium cations ([C n C 1 im] with n = 2, 4, 6, 8, 10 or 12) combined with the perfluorobutanesulfonate anion was used. The surface tensions of the investigated liquid salts are considerably lower than those reported for nonfluorinated ionic liquids. The most surprising and striking feature was the identification, for the first time, of a minimum at n = 8 in the surface tension versus the length of the IL cation alkyl side chain. Supported by molecular dynamic simulations it was found that this trend is a result of the competition between the two nonpolar domains (perfluorinated and aliphatic) on pointing towards the gas-liquid interface, a phenomenon which occurs in ionic liquids with perfluorinated anions. Furthermore, these ionic liquids present the lowest surface entropy reported to date.

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New aryl-containing fluorinated sulfonic acids and their ammonium salts, useful as electrolytes for fuel cells or ionic liquids

Cited by 28 publications

References 17 publications

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances

Influence of Nanosegregation on the Phase Behavior of Fluorinated Ionic Liquids

Influence of Nanosegregation on the Surface Tension of Fluorinated Ionic Liquids

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