Functionalization of fluorinated ionic liquids: A combined experimental-theoretical study

Abstract

We present new experimental and modeling data concerning imidazolium based-FILs synthesized with a hydroxyl group in the end of the cationic hydrogenated side chain and compared them with the analogous non-functionalized FILs in order to verify their suitability in the biomedical field.The thermophysical and thermodynamic properties of the neat coumpounds and the selfaggregation behavior of FILs in aqueous solutions were measured and compared with theoretical results from the soft-SAFT equation of state, in good agreement with each other. Results showed that the presence of the hydroxyl group increases the density and viscosity of pure compounds and aqueous mixtures, whereas the thermal stability, melting, free volume, ionicity and selfaggregation behavior decrease. These properties are improved with respect to the conventional perfluorosurfactants for the desired application, due to the full miscibility in water and the promising improved biocompatibility.

Thermal Stability of Ionic Liquids: Current Status and Prospects for Future Development

“…Hydroxyl functionalization has different effects on the thermal stability of ILs. [74,112], which can be attributed to the higher chemical activity and easier decomposition of the hydroxyethyl group [61] [74,112]. It could be speculated that the hydrogen bonding interaction between the hydroxyethyl group and anion results in this trend, and the higher intramolecular hydrogen bond interaction stabilizes ILs and block thermal decomposition reaction to some extent [74].…”

“…It can be concluded that the thermal stability of binary mixtures is determined by the ILs which could be reconstituted by all ions in the mixture [125]. In other words, the anions and cations can combine freely in the mixture [111,112]. Figure 15.…”

Unveiling the Influence of Non-Toxic Fluorinated Ionic Liquids Aqueous Solutions in the Encapsulation and Stability of Lysozyme

“…They have enhanced solubilization power due to the formation of three nanosegregated domains, one polar and two non-polar, and are able to dissolve polar, hydrogenated, and fluorinated solutes [18,19]. FILs are characterized by low surface tension, high surfactant power, elevated surface activity with a highly amphiphilic character, and consequently a high aggregation behavior [20][21][22][23]. The possibility to design FILs that are completely miscible in water [21][22][23], with negligible cytotoxicity and ecotoxicity [24,25], and maintaining all the characteristics mentioned above, makes them even more biocompatible.…”

“…FILs are characterized by low surface tension, high surfactant power, elevated surface activity with a highly amphiphilic character, and consequently a high aggregation behavior [20][21][22][23]. The possibility to design FILs that are completely miscible in water [21][22][23], with negligible cytotoxicity and ecotoxicity [24,25], and maintaining all the characteristics mentioned above, makes them even more biocompatible. FILs in a water-rich phase show smaller CACs than the conventional hydrogenated and fluorinated surfactants, which proves their rich aggregation behavior [21][22][23].…”

“…The possibility to design FILs that are completely miscible in water [21][22][23], with negligible cytotoxicity and ecotoxicity [24,25], and maintaining all the characteristics mentioned above, makes them even more biocompatible. FILs in a water-rich phase show smaller CACs than the conventional hydrogenated and fluorinated surfactants, which proves their rich aggregation behavior [21][22][23]. At least three different CACs were found for different FILs, which indicates the formation of different colloidal structures [21], having improved mechanisms of solubilization and opening the possibility of using FILs as protein stabilizers and as drug delivery systems.…”