When Functionalization Becomes Useful: Ionic Liquids with aSweet Appended Moiety Demonstrate Drastically ReducedToxicological Effects

Risultato della ricerca: Articlepeer review

Abstract

The growing number of applications of ionic liquids(ILs) in industry have brought attention to the green credentials ofsynthesis, as well as their cytotoxicities and ecotoxicities both fortheir use and accidental leakage into the environment. With theabovementioned properties in mind, we designed a class of ILswith either cations bearing a gluconamide motif and aliphatic sidechains or the anion incorporating a gluconic acid (derived fromfood waste) moiety. An IL with an imidazolium cation with anappended gluconic amide (bearing five hydroxyl groups) moietywas also synthesized for a useful comparison. Different structuralfeatures were considered, placing emphasis on the nature andlength of the alkyl chain and the nature of the anion. Forcomparison, two ILs, one with a hydroxyl group and anotherwithout any hydroxyl groups, were prepared. Apart from the typicalcharacterization of ILs, such as differential scanning calorimetry,thermogravimetric analysis, conductivity, and viscosity measurements, the main focus was placed on the evaluation of theircytotoxicities and ecotoxicities, performing tests with three cancer cell lines (HeLa, HTC-116, and MCF-7) and fish embryos(zebrafish). Data obtained have shed light on the relationship working between the physicochemical properties and thestructural features of the ILs. Interestingly, these ILs are able to inhibit cell growth only at very high concentrations (IC50 ≈10−3 M) and they do not affect the vitality of fish embryos, allowing them to be classified as harmless solvents. To our surprise,the data collected show that derivatization with the “sweet” residue on the imidazolium cation completely removes the wellknowntoxicity effects of imidazolium ILs.
Lingua originaleEnglish
pagine (da-a)926-938
Numero di pagine13
RivistaACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume8
Stato di pubblicazionePublished - 2020

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