Impact of Anions on the Partition Constant, Self-Diffusion, Thermal Stability, and Toxicity of Dicationic Ionic Liquids

Abstract

Partition constants (KD°), molecular dynamics (T1, T2, and DOSY measurements), thermal stability, and toxicity of dicationic ionic liquids (ILs) were determined. The dicationic ILs derived from 1,n-bis(3-methylimidazolim-1-yl)octane, [BisOct(MIM)2][2X] (in which X = Cl, Br, NO3, SCN, BF4, and NTf2), were evaluated to verify the influence of anion structure on the IL properties. A monocationic IL [Oct(MIM)][Br] was also monitored for comparison. In general, the solubility of the ILs followed the anion free energy of hydration (ΔG°hyd). The thermokinetic and thermodynamic functions of activation of the ILs were determined via thermogravimetric data, and it was observed that polyatomic anions influence the decomposition mechanism of these IL structures. Furthermore, [Oct(MIM)][Br] had a decomposition rate greater than that of the dicationic analogue, and the thermodynamic parameters of activation data corroborate these results. Finally, the dicationic ILs did not indicate toxic effects (LD50 > 40 mM).

Systematic Synthesis and Properties Evaluation of Dicationic Ionic Liquids, and a Glance Into a Potential New Field

“…Another crucial aspect of ILs is their potential toxicity, which has been scrutinized during the last 10 years. On this regard, the studies performed up to now showed promising toxicity profiles for DILs when compared with the corresponding monocationic ILs (Pretti et al, 2009; Frizzo et al, 2018; Montalbána et al, 2018).…”

Mefenoxam and pyraclostrobin: toxicity and in vitro inhibitory activity against Pythium insidiosum

“…2013; Frizzo et al . 2018). Around 500 C. elegans (L1) were transferred to microtubes containing different mefenoxam and pyraclostrobin concentrations in M9 buffer.…”

Antimicrobial and Toxicity Evaluation of Imidazolium-Based Dicationic Ionic Liquids with Dicarboxylate Anions

“…The worms were continuously shaken to stimulate oxygenation. After 1 h, the worms were washed three times with M9 buffer, and the survival assay was then performed [ 19 ].…”

“…Previous, imidazolium-based DILs [C 8 (MIM) 2 ][2X], in which X = Cl, Br, NO 3 , SCN, and BF 4 , and their toxicological effects against C. elegans were reported by us. In our early scanning, increasing concentrations of IL (0.01, 0.1, 1.0, and 10 mM) were added to the first stage of the worms (larval stage), which is more sensitive, and remained for 1 h. Results showed that the survival of above 90% of C. elegans indicated that these ILs do not have toxic effects at the concentrations evaluated [ 19 ].…”