71113-25-2Relevant articles and documents
Role of cationic head-group in cytotoxicity of ionic liquids: Probing changes in bilayer architecture using solid-state NMR spectroscopy
Fischer, Markus,Gahlay, Gagandeep Kaur,Kaur, Navleen,Kumar, Sandeep,Mithu, Venus Singh,Scheidt, Holger A.
, p. 954 - 963 (2021)
The effect of cationic head-group of ionic liquid on the structure and dynamics of phospholipid bilayer was studied to provide insights into the mechanism of ionic liquid-membrane interaction. The effect was observed using six ionic liquids containing benzimidazolium, imidazolium, pyrrolidinium, piperidinium, ammonium, and morpholinium based amphiphilic cations carrying a dodecyl alkyl chain. Unilamellar and multilamellar vesicles composed of zwitterionic 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) were used. Permeability of POPC bilayer was found to have a strong dependence on ionic liquid head-group structure. To probe the structural details of interaction, 31P and 2H based solid-state NMR measurements were performed. The cations differed in terms of their effect on the orientation and disorder in the phosphocholine moiety in lipid head-group as revealed by chemical shift anisotropy of 31P. Cations carrying an unshielded charge like benzimidazolium, imidazolium, and ammonium result in strong reorientation of phosphocholine moiety in lipid head-group. Large sized cations like benzimidazolium and piperidinium result in enhanced lipid chain dynamics as revealed by order parameter calculations of deuterated lipid chains. Relatively polar head-group of morpholinium cation neither impacts the phospholipid head-group nor chain packing. Our results suggest that there exists a direct correlation between ionic liquid head-group induced structural changes in bilayer and their ability to permeabilize/disrupt the membrane and be cytotoxic.
Newly designed flow reactor as an original method of synthesis of ionic liquids by ion-exchange reactions
Pawlowska-Zygarowicz, Anna
supporting information, (2021/11/16)
Optimization of chemical reactions is often costly and requires a significant investment in both materials and time. The solution to this type of difficulty may be the use of continuous flow systems. With the use of the newly designed continuous flow system, the method of synthesizing ionic liquids (ILs) by ion exchange was optimized. The flow rate of the substrates and the selection of the packing of the column in which the reactions were carried out (random packing or a chemical compound in the form of a solid, which was the source of the anion exchanged) were also optimized. The purity of the obtained ionic liquids and the progress of the reaction was determined using ion chromatography. Additionally, for the ionic liquids, which were the starting compounds for the ion exchange reaction, the basic physicochemical properties were determined, thus extending the data library available for chemical compounds belonging to the group of ionic liquids.
Aggregation behavior of long-chain piperidinium ionic liquids in ethylammonium nitrate
Dai, Caili,Du, Mingyong,Liu, Yifei,Wang, Shilu,Zhao, Jianhui,Chen, Ang,Peng, Dongxu,Zhao, Mingwei
, p. 20157 - 20169 (2015/03/13)
Micelles formed by the long-chain piperidinium ionic liquids (ILs) N-alkyl-N-methylpiperidinium bromide of general formula CnPDB (n = 12, 14, 16) in ethylammonium nitrate (EAN) were investigated through surface tension and dissipative particle dynamics (DPD) simulations. Through surface tension measurements, the critical micelle concentration (cmc), the effectiveness of surface tension reduction (Πcmc), the maximum excess surface concentration (Λmax) and the minimum area occupied per surfactant molecule (Amin) can be obtained. A series of thermodynamic parameters (ΔG0m, ΔH0m and ΔS0m) of micellization can be calculated and the results showed that the micellization was entropy-driven. In addition, the DPD simulation was performed to simulate the whole aggregation process behavior to better reveal the micelle formation process.
