Synthesis and properties of GABA-based ionic liquids and deep eutectic solvents

Satoshi Kitaoka , Natsuko Shimaike , Yuhei Kubo , Yukino Isshiki , Anju Furukawa , Kaoru Nobuoka
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Abstract

GABA-based ionic liquids (ILs) and deep eutectic solvents (DESs) were synthesized and their properties compared with those of ILs and DESs with similar structures. In ILs, using GABA as the anion, [N4444][GABA], [N2224][GABA] and [N4446][GABA] in combination with ammonium, [C2mim][GABA] in combination with imidazolium and [Ch][GABA] in combination with the biological substance choline were synthesized. Among the ILs under investigation, [N2224][GABA], [N4446][GABA] and [C2mim][GABA] were liquid at room temperature. In DESs, GABA was used as the hydrogen bond donor and three GABA-based DESs were prepared by combining [Ch][Cl], [L-Car][Cl], and [DL-Car][Cl] as hydrogen bond acceptors. Among these DESs, [L-Car][Cl] : GABA (1:1) and [DL-Car][Cl] : GABA (1:1) were shown to be liquid at room temperature. Comparing the viscosities of the prepared liquids showed that DESs was significantly higher than ILs. The viscosity increase was suggested to be due to the hydrogen bond acceptors of [L-Car][Cl] : GABA (1:1) and [DL-Car][Cl] : GABA (1:1) having carboxyl groups. The toxicity of GABA-based ILs and DESs was investigated using HeLa cells, which showed that their cytotoxicity was similar to or lower than that of GABA alone in HeLa cells.

Abstract Image

gaba基离子液体及深共晶溶剂的合成与性能研究
合成了基于gaba的离子液体(ILs)和深度共晶溶剂(DESs),并与相似结构的离子液体和深度共晶溶剂进行了性能比较。以GABA为阴离子,合成了[N4444][GABA]、[N2224][GABA]、[N4446][GABA]与铵结合、[C2mim][GABA]与咪唑结合、[Ch][GABA]与生物物质胆碱结合。在所研究的il中,[N2224][GABA], [N4446][GABA]和[C2mim][GABA]在室温下为液态。在DESs中,以GABA为氢键供体,以[Ch][Cl]、[L-Car][Cl]、[DL-Car][Cl]为氢键受体制备了3种GABA基DESs。其中,[L-Car][Cl]: GABA(1:1)和[DL-Car][Cl]: GABA(1:1)在室温下呈液态。对制备的液体粘度进行比较,发现DESs明显高于ILs。黏度增加的原因是[L-Car][Cl]: GABA(1:1)和[DL-Car][Cl]: GABA(1:1)的氢键受体含有羧基。利用HeLa细胞研究了GABA基il和DESs的毒性,结果表明它们在HeLa细胞中的细胞毒性与单独使用GABA相似或低于单独使用GABA的细胞毒性。
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CiteScore
3.70
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