Room temperature deep eutectic solvents of (1S)-(+)-10-camphorsulfonic acid and sulfobetaines: hydrogen bond-based mixtures with low ionicity and structure-dependent toxicity
Room temperature deep eutectic solvents of (1S)-(+)-10-camphorsulfonic acid and sulfobetaines: hydrogen bond-based mixtures with low ionicity and structure-dependent toxicity
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DOI：
10.1039/c5ra03932k
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发表时间：
2015-01-01
期刊：
影响因子：
3.9
通讯作者：
Tiecco, Matteo
中科院分区：
文献类型：
--
作者：
Cardellini, Fabio;Germani, Raimondo;Tiecco, Matteo
本工作制备并表征了十二种新型低共熔溶剂 (DES)。它们是 (1S)-(+)-10-樟脑磺酸 (CSA) 和具有脂肪族、芳香族和两亲性部分的不同结构的磺基甜菜碱 (SB) 的混合物。它们在室温下为液体，事实上，它们的熔点范围为 -5 摄氏度到 19 摄氏度，因此我们可以将这些混合物命名为 RTDES（室温低共熔溶剂）。这些两性离子 DES 的特征在于其粘度、电导率（因此通过 Walden 图显示离子性）、密度、表面张力和对真核模型细胞的毒性。收集的数据表明CSA和SB之间的相互作用可以归因于氢键而不是质子转移，因此它们不是离子液体。据我们所知，它们在瓦尔登图上的位置（靠近对角线的左侧部分）尚未在其他 DES 或离子液体系统中观察到，这表明这些混合物的离子度较低。进行基于 FTIR 的生物测定以确定这些混合物对真核模型细胞（酿酒酵母）的毒性。 DES 仅对细胞产生脱水作用，类似于 CaCl2（一种低细胞毒性盐）产生的脱水作用。这支持这些 DES 作为有前景的绿色介质。两亲性 SB DES 对细胞表现出更强的作用，并且可以描述此类的结构-活性趋势。通过将其中一种新型 DES 用于查耳酮合成，完成了对这些新型 DES 作为布朗斯台德催化剂介质的初步研究，该研究显示出有前景的催化和回收能力。
Twelve novel deep eutectic solvents (DESs) were prepared and characterized in this work. They are mixtures of (1S)-(+)-10-camphorsulfonic acid (CSA) and differently structured sulfobetaines (SBs) with aliphatic, aromatic and amphiphilic moieties. They are liquids at room temperature, their melting points span, in fact, from -5 degrees to 19 degrees C, so we can name these mixtures RTDESs (room temperature deep eutectic solvents). These zwitterionic DESs were characterized in terms of their viscosity, conductivity (and therefore ionicity via Walden plots), density, surface tension and toxicity on eukaryotic model cells. The collected data suggest that the interaction between CSA and the SBs can be ascribed as a hydrogen bond instead of a proton transfer, therefore they are not ionic liquids. To our knowledge, their position on the Walden plot, in the left portion close to the diagonal, has not yet been observed for other DESs or ionic liquid systems and indicates the low ionicity of these mixtures. A FTIR-based bioassay was performed to determine the toxicity of these mixtures on eukaryotic model cells (Saccharomyces cerevisiae). The DESs showed merely a dehydrating effect on the cells, similar to that produced by CaCl2, a low cell toxicity salt. This supports these DESs as promising green media. Amphiphilic SBs DESs showed a stronger effect on the cells and a structure-activity trend can be described for this class. A preliminary study on the use of these novel DESs as Bronsted catalyst media was accomplished by the use of one of them in chalcone synthesis, which showed promising catalytic and recycling capabilities.