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Preparation of protic ionic liquids containing cyclic oligosiloxane frameworks

机译：含环状低聚硅氧烷骨架的质子离子液体的制备

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Protic ionic liquids (PILs) containing cyclic oligosiloxanes with ammonium side-chain groups (Am-CyS-IL and 2Am-CyS-IL) were successfully prepared by the hydrolytic condensation of 3-aminopropyldimethoxymethylsilane and 3-(2-aminoethylamino)propyldimethoxymethylsilane, respectively, in a water/methanol (1?:?19 v/v) mixed solution of bis(trifluoromethanesulfonyl)imide (HNTf2). The differential scanning calorimetry (DSC) curves of Am-CyS-IL and 2Am-CyS-IL exhibited baseline shifts attributable to glass transition temperatures (Tg) of ?2 °C and 9 °C, respectively, and endothermic peaks at their melting temperatures (Tm) were not detected for both compounds, indicating their amorphous structures. In addition, fluidity was visually observed for each compound at ～35 °C and ～45 °C, respectively. On the basis of these results, we concluded that Am-CyS-IL and 2Am-CyS-IL were PILs. To investigate the influence of the kind of siloxane framework on the nature of the ionic liquid, we prepared polyhedral oligomeric silsesquioxanes (POSSs) containing the same side-chain groups and counteranions (Am-POSS and 2Am-POSS) from 3-aminopropyltrimethoxysilane and 3-(2-aminoethylamino)propyltrimethoxysilane, respectively, using an HNTf2 catalyst. Am-POSS had a Tg of 15 °C and a Tm of 193 °C, and 2Am-POSS had a Tg of 32 °C and a Tm of 208 °C, which were estimated by DSC analyses. Furthermore, fluidity was not observed below 150 °C for both compounds, indicating that these POSS compounds were not PILs. These results suggest that the cyclic oligosiloxane frameworks are an important factor for the preparation of siloxane-based PILs exhibiting fluidity at low temperature. In addition, the present PILs containing cyclic oligosiloxane frameworks exhibited relatively high decomposition temperatures (Td; Am-CyS-IL: Td5 = 351 °C and Td10 = 362 °C, 2Am-CyS-IL: Td5 = 294 °C and Td10 = 309 °C).
机译：分别通过3-氨基丙基二甲氧基甲基硅烷和3-（2-氨基乙基氨基）丙基二甲氧基甲基硅烷的水解缩合反应成功制备了含有带有铵侧链基团的环状低聚硅氧烷（Am-CyS-IL和2Am-CyS-IL）的质子离子液体（PIL） ，在水/甲醇（1？：？19 v / v）的双（三氟甲磺酰基）酰亚胺（HNTf 2 ）混合溶液中。 Am-CyS-IL和2Am-CyS-IL的差示扫描量热（DSC）曲线显示归因于玻璃化转变温度（ T g ）分别在2°C和9°C的温度下，未检测到其熔化温度下的吸热峰（ T m ）对于这两种化合物，表明它们的非晶结构。另外，在〜35℃和〜45℃下分别目视观察每种化合物的流动性。根据这些结果，我们得出结论，Am-CyS-IL和2Am-CyS-IL是PIL。为了研究硅氧烷骨架类型对离子液体性质的影响，我们从3-氨丙基三甲氧基硅烷和3制备了含有相同侧链基团和抗衡阴离子（Am-POSS和2Am-POSS）的多面体低聚倍半硅氧烷（POSSs）。 -（2-氨基乙基氨基）丙基三甲氧基硅烷，分别使用HNTf 2 催化剂。 Am-POSS的 T g 的温度为15°C， T m < / sub> 的温度为193°C，而2Am-POSS的 T g 的温度为32°C，而通过DSC分析估计的T m 为208°C。此外，两种化合物在150°C以下均未观察到流动性，表明这些POSS化合物不是PIL。这些结果表明，环状低聚硅氧烷骨架是制备在低温下显示出流动性的基于硅氧烷的PIL的重要因素。此外，目前的含有环状低聚硅氧烷骨架的PIL表现出较高的分解温度（ T d ; Am-CyS-IL： T d5 = 351°C和 T d10 = 362° C，2Am-CyS-IL： T d5 = 294°C和 T d10 = 309°C）。

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