The Effect of the Sulfur Position on the Melting Points of Lipidic 1-Methyl-3-Thiaalkylimidazolium Ionic Liquids

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• 作者：Richard A. O鈥橞rien ; Arsalan Mirjafari ; Kaila M. Mattson ; Samuel M. Murray ; Niloufar Mobarrez ; E. Alan Salter ; Andrzej Wierzbicki ; James H. Davis ; Jr. ; Kevin N. West
• 刊名：Journal of Physical Chemistry B
• 出版年：2014
• 出版时间：August 28, 2014
• 年：2014
• 卷：118
• 期：34
• 页码：10232-10239
• 全文大小：370K
• ISSN：1520-5207

文摘

A series of novel lipid-inspired ionic liquids have been synthesized employing the thiol鈥揺ne 鈥渃lick鈥?reaction in a single-step process. The thermal properties were determined by differential scanning calorimetry (DSC) and showed observable trends between the C₁₆, C₁₈, and C₂₀ analogues. The minimum melting points for each equivalent chain length series occur at sequential odd sulfur positions, 3, 5, and 7 for the C₁₆, C₁₈, and C₂₀ series, respectively. The magnitude of melting point depression relative to the saturated homologue is observed to have a strong dependence on the position of the sulfur in the side chain. Additionally, the sulfur position corresponding to the lowest melting point for a homologous series shifts further down the chain as the chain length is increased, indicating that the maximum effect takes place near the center of the ion and not the center of the thiaalkyl chain. This synthesis provides tunability and improved thermal stability for 1-methyl-3-thiaalkylimidazolium bistriflimides and insight into structure鈥損roperty relationships of lipidic ionic liquids.