本實驗使用酸鹼中和合成17種非質子型離子液體 (aprotic ionic liquids)，陽離子的部分以五圓環的吡咯啶 (pyrolidine)、六圓環的吡啶系列 (piperidine)、嗎啉 (morpholine)系列以及甘胺酸系列 (glycine-based)為基礎，分別加入醇基類、醚類以及烷烯類等取代基作為替換，陰離子的部分為(bis(trifluoromethanesulfonyl)amide)。
我們利用變溫的方式測量非質子型離子液體的黏度、密度、導電度的大小，並探討陰陽離子的結構變化對於整體離子液體的物理性質影響。另外也使用核磁共振(PGSE-NMR)的技術，量測陰陽離子在變溫條件下的擴散係數，經由Nernst-Einstein 方程式計算完全解離的莫爾導電度，並推算各離子液體的解離程度，瞭解非質子型離子液體的聚集現象。針對上述非質子型離子液體的物理性質探討其庫倫靜電力、氫鍵作用力、極性效應及凡得瓦爾力等分子間作用力的影響。
結果顯示，離子液體的黏度、密度會隨著溫度提升而下降，導電度與擴散係數則隨著溫度的提升而上升，黏度部分主要受到官能基的影響可以分三類，含有氫鍵取代基、極性取代基、非極性取代基，當有氫鍵的形成黏度越大，其次是受極性取代基的偶極-偶極作用力，凡得瓦力則是屬於微弱的作用力，另一個重要的考量因素是環效應影響，環效應造成六圓環離子液體的黏度為五圓環離子液體的1.4~1.7倍，導電度為0.6倍；密度的部分除了上述作用力因素外，還要考量到取代基碳鏈越長，單位體積下的質量會下降，造成密度降低；導電度以及擴散係數的部分，受到黏度效應以及作用力影響，趨勢會與黏度互成反比的走勢，但仍有與預測不符的部分需要進一步討論。
之後我們利用密度泛函理論B3LYP方法，在6-31G(d)基組上，對17組非質子型離子液體進行理論研究，通過幾何結構最佳化和頻率分析得到電位表面的穩定結構、電荷的分布情況、陰陽離子相互作用的能量，其中以氫鍵取代基的非質子型離子液體為最穩定結構，其次為極性取代基以及非極性取代基非質子型離子液體，並且利用Mulliken電荷分布的變化情況解釋陰、陽離子之間電子轉移以及誘導效應的發生。

Seventeen aprotic ionic liquids (aPILs) are prepared using acid-base neutralization reaction. These aprotic ionic liquids contain bis(trifluoromethanesufonyl)amide as anion and various oniums as cations. The cations are based on pyrrolidinium, piperidinium, morpholinium, and glycine-based ester with various functional groups.
In order to realize the structural relationship of cations and anions in ionic liquids, we measured the physicochemical properties, such as density, viscosity, and specific conductivity of these aprotic ionic liquids at variable temperatures. Furthermore, the self-diffusion coefficients of cation and anion in these aprotic ionic liquids were studied using pulsed gradient spin-echo NMR technique. To understand the influence of aggregation, we measured the equivalent conductivity and degree of dissociation by Stokes-Einstein equation. The possible effects of the physicochemical properties are derived from the intermolecular interactions, coulomb interaction, hydrogen bonding, polarizability effects, and van der Waals interactions.
The results indicate that viscosity, density, specific conductivity, and self-diffusion are different at various temperatures. Viscosity and density of aprotic ionic liquids increase with raising temperature. However, specific conductivity and self-diffusion decrease with raising temperature. The viscosity is influenced by various substituents of cations, various substituents cause different hydrogen-bond effect, polarized bond, and nonpolarized bond of cations. Hydrogen bonding, dipole-dipole, and van der Waals interactions increase viscosity and density of aprotic ionic liquids. The length of the cation side chain also affects the density, longer cation side chain has smaller density. The other important factor is the X-membered rings effect, the viscosity ratio of six-memberd rings: five-membered rings is 1.4~1.7 : 1, and the specific conductivity ratio of six-memberd rings : five-membered rings is 0.6~0.5 : 1. Compare with the tendency of viscosity of aprotic ionic liquids, the results of specific conductivity and self-difussion coefficient of aprotic ionic liquids versus viscosity show inverse ratio.
These aprotic ionic liquids are investigated with density functional theory at B3LYP/6-31G(d) level. Their electrostatic potential surfaces, optimized geometries, charge distribution, and the interactions between the cation and anion are discussed in detail. Theoretical results indicate that hydrogen-bond substituent of aprotic ionic liquids are more stable than polarized substituent and nonpolarized substituent of aprotic ionic liquids. The induced effect and electron transfer of aprotic ionic liquids are analyzed using the change of Mulliken charge.

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