基于红外光谱的离子液体溶液微观结构与相互作用研究
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摘要
离子液体是一种完全由阴阳离子组成的绿色环保溶剂,目前已经在许多领域有着广泛的应用。然而,由于其结构的特殊性,我们对其微观结构和相互作用的认识还非常有限,对其相互作用的作用机制、程度和本质还缺少了解,这也是限制离子液体推广和应用的重要原因。通过不同阴阳离子之间的组合,可以形成不计其数、功能性质迥异的离子液体。如若能通过对结构的分析,归纳总结出该类介质分子性能的普遍性规律,将对离子液体的分子设计和应用有着重要的指导作用。本论文采用谱学手段和量子化学计算相结合的方法,从分子层面上研究了离子液体的结构特点及其与各种介质分子之间的相互作用。
本论文首先运用二维相关红外光谱的方法研究了咪唑型离子液体随着水分子加入过程中的微观结构变化以及与水分子之间的相互作用。研究结果表明,随着离子液体／水混合体系中水分含量的增加,水分子优先与阴离子形成氢键作用,其次才与阳离子作用,最后,水分子包围的离子对结构是研究浓度范围内离子液体的主要存在形式。二维红外光谱展示了离子液体在水中溶剂化的动态过程。首先,离子液体中阴阳离子之间无限扩展的三维氢键网络结构逐步被破坏而形成离子团簇,然后离子团簇又进一步解离为水分子包围的离子对结构。同时,与离子液体的阴离子端和阳离子端作用的水分子团簇彼此相连,逐渐形成水分子的三维氢键网络的“类冰”结构。
与非质子型离子液体相比较,质子型离子液体具有一些非质子型离子液体所不具备或不及的性能,但是其微观结构和物理化学性质等的研究相对较少。本论文中,我们系统地对醋酸正丁胺型离子液体N4Ac及其水溶液的红外光谱性质进行了研究。红外光谱表明,N4Ac中正丁胺阳离子和醋酸根阴离子之间的存在着快速的质子转移平衡,阴阳离子之间的N-H…O强氢键作用极有可能是水溶液中质子型离子液体阴阳离子结合在一起的原因。通过对氢键N-H…O进行电子云密度拓扑分析(AIM)发现,水分子的加入使得N-H键的电子密度增大,醋酸根羰基氧原子与氢原子之间的电子密度变小。同时,我们也对咪唑类质子型离子液体醋酸N-甲基咪唑[Mim][Ac]和甲酸N-甲基咪唑[Mim][HCOO]的红外光谱以及相互作用进行了对比研究。结合电导率的测量,我们对质子型离子液体在水中的微观结构与宏观性质之间的关系做了关联。
除了与水分子的相互作用外,离子液体与有机溶剂分子之间的相互作用研究也是非常重要的一个研究课题。本论文采用红外光谱和量子化学计算相结合的方法,研究了离子液体与有机溶剂二甲亚砜(DMSO)之间的相互作用,解释了体系中蓝移氢键的成因及本质。通过精心设计红外光谱对比实验,不仅定性而且定量地探索了DMSO-d6与离子液体之间形成的直接氢键作用和间接氢键作用,分别在DMSO-d6的甲基C-D伸缩振动峰频率(νCD)蓝移中的贡献。研究表明,在[Bmim][BF4]/DMSO-d6体系中,DMSO-d6中的甲基C-D与离子液体阴离子[BF4]-之间的直接氢键作用对νCD蓝移的作用是非常小的。然而,DMSO-d6中的S=O基团与离子液体咪唑阳离子的C2-H形成氢键作用后对DMSO-d6甲基VCD蓝移的间接作用却是非常显著的。对比DMSO-d6/H2O体系中的νCD蓝移现象,我们发现DMSO-d6分子中的甲基C-H与水分子之间的直接氢键水合作用,是导致νCD蓝移的主要原因。结合量子化学计算的方法,我们深层次地揭示了两个体系中蓝移氢键是由于电荷转移及分子轨道的重新杂化所导致的。
通过以上研究,本论文主要借助谱学方法,并结合一定的理论计算,多方面多角度地对离子液体的微观结构和相互作用进行了研究,总结了离子介质中微观结构和相互作用之间的一些内在联系,构建了应用谱学和理论计算方法研究离子液体体系结构-性能关系的基本框架,为进一步研究离子液体中的结构-性能关系以及离子液体的分子设计打下了坚实的基础。
Ionic Liquids (ILs) are liquids formed solely of ions, and they are finding increasing use in many areas of technology and science. The most prominent feature of Ionic Liquids is that they can be designed for a particular application or to be present a specific set of intrinsic properties. Therefore, the study of the structure-activity relationship is the foundation of the molecule design and application of ionic liquids. In this thesis, by a combination of spectra properties and quantum calculations, we have systematically investigated the structural properties of Ionic Liquids and their interactions with other solvents or gas molecules, especially the hydrogen bond interaction.
Water is an impurity commonly presented in ILs since all known ILs can absorb water from the air, traces of water are thought to be ubiquitous in these materials. Therefore, it is of vital importance to investigate the interactions between ionic liquids and water. First, we have investigated the microscopic structure changes and the interactions of ionic liquids with the dilution of water molecules by two-dimensional correlation analysis spectroscopy. The result indicates that, water molecules are more prone to interact with the anions first, and then interact with the cation. The extended H-bond network between cations and anions of pure ILs is destroyed gradually into huge ionic clusters, and then the ionic clusters are further dissociated into solvent-surrounded ionic pairs. Finally, the ionic pairs become the dominant form of the ILs in bulk water. Meanwhile, small water clusters bounded to both the anion part and cation part of the ionic pairs are connecting with each other, thereby a percolating network of "ice-like" water molecules is found in the mixtures.
Aprotic Ionic liquids, such as imidazolium-based Ionic-Liquids, have been extensively studied. However, the protic Ionic Liquids, which can be considered as a unique subclass of ILs, are relatively less studied. We have systematically investigated the infrared spectrum and interactons in some protic ionic liquids, such as n-butylammonium acetate (N4Ac), N-methyl imidazolium acetate ([Mim][Ac]) as well as N-methyl imidazolium acetate ([Mim][HCOO]). We have found out that the fast proton transfer equilibrium may be responsible for the cohesion of cations and anions when protic ionic liquids dissolved in aqueous solutions. The AIM analysis of the hydrogen bond N-H…O in N4Ac indicates that small amount of water molecules stabilized the ionic pairs of ILs. Meantime, by the conductivity measurement of the protic ionic liquids, we have predicted their microscopic structures.
Recently, Ionic liquids have been widely used in the solvent extraction and separation process. The exploring of the way ionic liquids interacting with organic molecules will shed light on the mechemincs of chemical reactions with ionic liquids. By a series of carefully designed comparative infrared spectroscopic studies, we have quantitively identified the different role played by the direct hydrogen-bond interaction and the indirect hydrogen-bond respectively in the blue-shift of the C-D stretching vibrations of DMSO-d6 methyl group in DMSO-d6/[Bmim][BF4] complexes. Results based on FTIR studies indicate that the direct interaction of C-D…F between DMSO-d6 and the anion [BF4]ˉplays a minor role in the blue-shift of vCD in the mixtures of DMSO-d6/ILs. Whereas, the indirect influence of the hydrogen bond formed by the nearby functional group S=O with C2-H of the cation significantly contributes to the blue-shift of vcD, as can be inferred from the significant differences of the blue-shift in [Bmim][BF4] and 1-buty1-2,3-dimethylimidazolium tetrafluoroborate ([Bm2im][BF4]). In contrast, in the case of DMSO-d6/F2O mixtures, direct hydration of C-H…O between the methyl groups of DMSO-d6 with the oxygen atom of water is mainly responsible for the blue shift of vcD·Furthermore, theoretical calculations revealed that charge migrations as well as rehybridization have a dominant effect on the blue-shift in both mixtures.
All in all, by combinations of spectroscopic studies as well as quantum calculations, the relationship between microscopic structures and interactions of ionic liquids is successfully revealed. The frame of studing on the structure-property in ionic liquid is established in the systems. We expect that these methods will shed light on further investigations and may help with the designing of ILs.
本论文首先运用二维相关红外光谱的方法研究了咪唑型离子液体随着水分子加入过程中的微观结构变化以及与水分子之间的相互作用。研究结果表明,随着离子液体／水混合体系中水分含量的增加,水分子优先与阴离子形成氢键作用,其次才与阳离子作用,最后,水分子包围的离子对结构是研究浓度范围内离子液体的主要存在形式。二维红外光谱展示了离子液体在水中溶剂化的动态过程。首先,离子液体中阴阳离子之间无限扩展的三维氢键网络结构逐步被破坏而形成离子团簇,然后离子团簇又进一步解离为水分子包围的离子对结构。同时,与离子液体的阴离子端和阳离子端作用的水分子团簇彼此相连,逐渐形成水分子的三维氢键网络的“类冰”结构。
与非质子型离子液体相比较,质子型离子液体具有一些非质子型离子液体所不具备或不及的性能,但是其微观结构和物理化学性质等的研究相对较少。本论文中,我们系统地对醋酸正丁胺型离子液体N4Ac及其水溶液的红外光谱性质进行了研究。红外光谱表明,N4Ac中正丁胺阳离子和醋酸根阴离子之间的存在着快速的质子转移平衡,阴阳离子之间的N-H…O强氢键作用极有可能是水溶液中质子型离子液体阴阳离子结合在一起的原因。通过对氢键N-H…O进行电子云密度拓扑分析(AIM)发现,水分子的加入使得N-H键的电子密度增大,醋酸根羰基氧原子与氢原子之间的电子密度变小。同时,我们也对咪唑类质子型离子液体醋酸N-甲基咪唑[Mim][Ac]和甲酸N-甲基咪唑[Mim][HCOO]的红外光谱以及相互作用进行了对比研究。结合电导率的测量,我们对质子型离子液体在水中的微观结构与宏观性质之间的关系做了关联。
除了与水分子的相互作用外,离子液体与有机溶剂分子之间的相互作用研究也是非常重要的一个研究课题。本论文采用红外光谱和量子化学计算相结合的方法,研究了离子液体与有机溶剂二甲亚砜(DMSO)之间的相互作用,解释了体系中蓝移氢键的成因及本质。通过精心设计红外光谱对比实验,不仅定性而且定量地探索了DMSO-d6与离子液体之间形成的直接氢键作用和间接氢键作用,分别在DMSO-d6的甲基C-D伸缩振动峰频率(νCD)蓝移中的贡献。研究表明,在[Bmim][BF4]/DMSO-d6体系中,DMSO-d6中的甲基C-D与离子液体阴离子[BF4]-之间的直接氢键作用对νCD蓝移的作用是非常小的。然而,DMSO-d6中的S=O基团与离子液体咪唑阳离子的C2-H形成氢键作用后对DMSO-d6甲基VCD蓝移的间接作用却是非常显著的。对比DMSO-d6/H2O体系中的νCD蓝移现象,我们发现DMSO-d6分子中的甲基C-H与水分子之间的直接氢键水合作用,是导致νCD蓝移的主要原因。结合量子化学计算的方法,我们深层次地揭示了两个体系中蓝移氢键是由于电荷转移及分子轨道的重新杂化所导致的。
通过以上研究,本论文主要借助谱学方法,并结合一定的理论计算,多方面多角度地对离子液体的微观结构和相互作用进行了研究,总结了离子介质中微观结构和相互作用之间的一些内在联系,构建了应用谱学和理论计算方法研究离子液体体系结构-性能关系的基本框架,为进一步研究离子液体中的结构-性能关系以及离子液体的分子设计打下了坚实的基础。
Ionic Liquids (ILs) are liquids formed solely of ions, and they are finding increasing use in many areas of technology and science. The most prominent feature of Ionic Liquids is that they can be designed for a particular application or to be present a specific set of intrinsic properties. Therefore, the study of the structure-activity relationship is the foundation of the molecule design and application of ionic liquids. In this thesis, by a combination of spectra properties and quantum calculations, we have systematically investigated the structural properties of Ionic Liquids and their interactions with other solvents or gas molecules, especially the hydrogen bond interaction.
Water is an impurity commonly presented in ILs since all known ILs can absorb water from the air, traces of water are thought to be ubiquitous in these materials. Therefore, it is of vital importance to investigate the interactions between ionic liquids and water. First, we have investigated the microscopic structure changes and the interactions of ionic liquids with the dilution of water molecules by two-dimensional correlation analysis spectroscopy. The result indicates that, water molecules are more prone to interact with the anions first, and then interact with the cation. The extended H-bond network between cations and anions of pure ILs is destroyed gradually into huge ionic clusters, and then the ionic clusters are further dissociated into solvent-surrounded ionic pairs. Finally, the ionic pairs become the dominant form of the ILs in bulk water. Meanwhile, small water clusters bounded to both the anion part and cation part of the ionic pairs are connecting with each other, thereby a percolating network of "ice-like" water molecules is found in the mixtures.
Aprotic Ionic liquids, such as imidazolium-based Ionic-Liquids, have been extensively studied. However, the protic Ionic Liquids, which can be considered as a unique subclass of ILs, are relatively less studied. We have systematically investigated the infrared spectrum and interactons in some protic ionic liquids, such as n-butylammonium acetate (N4Ac), N-methyl imidazolium acetate ([Mim][Ac]) as well as N-methyl imidazolium acetate ([Mim][HCOO]). We have found out that the fast proton transfer equilibrium may be responsible for the cohesion of cations and anions when protic ionic liquids dissolved in aqueous solutions. The AIM analysis of the hydrogen bond N-H…O in N4Ac indicates that small amount of water molecules stabilized the ionic pairs of ILs. Meantime, by the conductivity measurement of the protic ionic liquids, we have predicted their microscopic structures.
Recently, Ionic liquids have been widely used in the solvent extraction and separation process. The exploring of the way ionic liquids interacting with organic molecules will shed light on the mechemincs of chemical reactions with ionic liquids. By a series of carefully designed comparative infrared spectroscopic studies, we have quantitively identified the different role played by the direct hydrogen-bond interaction and the indirect hydrogen-bond respectively in the blue-shift of the C-D stretching vibrations of DMSO-d6 methyl group in DMSO-d6/[Bmim][BF4] complexes. Results based on FTIR studies indicate that the direct interaction of C-D…F between DMSO-d6 and the anion [BF4]ˉplays a minor role in the blue-shift of vCD in the mixtures of DMSO-d6/ILs. Whereas, the indirect influence of the hydrogen bond formed by the nearby functional group S=O with C2-H of the cation significantly contributes to the blue-shift of vcD, as can be inferred from the significant differences of the blue-shift in [Bmim][BF4] and 1-buty1-2,3-dimethylimidazolium tetrafluoroborate ([Bm2im][BF4]). In contrast, in the case of DMSO-d6/F2O mixtures, direct hydration of C-H…O between the methyl groups of DMSO-d6 with the oxygen atom of water is mainly responsible for the blue shift of vcD·Furthermore, theoretical calculations revealed that charge migrations as well as rehybridization have a dominant effect on the blue-shift in both mixtures.
All in all, by combinations of spectroscopic studies as well as quantum calculations, the relationship between microscopic structures and interactions of ionic liquids is successfully revealed. The frame of studing on the structure-property in ionic liquid is established in the systems. We expect that these methods will shed light on further investigations and may help with the designing of ILs.
引文
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