Qiao Lizhen, Wang Shuangyuan, Li Hua, Shan Yuanhong, Dou Abo, Shi Xianzhe, Xu Guowang
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
J Chromatogr A. 2014 Sep 19;1360:240-7. doi: 10.1016/j.chroma.2014.07.096. Epub 2014 Aug 7.
Glucaminium-based ionic liquids are a new class of recently developed ionic liquids and prepared by functionalizing the amine group of N-methyl-d-glucamine, which renders them good hydrophilicity due to the presence of the glucose structure and charged quaternary ammonium group. In the present study, a glucaminium-based ionic liquid N,N-diallyl-N-methyl-d-glucaminium bromide was synthesized and subsequently bonded to the surface of 3-mercaptopropyl modified silica materials through "thiol-ene" click chemistry. The obtained stationary phase was characterized by elemental analysis and infrared spectroscopy, and then packed as a HPLC column. A mixture of five nucleosides was used to characterize the separation performance of the obtained column under HILIC mode and the column efficiency was determined with cytidine as the test solute, reaching 80,000plates/m. Then, the retention behavior was evaluated by investigating the effect of various chromatographic factors on retention of different types of solutes, and the results revealed that the developed surface-confined glucaminium-based ionic liquid stationary phase exhibited a hydrophilic interaction/anion-exchange mixed-mode retention mechanism. Finally, two mixtures of nucleotides and flavonoids were separated on the glucaminium-based ionic liquid column, respectively under hydrophilic interaction and hydrophilic interaction/anion-exchange mixed-mode chromatography. In conclusion, the multimodal retention capabilities of the glucaminium-based ionic liquid column could offer a wider range of retention behavior and flexible selectivity toward polar and hydrophilic compounds.
基于葡甲胺的离子液体是一类新开发的离子液体，通过对N-甲基-D-葡甲胺的胺基进行功能化制备而成，由于存在葡萄糖结构和带电荷的季铵基团，使其具有良好的亲水性。在本研究中，合成了一种基于葡甲胺的离子液体N,N-二烯丙基-N-甲基-D-葡甲胺溴化物，随后通过“硫醇-烯”点击化学将其键合到3-巯基丙基修饰的硅胶材料表面。通过元素分析和红外光谱对所得固定相进行表征，然后将其填充为高效液相色谱柱。使用五种核苷的混合物来表征所得色谱柱在亲水作用色谱模式下的分离性能，并以胞苷作为测试溶质测定柱效，达到80,000理论塔板数/米。然后，通过研究各种色谱因素对不同类型溶质保留的影响来评估保留行为，结果表明，所开发的表面受限的基于葡甲胺的离子液体固定相表现出亲水作用/阴离子交换混合模式保留机制。最后，分别在亲水作用色谱和亲水作用/阴离子交换混合模式色谱下，在基于葡甲胺的离子液体柱上分离了两种核苷酸和黄酮类化合物的混合物。总之，基于葡甲胺的离子液体柱的多模式保留能力可为极性和亲水性化合物提供更广泛的保留行为和灵活的选择性。
