A symmetric chiral aromatic polyamide modified silica material combining rigid-flexible and application in liquid chromatography

Abstract

The development of new separation materials is an effective way to improve the separation efficiency of chiral and achiral analytes. Here, a C3-symmetric chiral tricarboxylic acid compound was prepared and successfully immobilized onto the surface of porous silica particles by a one-pot synthesis strategy. The resulting material (TPHs-SiO2) was composed of symmetric chiral aromatic polyamide with a combination of rigid-flexibility, which gave it both chiral and hydrophilic interaction/ion exchange (HILIC/IEC) characteristics. TPHs-SiO2 as a new stationary phase for liquid chromatography can separate 1-phenyl-ethanol, 1-phenyl-propanol, 1-phenyl-1,2-ethylene glycol, 4-chloro-a-methylbenzyl alcohol, ofloxacin and mandelic acid in normal phase chromatography (NPLC) with resolutions of 2.69, 5.89, 4.49, 1.04, 1.73 and 5.47, respectively, thus indicating that TPHs-SiO2 has chiral resolution performance. TPHs-SiO2 can also achieve the separation of achiral compounds, such as nucleosides, nucleotides, and aniline compounds in HILIC/IEC mode. Therefore, the prepared stationary phase can be used as an ideal multifunctional separation material with chiral separation capability and mixed-mode separation capability (HILIC/IEC), realizing the separation of chiral compounds and different types of compounds. This work provides a new idea and method for developing multifunctional separation materials with multi-selectivity and high efficiency, that has important theoretical and application value.