Preparation of polysaccharide-based chiral stationary phases on SiO2@Ag core–shell particles by means of coating and intermolecular polycondensation and comparative liquid chromatography enantioseparations

Abstract

Material with a core-shell structure based on a porous silica core and Ag nanoparticles (AgNPs) as shell (SiO@Ag) was prepared with the seed growth method. Cellulose derivatives as chiral selectors were coated on the surfaces of SiO@Ag particles by means of coating and intermolecular polycondensation as chiral stationary phases (CSPs), respectively. Fifteen racemates were used to evaluate their chiral recognition ability by high-performance liquid chromatography (HPLC). The results implied that the CSPs based on SiO@Ag particles obtained stronger interaction with the analytes leading to better enantioseparation due to the existence of AgNPs on the surfaces of silica gel, compared with a cellulose derivative-modified silica column. In addition, the new CSPs showed special selectivity for ketone enantiomers, and AgNPs played a synergistic effect with cellulose derivatives on enantioseparation. Graphical abstract Schematic of SiO@Ag stationary phase.

Recent progress in the development of chiral stationary phases for high‐performance liquid chromatography

“…Li et al prepared polysaccharide-based CSPs by immobilizing cellulose tris-(3,5-dimethylphenylcarbamate) on SiO 2 @AgNPs or SiO 2 @AuNPs core-shell particles. The enantioselectivities of the CSPs were improved in comparison with the cellulose derivative-modified silica columns due to the presence of Ag nanoparticles or Au nanoparticles on the silica gel surface [136,137]. Chankvetadze and coworkers first reported the use of superficially porous particles to produce polysaccharide-based CSPs for HPLC in 2012 [138].…”

Chiral Stationary Phases for Liquid Chromatography: Recent Developments

“…Generally, for the new derivatives, the effect of different substituents on chiral recognition has been discussed [94,95,96,97]. Additionally, the effect of mobile phase composition on enantioseparation was also explored [94,95,96,98,99].…”

“…Another different approach for preparation of chromatographic support was reported by Li et al [99], who functionalized core-shell silver particles with cellulose derivatives through coating and intermolecular polycondensation and developed CSP58. A synergetic effect between silver and cellulose was observed considering the high values of resolution (Rs = 2.61) and enantioseparation (α = 8.42).…”

“…A synergetic effect between silver and cellulose was observed considering the high values of resolution (Rs = 2.61) and enantioseparation (α = 8.42). This CSP demonstrated a particular selectivity toward analytes having the functional group ketone [99].…”

Modular and conservative procedure for the quantification of amino functionalities bonded to solid porous matrices

“…[9][10][11][12] Amino-functionalized solid materials play an important role also as essential components of stationary phases in chromatographic techniques. [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] Indeed, amino phases with…”