Preparation and evaluation of partially‐substituted 3‐chloro‐4‐methylphenylcarbamate‐β‐cyclodextrin bonded silica particles as chiral stationary phase for multi‐mode HPLC

Abstract

3‐Chloro‐4‐methylphenylcarbamate‐(3‐(2‐O‐β‐cyclodextrin)‐2‐hydroxypropoxy)‐propylsilyl‐appended silica particles (CMP‐CD‐HPS), a new type of partially‐substituted cyclodextrin‐bonded phase, have been successfully synthesized and applied as a chiral stationary phase in high‐performance liquid chromatography under multi‐mode conditions including normal phase, reversed phase, and polar organic mobile phase conditions. Chemical characterization for the CMP‐CD‐HPS was carried out by elemental analysis. The chromatographic performance of CMP‐CD‐HPS‐packed column was evaluated by separating the positional isomers of nitrophenol and nitraniline and the enantiomers of some chiral drug compounds. The separation results show that CMP‐CD‐HPS exhibited excellent selectivity for separating the positional isomers of disubstituted benzenes and the enantiomers of the chiral drugs. The hydroxyl residues of partially‐substituted β‐cyclodextrin and the stable spacer linking to secondary hydroxyl site of the β‐cyclodextrin in the new CMP‐CD‐HPS phase play important roles in the chromatographic separations.

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

“…In addition to the partially substituted CD derivatives, fully derivatized CD derivatives, in which all of the hydroxyl groups at the C-2, C-3, and C-6 positions are functionalized, also have been widely used as CSPs for HPLC separation of enantiomers. Recently, a series of fully phenylcarbamoylated CD derivatives have been bonded onto silica gel to prepare CSPs for HPLC via various reactions and spacers [61][62][63][64][65][66][67][68]. Most of the studies focused on the introduction of different substituents to the benzene rings because the introduction of either electron-withdrawing or electron-donating substituents on the phenyl ring of phenylcarbamoylated CD CSPs generally improves enantioselectivity toward some racemates [69][70][71].…”

Chiral Inorganic mesoporous materials used as the stationary phase in GC

“…Scientists have conducted extensive research on mesoporous silica, mainly in the following categories: M41S [11][12][13][14], SBA [15][16][17], KIT [3,18], MSU [19], FDU [20], HMS [21], HOM [22] and AMS [23][24][25], in which the abbreviations represent different mesoporous materials that belong to different series. Most chirality exists in organic materials [26,27], and only rarely in inorganic materials. The organic-inorganic hybrid materials combine the advantages of organic and inorganic units and are widely used in the fields of separation, Article Related Abbreviations: CMS, chiral mesoporous silica; CTAB, cetyltrimethylammonium bromide; TEOS, tetraethoxysilane; TMAPS, N-trimethoxysilylpropyl-N,N,N-trimethyl-ammonium chloride.…”

“…Scientists have conducted extensive research on mesoporous silica, mainly in the following categories: M41S , SBA , KIT , MSU , FDU , HMS , HOM and AMS , in which the abbreviations represent different mesoporous materials that belong to different series. Most chirality exists in organic materials , and only rarely in inorganic materials. The organic–inorganic hybrid materials combine the advantages of organic and inorganic units and are widely used in the fields of separation, catalysis and electronics.…”