Preparation of Perphenylcarbamoylated β-Cyclodextrin-silica Hybrid Monolithic Column with “One-Pot” Approach for Enantioseparation by Capillary Liquid Chromatography

Abstract

Perphenylcarbamoylated β-cyclodextrin-silica (Ph-β-CD-silica) hybrid monolithic columns for enantioseparation in capillary liquid chromatography (cLC) have been prepared by a "one-pot" approach via the polycondensation of alkoxysilanes and in situ copolymerization of mono (6(A)-N-allylamino-6(A)-deoxy)-Ph-β-CD and vinyl group on the precondensed siloxanes. The morphologies of the Ph-β-CD-silica hybrid monolithic columns were characterized by optical microscopy and scanning electron microscopy (SEM), showing the uniform monolithic matrixes tightly bonded onto the capillary wall. The content of Ph-β-CD incorporated in monolithic matrix by the "one-pot" approach was ca. 2.9 times higher than that by postmodification method. The permeability of the Ph-β-CD-silica chiral hybrid monolithic column was 3.63 × 10(-14) m(2), and the minimum plate height was 12 μm corresponding to 83,300 theoretical plates/meter. Enantioseparations of 13 racemates were achieved by the Ph-β-CD-silica hybrid monolithic column. In this work, since the prepolymerization system mainly consisted of organic solvent (methanol (MeOH), N,N-dimethylformamide (DMF)), the limitation and difficulty of the use of water insoluble organic monomers in the previously reported "one-pot" method was circumvented. Therefore, various β-CD derivatives as well as other hydrophobic monomers could thus be used to prepare organic-silica hybrid monolithic columns with the "one-pot" process.

Synthesis of boronate-silica hybrid affinity monolith via a one-pot process for specific capture of glycoproteins at neutral conditions

“…The AAPBA-silica hybrid affinity monolith was synthesized via a one-pot procedure, which mainly involved two major steps as mentioned in the literatures [26][27][28][29]: the polycondensation between the hydrolyzed alkoxysilanes TMOS and VTMS to form vinyl-silica hybrid monolithic matrix at a relatively low temperature, and the copolymerization of vinyl functional groups on the vinyl-silica hybrid monolithic matrix and the organic monomer AAPBA at a proper higher temperature. The synthetic scheme of the AAPBA-silica hybrid affinity monolith is shown in Fig.…”

“…In this process, the polycondensation and copolymerization of the organic and inorganic monomers were carried out orderly by controlling at proper temperatures. The "one-pot" synthesis method is simple, convenient and time-saving, and it has been used to fabricate a series of organic-silica hybrid monolith with different organic monomers for the chromatographic analysis [26][27][28][29]. These researches provided a facile approach for covalent incorporation of different organic moieties into the silica monolith to prepare various organic-silica hybrid monoliths.…”

Recent advances in preparation and application of hybrid organic‐silica monolithic capillary columns

“…Consequently, the incompatibility between hydrophobic organic monomer and aqueous prepolymerization mixture limits to form a homogeneous solution in the "one-pot" process. To address this problem, we [76,77] further developed a novel polymerization system composed of water, organic solvent (methanol and DMF), and CTAB, which acts as supramolecular template to form desired pores in the sol-gel monolith. We first synthesized a chiral monomer, mono (6 A -N-allylamino-6…”

“…A -deoxy)-perphenylcarbamoylated-␤-CD (Ph-␤-CD), and then the hybrid Ph-␤-CD-silica monolith was successfully fabricated by a "one-pot" approach via the polycondensation of VTMS and TMOS and in situ copolymerization of chiral monomer [76]. More than ten racemates could be well enantioseparated on the resulting hybrid monolith by CLC.…”

Recent advances in monolithic columns for protein and peptide separation by capillary liquid chromatography

“…Recently, a novel "one-pot" preparation approach has been developed by the group of Zou [44][45][46][47] to prepare organic-silica hybrid monoliths via the polycondensation of hydrolyzed alkoxysilanes of tetramethoxysilane and vinyltrimethoxysilane at a relatively low temperature and then the copolymerization of organic monomers with the vinyl-silica matrix formed at a relatively high temperature, as shown in Fig. 2.…”