Related Experiment Video
Updated: Jul 1, 2025

Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
Preparation and evaluation of two chiral stationary phases based on imidazolyl-functionalized bromoethoxy
1Department of Chemistry, Research Center for Analytical Sciences, College of Sciences, Northeastern University, Shenyang 110819, China; CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China.
Abstract:
Chiral pillar[5]arene-based mesoporous silica, an emerging class of chiral structure, possesses excellent characteristics such as abundant chiral active sites, encapsulated cavity and excellent chiral modification, which make them a promising candidate as new chiral stationary phases (CSPs) in enantioseparation. In this study, two imidazole-containing (S)-1-(4-phenyl-1H-imidazol-2-yl)ethanamine and (S)-Histidinol were respectively modified to bromoethoxy pillar[5]arene-bonded silica to construct new chiral stationary phases (sPIE-BP5-Sil and sHol-BP5-Sil) for the separation and analysis of enantiomers. The separation conditions such as mobile phase composition, flow rate and temperature were optimized. Under optimal conditions, both sPIE-BP5-Sil and sHol-BP5-Sil showed good separation performance for different types of enantiomers. Interestingly, sPIE-BP5-Sil and sHol-BP5-Sil showed better enantioselectivity for chiral aromatic compounds and chiral aliphatic compounds, respectively. This enantioseparation result was closely related to the presence of additional aromatic rings and abundant hydroxyl groups in the side chains of the two chiral groups. In addition, the enantioseparation process was further studied by molecular docking simulation. Therefore, this work provided a new strategy for the preparation and application of imidazolyl-derived pillar[5]arene-based chiral stationary phases, which can be efficiently used for screening and separating enantiomers.
Related Concept Videos
Silica Gel Column Chromatography: Overview
Polar components tend to bind strongly to the silica gel, causing them to move slowly through the column. In contrast, nonpolar compounds...
High-Performance Liquid Chromatography: Introduction
In HPLC, two phases play a critical role in the separation process:
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Gas Chromatography: Types of Columns and Stationary Phases
For an analyte to remain on the column for a sufficient amount of time, it must exhibit some level of compatibility (or...
Prochirality
Preparation and Reactions of Sulfides

