Department of Chemistry, Adam Mickiewicz University, Poznan, Poland.
J Sep Sci. 2011 Sep;34(18):2391-6. doi: 10.1002/jssc.201100395. Epub 2011 Jul 21.
A new Pirkle-anion exchange hybrid-type chiral stationary phase (CSP-1) has been synthesized by immobilizing 10,11-didehydroquinine 3,5-dinitrophenylcarbamate onto 3-azidopropyl silica gel using click chemistry (1,3-dipolar Huisgen cycloaddition). This chiral selector and CSP contain a strong π-accepting 3,5-dinitrophenyl residue besides the π-basic quinoline group and an ionizable tertiary amino group. In concert with ion pairing it offers π-donor-π-acceptor interactions resulting in an enhancement of the selectivity toward specific π-donating analytes such as aryloxypropionic acids and profens. A representative set of these analytes has been investigated under various chromatographic conditions (polar-organic, reversed- and normal-phase) leading to base-line enantioseparations with selectivity (α) values up to 1.8. Control experiments with related quinine tert-butylcarbamate phase grafted onto the surface either by thioether (Chiralpak QN-AX) or 1,2,3-triazole linker revealed the impact of the additional aromatic moiety in the chiral selector motif.
一种新型的 Pirkle-阴离子交换杂化型手性固定相（CSP-1）已经通过点击化学（1,3-偶极环加成）将 10,11-二去氢奎宁 3,5-二硝基苯甲酰基氨基甲酸酯固定在 3-叠氮丙基硅胶上合成得到。这种手性选择剂和 CSP 除了具有π-碱性喹啉基团和可离子化的叔氨基外，还含有一个强的π-接受 3,5-二硝基苯基残基。与离子配对一起，它提供了π-供体-π-受体相互作用，从而增强了对特定的π-供电子分析物的选择性，如芳氧基丙酸和丙洛芬。在各种色谱条件（极性有机、反相和正相）下对这些分析物进行了研究，得到了基线对映体分离，选择性（α）值高达 1.8。用硫醚（Chiralpak QN-AX）或 1,2,3-三唑键合到表面的相关奎宁叔丁基氨基甲酸酯的对照实验表明了手性选择剂结构中额外芳基部分的影响。
