Department of Chemistry and Biochemistry, University of Texas at Arlington, 76019, USA.
Anal Bioanal Chem. 2011 Mar;399(7):2445-61. doi: 10.1007/s00216-010-4615-6. Epub 2011 Jan 4.
Three new polymeric chiral stationary phases were synthesized based on (1S,2S)-1,2-bis(2,4,6-trimethylphenyl)ethylenediamine, (1S,2S)-1,2-bis(2-chlorophenyl)ethylenediamine, and (1S,2S)-1,2-di-1-naphthylethylenediamine via a simple free-radical-initiated polymerization in solution. These monomers are structurally related to (1S,2S)-1,2-diphenylethylenediamine which is the chiral monomer used for the commercial P-CAP-DP polymeric chiral stationary phase (CSP). The performance of these three new chiral stationary phases were evaluated in normal phase high-performance liquid chromatography (HPLC) and supercritical fluid chromatography and the results were compared with those of the P-CAP-DP column. All three new phases showed enantioselectivity for a large number of racemates with a variety of functional groups, including amines, amides, alcohols, amino acids, esters, imines, thiols, and sulfoxides. In normal phase, 68 compounds were separated with 28 baseline separations (Rs ≥ 1.5) and in SFC, 65 compounds were separated with 24 baseline separations. In total 72 out of 100 racemates were separated by these CSPs with 37 baseline separations. Complimentary separation capabilities were observed for many analytes. The new polymeric CSPs showed similar or better enantioselectivities compared with the commercial column in both HPLC and SFC. However, faster separations were achieved on the new stationary phases. Also, it was shown that these polymeric stationary phases have good sample loading capacities while maintaining enantioselectivity.
基于（1S,2S）-1,2-双（2,4,6-三甲基苯基）乙二胺、（1S,2S）-1,2-双（2-氯苯基）乙二胺和（1S,2S）-1,2-双-1-萘基乙二胺，通过简单的自由基引发聚合在溶液中合成了三种新型聚合物手性固定相。这些单体与（1S,2S）-1,2-二苯基乙二胺在结构上有关，后者是商业 P-CAP-DP 聚合物手性固定相（CSP）所用的手性单体。在正相高效液相色谱（HPLC）和超临界流体色谱中评估了这三种新型手性固定相的性能，并将结果与 P-CAP-DP 柱的结果进行了比较。所有三种新相都对具有多种官能团的大量外消旋体表现出对映选择性，包括胺、酰胺、醇、氨基酸、酯、亚胺、硫醇和亚砜。在正相条件下，68 种化合物得到分离，其中 28 种达到基线分离（Rs≥1.5），在 SFC 中，65 种化合物得到分离，其中 24 种达到基线分离。共有 72 种外消旋体被这些 CSP 分离，其中 37 种达到基线分离。许多分析物观察到互补的分离能力。与商业柱相比，新的聚合物 CSP 在 HPLC 和 SFC 中均表现出相似或更好的对映选择性。然而，在新的固定相上实现了更快的分离。此外，还表明这些聚合物固定相具有良好的样品负载能力，同时保持对映选择性。
