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首页> 外文期刊>Journal of Applied Polymer Science >Synthesis and Characterization of Macroporous Silica Modified with Optically Active Poly[N-(oxazolinylphenyl)acrylamide] Derivatives for Potential Application as Chiral Stationary Phases
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Synthesis and Characterization of Macroporous Silica Modified with Optically Active Poly[N-(oxazolinylphenyl)acrylamide] Derivatives for Potential Application as Chiral Stationary Phases

机译：光学活性聚[N-（恶唑啉基苯基）丙烯酰胺]衍生物修饰的大孔二氧化硅的合成与表征，可用于手性固定相

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摘要

Enantiopure acrylamide derivatives, (S)-N-[o-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]acrylamideand (R)-N4o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)pheny-l]acrylamide, were synthesized through the acylation ofchiral 2-oxazolinylanilines. The radical polymerization ofthe chiral monomers was carried out with (3-mercaptopro-pyl)trimethoxysilane as a chain-transfer agent to obtain thecorresponding optically active prepolymers with a trime-thoxysilyl group. By immobilizing the prepolymers onporous silica gel via the grafting-to method, we prepareda new chiral stationary phase (CSP) and characterized itby elemental analysis, thermogravimetry, and Fouriertransform infrared spectroscopy. The enantioseparationcapacities of the CSPs were evaluated with high-perform-ance liquid chromatography toward several racemic compounds, including 1,1'-bi-2-naphthol, benzoin, 2-amino-1-butanol, and loxoprofen sodium under thenormal-phase mode. The results indicate that the CSPsexhibited improved chromatographic performancescompared to their brush-type analogs obtained by thealternative grafting-from approach. Also, the columnpacked with poly{(R)-N-[o-(4-phenyl-4,5-dihydro-1,3-oxa-zol-2-yl)phenyl]acrylamide}-bonded silica was found tohave an extent of enantioselectivity in the chiral resolutionof some unmodified amino acids with reversed-phase eluents.
机译：对映体纯丙烯酰胺衍生物，（S）-N- [邻-（4-甲基-4,5-二氢-1,3-恶唑-2-基）苯基]丙烯酰胺和（R）-N4o-（4-苯基-4，通过手性2-恶唑啉基苯胺的酰化反应合成了5-二氢-1,3-恶唑-2-基）苯基-1]丙烯酰胺。用（3-巯基-丙基）三甲氧基硅烷作为链转移剂进行手性单体的自由基聚合，得到相应的具有偏苯三甲氧基甲硅烷基的光学活性预聚物。通过接枝法将预聚物固定在多孔硅胶上，我们制备了一种新的手性固定相（CSP），并通过元素分析，热重分析和傅里叶变换红外光谱对其进行了表征。在正相模式下，通过高效液相色谱对几种外消旋化合物（包括1,1'-联-2-萘酚，安息香，2-氨基-1-丁醇和洛索洛芬钠）的CSP对映体分离能力进行了评估。 。结果表明，与通过交替接枝方法获得的刷型类似物相比，CSP的色谱性能有所提高。另外，发现填充有聚{（R）-N- [邻-（4-苯基-4,5-二氢-1,3-氧杂-zol-2-基）苯基]丙烯酰胺}键合的硅胶的色谱柱具有反相洗脱液对一些未修饰氨基酸的手性拆分中对映选择性的变化程度

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