四氧杂杯“2”芳烃“2”三嗪键合硅胶固定相的合成及色谱性能与应用研究
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摘要
杯芳烃作为继冠醚和环糊精之后的第三代超分子化合物,是一个很好的分子平台,非常容易进行结构修饰。杂原子杯杂芳烃由杯芳烃衍生化而来,即杯芳烃的桥联C原子被N、O、S、P等杂原子所取代,苯酚骨架基团被芳杂环如呋哺、噻吩、吲哚、吡啶等取代。桥联杂原子或芳杂环的引入使这类大环化合物与传统的杯芳烃相比,在结构和性能识别方面都发生了很大的变化。本论文系统的研究了四氧杂杯[2]芳烃[2]三嗪固定相的制备、表征及其色谱行为,并将该固定相应用于环境样品中苯并芘的测定及食品中三聚氰胺的分离测定,得到了较好的结果,具体包括以下三部分内容：
1.制备了四氧杂杯[2]芳烃[2]三嗪键合硅胶固定相,并采用红外光谱、元素分析和热重分析进行了表征。分析结果表明键合量达到0.367 mmol/g,热分解温度为280℃以上,表明其具有良好的热稳定性。
2.采用多环芳烃,苯二酚、苯二胺、氨基苯酚的位置异构体及一些苯的单取代物作为溶质研究了四氧杂杯[2]芳烃[2]三嗪固定相的色谱行为,并与C18商品柱的色谱行为进行了比较,结果表明该固定相不仅存在疏水作用,还存在氢键作用、p-p作用和包结作用等。另外奶粉样品中三聚氰胺也得到了较好的分离测定,为三聚氰胺的测定提供了新的分离介质和分析方法。
3.采用HPLC/FLD的方法,将四氧杂杯[2]芳烃[2]三嗪键合硅胶固定相(TOA2T2)应用于大气、土壤及水体中苯并芘的测定,在0.8-20 ng/mL浓度范围内呈良好的线性关系(R2=0.999),重现性良好(峰面积RSD=2.55%),检出限为0.2 ng/mL,加标回收率在96%-101%之间,结果较满意。
As the third-generation supermolecules after crown ethers and cyclodextrins, calixarenes are quite good molecule platforms, the structures of which are easily modified. Heterocalix[n]heteroarenes are synthesized from calixarene derivations, that is, the bridged carbon atoms of calixarenes are substituted by heteroatoms such as nitrogen,oxygen,sulfur,phosphorus et.al and phenol skeleton groups are substituted by aromatic heterocyclics such as furan,thiophene,indole,pyridine et.al. The introduction of bridged heteroatoms and aromatic heterocyclics bring great changes to structures and recognition performans of such macrocycles,compared to traditional calixarenes.This paper studied the preparation,characteration and chromatographic behaviors of silica-bonded tetraoxocalix[2]arene[2]triazine stationary phase and applied it to the determination of benzopyrene in environment samples and melamine in food,obtaining good results. This paper specifically included the following three parts:
1 Silica-bonded tetraoxocalix[2]arene[2]triazine stationary phase was synthesized and characterized by IR, EA and TG. Analysis results showed that banding quantity was 0.367 mmol/g and thermal decomposition temperature was over 280℃, demonstrating that it had good thermal stability.
2 The chromatographic behaviors of silica-bonded tetraoxocalix[2]arene[2]triazine stationary phase were investigated by using polycyclic aromatic hydrocarbons, positional isomers of hydroquinone,phenylenediamine and aminophenol, and several monosubstituted benzenes.When compared to commercial C18, the results showed that the new bonded stationary phase interact with solutes by hydrophobic as well as hydrogen bonding, p-p and inclusion effect et al.In addition,the melamine in milk samples obtained good separation and determination, which provided a new separation media and a new analysis method for the determination of melamine.
3 The silica-bonded tetraoxocalix[2]arene[2]triazine stationary phase (TOA2T2) was applied to determinations of benzo(a)pyrene in air, soil and water by HPLC/FLD. The results are satisfactory with a good linear relationship in the range of 0.8-20 ng/mL(R2=0.999), good reproducibility (peak area RSD=2.55 %), detection limt 0.2ng/mL, recoveries 96%-101%.
1.制备了四氧杂杯[2]芳烃[2]三嗪键合硅胶固定相,并采用红外光谱、元素分析和热重分析进行了表征。分析结果表明键合量达到0.367 mmol/g,热分解温度为280℃以上,表明其具有良好的热稳定性。
2.采用多环芳烃,苯二酚、苯二胺、氨基苯酚的位置异构体及一些苯的单取代物作为溶质研究了四氧杂杯[2]芳烃[2]三嗪固定相的色谱行为,并与C18商品柱的色谱行为进行了比较,结果表明该固定相不仅存在疏水作用,还存在氢键作用、p-p作用和包结作用等。另外奶粉样品中三聚氰胺也得到了较好的分离测定,为三聚氰胺的测定提供了新的分离介质和分析方法。
3.采用HPLC/FLD的方法,将四氧杂杯[2]芳烃[2]三嗪键合硅胶固定相(TOA2T2)应用于大气、土壤及水体中苯并芘的测定,在0.8-20 ng/mL浓度范围内呈良好的线性关系(R2=0.999),重现性良好(峰面积RSD=2.55%),检出限为0.2 ng/mL,加标回收率在96%-101%之间,结果较满意。
As the third-generation supermolecules after crown ethers and cyclodextrins, calixarenes are quite good molecule platforms, the structures of which are easily modified. Heterocalix[n]heteroarenes are synthesized from calixarene derivations, that is, the bridged carbon atoms of calixarenes are substituted by heteroatoms such as nitrogen,oxygen,sulfur,phosphorus et.al and phenol skeleton groups are substituted by aromatic heterocyclics such as furan,thiophene,indole,pyridine et.al. The introduction of bridged heteroatoms and aromatic heterocyclics bring great changes to structures and recognition performans of such macrocycles,compared to traditional calixarenes.This paper studied the preparation,characteration and chromatographic behaviors of silica-bonded tetraoxocalix[2]arene[2]triazine stationary phase and applied it to the determination of benzopyrene in environment samples and melamine in food,obtaining good results. This paper specifically included the following three parts:
1 Silica-bonded tetraoxocalix[2]arene[2]triazine stationary phase was synthesized and characterized by IR, EA and TG. Analysis results showed that banding quantity was 0.367 mmol/g and thermal decomposition temperature was over 280℃, demonstrating that it had good thermal stability.
2 The chromatographic behaviors of silica-bonded tetraoxocalix[2]arene[2]triazine stationary phase were investigated by using polycyclic aromatic hydrocarbons, positional isomers of hydroquinone,phenylenediamine and aminophenol, and several monosubstituted benzenes.When compared to commercial C18, the results showed that the new bonded stationary phase interact with solutes by hydrophobic as well as hydrogen bonding, p-p and inclusion effect et al.In addition,the melamine in milk samples obtained good separation and determination, which provided a new separation media and a new analysis method for the determination of melamine.
3 The silica-bonded tetraoxocalix[2]arene[2]triazine stationary phase (TOA2T2) was applied to determinations of benzo(a)pyrene in air, soil and water by HPLC/FLD. The results are satisfactory with a good linear relationship in the range of 0.8-20 ng/mL(R2=0.999), good reproducibility (peak area RSD=2.55 %), detection limt 0.2ng/mL, recoveries 96%-101%.
引文
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