超支化硅碳烷—硅基杂化功能材料的制备及其在色谱领域的应用
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摘要
作为一种新兴的功能高分子,超支化大分子拥有三维立体结构和末端可功能化修饰的优点。充分利于这种物理与化学优势,并将其应用于各材料前沿领域是一个研究热点。
本论文工作基于硅碳烷树枝状大分子为有机组分,充分利用其独特的物理化学性质,于其末端键合具有分离功能苯基、C8、环糊精的官能团,依据采用的色谱形式不同,运用不同的化学键合手段：或是直接对于稳定形态的硅胶进行化学键合,或是以前驱体的形式参与到溶胶-凝胶过程中,从而制备出几种不同物理形态的无机硅胶-硅碳烷超支化(或树枝状)功能大分子杂化材料,并在此基础上分别制备出了苯基树状大分子-硅胶固定相的高效液相色谱柱、苯基超支化大分子-硅胶杂化涂层的毛细管气相色谱柱和固相微萃取头、环糊精超支化大分子毛细管色谱柱,分别进行了色谱分离表达与制样水平表达,对这类物质作为色谱分离与制样材料的能力进行了有效评价。
采用硅氢加成和格氏取代的方法,对于硅碳烷树枝状大分子进行末端苯基改性,将其化学键合到5μm硅胶球体外表面。对产物采用红外光谱、元素分析和憎水性实验进行表征。采用苯酚、甲苯与4-氯代硝基苯进行了色谱性能评价。依据对甲苯和4-氯代硝基苯的出峰顺序与柱评价,提出了基于树枝状大分子硅胶键合固定相的液相色谱分离模式作用三因素：末端结构,枝臂结构与笼结构。它们对于混合物的共同作用决定了出峰顺序的先后。
双连续结构是整体柱色谱材料的必要结构。通过调整双亲大分子聚乙二醇的用量和溶胶-凝胶温度对正硅酸乙酯进行酸性水解,使用扫描电镜对产物进行形貌观察,在获取微区得以充分发展的、具有一定双连续结构的无机硅胶基础上,将合成的具有可水解的C8末端基的硅碳烷树状分子作为共水解前驱体,与正硅酸乙酯在优化条件下进行溶胶-凝胶反应,通过调整r(PEO单体单元/TEOS摩尔比)值和反应温度,进一步优化反应条件,制备出具有双连续结构的C8末端基的硅碳烷树枝状大分子-硅胶杂化双连续结构的整体材料。
开管毛细管柱内表面的化学修饰改性是毛细管气相色谱法与电色谱法的工作基础。充分利用超支化大分子的物理化学优势,合成出末端具有苯基的超支化硅碳烷大分子。采用溶胶-凝胶法,将清洗、去活、固载、陈化于一体,制备了无机硅胶-有机硅碳烷超支化大分子杂化物表面涂层的薄膜材料。应力开裂是在溶胶-凝胶工艺中获取均匀材料必需要克服的问题。通过对于大量样本在无机酸的催化作用下溶胶凝胶的动态演变过程的观察与分析,结合溶胶-凝胶原理,揭示了无机酸性催化剂作用于溶胶体系因组份分散不匀而使应力集中突发、进而不利于制备出结构均匀的薄膜材料的内在原因。色谱分离实验表明以这种催化剂进行溶胶凝胶反应所制备的色谱柱体材料由于在凝胶过程中产生大量裂纹,严重影响了毛细管色谱柱对于同系物的分离。采用三氟乙酸作为催化剂,依靠大气中的水份作为反应水源,进行溶胶凝胶反应制柱,在与无机酸催化制柱同样的配方与实验条件下,通过所得毛细管柱对同系物的分离实验,柱性能得以极大改善。进一步的痕量分析结果表明,苯基超支化硅碳烷-硅胶杂化结构柱在10米长度条件下拥有lppm级的痕量分析能力,其性能优越于国内30米长的5%苯基-PDMS毛细管柱。
固相微萃取是近来发展起来的色谱分析制样技术。固相微萃取头是这个技术的核心部件。而固相微萃取头的表面涂层性能在很大程度上决定了制样水平,直接影响分析表达能力。在前面的工作基础上,采用溶胶-凝胶法,制备了内壁涂敷有硅碳烷超支化大分子的毛细管固相微萃取头和以甲基苯基二乙氧基硅烷作为水解前驱体的毛细管固相微萃取头。通过对比两者的萃取性能,结果显示：苯基硅碳烷超支化大分子具有富集量大、迅速达到吸附平衡的能力。萃取性能优于相同工艺与配方下的甲基苯基二乙氧基硅烷制备的固相微萃取头。对1ppm苯/水溶液进行固相微萃取,性能优越于国外商品Supelco萃取头。
环糊精是手性分离固定相中常用的手性载体。本文将环糊精键合于硅碳烷超支化大分子末端,进行了红外光谱分析。并作为色谱手性分离材料使用,制备了毛细管色谱柱,并对于同系物、同分异构体与对映异构体进行了分离测试。实验结果表明,环糊精-硅碳烷超支化大分子作为手性分离固定相,不仅能够对于常规同系物苯类、丙烯酸酯类等物质进行很好的分离性能,尤其宝贵的是,它可以将苯基超支化柱不能给以很好区分的同分异构体二甲苯类和无法给以区分的对映异构体酒石酸类很好地拆分开来,充分表达了手性固定相的独特分离性能。使所制备色谱柱具有多种分离能力的优势。
Three dimensional structure and multi-ended groups afford hyperbranched polymers (including dendrimer) advantage functionalities in many fields, and have attracted more and more attention recently.
In full use of the advantages of the three-dimentional structure and chemcial agility, dendrimer and hyperbranched macromolecules with C8group, phenyl group, and cyclodextrin group are synthesized and used as stationary phases and microextraction coating by different forms in accordance with specific applications
In high performance liquid chromatography, phenyl-allyl-ended carbosilane dendrimer is hydrosilylated with MeHSiCl2and is bonded to5μm silica gel. The affoded surface modified silica gel is characterized by IR, element analysis and hydrophobicity test. Column evaluation by peak sequence of toluene and2-choloride-nitro-benzene indicates that a multi-functional interaction modle plays an important role in separation process-they are predicted as end group-analyte interaction, branch-analyte interaction and capsulation interaction.
Monolithic materials are recent interest especially in liquid chromatography field. Polyethylene glycol(PEG) is used as phase modulator in acid-catalyzed tetraethoxysilane/water(TEOS) system. Continuous structure with different morphology,"r" value, which represents the number ratio of PEG monomer unit to tetrethoxysilane, together with temperature, have important role in formation of this bi-continuous morphology. C8-ended hyperbranched carbosliane is synthesized and characterized by IR and1HNMR, and is bonded with hydrolyzable ethoxyl group by hydrosilylation with triethoxysilane. Co-hydrolyzed with tetraethoxysilane in optimized condition, bi-continuous structure with hyperbranched carbosilane is obtained.
Benzyl terminated carbosilane hyperbranched polymer is synthesized and characterized by IR,1H NMR,13C NMR. It is hydrosilylated with triethoxysilane and hydrolyzed with tetraethoxysilane with inorganic acid/organic acid as catalyst specifically. Obtained morphologies are carefully studied. Great number of cracks occurred in gel body in sol-gel process with catalysis by inorganic acid. This has negative effects to chromatography process. The column coated with hydrolyzable phenyl-ended hyperbranched carbosilane with trifluoroacetic acid catalysis by sol-gel process gives excellent performance in separatioin of homologues. Experiment analysis reveals that the column has ability to detect1ppm trace amount analytes.
Based on the work above, benzyl-terminated hyperbranched carbosilane is further used as fused silica inner wall coating and finds its application in microextraction field. A contrasting column coated with phenylmethyldiethoxylsilane is prepard in the same conditions as that of hyperbranched polymer coating. Experiments reveals that hyperbranched structure coating have much larger absorption amount than phenylmethyldiethoxylsilane coating (by ten fold) and reaches absorption balance point in much shorter time(20mins). Trace analysis by this coating reveals excellent property. An experiment is designed to test the comprehensive performance of the home-made hyperbranched carbosilane bearing SPME/Capillary Gas Chromatography combination model vs a commercial SPME/capillary model. Testing results show that the combined function of hyperbranched column/hyperbranched microextraction coating possess prominent property than commercial model. Sharp peaks at the challenge of trace analysis of1ppm benzyl/water sample are obtained.
β-Cyclodextrin react with allyl-ended hyperbranched carbosilane and the product is characterized by IR. Fused silica capillary is filled with β-cyclodextrin-hyperbranched carbosilane and the resulted chromatography property is tested. Homologues, isomers and especially enantiomers get base-line separated. The unique three-dimention structure of hyperbranched carbosilane combines well with the guest-inclusion function of β cyclodextrin and give perfect behavior as stationary phase in chromatography.
本论文工作基于硅碳烷树枝状大分子为有机组分,充分利用其独特的物理化学性质,于其末端键合具有分离功能苯基、C8、环糊精的官能团,依据采用的色谱形式不同,运用不同的化学键合手段：或是直接对于稳定形态的硅胶进行化学键合,或是以前驱体的形式参与到溶胶-凝胶过程中,从而制备出几种不同物理形态的无机硅胶-硅碳烷超支化(或树枝状)功能大分子杂化材料,并在此基础上分别制备出了苯基树状大分子-硅胶固定相的高效液相色谱柱、苯基超支化大分子-硅胶杂化涂层的毛细管气相色谱柱和固相微萃取头、环糊精超支化大分子毛细管色谱柱,分别进行了色谱分离表达与制样水平表达,对这类物质作为色谱分离与制样材料的能力进行了有效评价。
采用硅氢加成和格氏取代的方法,对于硅碳烷树枝状大分子进行末端苯基改性,将其化学键合到5μm硅胶球体外表面。对产物采用红外光谱、元素分析和憎水性实验进行表征。采用苯酚、甲苯与4-氯代硝基苯进行了色谱性能评价。依据对甲苯和4-氯代硝基苯的出峰顺序与柱评价,提出了基于树枝状大分子硅胶键合固定相的液相色谱分离模式作用三因素：末端结构,枝臂结构与笼结构。它们对于混合物的共同作用决定了出峰顺序的先后。
双连续结构是整体柱色谱材料的必要结构。通过调整双亲大分子聚乙二醇的用量和溶胶-凝胶温度对正硅酸乙酯进行酸性水解,使用扫描电镜对产物进行形貌观察,在获取微区得以充分发展的、具有一定双连续结构的无机硅胶基础上,将合成的具有可水解的C8末端基的硅碳烷树状分子作为共水解前驱体,与正硅酸乙酯在优化条件下进行溶胶-凝胶反应,通过调整r(PEO单体单元/TEOS摩尔比)值和反应温度,进一步优化反应条件,制备出具有双连续结构的C8末端基的硅碳烷树枝状大分子-硅胶杂化双连续结构的整体材料。
开管毛细管柱内表面的化学修饰改性是毛细管气相色谱法与电色谱法的工作基础。充分利用超支化大分子的物理化学优势,合成出末端具有苯基的超支化硅碳烷大分子。采用溶胶-凝胶法,将清洗、去活、固载、陈化于一体,制备了无机硅胶-有机硅碳烷超支化大分子杂化物表面涂层的薄膜材料。应力开裂是在溶胶-凝胶工艺中获取均匀材料必需要克服的问题。通过对于大量样本在无机酸的催化作用下溶胶凝胶的动态演变过程的观察与分析,结合溶胶-凝胶原理,揭示了无机酸性催化剂作用于溶胶体系因组份分散不匀而使应力集中突发、进而不利于制备出结构均匀的薄膜材料的内在原因。色谱分离实验表明以这种催化剂进行溶胶凝胶反应所制备的色谱柱体材料由于在凝胶过程中产生大量裂纹,严重影响了毛细管色谱柱对于同系物的分离。采用三氟乙酸作为催化剂,依靠大气中的水份作为反应水源,进行溶胶凝胶反应制柱,在与无机酸催化制柱同样的配方与实验条件下,通过所得毛细管柱对同系物的分离实验,柱性能得以极大改善。进一步的痕量分析结果表明,苯基超支化硅碳烷-硅胶杂化结构柱在10米长度条件下拥有lppm级的痕量分析能力,其性能优越于国内30米长的5%苯基-PDMS毛细管柱。
固相微萃取是近来发展起来的色谱分析制样技术。固相微萃取头是这个技术的核心部件。而固相微萃取头的表面涂层性能在很大程度上决定了制样水平,直接影响分析表达能力。在前面的工作基础上,采用溶胶-凝胶法,制备了内壁涂敷有硅碳烷超支化大分子的毛细管固相微萃取头和以甲基苯基二乙氧基硅烷作为水解前驱体的毛细管固相微萃取头。通过对比两者的萃取性能,结果显示：苯基硅碳烷超支化大分子具有富集量大、迅速达到吸附平衡的能力。萃取性能优于相同工艺与配方下的甲基苯基二乙氧基硅烷制备的固相微萃取头。对1ppm苯/水溶液进行固相微萃取,性能优越于国外商品Supelco萃取头。
环糊精是手性分离固定相中常用的手性载体。本文将环糊精键合于硅碳烷超支化大分子末端,进行了红外光谱分析。并作为色谱手性分离材料使用,制备了毛细管色谱柱,并对于同系物、同分异构体与对映异构体进行了分离测试。实验结果表明,环糊精-硅碳烷超支化大分子作为手性分离固定相,不仅能够对于常规同系物苯类、丙烯酸酯类等物质进行很好的分离性能,尤其宝贵的是,它可以将苯基超支化柱不能给以很好区分的同分异构体二甲苯类和无法给以区分的对映异构体酒石酸类很好地拆分开来,充分表达了手性固定相的独特分离性能。使所制备色谱柱具有多种分离能力的优势。
Three dimensional structure and multi-ended groups afford hyperbranched polymers (including dendrimer) advantage functionalities in many fields, and have attracted more and more attention recently.
In full use of the advantages of the three-dimentional structure and chemcial agility, dendrimer and hyperbranched macromolecules with C8group, phenyl group, and cyclodextrin group are synthesized and used as stationary phases and microextraction coating by different forms in accordance with specific applications
In high performance liquid chromatography, phenyl-allyl-ended carbosilane dendrimer is hydrosilylated with MeHSiCl2and is bonded to5μm silica gel. The affoded surface modified silica gel is characterized by IR, element analysis and hydrophobicity test. Column evaluation by peak sequence of toluene and2-choloride-nitro-benzene indicates that a multi-functional interaction modle plays an important role in separation process-they are predicted as end group-analyte interaction, branch-analyte interaction and capsulation interaction.
Monolithic materials are recent interest especially in liquid chromatography field. Polyethylene glycol(PEG) is used as phase modulator in acid-catalyzed tetraethoxysilane/water(TEOS) system. Continuous structure with different morphology,"r" value, which represents the number ratio of PEG monomer unit to tetrethoxysilane, together with temperature, have important role in formation of this bi-continuous morphology. C8-ended hyperbranched carbosliane is synthesized and characterized by IR and1HNMR, and is bonded with hydrolyzable ethoxyl group by hydrosilylation with triethoxysilane. Co-hydrolyzed with tetraethoxysilane in optimized condition, bi-continuous structure with hyperbranched carbosilane is obtained.
Benzyl terminated carbosilane hyperbranched polymer is synthesized and characterized by IR,1H NMR,13C NMR. It is hydrosilylated with triethoxysilane and hydrolyzed with tetraethoxysilane with inorganic acid/organic acid as catalyst specifically. Obtained morphologies are carefully studied. Great number of cracks occurred in gel body in sol-gel process with catalysis by inorganic acid. This has negative effects to chromatography process. The column coated with hydrolyzable phenyl-ended hyperbranched carbosilane with trifluoroacetic acid catalysis by sol-gel process gives excellent performance in separatioin of homologues. Experiment analysis reveals that the column has ability to detect1ppm trace amount analytes.
Based on the work above, benzyl-terminated hyperbranched carbosilane is further used as fused silica inner wall coating and finds its application in microextraction field. A contrasting column coated with phenylmethyldiethoxylsilane is prepard in the same conditions as that of hyperbranched polymer coating. Experiments reveals that hyperbranched structure coating have much larger absorption amount than phenylmethyldiethoxylsilane coating (by ten fold) and reaches absorption balance point in much shorter time(20mins). Trace analysis by this coating reveals excellent property. An experiment is designed to test the comprehensive performance of the home-made hyperbranched carbosilane bearing SPME/Capillary Gas Chromatography combination model vs a commercial SPME/capillary model. Testing results show that the combined function of hyperbranched column/hyperbranched microextraction coating possess prominent property than commercial model. Sharp peaks at the challenge of trace analysis of1ppm benzyl/water sample are obtained.
β-Cyclodextrin react with allyl-ended hyperbranched carbosilane and the product is characterized by IR. Fused silica capillary is filled with β-cyclodextrin-hyperbranched carbosilane and the resulted chromatography property is tested. Homologues, isomers and especially enantiomers get base-line separated. The unique three-dimention structure of hyperbranched carbosilane combines well with the guest-inclusion function of β cyclodextrin and give perfect behavior as stationary phase in chromatography.
引文
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