硅基质核—壳结构分子印迹纳米材料的制备及应用
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摘要
本工作的主要内容是硅基质核-壳结构分子印迹纳米材料的制备及其在食品和环境安全及生物分离分析中的应用。论文内容包括如下六部分：
第一部分：绪论。综述了分子印迹技术的分类及其面临的挑战；结合纳米材料和溶胶-凝胶技术的分子印迹技术。此外，还对本论文的选题意义、内容及创新性进行了简要的介绍。
第二部分：磺胺类药物分子印迹纳米硅球的制备及应用。采用溶胶-凝胶技术合成了粒径约为80nm的硅球。通过硅烷化试剂3-氨丙基三乙氧基硅烷，使氨基接枝到硅球表面；再通过丙烯酰氯与氨基间的作用，使丙烯酰基接枝到硅球表面。以磺胺甲噁唑为模板分子，采用表面分子印迹技术，在功能单体、交联剂和引发剂的共同作用下，将印迹层包覆在接枝有丙烯酰基的硅球表面，制得磺胺甲噁唑分子印迹纳米硅球。与本体分子印迹技术制得的块状聚合物相比较，所得分子印迹纳米硅球的识别位点均位于硅纳米粒子表面，易于模板分子接近，具有更快的动力学速度，更高的吸附能力和选择性。将其作为吸附材料，实现了对牛奶和鸡蛋中磺胺嘧啶和磺胺甲噁唑选择性地富集和测定。建立了一种离线的分子印迹固相萃取与高效液相色谱联用的有效检测食品中磺胺类药物残留的新方法。
第三部分：雌酮分子印迹碳纳米管的制备及应用。以包硅碳纳米管作为载体，雌酮作为模板分子，采用半共价印迹法，制得了雌酮的分子印迹碳纳米管。通过等温吸附和选择性吸附实验及Scatchard分析对所得分子印迹碳纳米管的吸附性能进行了考察。实验结果证明，其选择性吸附性能好，动力学吸附速度快，不同批次间的重现性良好。将其应用于环境水样中痕量雌酮的去除，去除效果令人满意。建立了一种价格低廉，合成方法简单，可大批量合成碳纳米管分子印迹聚合物的新方法。
第四部分：三氯生分子印迹碳纳米管的制备及应用。以包硅碳纳米管作为载体，三氯生作为模板分子，采用溶胶-凝胶技术，制得了三氯生的分子印迹碳纳米管。通过一系列的吸附实验对所制备的分子印迹碳纳米管的吸附性能进行了考察。实验结果显示，制得的聚合物不仅选择性吸附性能好、动力学吸附速度快、不同批次间的重现性好，且可多次循环使用。将其作为吸附材料，实现了对环境水样中三氯生的选择性富集和测定。建立了一种可选择性检测环境水样中三氯生含量的新方法。
第五部分：蛋白质磁性分子印迹纳米粒子的制备及应用。采用水热法合成了粒径均一，磁性能良好，粒径约200nm的磁性纳米粒子。结合表面分子印迹技术和溶胶-凝胶技术的优势，以所得磁性纳米粒子作为载体，以四种不同等电点的蛋白质（牛血清白蛋白，pI=4.9；牛血红蛋白，pI=6.9；核糖核酸酶A，pI=9.4；溶菌酶，pI=11.2）作为模板分子，采用固定模板蛋白的方法，制备了不同等电点蛋白质的磁性分子印迹纳米粒子。所得各种聚合物对相应的模板蛋白均表现出很好的选择吸附性能及极快的分离速度。其中，牛血红蛋白分子印迹磁性纳米粒子的吸附量最大，印迹效果最好。将其用于混合蛋白样品和牛血中牛血红蛋白的去除，去除效果良好，且可将去除的牛血红蛋白洗脱富集。建立了一种对不同等电点的蛋白质都适用的制备磁性分子印迹纳米粒子的通用方法。
第六部分：蛋白质温敏磁性分子印迹纳米粒子的制备及应用。以表面接枝有双键的磁性纳米粒子作为载体，以廉价的牛血清白蛋白作为替代模板，以具有温敏响应的N-异丙基丙烯酰胺作为主要功能单体，采用表面分子印迹技术，制备了一种新型的磁性温敏牛血清白蛋白分子印迹纳米粒子，以实现对价格相对昂贵的人血清白蛋白的选择性富集。对聚合、吸附及洗脱条件进行了系统的考察。所得磁性温敏分子印迹纳米粒子可快速达到吸附平衡，实现快速磁性分离，对人血清白蛋白有良好的选择性吸附性能，对温度和盐度都有一定的智能响应，通过对温度的改变即可实现对人血清白蛋白的吸附和解吸。将其应用于牛血样中的牛血清白蛋白和人血样中的人血清白蛋白的选择性去除和富集，效果良好。建立了一种制备可通过温度的改变就实现对人血清白蛋白选择性去除和富集的廉价的磁性分子印迹纳米粒子的新方法。
This thesis is involved in the preparation and application of molecularlyimprinted polymers based on silica-coated nanomaterials. It consists of six chapters.
In chapter one, the general introduction included the classification andchallenges of molecular imprinting technique (MIT), MIT combined with thecharacteristics of nanomaterials and sol-gel technique. Additionally, the aim,significance and innovation of this thesis were also briefly presented.
In chapter two, silica-coated molecularly imprinted polymer nanospheres for theselective analysis of sulfonamides in food samples were prepared. Themonodispersed SiO_2nanoparticles of diameter80nm were amino-modified byreaction with3-aminopropyltriethoxylsilane. The acryloyl monolayer was thengrafted onto the amine-modified SiO_2nanoparticles. Finally, the molecular imprintingpolymers (MIPs) films were coated onto the surface of SiO_2nanoparticles by thecopolymerization of the vinyl end groups with functional monomer, cross-linkingagent, initiator, and template molecule (sulfamethoxazole, SMO) to obtain MIPsnanoparticles for SMO (SiO_2@SMO-MIPs). The resulted SiO_2@SMO-MIPs hadbetter site accessibility, faster binding kinetics, higher binding capacity and selectivitycompared with MIPs prepared by traditional bulk polymerization. The feasibility ofremoving SMO and sulfadiazine from food samples was proved by the use of spikedmilk and eggs. Using the SiO_2@SMO-MIPs materials as sorbents, a new off-linemolecular imprinting solid phase extraction-high performance liquid chromatographymethod was developed.
In chapter three, carbon nanotubes (CNTs) functionalized with MIPs foradvanced removal of estrone were prepared. The obtained MIPs for estrone(CNTs@Est-MIPs) nanocomposites with a well-defined core-shell structure wereobtained using a semi-covalent imprinting strategy. The adsorption properties weredemonstrated by equilibrium rebinding experiments and Scatchard analysis. Theresults demonstrated that the CNTs@Est-MIPs possess favourable selectivity, highcapacity and fast kinetics for template molecule uptake. The synthetic process was quite simple, and the different batches of synthesized CNTs@Est-MIPsnanocomposites showed good reproducibility in template binding. The preparedCNTs@Est-MIPs nanocomposites exhibited high removal efficiency as a sorbent forestrone in water samples.
In chapter four, molecularly imprinted polymers for triclosan on CNTs coatedwith silica (CNTs@TCS-MIPs) combining a surface molecular imprinting techniquewith a sol-gel process were prepared. The adsorption properties of the polymers weredemonstrated by a series of rebinding experiments. The prepared imprinted materialsexhibited fast kinetics, high capacity and favorable selectivity. Different batches ofCNTs@TCS-MIPs showed good reproducibility and the reusability of MIPs withoutany deterioration in capacity was demonstrated for at least six repeated cycles. TheMIPs developed could be used for the selective adsorption and determination oftriclosan from environmental matrices.
In chapter five, molecularly imprinted polymers functionalized with magneticnanoparticles for the recognition and enrichment of protein were prepared. Themonodispersed Fe_3O_4nanoparticles of diameter200nm were prepared through amodified solvothermal reaction. Four proteins (bovine serum albumin (BSA, pI=4.9),bovine hemoglobin (BHb, pI=6.9), ribonuclease A (RNase A, pI=9.4) andlysozyme (Lyz, pI=11.2)) with different isoelectric points were chosen as thetemplates. The magnetic protein-MIPs were synthesized by combining surfaceimprinting with a sol-gel process based on covalent template immobilization on thesurface of Fe_3O_4. The adsorption ability of different magnetic protein-MIPs torelevant template proteins were all higher than for the other three proteins. Therefore,this general method studied in this paper was proven to be amenable to different kindsof proteins with different isoelectric points. The magnetic MIPs of BHb (Fe_3O_4@BHb-MIPs) showed the best imprinting effect and the highest adsorption capacity amongthe four proteins. The resulted Fe_3O_4@BHb-MIPs could not only selectively extract atarget protein from mixed proteins but also specifically capture the protein BHb froma real sample of bovine blood.
In chapter six, thermosensitive molecularly imprinted polymers functionalizedwith magnetic nanoparticles of BSA for the recognition and enrichment of human serum albumin (HSA) were prepared. The main monomer N-isopropylacrylamidewas introduced as a thermosensitive element. BSA was chosen as dummy templatefor HSA. The MIPs films were coated onto the surface of Fe_3O_4by thecopolymerization of the vinyl end groups with functional monomer, cross-linkingagent (N, N-methylenebisacrylamide), initiator (ammonium persulfate), and templatemolecule to obtain MIPs of BSA (Fe_3O_4@BSA-MIPs). The conditions ofpolymerization, adsorption and elution was systematically investigated. Fe_3O_4@BSA-MIPs possessed easy accessibility to the recognition sites and showed fastkinetics, high capacity and favorable selectivity. Fe_3O_4@BSA-MIPs could not onlyrespond to temperature and ionic strength, and achieve adsorption-desorption cyclesthrough changing the temperature, but also be successfully applicated in the selectiveenrichment of BSA or HSA from mixed proteins and bovine blood or human blood.
第一部分：绪论。综述了分子印迹技术的分类及其面临的挑战；结合纳米材料和溶胶-凝胶技术的分子印迹技术。此外，还对本论文的选题意义、内容及创新性进行了简要的介绍。
第二部分：磺胺类药物分子印迹纳米硅球的制备及应用。采用溶胶-凝胶技术合成了粒径约为80nm的硅球。通过硅烷化试剂3-氨丙基三乙氧基硅烷，使氨基接枝到硅球表面；再通过丙烯酰氯与氨基间的作用，使丙烯酰基接枝到硅球表面。以磺胺甲噁唑为模板分子，采用表面分子印迹技术，在功能单体、交联剂和引发剂的共同作用下，将印迹层包覆在接枝有丙烯酰基的硅球表面，制得磺胺甲噁唑分子印迹纳米硅球。与本体分子印迹技术制得的块状聚合物相比较，所得分子印迹纳米硅球的识别位点均位于硅纳米粒子表面，易于模板分子接近，具有更快的动力学速度，更高的吸附能力和选择性。将其作为吸附材料，实现了对牛奶和鸡蛋中磺胺嘧啶和磺胺甲噁唑选择性地富集和测定。建立了一种离线的分子印迹固相萃取与高效液相色谱联用的有效检测食品中磺胺类药物残留的新方法。
第三部分：雌酮分子印迹碳纳米管的制备及应用。以包硅碳纳米管作为载体，雌酮作为模板分子，采用半共价印迹法，制得了雌酮的分子印迹碳纳米管。通过等温吸附和选择性吸附实验及Scatchard分析对所得分子印迹碳纳米管的吸附性能进行了考察。实验结果证明，其选择性吸附性能好，动力学吸附速度快，不同批次间的重现性良好。将其应用于环境水样中痕量雌酮的去除，去除效果令人满意。建立了一种价格低廉，合成方法简单，可大批量合成碳纳米管分子印迹聚合物的新方法。
第四部分：三氯生分子印迹碳纳米管的制备及应用。以包硅碳纳米管作为载体，三氯生作为模板分子，采用溶胶-凝胶技术，制得了三氯生的分子印迹碳纳米管。通过一系列的吸附实验对所制备的分子印迹碳纳米管的吸附性能进行了考察。实验结果显示，制得的聚合物不仅选择性吸附性能好、动力学吸附速度快、不同批次间的重现性好，且可多次循环使用。将其作为吸附材料，实现了对环境水样中三氯生的选择性富集和测定。建立了一种可选择性检测环境水样中三氯生含量的新方法。
第五部分：蛋白质磁性分子印迹纳米粒子的制备及应用。采用水热法合成了粒径均一，磁性能良好，粒径约200nm的磁性纳米粒子。结合表面分子印迹技术和溶胶-凝胶技术的优势，以所得磁性纳米粒子作为载体，以四种不同等电点的蛋白质（牛血清白蛋白，pI=4.9；牛血红蛋白，pI=6.9；核糖核酸酶A，pI=9.4；溶菌酶，pI=11.2）作为模板分子，采用固定模板蛋白的方法，制备了不同等电点蛋白质的磁性分子印迹纳米粒子。所得各种聚合物对相应的模板蛋白均表现出很好的选择吸附性能及极快的分离速度。其中，牛血红蛋白分子印迹磁性纳米粒子的吸附量最大，印迹效果最好。将其用于混合蛋白样品和牛血中牛血红蛋白的去除，去除效果良好，且可将去除的牛血红蛋白洗脱富集。建立了一种对不同等电点的蛋白质都适用的制备磁性分子印迹纳米粒子的通用方法。
第六部分：蛋白质温敏磁性分子印迹纳米粒子的制备及应用。以表面接枝有双键的磁性纳米粒子作为载体，以廉价的牛血清白蛋白作为替代模板，以具有温敏响应的N-异丙基丙烯酰胺作为主要功能单体，采用表面分子印迹技术，制备了一种新型的磁性温敏牛血清白蛋白分子印迹纳米粒子，以实现对价格相对昂贵的人血清白蛋白的选择性富集。对聚合、吸附及洗脱条件进行了系统的考察。所得磁性温敏分子印迹纳米粒子可快速达到吸附平衡，实现快速磁性分离，对人血清白蛋白有良好的选择性吸附性能，对温度和盐度都有一定的智能响应，通过对温度的改变即可实现对人血清白蛋白的吸附和解吸。将其应用于牛血样中的牛血清白蛋白和人血样中的人血清白蛋白的选择性去除和富集，效果良好。建立了一种制备可通过温度的改变就实现对人血清白蛋白选择性去除和富集的廉价的磁性分子印迹纳米粒子的新方法。
This thesis is involved in the preparation and application of molecularlyimprinted polymers based on silica-coated nanomaterials. It consists of six chapters.
In chapter one, the general introduction included the classification andchallenges of molecular imprinting technique (MIT), MIT combined with thecharacteristics of nanomaterials and sol-gel technique. Additionally, the aim,significance and innovation of this thesis were also briefly presented.
In chapter two, silica-coated molecularly imprinted polymer nanospheres for theselective analysis of sulfonamides in food samples were prepared. Themonodispersed SiO_2nanoparticles of diameter80nm were amino-modified byreaction with3-aminopropyltriethoxylsilane. The acryloyl monolayer was thengrafted onto the amine-modified SiO_2nanoparticles. Finally, the molecular imprintingpolymers (MIPs) films were coated onto the surface of SiO_2nanoparticles by thecopolymerization of the vinyl end groups with functional monomer, cross-linkingagent, initiator, and template molecule (sulfamethoxazole, SMO) to obtain MIPsnanoparticles for SMO (SiO_2@SMO-MIPs). The resulted SiO_2@SMO-MIPs hadbetter site accessibility, faster binding kinetics, higher binding capacity and selectivitycompared with MIPs prepared by traditional bulk polymerization. The feasibility ofremoving SMO and sulfadiazine from food samples was proved by the use of spikedmilk and eggs. Using the SiO_2@SMO-MIPs materials as sorbents, a new off-linemolecular imprinting solid phase extraction-high performance liquid chromatographymethod was developed.
In chapter three, carbon nanotubes (CNTs) functionalized with MIPs foradvanced removal of estrone were prepared. The obtained MIPs for estrone(CNTs@Est-MIPs) nanocomposites with a well-defined core-shell structure wereobtained using a semi-covalent imprinting strategy. The adsorption properties weredemonstrated by equilibrium rebinding experiments and Scatchard analysis. Theresults demonstrated that the CNTs@Est-MIPs possess favourable selectivity, highcapacity and fast kinetics for template molecule uptake. The synthetic process was quite simple, and the different batches of synthesized CNTs@Est-MIPsnanocomposites showed good reproducibility in template binding. The preparedCNTs@Est-MIPs nanocomposites exhibited high removal efficiency as a sorbent forestrone in water samples.
In chapter four, molecularly imprinted polymers for triclosan on CNTs coatedwith silica (CNTs@TCS-MIPs) combining a surface molecular imprinting techniquewith a sol-gel process were prepared. The adsorption properties of the polymers weredemonstrated by a series of rebinding experiments. The prepared imprinted materialsexhibited fast kinetics, high capacity and favorable selectivity. Different batches ofCNTs@TCS-MIPs showed good reproducibility and the reusability of MIPs withoutany deterioration in capacity was demonstrated for at least six repeated cycles. TheMIPs developed could be used for the selective adsorption and determination oftriclosan from environmental matrices.
In chapter five, molecularly imprinted polymers functionalized with magneticnanoparticles for the recognition and enrichment of protein were prepared. Themonodispersed Fe_3O_4nanoparticles of diameter200nm were prepared through amodified solvothermal reaction. Four proteins (bovine serum albumin (BSA, pI=4.9),bovine hemoglobin (BHb, pI=6.9), ribonuclease A (RNase A, pI=9.4) andlysozyme (Lyz, pI=11.2)) with different isoelectric points were chosen as thetemplates. The magnetic protein-MIPs were synthesized by combining surfaceimprinting with a sol-gel process based on covalent template immobilization on thesurface of Fe_3O_4. The adsorption ability of different magnetic protein-MIPs torelevant template proteins were all higher than for the other three proteins. Therefore,this general method studied in this paper was proven to be amenable to different kindsof proteins with different isoelectric points. The magnetic MIPs of BHb (Fe_3O_4@BHb-MIPs) showed the best imprinting effect and the highest adsorption capacity amongthe four proteins. The resulted Fe_3O_4@BHb-MIPs could not only selectively extract atarget protein from mixed proteins but also specifically capture the protein BHb froma real sample of bovine blood.
In chapter six, thermosensitive molecularly imprinted polymers functionalizedwith magnetic nanoparticles of BSA for the recognition and enrichment of human serum albumin (HSA) were prepared. The main monomer N-isopropylacrylamidewas introduced as a thermosensitive element. BSA was chosen as dummy templatefor HSA. The MIPs films were coated onto the surface of Fe_3O_4by thecopolymerization of the vinyl end groups with functional monomer, cross-linkingagent (N, N-methylenebisacrylamide), initiator (ammonium persulfate), and templatemolecule to obtain MIPs of BSA (Fe_3O_4@BSA-MIPs). The conditions ofpolymerization, adsorption and elution was systematically investigated. Fe_3O_4@BSA-MIPs possessed easy accessibility to the recognition sites and showed fastkinetics, high capacity and favorable selectivity. Fe_3O_4@BSA-MIPs could not onlyrespond to temperature and ionic strength, and achieve adsorption-desorption cyclesthrough changing the temperature, but also be successfully applicated in the selectiveenrichment of BSA or HSA from mixed proteins and bovine blood or human blood.
引文
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