分子印迹聚合物、量子点及其复合微球的制备
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摘要
分子印迹技术和量子点技术都是近十几年发展起来的高分子材料技术,被广泛应用于各个领域,在食品安全领域也均具有重要的作用。本论文分别以4-甲基咪唑(4-MI)、三聚氰胺(MA)、氨基甲酸乙酯(EC)为模板分子,利用沉淀聚合法分别制备了三种分子印迹聚合物,利用油酸、油胺为混合稳定剂在液体石蜡中绿色制备了CdSe量子点和CdSe/CdS核壳量子点,在此基础上组合了分子印迹技术和量子点技术,制备了荧光分子印迹复合微球,现总结如下：
1.以4-MI为模板分子,α-甲基丙烯酸(MAA)为功能单体,乙二醇二甲基丙烯酸酯(EGDMA)为交联剂,偶氮二异丁腈(AIBN)为引发剂,在乙腈中通过沉淀聚合制备了分子印迹聚合物。用紫外分光光度法对4-MI与MAA的相互作用进行了分析,结果表明主客体主要存在形式为,1个4-MI与1个MAA通过氢键相互作用。利用Langmuir数学模型对吸附特性进行了分析,Scatchard分析显示印迹聚合物的最大吸附量Bmax=221.14μmol/g和解吸常数KD=1.8mmo1/L。同时对印迹聚合物的吸附选择性和吸附动力学进行了初步研究。
2.以MA为模板分子,MAA为功能单体,EGDMA为交联剂,AIBN为引发剂,在乙腈-乙二醇(20：1,v/v)混合溶剂中沉淀聚合制备了分子印迹聚合物微球。1H-NMR和紫外光谱方法研究表明,MA与MAA分子通过协同氢键作用形成1：2型氢键配合物。利用扫描电镜和红外光谱对聚合物微球的结构进行了表征。结果表明,印迹聚合物近似圆球形,粒径约为400-500nm,且大于非印迹聚合物微球,表面存在大量的结合位点。通过静态平衡吸附实验研究了聚合物微球对模板分子的结合能力,印迹聚合物微球在4h后逐渐达到吸附平衡,Scatchard分析表明,印迹聚合物微球主要存在两类不同的结合位点,最大表观结合量(Qmax)和平衡离解常数(Kd)分别为Qmax1=22.97μmol/g, Kd1=0.14×10-3 mol/L; Qmax2=157.65μmol/g,Kd2= 2.55×10-3mol/L,计算得出表观印迹效率和有效印迹效率分别为68%和58%。
3.改变传统沉淀聚合的合成条件,以液体石蜡和甲苯的混合液为溶剂和致孔剂,以EC为模板分子,MAA为功能单体,EGDMA为交联剂,AIBN为引发剂,制备了单分散微米级分子印迹聚合物微球。1H-NMR、红外光谱及计算机模拟研究表明EC分子与MAA之间具有较强的氢键作用。利用扫描电镜、红外光谱及示差扫描量热仪对聚合物微球的结构进行了表征,结果表明,印迹微球表面具有能够识别模板分子的基团,且微球粒径较大(约为4.32μm)、热稳定性好,有望应用于固相萃取及液相色谱填料等方面。
4.以液体石蜡作为高温反应溶剂,以油酸和油胺为混合稳定剂,利用高温热解法一步合成了高质量的CdSe量子点。通过紫外-可见吸收光谱、荧光发射光谱、红外光谱和X射线衍射等手段对量子点的光学性质和结构进行了表征。结果表明,油胺/油酸混合表面活性剂稳定的量子点吸收光谱峰形更加尖锐,荧光发射光谱半峰宽更窄,从42nm减小到32nm。反应温度和反应时间均对量子点的生长过程和光学性质有明显影响,220℃下反应10 min,荧光量子产率可达26.4%。CdSe量子点为立方晶型,平均直径d=3.6nm,荧光半峰宽较窄(32-39 nm),表面同时包覆了油酸和油胺,具有良好的光稳定性。
5.用油酸和油胺为混合修饰剂,在CdSe量子点表面包裹CdS,进一步制备了性能优越的CdSe/CdS核壳量子点。该量子点结构为闪锌矿结构,立方晶型,其壳层CdS是外延生长在CdSe量子点核表面的,颗粒近似圆形,平均直径d=4.5nm。与核CdSe量子点相比,核壳型的CdSe/CdS量子点的紫外吸收峰和荧光发射峰分别红移了25nm和15nm。CdSe/CdS核壳量子点的荧光强度要明显高于CdSe量子点,紫外激发4h后量子产率高达60.7%,且光稳定性较好。
6.将量子点技术与分子印迹技术相结合,以EC为模板分子,MAA为功能单体,EGDMA为交联剂,CdSe/CdS核壳量子点为荧光组分,光热联合引发,共沉淀聚合法制备了荧光分子印迹复合微球。将制备的荧光分子印迹复合微球用于EC的检测,在浓度范围1 mmol/L～5 mmol/L内具有良好的线性关系,回归方程为ln(F0/F)=0.03419[Q]-0.00739,猝灭常数Ksv为3.419×10-2L/mmol,线性相关系数R2为0.994,说明氨基甲酸乙酯对荧光分子印迹复合微球的具有较好的猝灭作用,可以进一步详细研究,以实现对EC的快速准确的检测。
Molecularly imprinted technology and quantum dots technology are both polymer materials technology which have developed over recent decades and are widely used in various fields including the field of food safety. In this paper, three molecularly imprinted polymers are respectively prepared using 4-MI、MA and EC EC as template by precipitation polymerization. Oleic acid and Oleic acid are used as mixed stabilizers prepareing the CdSe and CdSe/CdS quantum dots. Based on the above, we combine molecular imprinted technology with the quantum dots technology to prepare fluorescent molecularly imprinted composite microspheres. Summarized as follows:
1. Uniformly imprinted polymer microspheres are prepared by precipitation polymerization in acetonitrile.4-MI(4-methyl imiadzole), MAA(methacrylic acid), EGDMA(ethylene glycol dimethacrylate) and AIBN(azobisisobutyronitrile) are used as template, functional monomer, cross-linker and initiator, respectively. UV spectra is used to demonstrate the mechanism of the interaction between 4-MI and MAA. It is found that one 4-MI is entrapped by one MAA molecules in acetonitrile. Langmuir model is used to fit the adsorption data, the results show that the 4-MI imprinted polymer microspheres show specific binding sites to the 4-MI.The data obtained in equilibrium adsorption experiments are processed by Scatchard analysis, the dissociation contents (KD) and the apparent maximum binding capacity(Bmsx) are KD=1.8mmol/L,Bmax=221.14μmol/g. The 4-MI imprinted polymers have showed high affinity to 4-MI.
2. Uniformly molecularly imprinted polymer microspheres are prepared by precipitation polymerization of MAA and EGDMA using melamine as template in acetonitrile-ethylene glycol mixed solvent (20:1, v/v).1H-NMR and UV spectrometry are employed to demonstrate the mechanism of the interaction between Melamine and MAA, and the results show that the Melamine-MAA complexes of 1:2 mole ratio is obtained by cooperative hydrogen bonding. The adsorption efficiency is investigated by equilibrium adsorption experiments. The data obtained showed that the imprinted polymer microspheres reach equilibrium after 4h and have higher adsorption efficiency compared to the non-imprinted polymer microspheres, which have the same chemical composition. Scatchard analysis reveals that the apparent maximum binding capacity and the dissociation contents are Qmaxi=22.97μmol/g, Kd1=0.14×10-3mol/L for high affinity binding sites and Qmax2=157.65μmol/g, Kd2=2.55×10-3mol/L for low affinity binding sites, respectively. Thus, the apparent imprinting efficiency and the effective imprinting efficiency are calculated 68% and 58%, respectively.
3. We change the conditions of traditional precipitation polymerization. The monodisperse micron molecularly imprinted polymers microspheres are prepared by using EC as template, MAA as functional monomer, AIBN as initiator, EGDMA as cross linker, and the mixture of liquid paraffin and toluene as solvent and porogen, respectively. 1H-NMR, IR and computer are employed to demonstrate that there is strong hydrogen bonding between EC and MAA. Scanning electron microscopy, IR and Dynamic Rheometry are applied to indicate the characterization of the structure of the polymers microspheres. The above results demonstrated that the surface of microspheres has the imprinting hole which can recognize the template molecular. In addition, the microspheres with a good thermal stability, are comparatively large in size (approximately 4.32μm). As a result, it may be used in solid-phase extraction and chromatography packing.
4. A greener synthetic route to highly luminescent CdSe quantum dots (QDs) is reported in this paper. Oleylamine and oleic acid are used instead of phosphonic acids (HPA or TDPA) as the stabilizer. Paraffin liquid, which is a natural, nontoxic, and cheap solvent, is used to replace tri-n-octylphosphine oxide (TOPO) as the solvent for the synthesis of CdSe QDs at relatively low temperatures. CdSe quantum dots capped by the oleylamine/oleic acid have sharper UV-vis absorption spectra peaks and more narrow fluorescence full-width at half-maximum(FWHW), and reduced from 42 nm to 32 nm. Reaction temperature and reaction time have a significant effect on the growth process and optical properties of the obtained CdSe quantum dots. The fluorescet quantum yield of obtained CdSe quantum dots that reacts within 15 min at 220℃can reach up to 26%. The cubic CdSe QDs with the surface coating of oleic acid and oil-amine together prepared by the proposed method, have narrow FWHW (32-39 nm) and good light stability.
5. The CdSe/CdS core-shell quantum dots with predominant quality are prepared by using oleic acid and oleylamine as mixed modifier, and are wrapped with CdS. The structure of CdSe/CdS QDs are sphalerite and cubic, the shell grow epitaxially on the surface of the core of CdSe QDs, and particles are roughly spherical with a diameter d=4.5 nm. Compared with nuclear CdSe QDs, UV absorption peak and Fluorescence emission peak of the core-shell CdSe/CdS QDs are red shift 25 nm and 15 nm respectively. The fluorescence intensity of CdSe/CdS core-shell quantum dots is much higher than that of CdSe QDs, and production rate can reach up to 60.7% after 4 hours ultraviolet optical excitation.
6. The fluorescent molecularly imprinted composite microspheres are prepared by coprecipitation polymerization of MAA, EGDMA and CdSe/CdS core-shell quantum dots using EC as template, which are used for determination of EC. The data obtained shows that there is a good linear relationship between EC and fluorescent intensity in the range of 1 mmol/L～5 mmol/L. The Stern-Volmer plots with a linear correlation coefficient R2=0.994 was ln(Fo/F)=0.03419[Q]-0.00739, and the quenching constant Ksv is 3.419×10-2 L/mmol. The above results indicate that EC can especially and proportionally quench the fluorescence of the fluorescent molecularly imprinted composite microspheres, and further study should be conducted to establish an accurate and rapid detection method for EC.
1.以4-MI为模板分子,α-甲基丙烯酸(MAA)为功能单体,乙二醇二甲基丙烯酸酯(EGDMA)为交联剂,偶氮二异丁腈(AIBN)为引发剂,在乙腈中通过沉淀聚合制备了分子印迹聚合物。用紫外分光光度法对4-MI与MAA的相互作用进行了分析,结果表明主客体主要存在形式为,1个4-MI与1个MAA通过氢键相互作用。利用Langmuir数学模型对吸附特性进行了分析,Scatchard分析显示印迹聚合物的最大吸附量Bmax=221.14μmol/g和解吸常数KD=1.8mmo1/L。同时对印迹聚合物的吸附选择性和吸附动力学进行了初步研究。
2.以MA为模板分子,MAA为功能单体,EGDMA为交联剂,AIBN为引发剂,在乙腈-乙二醇(20：1,v/v)混合溶剂中沉淀聚合制备了分子印迹聚合物微球。1H-NMR和紫外光谱方法研究表明,MA与MAA分子通过协同氢键作用形成1：2型氢键配合物。利用扫描电镜和红外光谱对聚合物微球的结构进行了表征。结果表明,印迹聚合物近似圆球形,粒径约为400-500nm,且大于非印迹聚合物微球,表面存在大量的结合位点。通过静态平衡吸附实验研究了聚合物微球对模板分子的结合能力,印迹聚合物微球在4h后逐渐达到吸附平衡,Scatchard分析表明,印迹聚合物微球主要存在两类不同的结合位点,最大表观结合量(Qmax)和平衡离解常数(Kd)分别为Qmax1=22.97μmol/g, Kd1=0.14×10-3 mol/L; Qmax2=157.65μmol/g,Kd2= 2.55×10-3mol/L,计算得出表观印迹效率和有效印迹效率分别为68%和58%。
3.改变传统沉淀聚合的合成条件,以液体石蜡和甲苯的混合液为溶剂和致孔剂,以EC为模板分子,MAA为功能单体,EGDMA为交联剂,AIBN为引发剂,制备了单分散微米级分子印迹聚合物微球。1H-NMR、红外光谱及计算机模拟研究表明EC分子与MAA之间具有较强的氢键作用。利用扫描电镜、红外光谱及示差扫描量热仪对聚合物微球的结构进行了表征,结果表明,印迹微球表面具有能够识别模板分子的基团,且微球粒径较大(约为4.32μm)、热稳定性好,有望应用于固相萃取及液相色谱填料等方面。
4.以液体石蜡作为高温反应溶剂,以油酸和油胺为混合稳定剂,利用高温热解法一步合成了高质量的CdSe量子点。通过紫外-可见吸收光谱、荧光发射光谱、红外光谱和X射线衍射等手段对量子点的光学性质和结构进行了表征。结果表明,油胺/油酸混合表面活性剂稳定的量子点吸收光谱峰形更加尖锐,荧光发射光谱半峰宽更窄,从42nm减小到32nm。反应温度和反应时间均对量子点的生长过程和光学性质有明显影响,220℃下反应10 min,荧光量子产率可达26.4%。CdSe量子点为立方晶型,平均直径d=3.6nm,荧光半峰宽较窄(32-39 nm),表面同时包覆了油酸和油胺,具有良好的光稳定性。
5.用油酸和油胺为混合修饰剂,在CdSe量子点表面包裹CdS,进一步制备了性能优越的CdSe/CdS核壳量子点。该量子点结构为闪锌矿结构,立方晶型,其壳层CdS是外延生长在CdSe量子点核表面的,颗粒近似圆形,平均直径d=4.5nm。与核CdSe量子点相比,核壳型的CdSe/CdS量子点的紫外吸收峰和荧光发射峰分别红移了25nm和15nm。CdSe/CdS核壳量子点的荧光强度要明显高于CdSe量子点,紫外激发4h后量子产率高达60.7%,且光稳定性较好。
6.将量子点技术与分子印迹技术相结合,以EC为模板分子,MAA为功能单体,EGDMA为交联剂,CdSe/CdS核壳量子点为荧光组分,光热联合引发,共沉淀聚合法制备了荧光分子印迹复合微球。将制备的荧光分子印迹复合微球用于EC的检测,在浓度范围1 mmol/L～5 mmol/L内具有良好的线性关系,回归方程为ln(F0/F)=0.03419[Q]-0.00739,猝灭常数Ksv为3.419×10-2L/mmol,线性相关系数R2为0.994,说明氨基甲酸乙酯对荧光分子印迹复合微球的具有较好的猝灭作用,可以进一步详细研究,以实现对EC的快速准确的检测。
Molecularly imprinted technology and quantum dots technology are both polymer materials technology which have developed over recent decades and are widely used in various fields including the field of food safety. In this paper, three molecularly imprinted polymers are respectively prepared using 4-MI、MA and EC EC as template by precipitation polymerization. Oleic acid and Oleic acid are used as mixed stabilizers prepareing the CdSe and CdSe/CdS quantum dots. Based on the above, we combine molecular imprinted technology with the quantum dots technology to prepare fluorescent molecularly imprinted composite microspheres. Summarized as follows:
1. Uniformly imprinted polymer microspheres are prepared by precipitation polymerization in acetonitrile.4-MI(4-methyl imiadzole), MAA(methacrylic acid), EGDMA(ethylene glycol dimethacrylate) and AIBN(azobisisobutyronitrile) are used as template, functional monomer, cross-linker and initiator, respectively. UV spectra is used to demonstrate the mechanism of the interaction between 4-MI and MAA. It is found that one 4-MI is entrapped by one MAA molecules in acetonitrile. Langmuir model is used to fit the adsorption data, the results show that the 4-MI imprinted polymer microspheres show specific binding sites to the 4-MI.The data obtained in equilibrium adsorption experiments are processed by Scatchard analysis, the dissociation contents (KD) and the apparent maximum binding capacity(Bmsx) are KD=1.8mmol/L,Bmax=221.14μmol/g. The 4-MI imprinted polymers have showed high affinity to 4-MI.
2. Uniformly molecularly imprinted polymer microspheres are prepared by precipitation polymerization of MAA and EGDMA using melamine as template in acetonitrile-ethylene glycol mixed solvent (20:1, v/v).1H-NMR and UV spectrometry are employed to demonstrate the mechanism of the interaction between Melamine and MAA, and the results show that the Melamine-MAA complexes of 1:2 mole ratio is obtained by cooperative hydrogen bonding. The adsorption efficiency is investigated by equilibrium adsorption experiments. The data obtained showed that the imprinted polymer microspheres reach equilibrium after 4h and have higher adsorption efficiency compared to the non-imprinted polymer microspheres, which have the same chemical composition. Scatchard analysis reveals that the apparent maximum binding capacity and the dissociation contents are Qmaxi=22.97μmol/g, Kd1=0.14×10-3mol/L for high affinity binding sites and Qmax2=157.65μmol/g, Kd2=2.55×10-3mol/L for low affinity binding sites, respectively. Thus, the apparent imprinting efficiency and the effective imprinting efficiency are calculated 68% and 58%, respectively.
3. We change the conditions of traditional precipitation polymerization. The monodisperse micron molecularly imprinted polymers microspheres are prepared by using EC as template, MAA as functional monomer, AIBN as initiator, EGDMA as cross linker, and the mixture of liquid paraffin and toluene as solvent and porogen, respectively. 1H-NMR, IR and computer are employed to demonstrate that there is strong hydrogen bonding between EC and MAA. Scanning electron microscopy, IR and Dynamic Rheometry are applied to indicate the characterization of the structure of the polymers microspheres. The above results demonstrated that the surface of microspheres has the imprinting hole which can recognize the template molecular. In addition, the microspheres with a good thermal stability, are comparatively large in size (approximately 4.32μm). As a result, it may be used in solid-phase extraction and chromatography packing.
4. A greener synthetic route to highly luminescent CdSe quantum dots (QDs) is reported in this paper. Oleylamine and oleic acid are used instead of phosphonic acids (HPA or TDPA) as the stabilizer. Paraffin liquid, which is a natural, nontoxic, and cheap solvent, is used to replace tri-n-octylphosphine oxide (TOPO) as the solvent for the synthesis of CdSe QDs at relatively low temperatures. CdSe quantum dots capped by the oleylamine/oleic acid have sharper UV-vis absorption spectra peaks and more narrow fluorescence full-width at half-maximum(FWHW), and reduced from 42 nm to 32 nm. Reaction temperature and reaction time have a significant effect on the growth process and optical properties of the obtained CdSe quantum dots. The fluorescet quantum yield of obtained CdSe quantum dots that reacts within 15 min at 220℃can reach up to 26%. The cubic CdSe QDs with the surface coating of oleic acid and oil-amine together prepared by the proposed method, have narrow FWHW (32-39 nm) and good light stability.
5. The CdSe/CdS core-shell quantum dots with predominant quality are prepared by using oleic acid and oleylamine as mixed modifier, and are wrapped with CdS. The structure of CdSe/CdS QDs are sphalerite and cubic, the shell grow epitaxially on the surface of the core of CdSe QDs, and particles are roughly spherical with a diameter d=4.5 nm. Compared with nuclear CdSe QDs, UV absorption peak and Fluorescence emission peak of the core-shell CdSe/CdS QDs are red shift 25 nm and 15 nm respectively. The fluorescence intensity of CdSe/CdS core-shell quantum dots is much higher than that of CdSe QDs, and production rate can reach up to 60.7% after 4 hours ultraviolet optical excitation.
6. The fluorescent molecularly imprinted composite microspheres are prepared by coprecipitation polymerization of MAA, EGDMA and CdSe/CdS core-shell quantum dots using EC as template, which are used for determination of EC. The data obtained shows that there is a good linear relationship between EC and fluorescent intensity in the range of 1 mmol/L～5 mmol/L. The Stern-Volmer plots with a linear correlation coefficient R2=0.994 was ln(Fo/F)=0.03419[Q]-0.00739, and the quenching constant Ksv is 3.419×10-2 L/mmol. The above results indicate that EC can especially and proportionally quench the fluorescence of the fluorescent molecularly imprinted composite microspheres, and further study should be conducted to establish an accurate and rapid detection method for EC.
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