基于电聚合技术的新型分子印迹传感器的研究和应用
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摘要
作为传感器中最重要的研究方向之一，分子印迹电化学传感器的研究在近十年中取得了巨大进展。分子印迹聚合物膜在电化学转换器表面的固定化方法有涂膜法、原位引发聚合法和电化学聚合法等，其中电化学聚合法因具有制备简单、膜厚可控、膜与电极附着力强、重现性好等优点而成为非常有潜力的制备方法。本研究采用电化学聚合技术，分别基于分子间力和共价键力构建了五种新型的分子印迹电化学传感器。基于分子间力的印迹传感器的制备是以含有双官能团的邻苯二胺为单体，以分子量相当但含羟基个数不同的三氯生、己烯雌酚、沙丁胺醇为模板分子，探讨分子中羟基的个数对于印迹效应的影响；此外，为增强传感器的灵敏度，于电极表面引入纳米材料，采用对比实验证实了碳纳米管的增敏效应。基于共价键力的印迹传感器的制备是以含有双官能团的间氨基苯硼酸为单体，以邻二醇类物质多巴胺为模板，构建具有特异识别功能的新型传感器。论文的主要创新性工作如下：
1.综述了基于电化学聚合技术的分子印迹传感器的主要研究现状，对电聚合膜制备过程中单体的选择、模板的去除以及电聚合分子印迹膜在传感器领域的应用进行了重点评述，对其不足及未来的发展进行了讨论。
2.以具有双官能团的邻苯二胺为单体，以含一个羟基的三氯生为模板，基于分子间的相互作用力，采用电聚合法制备了三氯生分子印迹电化学传感器。用QCM（QuartzCrystal Microbalance）技术测量了膜的厚度，测定的膜厚为纳米级。探索了聚合介质、聚合电位、聚合扫描圈数、模板去除方式对印迹电极性能的影响。三氯生分子含一个羟基官能团，与聚合物骨架的氢键力较弱，模板容易被洗脱，用0.10mol/L NaOH溶液洗脱10min时即可去除模板。采用循环伏安法、电化学交流阻抗法对印迹传感器的性能进行了表征。以铁氰化钾溶液为电化学探针，采用间接分析法对三氯生进行测定，线性范围为2.0×10~(-7)~3.0×10~(-6)mol/L，检测限为8.0×10~(-8)mol/L。相对于裸电极，该传感器对结构类似物有良好的选择性。
3.为进一步验证邻苯二胺作为电聚合分子印迹单体的广泛适应性，以邻苯二胺为单体，以含两个羟基的己烯雌酚为模板，基于分子间的相互作用力，采用电化学聚合法制备了己烯雌酚分子印迹电化学传感器。当聚合介质为PBS缓冲溶液（pH7.2）、聚合电位为0~0.8V、聚合圈数为20时，可制得性能稳定的分子印迹聚合物膜。己烯雌酚含有两个羟基，与聚合物骨架的氢键力较强，相对于三氯生印迹的传感器，模板的洗脱较困难，但同时在聚合物膜中产生的印迹点也增多，线性范围相应变宽。将含模板的聚合物电极于50%的乙醇水溶液浸泡10min时可去除模板。以铁氰化钾溶液为电化学探针，采用间接分析法对己烯雌酚进行测定，线性范围为1.0×10~(-7)~5.1×10~(-6)mol/L，检测限为3.0×10~(-8)mol/L。该印迹电极对结构类似物质选择性良好。
4.为提高电聚合分子印迹传感器的灵敏度，在采用电聚合法制备分子印迹聚合物膜之前，先于电极表面修饰碳纳米材料层，利用纳米材料的高比表面、高导电性提高传感器的灵敏度。为验证纳米材料的增敏效果，首先以三氯生为模板，以邻苯二胺为单体，以单壁碳纳米管修饰的玻碳电极为工作电极，采用电聚合技术，在碳纳米管修饰玻碳电极表面制备分子印迹聚合物膜。对比试验表明，单壁碳纳米管具有显著的增敏效应。在此基础上，以沙丁胺醇为模板分子，以碳纳米管修饰的玻碳电极为工作电极，采用循环伏安法制备了沙丁胺醇分子印迹电化学传感器。相对于三氯生和己烯雌酚，含有三个羟基的沙丁胺醇与单体间的氢键结合力最大，洗脱困难，需采用电化学法去除模板，但同时嵌入聚合物膜中的印迹点增多，线性范围显著拓宽。采用线性溶出伏安法对沙丁胺醇进行测试，在最佳条件下，峰电流与沙丁胺醇的浓度在2.0×10~(-7)~5.0×10~(-5)mol/L范围内呈线性关系，检测限为7.0×10~(-8)mol/L。实验结果表明，模板分子在碳纳米管修饰的印迹电极上的响应显著大于没有修饰碳纳米管层的印迹电极。印迹电极对沙丁胺醇有特异选择性，对共存物质有较强的抗干扰能力。
5.为进一步增强印迹传感器的选择性，以间氨基苯硼酸为单体，多巴胺为模板，基于间氨基苯硼酸和邻二羟基类物质多巴胺间的可逆共价键合作用，采用电聚合技术构建了共价键型的分子印迹电化学传感器。采用循环伏安法、电化学交流阻抗法对印迹电极的性能进行了表征。对印迹电极的制备条件进行了优化。当聚合介质为PBS溶液（pH7.0）、聚合电位为0~1.2V、扫描圈数为20圈时制备的印迹电极具有良好的稳定性及分子识别性。将含模板的电极于0.50mol/L H2SO4溶液中在0~1.5V循环扫描10圈，可去除模板。多巴胺在印迹电极上的氧化峰电流与浓度成线性关系，线性范围为0~6.0×10~(-5)mol/L，检测限为5.0×10~(-8)mol/L。制备的印迹电极对多巴胺呈现良好选择性，当溶液中含有等量的多巴胺和抗坏血酸时，抗坏血酸不干扰多巴胺的测定。
As one of the most important researches of electrochemical biosensors, molecularimprinting sensors obtained great achievements over the past10years. Several procedures areused to prepare molecularly imprinted polymer (MIP) films on transducer surfaces, includingdrop-coating or spin-coating of a solution of a pre-prepared polymer, in situ chemicalpolymerization and electropolymerization. In comparison with other procedures of MIP filmpreparation, the MIP films prepared by electropolymerization have superior properties withrespect to adherence to the transducer surface, simplicity and speed of preparation, easycontrol of the film thickness and high reproducibility. Five types of MIP sensors wereprepared respectively based on covalent or noncovalent interaction by electropolymerizationin this study. For the preparation of MIP sensors based on the noncovalent interaction,o-phenylenediamine with two functional groups is selected as the monomer. Triclosan,diethylstilbestrol and salbutamol, with the similar molecular weight but the different hydroxylnumber, were selected as the target molecules. The effect of hydroxyl number in templates onthe properties of MIP sensors was studied in detail. In order to increase the sensitivity ofsensors, carbon nano-material was modified on the surface of electrodes and the enhancedsensitivity was realized. In the preparation of MIP sensor based on the covalent interaction,3-aminophenylboronic acid was used as the monomer and dopamine was used as the targetmolecules, and a sensor with special recognition capacity towards dopamine was constructed.The main innovative works in this paper are described as follows:
1. An evaluation of literatures on the recent achivements aiming at the MIP sensors baseon electropolymerization is presented. The main focus is on the choice of functionalmonomers and the removal of templates in the electrosynthesized preparation of MIP films.The application of the electrosynthesized molecularly imprinted polymers (MIPs) asrecognition elements of chemical sensors is summarized. The future development and thelimitations in this research field are discussed.
2. Base on the noncovalent interaction, a MIP amperometric sensor was prepared byelectropolymerization using o-phenylenediamine (o-PD) as a monomer in the presence oftemplate triclosan which contains a hydroxyl group. Thickness of thepoly(o-phenylenediamine)(POPD) film with the nanometer was determined by QuartzCrystal Microbalance (QCM) technique. Factors affecting the properties of sensor, such as pHvalue of supporting electrolyte, polymerized potential, scan number and the ways of removingthe template were investigated in detail. The noncovalent interaction between the templateand the monomer is no strong because triclosan contains only one hydroxyl group. Thetemplate can be quickly removed by immersing the electrode in NaOH solution for10min.The sensor was applied for the detection of triclosan by an indirect method taking potassiumferricyanide, an electrochemical probe, as the mediator between the imprinted electrodes andsubstrate solutions. The sensor responses sensitively to triclosan over a linear range of2.0×107to3.0×106mol/L and the detection limit as low as8.0×108mol/L is obtained. Thissensor provides an efficient way for eliminating interferences from compounds with similar structures to that of triclosan compared to bare electrode.
3. In order to verify the flexibility of o-PD as a functional mononer used forelectropolymerized preparation of MIP, diethylstilbestrol, a molecular containing twohydroxyl groups, was selected as a template. The prepared MIP sensor had the best propertieswhen the electropolymerization of o-PD was conducted by cyclic voltammetry (20scans) inthe range of0~0.8V (scan rate50mV/s) in a PBS buffer (pH7.2). The interaction forcebetween the monomer and the template is still the noncovalent interaction, butdiethylstilbestrol with two hydroxyl groups can form more hydrogen bonds with the polymermatrix, which makes it is more difficult to remove the template from the polymer thantriclosan imprinted sensor.50%ethanol-water solution was used to get rid of diethylstilbestrolembedded in the polymer matrix and10min is needed in order to reach complete remove.The sensor was applied for the detection of diethylstilbestrol by an indirect method takingpotassium ferricyanide as the mediator between the imprinted electrodes and substratesolutions. The sensor responses sensitively to diethylstilbestrol over a linear range of1.0×10~(-7)~5.1×10~(-6)mol/L and a detection limit as low as3.0×10~(-8)mol/L is obtained. Thissensor provides an efficient way for eliminating interferences from compounds with similarstructures to that of diethylstilbestrol compared to bare electrode.
4. Carbon nano-materials have the excellent properties, such as the large surface area,high electrical conductivity, and are often used for the construction of sensors with highsensitivity. In order to improve the sensitivity of the MIP sensor, bare electrode was modifiedby carbon nano-materials before the formation of the MIP film. Triclosan imprinted sensorwas first prepared using o-PD as a monomer and a single-walled carbon nanotubes (SWNTs)modified GC electrode as a work electrode. Comparative trial between the bare electrode andthe SWNTs modified electrode verified the contribution of SWNTs to the enhanced sensitivity.Salbutamol imprinted SWNTs modified sensor was then prepared at the similarelectropolymerized conditions. Salbutamol contains three hydroxyl groups and can form morehydrogen bonds with the polymer matrix than both triclosan and diethylstilbestrol, whichmakes it embedded deeply in polymer matrix and very difficult to be removed. Onlyelectrochemical methods can remove the templates. On the other hand, with the increase ofhydrogen bonds between the monomer and the template, number of templates in the polymermatrix increases, the imprinted cavities increase and the linear range is widened accordingly.The sensor responses sensitively to salbutamol over the linear range of2.0×10~(-7)~5.0×10~(-5)mol/L and the detection limit as low as7.0×10~(-8)mol/L at the optimum conditions using linearstripping voltammetry. The results showed that SWNTs can increase the sensitivity of MIPsensors dramatically. The MIP sensor modified by SWNTs has the good recognition abilitytowards diethylstilbestrol.
5. In order to increase the selectivity of MIP sensors, a MIP sensor based on thereversible covalent interaction between3-aminophenylboronic acid (APB) and dopamine wasdeveloped. The boronic acid group is known to rapidly and reversibly form complexes withdiols in aqueous solution. Cyclic voltammetry and Electrochemical Impedance Spectroscopy(EIS) was performed to characterize the dopamine imprinted sensor. Factors affecting theproperties of sensor, such as pH value of supporting electrolyte, polymerized potential, scan number and the ways of removing the template were investigated in detail. The prepared MIPsensor had good stability and selectivity when the electropolymerization of APB wasconducted by cyclic voltammetry (20scans) in the range of0~1.2V (scan rate50mV/s) in aPBS buffer (pH7.0). The templates can be removed by potential cycling between0~1.5V (10scans) in0.50mol/L sulfuric acid. The response of the imprinted sensor to dopamine waslinearly proportional to its concentration over the range0~6.0×10~(-5)mol/L, with a lowdetection limit of5.0×10~(-8)mol/L. The imprinted sensor showed high recognition ability andaffinity for dopamine and could eliminate the interference of the same concentration ofascorbic acid.
1.综述了基于电化学聚合技术的分子印迹传感器的主要研究现状，对电聚合膜制备过程中单体的选择、模板的去除以及电聚合分子印迹膜在传感器领域的应用进行了重点评述，对其不足及未来的发展进行了讨论。
2.以具有双官能团的邻苯二胺为单体，以含一个羟基的三氯生为模板，基于分子间的相互作用力，采用电聚合法制备了三氯生分子印迹电化学传感器。用QCM（QuartzCrystal Microbalance）技术测量了膜的厚度，测定的膜厚为纳米级。探索了聚合介质、聚合电位、聚合扫描圈数、模板去除方式对印迹电极性能的影响。三氯生分子含一个羟基官能团，与聚合物骨架的氢键力较弱，模板容易被洗脱，用0.10mol/L NaOH溶液洗脱10min时即可去除模板。采用循环伏安法、电化学交流阻抗法对印迹传感器的性能进行了表征。以铁氰化钾溶液为电化学探针，采用间接分析法对三氯生进行测定，线性范围为2.0×10~(-7)~3.0×10~(-6)mol/L，检测限为8.0×10~(-8)mol/L。相对于裸电极，该传感器对结构类似物有良好的选择性。
3.为进一步验证邻苯二胺作为电聚合分子印迹单体的广泛适应性，以邻苯二胺为单体，以含两个羟基的己烯雌酚为模板，基于分子间的相互作用力，采用电化学聚合法制备了己烯雌酚分子印迹电化学传感器。当聚合介质为PBS缓冲溶液（pH7.2）、聚合电位为0~0.8V、聚合圈数为20时，可制得性能稳定的分子印迹聚合物膜。己烯雌酚含有两个羟基，与聚合物骨架的氢键力较强，相对于三氯生印迹的传感器，模板的洗脱较困难，但同时在聚合物膜中产生的印迹点也增多，线性范围相应变宽。将含模板的聚合物电极于50%的乙醇水溶液浸泡10min时可去除模板。以铁氰化钾溶液为电化学探针，采用间接分析法对己烯雌酚进行测定，线性范围为1.0×10~(-7)~5.1×10~(-6)mol/L，检测限为3.0×10~(-8)mol/L。该印迹电极对结构类似物质选择性良好。
4.为提高电聚合分子印迹传感器的灵敏度，在采用电聚合法制备分子印迹聚合物膜之前，先于电极表面修饰碳纳米材料层，利用纳米材料的高比表面、高导电性提高传感器的灵敏度。为验证纳米材料的增敏效果，首先以三氯生为模板，以邻苯二胺为单体，以单壁碳纳米管修饰的玻碳电极为工作电极，采用电聚合技术，在碳纳米管修饰玻碳电极表面制备分子印迹聚合物膜。对比试验表明，单壁碳纳米管具有显著的增敏效应。在此基础上，以沙丁胺醇为模板分子，以碳纳米管修饰的玻碳电极为工作电极，采用循环伏安法制备了沙丁胺醇分子印迹电化学传感器。相对于三氯生和己烯雌酚，含有三个羟基的沙丁胺醇与单体间的氢键结合力最大，洗脱困难，需采用电化学法去除模板，但同时嵌入聚合物膜中的印迹点增多，线性范围显著拓宽。采用线性溶出伏安法对沙丁胺醇进行测试，在最佳条件下，峰电流与沙丁胺醇的浓度在2.0×10~(-7)~5.0×10~(-5)mol/L范围内呈线性关系，检测限为7.0×10~(-8)mol/L。实验结果表明，模板分子在碳纳米管修饰的印迹电极上的响应显著大于没有修饰碳纳米管层的印迹电极。印迹电极对沙丁胺醇有特异选择性，对共存物质有较强的抗干扰能力。
5.为进一步增强印迹传感器的选择性，以间氨基苯硼酸为单体，多巴胺为模板，基于间氨基苯硼酸和邻二羟基类物质多巴胺间的可逆共价键合作用，采用电聚合技术构建了共价键型的分子印迹电化学传感器。采用循环伏安法、电化学交流阻抗法对印迹电极的性能进行了表征。对印迹电极的制备条件进行了优化。当聚合介质为PBS溶液（pH7.0）、聚合电位为0~1.2V、扫描圈数为20圈时制备的印迹电极具有良好的稳定性及分子识别性。将含模板的电极于0.50mol/L H2SO4溶液中在0~1.5V循环扫描10圈，可去除模板。多巴胺在印迹电极上的氧化峰电流与浓度成线性关系，线性范围为0~6.0×10~(-5)mol/L，检测限为5.0×10~(-8)mol/L。制备的印迹电极对多巴胺呈现良好选择性，当溶液中含有等量的多巴胺和抗坏血酸时，抗坏血酸不干扰多巴胺的测定。
As one of the most important researches of electrochemical biosensors, molecularimprinting sensors obtained great achievements over the past10years. Several procedures areused to prepare molecularly imprinted polymer (MIP) films on transducer surfaces, includingdrop-coating or spin-coating of a solution of a pre-prepared polymer, in situ chemicalpolymerization and electropolymerization. In comparison with other procedures of MIP filmpreparation, the MIP films prepared by electropolymerization have superior properties withrespect to adherence to the transducer surface, simplicity and speed of preparation, easycontrol of the film thickness and high reproducibility. Five types of MIP sensors wereprepared respectively based on covalent or noncovalent interaction by electropolymerizationin this study. For the preparation of MIP sensors based on the noncovalent interaction,o-phenylenediamine with two functional groups is selected as the monomer. Triclosan,diethylstilbestrol and salbutamol, with the similar molecular weight but the different hydroxylnumber, were selected as the target molecules. The effect of hydroxyl number in templates onthe properties of MIP sensors was studied in detail. In order to increase the sensitivity ofsensors, carbon nano-material was modified on the surface of electrodes and the enhancedsensitivity was realized. In the preparation of MIP sensor based on the covalent interaction,3-aminophenylboronic acid was used as the monomer and dopamine was used as the targetmolecules, and a sensor with special recognition capacity towards dopamine was constructed.The main innovative works in this paper are described as follows:
1. An evaluation of literatures on the recent achivements aiming at the MIP sensors baseon electropolymerization is presented. The main focus is on the choice of functionalmonomers and the removal of templates in the electrosynthesized preparation of MIP films.The application of the electrosynthesized molecularly imprinted polymers (MIPs) asrecognition elements of chemical sensors is summarized. The future development and thelimitations in this research field are discussed.
2. Base on the noncovalent interaction, a MIP amperometric sensor was prepared byelectropolymerization using o-phenylenediamine (o-PD) as a monomer in the presence oftemplate triclosan which contains a hydroxyl group. Thickness of thepoly(o-phenylenediamine)(POPD) film with the nanometer was determined by QuartzCrystal Microbalance (QCM) technique. Factors affecting the properties of sensor, such as pHvalue of supporting electrolyte, polymerized potential, scan number and the ways of removingthe template were investigated in detail. The noncovalent interaction between the templateand the monomer is no strong because triclosan contains only one hydroxyl group. Thetemplate can be quickly removed by immersing the electrode in NaOH solution for10min.The sensor was applied for the detection of triclosan by an indirect method taking potassiumferricyanide, an electrochemical probe, as the mediator between the imprinted electrodes andsubstrate solutions. The sensor responses sensitively to triclosan over a linear range of2.0×107to3.0×106mol/L and the detection limit as low as8.0×108mol/L is obtained. Thissensor provides an efficient way for eliminating interferences from compounds with similar structures to that of triclosan compared to bare electrode.
3. In order to verify the flexibility of o-PD as a functional mononer used forelectropolymerized preparation of MIP, diethylstilbestrol, a molecular containing twohydroxyl groups, was selected as a template. The prepared MIP sensor had the best propertieswhen the electropolymerization of o-PD was conducted by cyclic voltammetry (20scans) inthe range of0~0.8V (scan rate50mV/s) in a PBS buffer (pH7.2). The interaction forcebetween the monomer and the template is still the noncovalent interaction, butdiethylstilbestrol with two hydroxyl groups can form more hydrogen bonds with the polymermatrix, which makes it is more difficult to remove the template from the polymer thantriclosan imprinted sensor.50%ethanol-water solution was used to get rid of diethylstilbestrolembedded in the polymer matrix and10min is needed in order to reach complete remove.The sensor was applied for the detection of diethylstilbestrol by an indirect method takingpotassium ferricyanide as the mediator between the imprinted electrodes and substratesolutions. The sensor responses sensitively to diethylstilbestrol over a linear range of1.0×10~(-7)~5.1×10~(-6)mol/L and a detection limit as low as3.0×10~(-8)mol/L is obtained. Thissensor provides an efficient way for eliminating interferences from compounds with similarstructures to that of diethylstilbestrol compared to bare electrode.
4. Carbon nano-materials have the excellent properties, such as the large surface area,high electrical conductivity, and are often used for the construction of sensors with highsensitivity. In order to improve the sensitivity of the MIP sensor, bare electrode was modifiedby carbon nano-materials before the formation of the MIP film. Triclosan imprinted sensorwas first prepared using o-PD as a monomer and a single-walled carbon nanotubes (SWNTs)modified GC electrode as a work electrode. Comparative trial between the bare electrode andthe SWNTs modified electrode verified the contribution of SWNTs to the enhanced sensitivity.Salbutamol imprinted SWNTs modified sensor was then prepared at the similarelectropolymerized conditions. Salbutamol contains three hydroxyl groups and can form morehydrogen bonds with the polymer matrix than both triclosan and diethylstilbestrol, whichmakes it embedded deeply in polymer matrix and very difficult to be removed. Onlyelectrochemical methods can remove the templates. On the other hand, with the increase ofhydrogen bonds between the monomer and the template, number of templates in the polymermatrix increases, the imprinted cavities increase and the linear range is widened accordingly.The sensor responses sensitively to salbutamol over the linear range of2.0×10~(-7)~5.0×10~(-5)mol/L and the detection limit as low as7.0×10~(-8)mol/L at the optimum conditions using linearstripping voltammetry. The results showed that SWNTs can increase the sensitivity of MIPsensors dramatically. The MIP sensor modified by SWNTs has the good recognition abilitytowards diethylstilbestrol.
5. In order to increase the selectivity of MIP sensors, a MIP sensor based on thereversible covalent interaction between3-aminophenylboronic acid (APB) and dopamine wasdeveloped. The boronic acid group is known to rapidly and reversibly form complexes withdiols in aqueous solution. Cyclic voltammetry and Electrochemical Impedance Spectroscopy(EIS) was performed to characterize the dopamine imprinted sensor. Factors affecting theproperties of sensor, such as pH value of supporting electrolyte, polymerized potential, scan number and the ways of removing the template were investigated in detail. The prepared MIPsensor had good stability and selectivity when the electropolymerization of APB wasconducted by cyclic voltammetry (20scans) in the range of0~1.2V (scan rate50mV/s) in aPBS buffer (pH7.0). The templates can be removed by potential cycling between0~1.5V (10scans) in0.50mol/L sulfuric acid. The response of the imprinted sensor to dopamine waslinearly proportional to its concentration over the range0~6.0×10~(-5)mol/L, with a lowdetection limit of5.0×10~(-8)mol/L. The imprinted sensor showed high recognition ability andaffinity for dopamine and could eliminate the interference of the same concentration ofascorbic acid.
引文
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