基于荧光分子印迹材料与表面增强拉曼基底对五氯酚的检测
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摘要
五氯酚(PCP)作为有机氯农药广泛地用作杀菌剂、杀藻剂、杀虫剂和除草剂,以及木材防腐剂。由于其化学性质稳定、残效期长、毒性高,对生物体具有广谱毒性和致突变性,属于我国严格控制的环境污染物。在美国环保局公布的优先污染物分类表中,PCP位列其中。实验室检测PCP的常用方法有气相色谱法,比色法,高效液相色谱法,气相色谱-质谱法联用,在上述几种方法中,比色法专一性和灵敏度差；气相色谱-质谱法不仅灵敏度高,精确度好,而且分辨率高。但这类方法除需要使用昂贵的仪器设备外,还经常面临常规检测中繁琐费时的样品提取、净化、衍生化等前处理步骤,检测时间很长,检测费用很高,不利于大规模样品的检测。由于PCP的存在基质体系比较复杂,能够快速检测而避免其他物质的干扰是一个重要的课题。针对此,本论文采取两种手段来选择性的检测PCP,这是本文的主要目标。一种是利用分子印迹技术。分子印迹技术是指制备对某一特定目标分子具有特异选择性的聚合物,即分子印迹聚合物的过程,常被形象地描绘为制造识别“分子钥匙”的“人工锁”的技术。分子印迹是在模板分子周围形成一个高度交联的刚性高分子,除去模板分子后在聚合物的网络结构中留下具有结合能力的反应基团,对模板客体分子表现高度的选择识别性能,因此在识别富集和识别分析中具有美好的应用前景。利用分子印迹材料可以对PCP进行选择性的吸附分离,但是分子印迹聚合物本身没有信号输出,需要后续的洗脱检测。我们将量子点引入分子印迹材料中,利用其荧光信号来监测分子印迹材料的吸附情况。在分析测试中,利用分子本身的信号输出进行检测是最直接最准确的方法。表面增强拉曼散射(SERS)可以提供分析物的结构特征指纹信息,具有高灵敏性、高选择性和快速的特点,在许多重要化学物质和生物分子的检测中具有潜在的应用价值。因此,我们选择的第二种手段是利用表面增强拉曼散射对PCP进行检测。在SERS中,合成一种具有强的增强因子的可靠的基底是很重要的研究方向。在铜箔或铝箔等平面结构上合成金属纳米结构因其高增强因子和容易储备等优点常常用于SERS快速检测。
本论文中,利用分子印迹材料来选择性的将PCP分离出来,依据印迹材料中量子点的信号变化来检测PCP。基于PCP本身的拉曼信号检测的要求,合成了一种高增强因子的SERS基底。在此基础上,分别发展了以荧光分子印迹材料和银质铜基拉曼基底为探针检测PCP的应用。论文主要内容归纳如下：
1.合成了一种负载了磁性Fe304纳米颗粒和ZnS:Mn2+量子点的PCP的分子印迹材料。将Fe304纳米颗粒加入到印迹材料中可以在外加磁场存在下进行磁分离,方便分离过程。复合材料中的ZnS:Mn2+量子点可以提供输出信号,用于监测吸附到印迹材料上的PCP的量,进而来衡量印迹的效率。所得的印迹材料用X射线粉末衍射(XRD),透射电子显微镜(TEM),傅立叶变换红外(FTIR)来表征。小角X射线衍射和氮气吸附脱附分析表明所得印迹材料具有短程周期性介孔结构。研究了磁性印迹材料的吸附行为,介孔的存在使得吸附很快达到平衡,并且印迹材料比非印迹材料对PCP的吸附容量要大。利用ZnS:Mn2+量子点的荧光信号监测了PCP的吸附量的变化。常见的离子如K+, Na+, Ca2+, Mg2+, Cl-, CO32对磁性荧光印迹材料对PCP的检测的影响很小与其他芳香族化合物如2,4-二氯苯氧乙酸(2,4-d),2,4-二氯苯酚(2,4-dp)和苯酚(phOH)相比,合成的印迹材料对PCP有更好的亲和作用。将这种材料用于泉水和自来水样的检测中得到较好的回收率,分别是101%和97%。
2.研究了PCP对ZnS:Mn2+量子点的两个发光峰的不同影响的原因,并基于此建立了一种荧光比率法来检测PCP。在本工作中,在水相中合成了ZnS:Mn2+量子点,这种量子点有缺陷发光(467nm)和杂质离子发光(595nm)两个发光峰。当PCP加入到量子点溶液中时,两个峰对PCP的响应不同,杂质离子发光被淬灭而缺陷发光强度基本没有变化。我们通过对ZnS:Mn2+量子点的两个发光峰不寿命进行测试,推断了PCP对两个发光峰影响不同是由于两者寿命相差约6个数量级,导致了淬灭效率的差异,并依此建立了荧光比率法来测试对PCP。为了提高对PCP的选择性,对ZnS:Mn2+量子点进行了表面印迹。首先对ZnS:Mn2+量子点用巯丙基硅烷修饰,之后加入到以PCP为模板,氨丙基三乙氧基硅烷(APTES)为功能单体的混合液中,正硅酸四乙酯(TEOS)为交联剂进行印迹。对合成的荧光印迹材料用了XRD、TEM、FTIR进行表征。同时用ZnS:Mn2+量子点的荧光比率(F467/F595)来衡量印迹的效率,结果表明F467/F595与PCP的加入量在0-5μmoL-1范围内呈线性关系。与其它结构类似物相比,合成的荧光印迹材料对PCP亲和作用更强。常见离子对荧光比率法检测PCP基本没有影响。因此,基于这种方法,我们把合成的荧光印迹材料应用于泉水和自来水两种实际水样中PCP的检测,得到了较好的回收率。
3.为了利用PCP的拉曼信号来检测,我们以硝酸银、氢氟酸为原料在铜箔上合成了银的微纳结构。硝酸银与铜箔基于置换反应会在铜箔上沉积银单质。在氟离子存在的情况下,铜的电极电势φθ(Cu2+/Cu)=0.3419V变为了0.2353V,与银的电极电势φθ(Ag+/Ag)=0.7996V电势差变大,反应更容易进行。调节硝酸银的浓度、银离子和氟离子的配比以及反应时间等参数来优化合成的基底。将所合成的基底进行XRD、SEM的表征,利用巯基苯胺来标定合成基底的SERS效果。最终选择在硝酸银浓度为10mmol L-1,银离子与氟离子比例为1：10,反应时间为60s时合成的基底用于PCP的检测。
As an organochlorine pesticide, pentachlorophenol (PCP) has been widely used as fungicides, algicides, herbicides and wood preservatives. Because of its chemical stability, high toxicity and mutagenicity, PCP has been listed as strictly controlled envioremental pollutants in China. Envioremental Protection Agency in U.S. also classified it as a priority pollution. Common methods for PCP detection in lab include gas chromatography (GC), high performance liquid chromatography (HPLC), colcorimetry and gas chromatography-mass spectrometry (GC-MS). However, drawbacks exist in the methods. In colorimetry method, specificity and sensitivity are relatively poor. Although GC-MS method is able to give a high sensitivity, accuracy and resolution detection, such a method needs expensive equipments and cumbersome, time-consuming routine sample extraction, purification, derivatization, making it not suitable to large-scale sample testing. As PCP existence condition is relatively complex, it is an important issue to detect PCP quickly without interface of the other co-existant substances. In this paper, two proposals were chosen to sense PCP with high selectivity. This is the main objective of this paper. One way is using molecular imprinting technique. Molecular imprinting technique is a progress to prepare a matrix with specific selectivity to a particular target molecule. Molecularly imprinted polymers (MIPs) are complentary in spatial structure and functionality to template and promising in enrichment and analysis indentically. MIPs of PCP can be synthesized to adsorb and seprate selectively. However, MIPs cannot give the output signal. Quantum dots (QDs) were introduced to MIPs, making it possible to monitor the adsorption. In analytical testing, the most direct and accurate method for detection is using the output signal of the analyte. Surface enhanced Raman scattering (SERS) can provide the fingerprint information of analyte, with potential application in the detection of chemicals and biological molecules for the characterization of high sensitivity and selectivity. Therefore, the second proposal to detect PCP is using SERS.
In this paper, fluorescent molecularly imprinted matrix and SERS substrates were synthesized for the detection of PCP with fluorescent and Raman spectra. The main contents can be summarized as follows:
1. An imprinted silica matrix of PCP co-loaded with FeO4nanoparticles and ZnS:Mn2+QDs was fabricated. The introduction of Fe3O4nanoparticles to the imprinted matrix provided an easy way to separate PCP under an external magnetic field. ZnS:Mn2+QDs offered a readout signal to monitor the amount of PCP bound to the imprinted matrix and evaluate the efficiency of imprinting. X-ray diffraction, transmission electron microscopy, Fourier transform infrared spectroscopy were used to characterize the imprinted matrix. The low angle X-ray diffraction and N2adsorption-desorption analysis indicated a periodic mesoporous structure. The adsorption of magnetic imprinted matrix was studied. The adsorption reached equilibrium quickly because of the mesoporous structure. The as-synthesized imprinted matrix preferred to adsorb PCP rather than the other aromatic compounds like2,4-dichlorophenoxy acetic acid,2,4-dichlorophenol and phenol. The common ions like K+, Na+, Ca2+, Mg2+, Cl-,CO32-interfaced little to the detection. The recoveries of spiked PCP in spring water and tap water with Fe3O4-ZnS:Mn2+co-loaded MIPsare101%and97%, respectively.
2. The two emissions of ZnS:Mn2+QDs exhibited different responces when PCP was added. A ratiometric fluorescent method was established to detect PCP. In this work, water soluble ZnS:Mn2+QDs were synthesized with defect-related emission (467nm) and impurity emission (595nm). When PCP was added, impurity emission was quenched whileas defect-related emission changed little. The fluorescent lifetimes of the two emissions were measured. A possible reason was deduced for this phenomenane. The lifetime of impurity emission is about6magnitudes longer than defect-related emission, which affect the quenching efficiency. To improve the selectivity to PCP, surface imprinting was fabricated on ZnS:Mn2+QDs. PCP was preassembled with the functional monomer3-aminopropyltriethoxysilane (APTES) and copolymerized with cross-linkers tetraethoxysilane (TEOS). The as synthesized fluorescent imprinted matrix was characterized with XRD, TEM and FTIR. The ratio of two emission bands (F467/F595) was employed to evalue the efficiency of the imprinting. The ratio (F467/F595) exhibited a linearship with PCP concentration range of0-5μmol L-1. Compared with the other structural analogues, fluorescent imprinted matrix exhibited more affinity to PCP. Great recoveries were obtained in real sample detection with this approach.
3. Silver structures were obtained on copper foil by the galvanic displacement reaction between copper and silver nitrate in the presence of hydrogen fluoride for the detection of PCP. The electrode potential of copper changed from0.3419V to0.2353V in the presence of fluoride ions. The electric potential difference of copper and silver nitrate (0.7996V) became larger, promoting the reaction. Experimental conditions like the concentration of silver nitrate, ratio of silver ion and fluoride ion and reaction time were optimized to obtain substrates with high enhancement factor. Substrates prepared with10m mol L-1silver nitrate, ratio of silver ion and fluoride ion1:10and reaction time of60s were used for the SERS detection of PCP.
本论文中,利用分子印迹材料来选择性的将PCP分离出来,依据印迹材料中量子点的信号变化来检测PCP。基于PCP本身的拉曼信号检测的要求,合成了一种高增强因子的SERS基底。在此基础上,分别发展了以荧光分子印迹材料和银质铜基拉曼基底为探针检测PCP的应用。论文主要内容归纳如下：
1.合成了一种负载了磁性Fe304纳米颗粒和ZnS:Mn2+量子点的PCP的分子印迹材料。将Fe304纳米颗粒加入到印迹材料中可以在外加磁场存在下进行磁分离,方便分离过程。复合材料中的ZnS:Mn2+量子点可以提供输出信号,用于监测吸附到印迹材料上的PCP的量,进而来衡量印迹的效率。所得的印迹材料用X射线粉末衍射(XRD),透射电子显微镜(TEM),傅立叶变换红外(FTIR)来表征。小角X射线衍射和氮气吸附脱附分析表明所得印迹材料具有短程周期性介孔结构。研究了磁性印迹材料的吸附行为,介孔的存在使得吸附很快达到平衡,并且印迹材料比非印迹材料对PCP的吸附容量要大。利用ZnS:Mn2+量子点的荧光信号监测了PCP的吸附量的变化。常见的离子如K+, Na+, Ca2+, Mg2+, Cl-, CO32对磁性荧光印迹材料对PCP的检测的影响很小与其他芳香族化合物如2,4-二氯苯氧乙酸(2,4-d),2,4-二氯苯酚(2,4-dp)和苯酚(phOH)相比,合成的印迹材料对PCP有更好的亲和作用。将这种材料用于泉水和自来水样的检测中得到较好的回收率,分别是101%和97%。
2.研究了PCP对ZnS:Mn2+量子点的两个发光峰的不同影响的原因,并基于此建立了一种荧光比率法来检测PCP。在本工作中,在水相中合成了ZnS:Mn2+量子点,这种量子点有缺陷发光(467nm)和杂质离子发光(595nm)两个发光峰。当PCP加入到量子点溶液中时,两个峰对PCP的响应不同,杂质离子发光被淬灭而缺陷发光强度基本没有变化。我们通过对ZnS:Mn2+量子点的两个发光峰不寿命进行测试,推断了PCP对两个发光峰影响不同是由于两者寿命相差约6个数量级,导致了淬灭效率的差异,并依此建立了荧光比率法来测试对PCP。为了提高对PCP的选择性,对ZnS:Mn2+量子点进行了表面印迹。首先对ZnS:Mn2+量子点用巯丙基硅烷修饰,之后加入到以PCP为模板,氨丙基三乙氧基硅烷(APTES)为功能单体的混合液中,正硅酸四乙酯(TEOS)为交联剂进行印迹。对合成的荧光印迹材料用了XRD、TEM、FTIR进行表征。同时用ZnS:Mn2+量子点的荧光比率(F467/F595)来衡量印迹的效率,结果表明F467/F595与PCP的加入量在0-5μmoL-1范围内呈线性关系。与其它结构类似物相比,合成的荧光印迹材料对PCP亲和作用更强。常见离子对荧光比率法检测PCP基本没有影响。因此,基于这种方法,我们把合成的荧光印迹材料应用于泉水和自来水两种实际水样中PCP的检测,得到了较好的回收率。
3.为了利用PCP的拉曼信号来检测,我们以硝酸银、氢氟酸为原料在铜箔上合成了银的微纳结构。硝酸银与铜箔基于置换反应会在铜箔上沉积银单质。在氟离子存在的情况下,铜的电极电势φθ(Cu2+/Cu)=0.3419V变为了0.2353V,与银的电极电势φθ(Ag+/Ag)=0.7996V电势差变大,反应更容易进行。调节硝酸银的浓度、银离子和氟离子的配比以及反应时间等参数来优化合成的基底。将所合成的基底进行XRD、SEM的表征,利用巯基苯胺来标定合成基底的SERS效果。最终选择在硝酸银浓度为10mmol L-1,银离子与氟离子比例为1：10,反应时间为60s时合成的基底用于PCP的检测。
As an organochlorine pesticide, pentachlorophenol (PCP) has been widely used as fungicides, algicides, herbicides and wood preservatives. Because of its chemical stability, high toxicity and mutagenicity, PCP has been listed as strictly controlled envioremental pollutants in China. Envioremental Protection Agency in U.S. also classified it as a priority pollution. Common methods for PCP detection in lab include gas chromatography (GC), high performance liquid chromatography (HPLC), colcorimetry and gas chromatography-mass spectrometry (GC-MS). However, drawbacks exist in the methods. In colorimetry method, specificity and sensitivity are relatively poor. Although GC-MS method is able to give a high sensitivity, accuracy and resolution detection, such a method needs expensive equipments and cumbersome, time-consuming routine sample extraction, purification, derivatization, making it not suitable to large-scale sample testing. As PCP existence condition is relatively complex, it is an important issue to detect PCP quickly without interface of the other co-existant substances. In this paper, two proposals were chosen to sense PCP with high selectivity. This is the main objective of this paper. One way is using molecular imprinting technique. Molecular imprinting technique is a progress to prepare a matrix with specific selectivity to a particular target molecule. Molecularly imprinted polymers (MIPs) are complentary in spatial structure and functionality to template and promising in enrichment and analysis indentically. MIPs of PCP can be synthesized to adsorb and seprate selectively. However, MIPs cannot give the output signal. Quantum dots (QDs) were introduced to MIPs, making it possible to monitor the adsorption. In analytical testing, the most direct and accurate method for detection is using the output signal of the analyte. Surface enhanced Raman scattering (SERS) can provide the fingerprint information of analyte, with potential application in the detection of chemicals and biological molecules for the characterization of high sensitivity and selectivity. Therefore, the second proposal to detect PCP is using SERS.
In this paper, fluorescent molecularly imprinted matrix and SERS substrates were synthesized for the detection of PCP with fluorescent and Raman spectra. The main contents can be summarized as follows:
1. An imprinted silica matrix of PCP co-loaded with FeO4nanoparticles and ZnS:Mn2+QDs was fabricated. The introduction of Fe3O4nanoparticles to the imprinted matrix provided an easy way to separate PCP under an external magnetic field. ZnS:Mn2+QDs offered a readout signal to monitor the amount of PCP bound to the imprinted matrix and evaluate the efficiency of imprinting. X-ray diffraction, transmission electron microscopy, Fourier transform infrared spectroscopy were used to characterize the imprinted matrix. The low angle X-ray diffraction and N2adsorption-desorption analysis indicated a periodic mesoporous structure. The adsorption of magnetic imprinted matrix was studied. The adsorption reached equilibrium quickly because of the mesoporous structure. The as-synthesized imprinted matrix preferred to adsorb PCP rather than the other aromatic compounds like2,4-dichlorophenoxy acetic acid,2,4-dichlorophenol and phenol. The common ions like K+, Na+, Ca2+, Mg2+, Cl-,CO32-interfaced little to the detection. The recoveries of spiked PCP in spring water and tap water with Fe3O4-ZnS:Mn2+co-loaded MIPsare101%and97%, respectively.
2. The two emissions of ZnS:Mn2+QDs exhibited different responces when PCP was added. A ratiometric fluorescent method was established to detect PCP. In this work, water soluble ZnS:Mn2+QDs were synthesized with defect-related emission (467nm) and impurity emission (595nm). When PCP was added, impurity emission was quenched whileas defect-related emission changed little. The fluorescent lifetimes of the two emissions were measured. A possible reason was deduced for this phenomenane. The lifetime of impurity emission is about6magnitudes longer than defect-related emission, which affect the quenching efficiency. To improve the selectivity to PCP, surface imprinting was fabricated on ZnS:Mn2+QDs. PCP was preassembled with the functional monomer3-aminopropyltriethoxysilane (APTES) and copolymerized with cross-linkers tetraethoxysilane (TEOS). The as synthesized fluorescent imprinted matrix was characterized with XRD, TEM and FTIR. The ratio of two emission bands (F467/F595) was employed to evalue the efficiency of the imprinting. The ratio (F467/F595) exhibited a linearship with PCP concentration range of0-5μmol L-1. Compared with the other structural analogues, fluorescent imprinted matrix exhibited more affinity to PCP. Great recoveries were obtained in real sample detection with this approach.
3. Silver structures were obtained on copper foil by the galvanic displacement reaction between copper and silver nitrate in the presence of hydrogen fluoride for the detection of PCP. The electrode potential of copper changed from0.3419V to0.2353V in the presence of fluoride ions. The electric potential difference of copper and silver nitrate (0.7996V) became larger, promoting the reaction. Experimental conditions like the concentration of silver nitrate, ratio of silver ion and fluoride ion and reaction time were optimized to obtain substrates with high enhancement factor. Substrates prepared with10m mol L-1silver nitrate, ratio of silver ion and fluoride ion1:10and reaction time of60s were used for the SERS detection of PCP.
引文
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