基于新型对亚苯基亚乙炔基衍生物的小分子化学/生物传感研究
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摘要
复杂的食品、药品、生物样品、环境样品中相关小分子的定性定量检测,是食品安全与卫生、疾病预防与诊断、环境污染与监测的核心问题。发展快速、简单、灵敏的用于复杂样品中单组份或多组份检测的新方法具有重要意义。化学/生物传感检测技术作为新型的检测技术已被广泛用于复杂的食品、药品、生物样品和环境样品中的相关小分子的定性定量检测。而创新传感方法,开发高效和信号放大的新型传感材料,是制备高灵敏度和高选择性传感器的关键。
本学位论文对化学/生物传感器进行了简要概述,重点对新型化学传感器的设计与构建,尤其对纳米材料、电子媒介体和分子导线等在化学和生物传感领域的应用进行了详细综述。作为一类极为重要的分子导线,低聚对亚苯基亚乙炔基衍生物以其所具有的诸如整流、存储和开关等奇特性质而被广泛应用于分子电子学的各个方面。利用此类化合物的优良光电性质,可望建立一些对小分子检测具有灵敏响应特性的检测方法。基于此,本论文中设计并合成两类功能化对亚苯基亚乙炔基类化合物,结合纳米材料和环糊精等构建了系列具有优异传感性能的传感器并用于生命体系和环境体系中相关小分子的检测。主要工作内容如下：
1.通过亲电取代、亲电加成、加成消去、Sonogashira偶联等反应合成了四种共轭对亚苯基亚乙炔基化合物,即N-甲基-4-(4-硫代乙酸苯酯基-2-乙炔基)-1,8-萘酰胺(化合物1),4-(4-硫代乙酸苯酯基-2-乙炔基)苯胺(化合物2),4-(4-甲硫醚苯基-2-乙炔基)苯胺(化合物3),N-甲基-4-(4-甲硫醚苯基-2-乙炔基)-1,8-萘酰胺(化合物4)。中间体和目标化合物均通过1H NMR、13C NMR、 MS和IR进行了结构表征。荧光和紫外光谱研究表明,这一系列化合物在有机溶剂如三氯甲烷或四氢呋喃中具有良好的光谱性质,而在水溶液中其荧光迅速被猝灭。在β-环糊精存在时,化合物2和3在水溶液中的荧光性质明显改善。光谱分析结果显示,荧光增强是由于化合物与β-环糊精形成了稳定的超分子包合物。详细探讨了该超分子包合反应过程,并推导了相应的包合机理。将化合物3与β-环糊精的超分子包合物用于水溶液中水杨醛的检测。在最优条件下,随着水杨醛的加入,超分子化合物的荧光被猝灭,据此可定量检测水杨醛,线性范围为0.6-240μM,检测下限为1×10-8M。
2.设计并合成了两种共轭对亚苯基亚乙炔基分子导线(4-(4-甲硫醚苯基-2-乙炔基)苯甲醛(化合物5)和4-(4-甲硫醚苯基-2-乙炔基)苯甲酸(化合物6),并对这两种化合物的结构进行了表征确认。详细研究了这两种化合物的光谱性质及其与β-环糊精的包合反应,探讨了超分子反应过程并推导了相应的包合机理。研究发现：随着包合物的形成,这两种化合物的荧光明显增强；在三聚氰胺的存在下,化合物5和6的环糊精包合物的荧光被猝灭,由此建立了灵敏检测水中三聚氰胺的新方法,检测范围为分别为0.15-10μM和0.15-25μM。
3.设计合成了一种新型的二茂铁乙炔衍生物,即4-(二茂铁基-2-乙炔基)苯胺(化合物7,简写为Fc-NH2)。该分子中含有苯乙炔骨架,封端基分别为二茂铁和氨基砌块,该化合物拥有优良的电化学性质,可以作为新型的电子媒介体用于构建电化学传感器。通过一锅法将石墨烯的水溶液和Fc-NH2溶液混合,制备了Fc-NH2/石墨烯复合物,滴于玻碳电极,再滴上一层Nafion膜,构建了新型Nafion/graphene/Fc-NH2修饰的玻碳电极。将Fc-NH2固定于石墨烯基体中,不但可以增强石墨烯复合物的电子传输性能和稳定性,同时也能有效防止二茂铁的泄露。研究表明,多巴胺(DA)在复合物修饰电极上的检测信号显著增强,石墨烯的电催化性能和二茂铁的电子媒介作用对检测信号的放大起主要作用。无论尿酸(UA)和抗坏血酸(AA)存在与否,多巴胺的电流响应与其浓度均呈良好的线性关系,线性范围分别为5×10-8-2×10-4M和1×10-7-4×10-4M,检测限分别为20和50nM。采用标准加入法,该修饰电极可很好地用于实际样品中多巴胺的检测。我们还进一步深入探讨了这一新检测方法中的信号放大的可能机理。
4.将新合成的新型的二茂铁乙炔衍生物,即4-(二茂铁基-2-乙炔基)苯胺(化合物7,Fc-NH2)与石墨烯片(GS)之间良好的相互作用制备了GS/chi/Fc-NH2复合物,并成功用于细胞色素c (Cytc)的固定,获得GS/chi/Fc-NH2/Cytc修饰电极。实验研究发现,GS/chi/Fc-NH2复合物可以实现Cytc与电极间的快速电子传递,GS/chi/Fc-NH2/Cytc修饰电极在-0.2V附近出现一对峰,对应于Cytc的可逆氧化还原峰。该电极对亚硝酸钠有良好的电催化作用,在0.1-150μM范围内呈良好的线性关系,检测限低至0.01μM。
5.设计、合成一种新型二茂铁乙炔衍生物,即4-(二茂铁基-2-乙炔基)硫代乙酸苯硫醇酯(化合物9,Fc-SAc),此化合物以低聚对弧苯基亚乙炔基作为骨架,以二茂铁和硫酯基为端基。将Fc-SAc的水解产物4-(二茂铁基-2-乙炔基)苯硫酚(Fc-SH)通过金-硫键固定在金纳米粒子(AuNPs)修饰电极表面,构建了新型、高灵敏芦丁传感器。将二茂铁乙炔衍生物结合纳米金、石墨烯／壳聚糖构建了两种不同的修饰电极,即Fc-S/AuNPs/GCE(电极1)和Fc-S/AuNPs/graphene-chitosan/GCE(电极2)。实验发现,芦丁在电极1上的电化学过程是受扩散控制,而在电极2上的电化学过程是受传质控制的。在最优实验条件下,电极1上芦丁检测的浓度线性范围为0.1-30μM,线性回归系数为0.998；而在电极2上,线性范围扩大至0.04-100μM,线性回归系数为0.997。研究表明,电极2检测芦丁的线性范围更宽、检测限更低、稳定性更好。
6.首次报道了一种双重信号放大检测平台用于超灵敏检测抗坏血酸(AA)、多巴胺(DA)、尿酸(UA)和乙酰氨基酚(AC)的四组份混合物。这一双重信号放大平台是由新合成的4-(二茂铁基-2-乙炔基)硫代乙酸苯硫醇酯(化合物9, Fc-SAc,)的水解产物4-(二茂铁基-2-乙炔基)苯硫酚(Fc-SH)修饰的金包磁纳米粒子(Au@Fe3O4)和石墨烯纳米片(GS)及玻碳电极构成。由于纳米材料如Au@Fe3O4纳米粒子和GS的催化作用以及二茂铁作为电子媒介体可加速电子传递,检测的灵敏度大大提高。新型Fc-SH修饰的Au@Fe3O4纳米复合物表现出良好的电化学性质和电催化性能。将Fc-S-Au@Fe3O4与GS/chitosan(石墨烯／壳聚糖)一锅法混合,可以得到Fc-S-Au@Fe3O4/GS/chitosan纳米复合物。将这一纳米复合物滴于玻碳电极表面,构建Fc-S-Au@Fe3O4/GS/chitosan/GCE修饰电极。实验发现此修饰电极可以用于AA、DA、UA和AC共存条件下各组份的灵敏检测。在50mVs-1的扫速下,四组份可以很好地分开,峰电位分别位于-0.03,0.15,0.26和0.37V, AA-DA, DA-UA和UA-AC的峰-峰电位差分别为0.18,0.11和0.11V。采用微分脉冲伏安法对四组份进行检测发现,各物质的峰电流都随着浓度的增加而增加。当保持其他三组份的浓度不变,只改变待测组分浓度时,四组份体系中AA、DA、UA和AC分别在5-100,0.5-80,2-120和0.5-35μM浓度范围内呈良好的线性关系。同时改变四组份的浓度时,AA、DA、UA和AC分别在6-350,0.5-50,1-100和0.2-30μM范围内呈良好的线性。根据三倍信噪比计算出AA、DA、UA和AC的最低检测限分别为1、0.08、0.1和0.01μM。
Quantitative and qualitative determination of physiologically-related species in complex food, medicine, biological matrixes, and environmental sample is the core issue of food safety, disease screening and diagnosis and sanitation, environmental monitoring and pollution. It is very important to develope fast, simple, sensitive methods for detection of individual and multiple components in the complex samples. Chemo/biosensing is a new detection technique, and has widely applied in food, medicine, biological matrixes and environmental samples. And innovativing sensing methods, developing effective and amflification material is the key to constructing biosensors for small molecules with higher sensitivity and selectivity.
In this dissertation, we briefly reviewed the chemo/biosensors, and especially stated how to design and construct new chemical sensors. The recent applications of nanomaterials, electron mediators and molecular wires in the area of chemo/biosensing were reviewed in detail. As one of important molecular wires, oligo-(phenylene-ethynylene)s (OPEs) derivatives have excellent properities such as rectifier, storage and switch, and have widely employed in molecular electronics area. Take advantage of the good optical and electrotronic properties, it is expected to build some sensitive detection methods for small molecules. Based on this, serials of new OPEs were synthesized and characterized. Combined with nanomaterials and β-cyclodextrin, several biosensors for life-related biomolecules were constructed. The main contents are as follows:
1. Four new conjugated oligo-phenylene-ethynylenes derivatives, N-methyl-4-(4-acetylthiophenylethynyl)-1,8-naphthalimide (1), thioacetic acid S-[4-(4-aminophenyl-ethynyl) phenyl]ester (2),4-methylthiophenylethynyl-benzenamine (3), and N-methyl-4-(4-methyl-thiophenyl-ethynyl)-1,8-naphthalimide (4), were synthesized by nucleophilic substitution, electrophilies addition and Sonogashira reactions. The structures of the four compounds were confirmed by1H NMR,13C NMR, MS and IR and their spectral characteristics were studied by ultraviolet and visible (UV-vis) spectroscopy as well as fluorescence spectroscopy in different mediums. It was found that the fluorescence properties of compounds2and3were notably improved in the aqueous solutions in the presence of β-cyclodextrin (β-CD). Spectral analysis supported the supposition that the fluorescence intensity enhancement was due to the formation of inclusion complex with β-CD. The supramolecular interaction was investigated in detail and the reaction mechanism was provided. A salicylaldehyde determination method in aqueous medium was established based on the supramolecular complex of compound3. Under the optimum conditions, the supramolecular complex exhibited a dynamic fluorescence response range for salicylaldehyde from0.6to240μM, with a detection limit of1×10-8M.
2. Two new conjugated oligo-phenylene-ethynylenes derivatives,4-((4-(methylthio) phenyl)ethynyl)benzaldehyde (5),4-((4-(methylthio) phenyl) ethynyl) benzoic acid)(6) were designed and synthesized for the first time. Their structures of the two compounds were thoroughly confirmed by1H NMR,13C NMR, MS and IR. The spectral characteristics were studied by UV-vis spectroscopy as well as fluorescence spectroscopy in different solvents. The inclusion processes with β-CD were investigated in detail and the possible inclusion mechanism was induced. It was found that the fluorescence intensity of the two compounds was enhanced after the complex was formed. In the presence of melamine, the fluorescence intensity of the supramolecular complex was quickly quenched. A simple melamine determination method in aqueous medium was established based on the supramolecular complex of β-CD with compound5and6. Under the optimum conditions, the supramolecular complex exhibited dynamic fluorescence response ranges for melamine from0.15-10μM and0.15-25μM, respectively.
3. A new ferrocene derivative (1-[(4-amino) phenyl ethynyl] ferrocene,(compound7, Fc-NH2) was synthesized for the first time. The ferrocene derivative molecule contained phenylethynyl skeleton, ferrocene and amino groups with excellent electrochemical property. Graphene/Fc-NH2nanocomposite was prepared by mixing graphene solution and Fc-NH2solution in one pot and the nanocomposite was utilized to construct Nafion/graphene/Fc-NH2modified glass carbon electrode (GCE). The ferrocene derivative immobilized on the graphene can enhance the charge-transport ability of the nanocomposite, stabilize the graphene and prevent the leakage of ferrocene. The detection signal of dopamine (DA) was significantly amplified on the Nafion/graphene/Fc-NH2/GCE. It was experimentally demonstrated that the signal enhancement is resulted from the synergy amplification effect of graphene and the Fc-NH2. The oxidation peak currents of DA were linearly related to the concentrations in the range of5×10-2×10-4M with the detection limit of20nM in the absence of urine acid (UA) and ascorbic acid (AA). In the presence of10-3M AA and10-4M UA, the linear response range was1×10-7-4×10-4M, and the detection limit was50nM at S/N=3. Using the proposed Nafion/Fc-NH2/graphene/GCE, DA was successfully determined in real samples with the standard addition method.
4. A new ferrocene-terminated phenylethynyaniline (Fc-NH2, compound7) was synthesized by Sonogashira reaction. The structures of the new intermediate and target compound were identified by IR,1H NMR,13C NMR, MS. Stable GS/chi/Fc-NH2complex was prepared combined with graphene, and the GS/chi/Fc-NH2/Cytc modified electrode was fabricated. It was found that Cytc can immobilize on GS/chi/Fc-NH2and the fast electron transfer can be realized between the electrode and Cytc molecules. There is a pair of peaks near-0.2V, which can be attributed to Cytc. The GS/chi/Fc-NH2/Cytc modified GCE shows good catalysis towards NaNO2, and it shows good linearity in the range of1×10-7-1.5×10-4M,0.1-150μM, and the determination limit is bellow at4×10-8M.
5. A new ferrocene benzyne derivative (Fc-SAc, compound9) that contained oligo-(phenylene-ethynylene) skeleton, ferrocene and thiolate terminal groups was firstly synthesized. The hydrolysis product of Fc-SAc (Fc-SH) was immobilized onto gold nanoparticles (AuNPs) modified glass carbon electrode (GCE) as sensing element for rutin detection with high sensitivity. The new sensing strategy was proposed by using two Fc-SH modified electrodes:Fc-S/AuNPs/GCE (Electrodel) and Fc-S/AuNPs/graphene-chitosan/GCE (Electrode2). The electrochemical oxidation of rutin on Electrode2was a diffusion-controlled process, which was different from a mass-controlled process on Electrode1. Under the optimal conditions, the peak currents of the sensors were linearly related to the concentrations of rutin. The linear response ranges were0.05-30μM and0.04-100μM with the regression coefficients of0.998and0.997on Electrodel and Electrode2, respectively. Electrode2presented wider linear range, superior sensitivity, lower detection limit and better stability on determination of rutin.
6. A double signal amplification platform for ultrasensitive simultaneous detection of a quaternary mixture of ascorbic acid (AA), dopamine (DA), uric acid (UA) and acetaminophen (AC) is fabricated by assembling newly synthesized ferrocene thiolate (phenylethynyl ferrocene thiolate, Fc-SAc, compound9) on core/shell structured Fe3O4@Au and coupling with graphene sheet/chitosan (GS/chitosan). By immobilization of the electron mediator on Fe3O4@Au nanoparticles (NPs), a Fe3O4@Au-S-Fc nanocomposite possessing excellent electric-catalytic and signal amplification behavior was obtained. Mixing the Fe3O4@Au-S-Fc with GS/chitosan, the Fe3O4@Au-S-Fc/GS/chitosan nanocomposites were obtained and utilized to construct a multicomponent sensor. Using the Fe3O4@Au-S-Fc/GS/chitosan modified glass carbon electrode (GCE), the double signal amplification strategy was realized by the synergistic catalytic effect of Fe3O4@Au NPs and GS, and the amplification effect of the ferrocene electron mediator. The individual and simultaneous determinations of AA, DA, UA and AC were performed using differential pulse voltammetry (DPV) with the modified electrode. This modified electrode exhibits potent and persistent electro-oxidation behavior followed by well-separated oxidation peaks towards AA, DA, UA and AC. For the quaternary mixture, the four compounds can be well separated from each other at a scan rate of50mVs-1with the peak potentials at-0.03,0.15,0.24and0.35V, respectively. The peak-to-peak potential separations of AA-DA, DA-UA and UA-AC were0.18,0.09and0.11V, respectively, which were large enough to determine AA, DA, UA and AC simultaneously. The catalytic peak currents were linearly dependent on the concentrations of AA, DA, UA and AC in the range of5-100,0.5-80,2-120and0.5-35μM, respectively, in the individual detection of each component under the condition of keeping the concentrations of the other3compounds constant. By simultaneously changing the concentrations of the4constituents, good linear current responses were obtained in the range of6-350,0.5-50,1-90and0.4-32μM for AA, DA, UA and AC, respectively. And the determination limits for AA, DA, UA and AC were1,0.2,0.3and0.05μM, respectively. The analytical performance of this sensor has been evaluated for simultaneous detection of AA, DA, UA and AC in serum and urine samples.
本学位论文对化学/生物传感器进行了简要概述,重点对新型化学传感器的设计与构建,尤其对纳米材料、电子媒介体和分子导线等在化学和生物传感领域的应用进行了详细综述。作为一类极为重要的分子导线,低聚对亚苯基亚乙炔基衍生物以其所具有的诸如整流、存储和开关等奇特性质而被广泛应用于分子电子学的各个方面。利用此类化合物的优良光电性质,可望建立一些对小分子检测具有灵敏响应特性的检测方法。基于此,本论文中设计并合成两类功能化对亚苯基亚乙炔基类化合物,结合纳米材料和环糊精等构建了系列具有优异传感性能的传感器并用于生命体系和环境体系中相关小分子的检测。主要工作内容如下：
1.通过亲电取代、亲电加成、加成消去、Sonogashira偶联等反应合成了四种共轭对亚苯基亚乙炔基化合物,即N-甲基-4-(4-硫代乙酸苯酯基-2-乙炔基)-1,8-萘酰胺(化合物1),4-(4-硫代乙酸苯酯基-2-乙炔基)苯胺(化合物2),4-(4-甲硫醚苯基-2-乙炔基)苯胺(化合物3),N-甲基-4-(4-甲硫醚苯基-2-乙炔基)-1,8-萘酰胺(化合物4)。中间体和目标化合物均通过1H NMR、13C NMR、 MS和IR进行了结构表征。荧光和紫外光谱研究表明,这一系列化合物在有机溶剂如三氯甲烷或四氢呋喃中具有良好的光谱性质,而在水溶液中其荧光迅速被猝灭。在β-环糊精存在时,化合物2和3在水溶液中的荧光性质明显改善。光谱分析结果显示,荧光增强是由于化合物与β-环糊精形成了稳定的超分子包合物。详细探讨了该超分子包合反应过程,并推导了相应的包合机理。将化合物3与β-环糊精的超分子包合物用于水溶液中水杨醛的检测。在最优条件下,随着水杨醛的加入,超分子化合物的荧光被猝灭,据此可定量检测水杨醛,线性范围为0.6-240μM,检测下限为1×10-8M。
2.设计并合成了两种共轭对亚苯基亚乙炔基分子导线(4-(4-甲硫醚苯基-2-乙炔基)苯甲醛(化合物5)和4-(4-甲硫醚苯基-2-乙炔基)苯甲酸(化合物6),并对这两种化合物的结构进行了表征确认。详细研究了这两种化合物的光谱性质及其与β-环糊精的包合反应,探讨了超分子反应过程并推导了相应的包合机理。研究发现：随着包合物的形成,这两种化合物的荧光明显增强；在三聚氰胺的存在下,化合物5和6的环糊精包合物的荧光被猝灭,由此建立了灵敏检测水中三聚氰胺的新方法,检测范围为分别为0.15-10μM和0.15-25μM。
3.设计合成了一种新型的二茂铁乙炔衍生物,即4-(二茂铁基-2-乙炔基)苯胺(化合物7,简写为Fc-NH2)。该分子中含有苯乙炔骨架,封端基分别为二茂铁和氨基砌块,该化合物拥有优良的电化学性质,可以作为新型的电子媒介体用于构建电化学传感器。通过一锅法将石墨烯的水溶液和Fc-NH2溶液混合,制备了Fc-NH2/石墨烯复合物,滴于玻碳电极,再滴上一层Nafion膜,构建了新型Nafion/graphene/Fc-NH2修饰的玻碳电极。将Fc-NH2固定于石墨烯基体中,不但可以增强石墨烯复合物的电子传输性能和稳定性,同时也能有效防止二茂铁的泄露。研究表明,多巴胺(DA)在复合物修饰电极上的检测信号显著增强,石墨烯的电催化性能和二茂铁的电子媒介作用对检测信号的放大起主要作用。无论尿酸(UA)和抗坏血酸(AA)存在与否,多巴胺的电流响应与其浓度均呈良好的线性关系,线性范围分别为5×10-8-2×10-4M和1×10-7-4×10-4M,检测限分别为20和50nM。采用标准加入法,该修饰电极可很好地用于实际样品中多巴胺的检测。我们还进一步深入探讨了这一新检测方法中的信号放大的可能机理。
4.将新合成的新型的二茂铁乙炔衍生物,即4-(二茂铁基-2-乙炔基)苯胺(化合物7,Fc-NH2)与石墨烯片(GS)之间良好的相互作用制备了GS/chi/Fc-NH2复合物,并成功用于细胞色素c (Cytc)的固定,获得GS/chi/Fc-NH2/Cytc修饰电极。实验研究发现,GS/chi/Fc-NH2复合物可以实现Cytc与电极间的快速电子传递,GS/chi/Fc-NH2/Cytc修饰电极在-0.2V附近出现一对峰,对应于Cytc的可逆氧化还原峰。该电极对亚硝酸钠有良好的电催化作用,在0.1-150μM范围内呈良好的线性关系,检测限低至0.01μM。
5.设计、合成一种新型二茂铁乙炔衍生物,即4-(二茂铁基-2-乙炔基)硫代乙酸苯硫醇酯(化合物9,Fc-SAc),此化合物以低聚对弧苯基亚乙炔基作为骨架,以二茂铁和硫酯基为端基。将Fc-SAc的水解产物4-(二茂铁基-2-乙炔基)苯硫酚(Fc-SH)通过金-硫键固定在金纳米粒子(AuNPs)修饰电极表面,构建了新型、高灵敏芦丁传感器。将二茂铁乙炔衍生物结合纳米金、石墨烯／壳聚糖构建了两种不同的修饰电极,即Fc-S/AuNPs/GCE(电极1)和Fc-S/AuNPs/graphene-chitosan/GCE(电极2)。实验发现,芦丁在电极1上的电化学过程是受扩散控制,而在电极2上的电化学过程是受传质控制的。在最优实验条件下,电极1上芦丁检测的浓度线性范围为0.1-30μM,线性回归系数为0.998；而在电极2上,线性范围扩大至0.04-100μM,线性回归系数为0.997。研究表明,电极2检测芦丁的线性范围更宽、检测限更低、稳定性更好。
6.首次报道了一种双重信号放大检测平台用于超灵敏检测抗坏血酸(AA)、多巴胺(DA)、尿酸(UA)和乙酰氨基酚(AC)的四组份混合物。这一双重信号放大平台是由新合成的4-(二茂铁基-2-乙炔基)硫代乙酸苯硫醇酯(化合物9, Fc-SAc,)的水解产物4-(二茂铁基-2-乙炔基)苯硫酚(Fc-SH)修饰的金包磁纳米粒子(Au@Fe3O4)和石墨烯纳米片(GS)及玻碳电极构成。由于纳米材料如Au@Fe3O4纳米粒子和GS的催化作用以及二茂铁作为电子媒介体可加速电子传递,检测的灵敏度大大提高。新型Fc-SH修饰的Au@Fe3O4纳米复合物表现出良好的电化学性质和电催化性能。将Fc-S-Au@Fe3O4与GS/chitosan(石墨烯／壳聚糖)一锅法混合,可以得到Fc-S-Au@Fe3O4/GS/chitosan纳米复合物。将这一纳米复合物滴于玻碳电极表面,构建Fc-S-Au@Fe3O4/GS/chitosan/GCE修饰电极。实验发现此修饰电极可以用于AA、DA、UA和AC共存条件下各组份的灵敏检测。在50mVs-1的扫速下,四组份可以很好地分开,峰电位分别位于-0.03,0.15,0.26和0.37V, AA-DA, DA-UA和UA-AC的峰-峰电位差分别为0.18,0.11和0.11V。采用微分脉冲伏安法对四组份进行检测发现,各物质的峰电流都随着浓度的增加而增加。当保持其他三组份的浓度不变,只改变待测组分浓度时,四组份体系中AA、DA、UA和AC分别在5-100,0.5-80,2-120和0.5-35μM浓度范围内呈良好的线性关系。同时改变四组份的浓度时,AA、DA、UA和AC分别在6-350,0.5-50,1-100和0.2-30μM范围内呈良好的线性。根据三倍信噪比计算出AA、DA、UA和AC的最低检测限分别为1、0.08、0.1和0.01μM。
Quantitative and qualitative determination of physiologically-related species in complex food, medicine, biological matrixes, and environmental sample is the core issue of food safety, disease screening and diagnosis and sanitation, environmental monitoring and pollution. It is very important to develope fast, simple, sensitive methods for detection of individual and multiple components in the complex samples. Chemo/biosensing is a new detection technique, and has widely applied in food, medicine, biological matrixes and environmental samples. And innovativing sensing methods, developing effective and amflification material is the key to constructing biosensors for small molecules with higher sensitivity and selectivity.
In this dissertation, we briefly reviewed the chemo/biosensors, and especially stated how to design and construct new chemical sensors. The recent applications of nanomaterials, electron mediators and molecular wires in the area of chemo/biosensing were reviewed in detail. As one of important molecular wires, oligo-(phenylene-ethynylene)s (OPEs) derivatives have excellent properities such as rectifier, storage and switch, and have widely employed in molecular electronics area. Take advantage of the good optical and electrotronic properties, it is expected to build some sensitive detection methods for small molecules. Based on this, serials of new OPEs were synthesized and characterized. Combined with nanomaterials and β-cyclodextrin, several biosensors for life-related biomolecules were constructed. The main contents are as follows:
1. Four new conjugated oligo-phenylene-ethynylenes derivatives, N-methyl-4-(4-acetylthiophenylethynyl)-1,8-naphthalimide (1), thioacetic acid S-[4-(4-aminophenyl-ethynyl) phenyl]ester (2),4-methylthiophenylethynyl-benzenamine (3), and N-methyl-4-(4-methyl-thiophenyl-ethynyl)-1,8-naphthalimide (4), were synthesized by nucleophilic substitution, electrophilies addition and Sonogashira reactions. The structures of the four compounds were confirmed by1H NMR,13C NMR, MS and IR and their spectral characteristics were studied by ultraviolet and visible (UV-vis) spectroscopy as well as fluorescence spectroscopy in different mediums. It was found that the fluorescence properties of compounds2and3were notably improved in the aqueous solutions in the presence of β-cyclodextrin (β-CD). Spectral analysis supported the supposition that the fluorescence intensity enhancement was due to the formation of inclusion complex with β-CD. The supramolecular interaction was investigated in detail and the reaction mechanism was provided. A salicylaldehyde determination method in aqueous medium was established based on the supramolecular complex of compound3. Under the optimum conditions, the supramolecular complex exhibited a dynamic fluorescence response range for salicylaldehyde from0.6to240μM, with a detection limit of1×10-8M.
2. Two new conjugated oligo-phenylene-ethynylenes derivatives,4-((4-(methylthio) phenyl)ethynyl)benzaldehyde (5),4-((4-(methylthio) phenyl) ethynyl) benzoic acid)(6) were designed and synthesized for the first time. Their structures of the two compounds were thoroughly confirmed by1H NMR,13C NMR, MS and IR. The spectral characteristics were studied by UV-vis spectroscopy as well as fluorescence spectroscopy in different solvents. The inclusion processes with β-CD were investigated in detail and the possible inclusion mechanism was induced. It was found that the fluorescence intensity of the two compounds was enhanced after the complex was formed. In the presence of melamine, the fluorescence intensity of the supramolecular complex was quickly quenched. A simple melamine determination method in aqueous medium was established based on the supramolecular complex of β-CD with compound5and6. Under the optimum conditions, the supramolecular complex exhibited dynamic fluorescence response ranges for melamine from0.15-10μM and0.15-25μM, respectively.
3. A new ferrocene derivative (1-[(4-amino) phenyl ethynyl] ferrocene,(compound7, Fc-NH2) was synthesized for the first time. The ferrocene derivative molecule contained phenylethynyl skeleton, ferrocene and amino groups with excellent electrochemical property. Graphene/Fc-NH2nanocomposite was prepared by mixing graphene solution and Fc-NH2solution in one pot and the nanocomposite was utilized to construct Nafion/graphene/Fc-NH2modified glass carbon electrode (GCE). The ferrocene derivative immobilized on the graphene can enhance the charge-transport ability of the nanocomposite, stabilize the graphene and prevent the leakage of ferrocene. The detection signal of dopamine (DA) was significantly amplified on the Nafion/graphene/Fc-NH2/GCE. It was experimentally demonstrated that the signal enhancement is resulted from the synergy amplification effect of graphene and the Fc-NH2. The oxidation peak currents of DA were linearly related to the concentrations in the range of5×10-2×10-4M with the detection limit of20nM in the absence of urine acid (UA) and ascorbic acid (AA). In the presence of10-3M AA and10-4M UA, the linear response range was1×10-7-4×10-4M, and the detection limit was50nM at S/N=3. Using the proposed Nafion/Fc-NH2/graphene/GCE, DA was successfully determined in real samples with the standard addition method.
4. A new ferrocene-terminated phenylethynyaniline (Fc-NH2, compound7) was synthesized by Sonogashira reaction. The structures of the new intermediate and target compound were identified by IR,1H NMR,13C NMR, MS. Stable GS/chi/Fc-NH2complex was prepared combined with graphene, and the GS/chi/Fc-NH2/Cytc modified electrode was fabricated. It was found that Cytc can immobilize on GS/chi/Fc-NH2and the fast electron transfer can be realized between the electrode and Cytc molecules. There is a pair of peaks near-0.2V, which can be attributed to Cytc. The GS/chi/Fc-NH2/Cytc modified GCE shows good catalysis towards NaNO2, and it shows good linearity in the range of1×10-7-1.5×10-4M,0.1-150μM, and the determination limit is bellow at4×10-8M.
5. A new ferrocene benzyne derivative (Fc-SAc, compound9) that contained oligo-(phenylene-ethynylene) skeleton, ferrocene and thiolate terminal groups was firstly synthesized. The hydrolysis product of Fc-SAc (Fc-SH) was immobilized onto gold nanoparticles (AuNPs) modified glass carbon electrode (GCE) as sensing element for rutin detection with high sensitivity. The new sensing strategy was proposed by using two Fc-SH modified electrodes:Fc-S/AuNPs/GCE (Electrodel) and Fc-S/AuNPs/graphene-chitosan/GCE (Electrode2). The electrochemical oxidation of rutin on Electrode2was a diffusion-controlled process, which was different from a mass-controlled process on Electrode1. Under the optimal conditions, the peak currents of the sensors were linearly related to the concentrations of rutin. The linear response ranges were0.05-30μM and0.04-100μM with the regression coefficients of0.998and0.997on Electrodel and Electrode2, respectively. Electrode2presented wider linear range, superior sensitivity, lower detection limit and better stability on determination of rutin.
6. A double signal amplification platform for ultrasensitive simultaneous detection of a quaternary mixture of ascorbic acid (AA), dopamine (DA), uric acid (UA) and acetaminophen (AC) is fabricated by assembling newly synthesized ferrocene thiolate (phenylethynyl ferrocene thiolate, Fc-SAc, compound9) on core/shell structured Fe3O4@Au and coupling with graphene sheet/chitosan (GS/chitosan). By immobilization of the electron mediator on Fe3O4@Au nanoparticles (NPs), a Fe3O4@Au-S-Fc nanocomposite possessing excellent electric-catalytic and signal amplification behavior was obtained. Mixing the Fe3O4@Au-S-Fc with GS/chitosan, the Fe3O4@Au-S-Fc/GS/chitosan nanocomposites were obtained and utilized to construct a multicomponent sensor. Using the Fe3O4@Au-S-Fc/GS/chitosan modified glass carbon electrode (GCE), the double signal amplification strategy was realized by the synergistic catalytic effect of Fe3O4@Au NPs and GS, and the amplification effect of the ferrocene electron mediator. The individual and simultaneous determinations of AA, DA, UA and AC were performed using differential pulse voltammetry (DPV) with the modified electrode. This modified electrode exhibits potent and persistent electro-oxidation behavior followed by well-separated oxidation peaks towards AA, DA, UA and AC. For the quaternary mixture, the four compounds can be well separated from each other at a scan rate of50mVs-1with the peak potentials at-0.03,0.15,0.24and0.35V, respectively. The peak-to-peak potential separations of AA-DA, DA-UA and UA-AC were0.18,0.09and0.11V, respectively, which were large enough to determine AA, DA, UA and AC simultaneously. The catalytic peak currents were linearly dependent on the concentrations of AA, DA, UA and AC in the range of5-100,0.5-80,2-120and0.5-35μM, respectively, in the individual detection of each component under the condition of keeping the concentrations of the other3compounds constant. By simultaneously changing the concentrations of the4constituents, good linear current responses were obtained in the range of6-350,0.5-50,1-90and0.4-32μM for AA, DA, UA and AC, respectively. And the determination limits for AA, DA, UA and AC were1,0.2,0.3and0.05μM, respectively. The analytical performance of this sensor has been evaluated for simultaneous detection of AA, DA, UA and AC in serum and urine samples.
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