荧光共轭聚合物在化学传感器上的应用
摘要
应用荧光化学传感技术进行物质快速，高选择性，高灵敏地研究的检测是当前研究的热点之一。而敏感试剂和测量方法的探索是提高痕量物质分析选择性和灵敏度的关键因素。共轭聚合物(CPs)己被广泛应用于生物传感和成像领域，此外共轭聚电解质(CPEs)综合了传统的共轭聚合物(CPs)优异的光电性质(如分子导线效应)和聚电解质的水或是醇溶性特点，同样也被广泛应用于光电器件，化学传感器以及生物成像等领域。本文主要工作包括两个体系的研究：
在第一章中，我们通过引入三嵌段的表面活性剂F127共聚物与共轭聚合物在水溶液中进行自组装，成功制备了粒径在50-100纳米的尺寸可控的球形纳米胶束。生物传感领域中共轭聚合物大多数不溶于水中，普通的共轭聚合物为了在水溶液中实现特定分析对象(DNA及生物分子相应的生化过程)的检测必须经过复杂修饰的共轭聚电解质。因此，我们研究并扩展能够在水溶液中实现传感性能的的共轭聚合物纳米材料。我们筛选出最佳的共轭聚合物和表面活性剂F127的浓度配比，比较不同共轭聚合物的猝灭效率后选择PFO和PF-PE作为的水溶液中的传感体系。通过动态光散射(DLS)、透射电镜(TEM)证实了在共轭聚合物(CPs)包覆后具有稳定纳米胶束结构，荧光(PL)和吸收光谱(UV)表明可以通过将不同的表面活性剂以及共轭聚合物(CPs)的浓度比来调节不同的发光性能。我们采用共轭聚合物纳米胶束来研究对苏丹红染料的传感检测，体系主要是通过利用染料色素的疏水性，当在水溶液中加入被检测物后，疏水的染料会被包含入纳米胶束内部和共轭聚合物有效接触，并且苏丹红染料能够有效猝灭共轭聚合物的荧光。苏丹红一号对PF-PE/F127和PFO/F127纳米胶束的猝灭常数分别1,040,480M-1和665,000M-1，要比它们在甲苯溶剂中的猝灭效率高出2个数量级。我们进一步研究了荧光猝灭机理发现由于苏丹红染料的电化学能级是被包含在共轭聚合物能级之间，因此较好的能及匹配使之能够发生电子的转移过程(PET)，它们在对苏丹2-4号的检测中也显示了很高的灵敏度，因此共轭聚合物纳米胶水对苏丹红染料具有较高的灵敏度和选择性，有望成为对疏水染料的选择性检测手段。
第二章中我们利用激光光散射技术(LLS)来研究三种不同侧链的共轭聚电解质(PF6NBr，PFSO3Na，PFN6SO)在甲醇中的光物理性质，通过光散射实验证明了三种聚电解质在甲醇中具有不同的构象和存在不同的聚集态，透射电镜的结果也证明了它们在溶液中存在不同的聚集态。我们进一步用荧光光谱证实了在水/甲醇混合溶液中聚集态对光
物理性质的影响。我们分别用甲基紫精(MV2+)和1,2-萘醌-4-磺酸钠(NQS-)作为阳离子猝灭剂和阴离子猝灭剂来进一步研究它们聚集态行为对猝灭效率的影响。对于PF6NBr，随着聚电解质浓度的增加，会通过静电相互吸引使猝灭剂结合导致猝灭；高浓度下的链构象发生强烈聚集会导致猝灭效率降低。然而对于PFSO3Na和PF6NSO，由于它们在溶液中有稳定的聚集态，它们的猝灭效率相比则影响较小。我们研究了在不同甲醇和水混合溶剂中的影响时发现，用NQS-作为猝灭剂时，PF6NBr和PF6NSO显示出较好的猝灭放大效率，PFSO3Na对MV2+有较好的猝灭放大效率，这个结果可以由聚合物在溶剂中较容易形成聚集体来解释。但两性聚电解质PF6NSO相对于PF6NBr和PFSO3Na猝灭效率则较低，而阴离子猝灭剂NQS-相比MV2+能够更好打破聚电解质的聚集态，从而导致了NQS-对PF6NSO更高的猝灭效率。CPEs的猝灭放大效应主要是猝灭剂和CPEs之间的静电吸引从而导致电子转移过程，从而导致激子在CPEs骨架上的长程快速迁移，实验结果表明，引起共轭聚电解质(CPEs)的猝灭放大效应的一个主要原因则是因为不同电性小分子猝灭剂的静电作用对聚集态的影响和聚电解质(CPEs)聚集态结构变化下共同影响导致的。
The application of fluorescent biosensor for analytes sensing is one of the hot spot inscience research. Rapid, high selectivity and high sensitivity study of analytes in biologicalchemical information is one of the frontier subjects in the biosensing. And sensitive reagentand exploration is to improve the trace analysis of the measuring methods of selectivity andsensitivity of the key factors. Conjugated polymers have been widely applied in biosensing,and conjugated polyelectrolyte (CPEs) is a kind of ionized in polar solvent functional groupsin the main chain of the conjugated polymers, which is combines traditional conjugatedpolymers excellent photoelectric properties, such as signal amplification and with goodwater-soluble characteristics of polyelectrolyte. Conjugated polyelectrolyte is also widelyapplied light electric parts and chemical sensors and biological imaging, etc. This paper mainwork includes the following aspects:
In this paper, Novel self-assembled water-soluble nanomicelles that by introducingcommercialized three block of surfactant Pluronic F127self-assembly with conjugatedpolymers in aqueous solution, and particle size distribution of spherical nanometer micelleswas successfully achieved in50-100nm. Conjugated polymers (CPs) with uniquephotophysical properties and electrical conductivity are considered as promising candidatesfor the development of fluorescent sensors. However, the application of Conjugated polymers(CPs) to bioimaging and sensing in aqueous environment is hindered by their poor watersolubilities, and Conjugated polymers (CPs) is not conducive to implement specific analysisobject in the aqueous solution (Such as DNA and corresponding biochemical processes ofbiological molecules) detection. Therefore, great efforts have been devoted to developingcolloidal stable conjugated polymer nanoparticles (NPs) in aqueous solution. We screeningout the appropriate concentration ratio of Pluronic F127and conjugated polymer, andoptimize the sensor system in the aqueous solution of conjugated polymers. The morphologyof the F127and conjugated polymers/F127micelles were observed with by dynamic lightscattering (DLS) and transmission electron microscopy (TEM). Fluorescence and absorptionspectroscopy characterization methods confirmed that different surfactants and conjugatedpolymer concentration ratios to adjust different luminous efficiency. The Fluorescent nanomicelles exhibited a highly selective fluorescence quenching by the prohibited foodadditive Sudan dyes, while not for the natural pigments: Capsanthin and Beta-carotene. It isalso possible that the trace amount of hydrophobic dye in the aqueous solution can becollected and enriched in the hydrophobic inner part of F127nanomicelles by thehydrophobic–hydrophobic interaction resulting in the enhancement of quenching effect. TheStern-Volmer constants (Ksv) of PF-PE/F127and PFO/F127for Sudan I were1,040,480M-1and665,000M-1, respectively, which were over100times higher than those of the sameconjugated polymers in the orgainc solvents. The detailed photochemical mechanism foramplified fluorescence quenching was revealed to be due to the more suitable matching of theLUMOs (lowest unoccupied molecular orbital) of the conjugated polymers with that of SudanI molecules, thusthe charge transfer between CPs and analytes and the enriching andcollecting effect micelles hydrophobic core. In the same conditions, CPs nanomicellesexhibited strong fluorescence responses toward other azo dyes, such as Sudan II, Sudan IIIand Sudan IV. It allowed the selectively determination of Sudan dye by a fluorescence method.Moreover, this strategy provides a general approach for extending the applications ofconjugated polymers.
In the second chapter, the effect of aggregation on the photophysical properties of threewater/alcohol-soluble conjugated polymers (CPEs),poly[9,9-bis((N,N,N-triethylammonium)-hexyl)-2,7-fluorene] dibromide (PF6NBr),poly[9,9-bis(4’-sulfonatobutyl)fluorene-co-alt-1,4-phenylene] sodium salt (PFSO3Na) andpoly[9,9-bis((N-(3-sulfonate-1-propyl)-N,N-diethylammonium)-hexyl)-2,7-fluorene](PF6NSO) has been studied through laser light scatterings (LLS) and quenching experiment.The results obtained by light scatterings reveal that three CPEs form different fluorescenceaggregates in methanol. Furthermore, fluorescence spectroscopy also reveals that CPEs formfluorescent aggregates in a mixture of methanol and water. Fluorescence quenching of thepolymers was examined using methyl viologen (MV2+)and1,2-naphthoquinone-4-sulfonate(NQS-) as a cationic quencher and anionic quencher, respectively.
The fluorescence intensity of PF6NBr decreases with increasing concentration, indicatingthat dominated by electrostatic attraction and aggregation induced less fluorescence quenching and the chain conformation controlled, and high concentrations of PF6NBr leadingchain conformation strong aggregation in methanol and cause the less quenching efficiency.In contrast, for both PFSO3Na and PF6NSO, the emission is less quenched in methanol due tothey have a stable state of aggregation in solution.
Accordingly, we investigated the quenching properties of three polyelectrolytes atdifferent methanol and water solvent ratio. However, PF6NBr and PF6NSO shows stronglyamplified quenching effect by NQS-, and PFSO3Na shows amplified quenching effect byMV2+in water. The results are explained by polymer is able to fold into an aggregation insolution. With regard to the PF6NBr and PFSO3Na, quenching efficiency of PF6NSO showeda high quenching efficiency due to NQS-break up polymers aggregates and show a betterquenching efficiency compare to MV2+. This work shows that the quenching of the CPEsinvolves electron transfer and is correlated to the conformational changes that occur uponbinding the quenchers to the polyelectrolyte (CPEs), which facilitates the long-distanceexciton rapid migration along CPEs backbone. Our work addresses an important fundamentalissue concerning quencher-induced amplified quenching effect for CPEs. The resultsunderscore the important role played by chain aggregation in promoting efficient excitontransport, which is the key to the amplified quenching effect.
在第一章中，我们通过引入三嵌段的表面活性剂F127共聚物与共轭聚合物在水溶液中进行自组装，成功制备了粒径在50-100纳米的尺寸可控的球形纳米胶束。生物传感领域中共轭聚合物大多数不溶于水中，普通的共轭聚合物为了在水溶液中实现特定分析对象(DNA及生物分子相应的生化过程)的检测必须经过复杂修饰的共轭聚电解质。因此，我们研究并扩展能够在水溶液中实现传感性能的的共轭聚合物纳米材料。我们筛选出最佳的共轭聚合物和表面活性剂F127的浓度配比，比较不同共轭聚合物的猝灭效率后选择PFO和PF-PE作为的水溶液中的传感体系。通过动态光散射(DLS)、透射电镜(TEM)证实了在共轭聚合物(CPs)包覆后具有稳定纳米胶束结构，荧光(PL)和吸收光谱(UV)表明可以通过将不同的表面活性剂以及共轭聚合物(CPs)的浓度比来调节不同的发光性能。我们采用共轭聚合物纳米胶束来研究对苏丹红染料的传感检测，体系主要是通过利用染料色素的疏水性，当在水溶液中加入被检测物后，疏水的染料会被包含入纳米胶束内部和共轭聚合物有效接触，并且苏丹红染料能够有效猝灭共轭聚合物的荧光。苏丹红一号对PF-PE/F127和PFO/F127纳米胶束的猝灭常数分别1,040,480M-1和665,000M-1，要比它们在甲苯溶剂中的猝灭效率高出2个数量级。我们进一步研究了荧光猝灭机理发现由于苏丹红染料的电化学能级是被包含在共轭聚合物能级之间，因此较好的能及匹配使之能够发生电子的转移过程(PET)，它们在对苏丹2-4号的检测中也显示了很高的灵敏度，因此共轭聚合物纳米胶水对苏丹红染料具有较高的灵敏度和选择性，有望成为对疏水染料的选择性检测手段。
第二章中我们利用激光光散射技术(LLS)来研究三种不同侧链的共轭聚电解质(PF6NBr，PFSO3Na，PFN6SO)在甲醇中的光物理性质，通过光散射实验证明了三种聚电解质在甲醇中具有不同的构象和存在不同的聚集态，透射电镜的结果也证明了它们在溶液中存在不同的聚集态。我们进一步用荧光光谱证实了在水/甲醇混合溶液中聚集态对光
物理性质的影响。我们分别用甲基紫精(MV2+)和1,2-萘醌-4-磺酸钠(NQS-)作为阳离子猝灭剂和阴离子猝灭剂来进一步研究它们聚集态行为对猝灭效率的影响。对于PF6NBr，随着聚电解质浓度的增加，会通过静电相互吸引使猝灭剂结合导致猝灭；高浓度下的链构象发生强烈聚集会导致猝灭效率降低。然而对于PFSO3Na和PF6NSO，由于它们在溶液中有稳定的聚集态，它们的猝灭效率相比则影响较小。我们研究了在不同甲醇和水混合溶剂中的影响时发现，用NQS-作为猝灭剂时，PF6NBr和PF6NSO显示出较好的猝灭放大效率，PFSO3Na对MV2+有较好的猝灭放大效率，这个结果可以由聚合物在溶剂中较容易形成聚集体来解释。但两性聚电解质PF6NSO相对于PF6NBr和PFSO3Na猝灭效率则较低，而阴离子猝灭剂NQS-相比MV2+能够更好打破聚电解质的聚集态，从而导致了NQS-对PF6NSO更高的猝灭效率。CPEs的猝灭放大效应主要是猝灭剂和CPEs之间的静电吸引从而导致电子转移过程，从而导致激子在CPEs骨架上的长程快速迁移，实验结果表明，引起共轭聚电解质(CPEs)的猝灭放大效应的一个主要原因则是因为不同电性小分子猝灭剂的静电作用对聚集态的影响和聚电解质(CPEs)聚集态结构变化下共同影响导致的。
The application of fluorescent biosensor for analytes sensing is one of the hot spot inscience research. Rapid, high selectivity and high sensitivity study of analytes in biologicalchemical information is one of the frontier subjects in the biosensing. And sensitive reagentand exploration is to improve the trace analysis of the measuring methods of selectivity andsensitivity of the key factors. Conjugated polymers have been widely applied in biosensing,and conjugated polyelectrolyte (CPEs) is a kind of ionized in polar solvent functional groupsin the main chain of the conjugated polymers, which is combines traditional conjugatedpolymers excellent photoelectric properties, such as signal amplification and with goodwater-soluble characteristics of polyelectrolyte. Conjugated polyelectrolyte is also widelyapplied light electric parts and chemical sensors and biological imaging, etc. This paper mainwork includes the following aspects:
In this paper, Novel self-assembled water-soluble nanomicelles that by introducingcommercialized three block of surfactant Pluronic F127self-assembly with conjugatedpolymers in aqueous solution, and particle size distribution of spherical nanometer micelleswas successfully achieved in50-100nm. Conjugated polymers (CPs) with uniquephotophysical properties and electrical conductivity are considered as promising candidatesfor the development of fluorescent sensors. However, the application of Conjugated polymers(CPs) to bioimaging and sensing in aqueous environment is hindered by their poor watersolubilities, and Conjugated polymers (CPs) is not conducive to implement specific analysisobject in the aqueous solution (Such as DNA and corresponding biochemical processes ofbiological molecules) detection. Therefore, great efforts have been devoted to developingcolloidal stable conjugated polymer nanoparticles (NPs) in aqueous solution. We screeningout the appropriate concentration ratio of Pluronic F127and conjugated polymer, andoptimize the sensor system in the aqueous solution of conjugated polymers. The morphologyof the F127and conjugated polymers/F127micelles were observed with by dynamic lightscattering (DLS) and transmission electron microscopy (TEM). Fluorescence and absorptionspectroscopy characterization methods confirmed that different surfactants and conjugatedpolymer concentration ratios to adjust different luminous efficiency. The Fluorescent nanomicelles exhibited a highly selective fluorescence quenching by the prohibited foodadditive Sudan dyes, while not for the natural pigments: Capsanthin and Beta-carotene. It isalso possible that the trace amount of hydrophobic dye in the aqueous solution can becollected and enriched in the hydrophobic inner part of F127nanomicelles by thehydrophobic–hydrophobic interaction resulting in the enhancement of quenching effect. TheStern-Volmer constants (Ksv) of PF-PE/F127and PFO/F127for Sudan I were1,040,480M-1and665,000M-1, respectively, which were over100times higher than those of the sameconjugated polymers in the orgainc solvents. The detailed photochemical mechanism foramplified fluorescence quenching was revealed to be due to the more suitable matching of theLUMOs (lowest unoccupied molecular orbital) of the conjugated polymers with that of SudanI molecules, thusthe charge transfer between CPs and analytes and the enriching andcollecting effect micelles hydrophobic core. In the same conditions, CPs nanomicellesexhibited strong fluorescence responses toward other azo dyes, such as Sudan II, Sudan IIIand Sudan IV. It allowed the selectively determination of Sudan dye by a fluorescence method.Moreover, this strategy provides a general approach for extending the applications ofconjugated polymers.
In the second chapter, the effect of aggregation on the photophysical properties of threewater/alcohol-soluble conjugated polymers (CPEs),poly[9,9-bis((N,N,N-triethylammonium)-hexyl)-2,7-fluorene] dibromide (PF6NBr),poly[9,9-bis(4’-sulfonatobutyl)fluorene-co-alt-1,4-phenylene] sodium salt (PFSO3Na) andpoly[9,9-bis((N-(3-sulfonate-1-propyl)-N,N-diethylammonium)-hexyl)-2,7-fluorene](PF6NSO) has been studied through laser light scatterings (LLS) and quenching experiment.The results obtained by light scatterings reveal that three CPEs form different fluorescenceaggregates in methanol. Furthermore, fluorescence spectroscopy also reveals that CPEs formfluorescent aggregates in a mixture of methanol and water. Fluorescence quenching of thepolymers was examined using methyl viologen (MV2+)and1,2-naphthoquinone-4-sulfonate(NQS-) as a cationic quencher and anionic quencher, respectively.
The fluorescence intensity of PF6NBr decreases with increasing concentration, indicatingthat dominated by electrostatic attraction and aggregation induced less fluorescence quenching and the chain conformation controlled, and high concentrations of PF6NBr leadingchain conformation strong aggregation in methanol and cause the less quenching efficiency.In contrast, for both PFSO3Na and PF6NSO, the emission is less quenched in methanol due tothey have a stable state of aggregation in solution.
Accordingly, we investigated the quenching properties of three polyelectrolytes atdifferent methanol and water solvent ratio. However, PF6NBr and PF6NSO shows stronglyamplified quenching effect by NQS-, and PFSO3Na shows amplified quenching effect byMV2+in water. The results are explained by polymer is able to fold into an aggregation insolution. With regard to the PF6NBr and PFSO3Na, quenching efficiency of PF6NSO showeda high quenching efficiency due to NQS-break up polymers aggregates and show a betterquenching efficiency compare to MV2+. This work shows that the quenching of the CPEsinvolves electron transfer and is correlated to the conformational changes that occur uponbinding the quenchers to the polyelectrolyte (CPEs), which facilitates the long-distanceexciton rapid migration along CPEs backbone. Our work addresses an important fundamentalissue concerning quencher-induced amplified quenching effect for CPEs. The resultsunderscore the important role played by chain aggregation in promoting efficient excitontransport, which is the key to the amplified quenching effect.
引文
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