有机/无机荧光材料的合成、表征及其在光化学传感方面的应用
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摘要
光化学传感器已经被广泛地应用于探测重金属离子。荧光化学传感器具有简单快速,选择性和灵敏度高等优点,而比色化学传感器则可以通过肉眼直接观测。在众多的有机染料探针中,罗丹明衍生物由于具有大的摩尔消光系数,高的量子产率和长的吸收和发射波长等优点而被广泛应用于构筑开／关型的荧光探针。与传统的有机染料和荧光蛋白相比,半导体纳米晶(常被称为量子点,QDs)具有更多迷人的优点,如高的水溶性,更大的摩尔消光系数,更高的荧光量子产率,宽的吸收光谱和窄的发射光谱,根据粒子大小可调控的荧光发射等。
在本文中,我们设计了一系列基于罗丹明衍生物和量子点的荧光探针,并研究了他们识别重金属离子Hg~(2+)和Cu~(2+)的性能。另外,我们利用静电纺丝技术制备了一系列荧光复合薄膜,为下一步开展基于纺丝薄膜传感材料的制备工作奠定了基础。具体内容如下：
1.设计合成了新颖的基于罗丹明衍生物的比色、荧光探针R01和RS1。然后,研究和比较了探针分子RO1和RS1对重金属离子的识别能力。利用汞的亲硫特性,通过硫离子的引入,实现了二者识别的金属离子由Cu~(2+)到Hg~(2+)的转变。对比二者对两类重金属离子的识别能力,探针RS1对Hg~(2+)表现出更优异的识别性能。具体的探测原理是基于酰胺螺环结构“开-关”的特征,对Hg~(2+)表现出高灵敏度、高选择性、快速、可逆的识别能力。将探针RS1应用于细胞成像研究,发现探针分子RS1可以探测识别活细胞中的Hg~(2+),证实该探针分子在生物体系中具有实际的应用价值。
2.设计合成了基于汞诱导脱硫化反应和罗丹明酰胺螺环结构“开-关”特征的化学计量计R02,通过紫外可见吸收光谱和荧光光谱的测试证实了该化学计量计对Hg~(2+)具有高的选择性,快的响应时间和较高的灵敏度。引入双键单元,期望通过双键聚合而形成高分子聚合物,然后利用静电纺丝技术制备荧光薄膜传感材料。通过上述表征证实了该化学计量计的优异识别性能,为下一步工作的开展奠定了基础。
3.通过溶胶-凝胶法用Si0_2将CdTe QDs和Fe_2O_3 NRs包裹起来,从而形成具有多重功能的CdTe/Fe_2O_3@SiO2核壳复合材料。通过一系列的表征手段充分证实了该核壳复合材料的成功制备。另外利用荧光光谱和超导量子干涉磁力仪观察并且表征了该材料具有荧光和磁性特征。将该材料作为荧光探针可以通过其荧光强度的猝灭来检测水溶液中Hg~(2+)的浓度。我们详细地研究了猝灭过程的机理,发现Hg~(2+)对探针荧光的猝灭是动态猝灭和静态猝灭共同作用的结果,而且其猝灭过程符合改进的Stern-Volmer公式,在1μM-10μM范围内呈现很好的线性关系。
4.通过联合水热反应和静电自组装技术简单、高效地制备了Fe3O4@C@CdTe复合多层核壳纳米材料。巧妙地选用聚阳离子电解质-聚二烯丙基二甲基胺盐酸盐(PDDA),该聚合物既可以作为负电荷的吸附剂,又能形成壳层有效地避免Fe304和量子点的直接接触,更有利于量子点的荧光。利用了多种表征手段,充分证实了多层核壳纳米材料的形成。通过样品振动磁强计测试了该复合材料的超顺磁性,并且证实了可以通过外加磁场的方式对复合材料实行简单的分离和回收。将制备的可回收复合材料作为荧光探针可以通过其荧光强度的猝灭来检测水溶液中Cu~(2+)的浓度。我们详细地研究了猝灭过程的机理,发现Cu~(2+)对探针荧光的猝灭是动态猝灭和静态猝灭共同作用的结果,而且其猝灭过程符合改进的Stern-Volmer公式,在1μM-10μM范围内呈现很好的线性关系。
5.利用静电纺丝技术制备罗丹明6G/PAN和稀土配合物/PAN荧光复合纳米纤维。对于罗丹明6G/PAN荧光复合纳米纤维,我们利用UV-Vis吸收光谱和荧光光谱详细地研究了在纺丝薄膜中引入不同浓度的Rh6G分子对其聚集状态的影响。通过与铸造薄膜的光学性质对比发现：由于纺丝纤维膜大的比表面积和纺丝过程中溶剂的快速挥发,导致了纺丝薄膜减弱了Rh6G分子的聚集形式,从而更有利于其J-型二聚体的形成。对于稀土配合物/PAN荧光复合纳米纤维,通过对比复合纳米纤维薄膜与稀土配合物粉末的光学性质,我们发现当稀土配合物被掺杂到PAN纤维中后,PAN介质对其赋予了一定的保护作用。由于聚合物链段的刚性结构和受到所谓笼效应的影响,掺杂到PAN介质中的稀土配合物分子彼此之间相互孤立,不仅减少了聚集体的形成,而且避免了有机配体分子的转动和与周围介质的作用,从而降低了非辐射去活化的过程,最终改善了稀土配合物的热稳定性,光稳定性,延长了其荧光寿命和提高了其荧光量子产率。综上所述,通过研究染料分子和稀土配合物引入前后光学性能的改善,证实了静电纺丝薄膜是一个引入荧光化合物的理想基质。
6.通过对静电纺丝纤维进行乙二胺改性和利用曼尼希反应成功地将荧光素共价键连接到PAN纳米纤维薄膜表面。经荧光光谱检测获得了较强的荧光信号,避免了由于物理掺杂而发生的泄露现象,充分证明了静电纺丝薄膜表面修饰的可行性,为构筑含有性能优异传感分子的纺丝薄膜传感器奠定了基础。
Fluorescent and colorimetric chemosensors have been developed to be useful tools for sensing heavy metal ions. Fluorescent chemosensors are attractive due to the simplicity and high detection limit. The advantage of colorimetric sensors is their capability to detect analyte by the naked eye. Among numerous indicators, rhodamine-based dyes are a kind of excellent candidate for the construction of an off/on-type fluorescent chemosensor due to their excellent spectroscopic properties of large molar extinction coefficients, high fluorescence quantum yields, and long absorption and emission wavelength elongated to visible region. Compared to traditional organic dyes and fluorescent proteins, semiconductor nanocrystals, often referred to quantum dots (QDs), have several intriguing advantages such as great water-solubility, large extinction coefficients, high photoluminescence efficiency, tunable size-dependent emission, wide absorption spectrum and sharp emission profile.
In this thesis, a series of new optical chemosensors based on rhodamine and quantum dots were synthesized and investigated for their applications in the detection of heavy metal cations (Hg~(2+), Cu~(2+)). In addition, rhodamine 6G and europium complexes are incorporated into polymer matrixes and electrospun into various composite nanofibers.The details are as follows:
1. Novel rhodamine-based highly sensitive and selective colorimetric and off-on fluorescent chemosensors (RO1 and RS1) for heavy metal ions is designed and prepared. The photophysical characterization and Hg~(2+)/Cu~(2+)-binding properties of sensor RS1/RO1 are investigated and compared. The sensor RS1 show more excellent sensing ability for Hg~(2+) due to the incorporation of the S atom. The signal change of the chemosensor RS1 is based on a specific metal ion induced reversible ring-opening mechanism of the rhodamine spirolactam. The response of the chemise nsor RS1 for Hg~(2+) ions is instantaneous and reversible. Moreover, this sensor is applied for in vivo imaging in Rat Schwann cells to confirm that RS1 can be used as a fluorescent probe for monitoring Hg~(2+) in living cells with satisfying results, which further demonstrates its value of practical applications in environmental and biological systems.
2. A rhodamine-based highly sensitive and selective chemodosimeter is designed and prepared. The system, which utilizes an irreversible Hg~(2+)-promoted oxadiazole forming reaction of rhodamine derivative RO2, is monitored by colorimetric and fluorescence intensity changes that respond instantaneously at room temperature. In addition, the C=C is also incorporated into the rhodamine derivative. Next. the polymer through this C=C will be synthesized and electrospun into nanofibers with sensing ability.
3. Novel multifunctional Hg~(2+) ions sensing nanocomposites were developed by applying SiO2 as the encapsulation agent to package Fe_2O_3 NRs and CdTe QDs. resulting in CdTe/Fe_2O_3@SiO2 core/shell nanostructures. The core/shell structural nanocomposites were confirmed by extensive characterizations. Photoluminescence (PL) spectroscopy and superconducting quantum interference device (SQUID) were used to investigate the optical and magnetic properties of the core/shell structural nanocomposites, respectively. The fluorescence of the obtained nanocomposites could be quenched effectively by Hg~(2+)ions. The quenching mechanism was studied and the results show the existence of both static and dynamic quenching processes.
4. A novel multifunctional microsphere with a fluorescent CdTe quantum dots (QDs) shell and a magnetic core (Fe3O4) has been successfully developed and prepared by a combination of the hydrothermal method and layer-by-layer (LBL) self-assembly technique. The resulting fluorescent Fe3O4@C@CdTe core/shell microspheres are utilized as a chemosensor for ultrasensitive Cu~(2+)ions detection. The fluorescence of the obtained chemosensor could be quenched effectively by Cu~(2+)ions. The quenching mechanism was studied and the results showed the existence of both static and dynamic quenching processes. The modified Stern-Volmer equation showed a good linear response (R2=0.9957) in the range of 1 to 10μM with a quenching constant (Ksv) of 4.9×104 M-1. Most importantly, magnetic measurements showed that the Fe3O4@C@CdTe core/shell microspheres were superparamagnetic and they could be separated and collected easily using a commercial magnet in 10s。
5. Novel fluorescent composite nanofibrous films of rhodamine 6G/PAN and europium complexes/PAN are prepared by electrospinning. The optical properties of electruspun nanofibrous films are studied. For the rhodamine 6G/PAN fluorescent composite nanofibrous films, we have used casting films as reference material to compare the aggregation states of incorporation of Rh6G in electrospun nanofibrous films and casting films. The large specific surface area of the nanofibers and fast evaporation of the solvents in the electrospinning process reduced the aggregation of Rh6G. For the europium complexes/PAN fluorescent composite nanofibrous films, the thermal-stability, photo-stability and photoluminescence properties of these composite nanofibers are studied in comparison to that of the pure europium complexes in detail. The results indicate that, the PAN can provide a rigid environment for the europium complexes, so the thermal-stability and photo- stability of composite nanofibers are considerably improved. Most importantly, the luminescent quantum efficiency and luminescence lifetime of the composite nanofibers are of great improvement. The results demonstrate that the electrospun films are an ideal material for incorporation of fluorescent dyes and europium complexes.
6. The Mannich reaction was successfully used in modification of the electrospun films surfaces. Further modification of electrospun films with fluorescent molecules presents the possibility of practical sensing applications of the electrospun films.
在本文中,我们设计了一系列基于罗丹明衍生物和量子点的荧光探针,并研究了他们识别重金属离子Hg~(2+)和Cu~(2+)的性能。另外,我们利用静电纺丝技术制备了一系列荧光复合薄膜,为下一步开展基于纺丝薄膜传感材料的制备工作奠定了基础。具体内容如下：
1.设计合成了新颖的基于罗丹明衍生物的比色、荧光探针R01和RS1。然后,研究和比较了探针分子RO1和RS1对重金属离子的识别能力。利用汞的亲硫特性,通过硫离子的引入,实现了二者识别的金属离子由Cu~(2+)到Hg~(2+)的转变。对比二者对两类重金属离子的识别能力,探针RS1对Hg~(2+)表现出更优异的识别性能。具体的探测原理是基于酰胺螺环结构“开-关”的特征,对Hg~(2+)表现出高灵敏度、高选择性、快速、可逆的识别能力。将探针RS1应用于细胞成像研究,发现探针分子RS1可以探测识别活细胞中的Hg~(2+),证实该探针分子在生物体系中具有实际的应用价值。
2.设计合成了基于汞诱导脱硫化反应和罗丹明酰胺螺环结构“开-关”特征的化学计量计R02,通过紫外可见吸收光谱和荧光光谱的测试证实了该化学计量计对Hg~(2+)具有高的选择性,快的响应时间和较高的灵敏度。引入双键单元,期望通过双键聚合而形成高分子聚合物,然后利用静电纺丝技术制备荧光薄膜传感材料。通过上述表征证实了该化学计量计的优异识别性能,为下一步工作的开展奠定了基础。
3.通过溶胶-凝胶法用Si0_2将CdTe QDs和Fe_2O_3 NRs包裹起来,从而形成具有多重功能的CdTe/Fe_2O_3@SiO2核壳复合材料。通过一系列的表征手段充分证实了该核壳复合材料的成功制备。另外利用荧光光谱和超导量子干涉磁力仪观察并且表征了该材料具有荧光和磁性特征。将该材料作为荧光探针可以通过其荧光强度的猝灭来检测水溶液中Hg~(2+)的浓度。我们详细地研究了猝灭过程的机理,发现Hg~(2+)对探针荧光的猝灭是动态猝灭和静态猝灭共同作用的结果,而且其猝灭过程符合改进的Stern-Volmer公式,在1μM-10μM范围内呈现很好的线性关系。
4.通过联合水热反应和静电自组装技术简单、高效地制备了Fe3O4@C@CdTe复合多层核壳纳米材料。巧妙地选用聚阳离子电解质-聚二烯丙基二甲基胺盐酸盐(PDDA),该聚合物既可以作为负电荷的吸附剂,又能形成壳层有效地避免Fe304和量子点的直接接触,更有利于量子点的荧光。利用了多种表征手段,充分证实了多层核壳纳米材料的形成。通过样品振动磁强计测试了该复合材料的超顺磁性,并且证实了可以通过外加磁场的方式对复合材料实行简单的分离和回收。将制备的可回收复合材料作为荧光探针可以通过其荧光强度的猝灭来检测水溶液中Cu~(2+)的浓度。我们详细地研究了猝灭过程的机理,发现Cu~(2+)对探针荧光的猝灭是动态猝灭和静态猝灭共同作用的结果,而且其猝灭过程符合改进的Stern-Volmer公式,在1μM-10μM范围内呈现很好的线性关系。
5.利用静电纺丝技术制备罗丹明6G/PAN和稀土配合物/PAN荧光复合纳米纤维。对于罗丹明6G/PAN荧光复合纳米纤维,我们利用UV-Vis吸收光谱和荧光光谱详细地研究了在纺丝薄膜中引入不同浓度的Rh6G分子对其聚集状态的影响。通过与铸造薄膜的光学性质对比发现：由于纺丝纤维膜大的比表面积和纺丝过程中溶剂的快速挥发,导致了纺丝薄膜减弱了Rh6G分子的聚集形式,从而更有利于其J-型二聚体的形成。对于稀土配合物/PAN荧光复合纳米纤维,通过对比复合纳米纤维薄膜与稀土配合物粉末的光学性质,我们发现当稀土配合物被掺杂到PAN纤维中后,PAN介质对其赋予了一定的保护作用。由于聚合物链段的刚性结构和受到所谓笼效应的影响,掺杂到PAN介质中的稀土配合物分子彼此之间相互孤立,不仅减少了聚集体的形成,而且避免了有机配体分子的转动和与周围介质的作用,从而降低了非辐射去活化的过程,最终改善了稀土配合物的热稳定性,光稳定性,延长了其荧光寿命和提高了其荧光量子产率。综上所述,通过研究染料分子和稀土配合物引入前后光学性能的改善,证实了静电纺丝薄膜是一个引入荧光化合物的理想基质。
6.通过对静电纺丝纤维进行乙二胺改性和利用曼尼希反应成功地将荧光素共价键连接到PAN纳米纤维薄膜表面。经荧光光谱检测获得了较强的荧光信号,避免了由于物理掺杂而发生的泄露现象,充分证明了静电纺丝薄膜表面修饰的可行性,为构筑含有性能优异传感分子的纺丝薄膜传感器奠定了基础。
Fluorescent and colorimetric chemosensors have been developed to be useful tools for sensing heavy metal ions. Fluorescent chemosensors are attractive due to the simplicity and high detection limit. The advantage of colorimetric sensors is their capability to detect analyte by the naked eye. Among numerous indicators, rhodamine-based dyes are a kind of excellent candidate for the construction of an off/on-type fluorescent chemosensor due to their excellent spectroscopic properties of large molar extinction coefficients, high fluorescence quantum yields, and long absorption and emission wavelength elongated to visible region. Compared to traditional organic dyes and fluorescent proteins, semiconductor nanocrystals, often referred to quantum dots (QDs), have several intriguing advantages such as great water-solubility, large extinction coefficients, high photoluminescence efficiency, tunable size-dependent emission, wide absorption spectrum and sharp emission profile.
In this thesis, a series of new optical chemosensors based on rhodamine and quantum dots were synthesized and investigated for their applications in the detection of heavy metal cations (Hg~(2+), Cu~(2+)). In addition, rhodamine 6G and europium complexes are incorporated into polymer matrixes and electrospun into various composite nanofibers.The details are as follows:
1. Novel rhodamine-based highly sensitive and selective colorimetric and off-on fluorescent chemosensors (RO1 and RS1) for heavy metal ions is designed and prepared. The photophysical characterization and Hg~(2+)/Cu~(2+)-binding properties of sensor RS1/RO1 are investigated and compared. The sensor RS1 show more excellent sensing ability for Hg~(2+) due to the incorporation of the S atom. The signal change of the chemosensor RS1 is based on a specific metal ion induced reversible ring-opening mechanism of the rhodamine spirolactam. The response of the chemise nsor RS1 for Hg~(2+) ions is instantaneous and reversible. Moreover, this sensor is applied for in vivo imaging in Rat Schwann cells to confirm that RS1 can be used as a fluorescent probe for monitoring Hg~(2+) in living cells with satisfying results, which further demonstrates its value of practical applications in environmental and biological systems.
2. A rhodamine-based highly sensitive and selective chemodosimeter is designed and prepared. The system, which utilizes an irreversible Hg~(2+)-promoted oxadiazole forming reaction of rhodamine derivative RO2, is monitored by colorimetric and fluorescence intensity changes that respond instantaneously at room temperature. In addition, the C=C is also incorporated into the rhodamine derivative. Next. the polymer through this C=C will be synthesized and electrospun into nanofibers with sensing ability.
3. Novel multifunctional Hg~(2+) ions sensing nanocomposites were developed by applying SiO2 as the encapsulation agent to package Fe_2O_3 NRs and CdTe QDs. resulting in CdTe/Fe_2O_3@SiO2 core/shell nanostructures. The core/shell structural nanocomposites were confirmed by extensive characterizations. Photoluminescence (PL) spectroscopy and superconducting quantum interference device (SQUID) were used to investigate the optical and magnetic properties of the core/shell structural nanocomposites, respectively. The fluorescence of the obtained nanocomposites could be quenched effectively by Hg~(2+)ions. The quenching mechanism was studied and the results show the existence of both static and dynamic quenching processes.
4. A novel multifunctional microsphere with a fluorescent CdTe quantum dots (QDs) shell and a magnetic core (Fe3O4) has been successfully developed and prepared by a combination of the hydrothermal method and layer-by-layer (LBL) self-assembly technique. The resulting fluorescent Fe3O4@C@CdTe core/shell microspheres are utilized as a chemosensor for ultrasensitive Cu~(2+)ions detection. The fluorescence of the obtained chemosensor could be quenched effectively by Cu~(2+)ions. The quenching mechanism was studied and the results showed the existence of both static and dynamic quenching processes. The modified Stern-Volmer equation showed a good linear response (R2=0.9957) in the range of 1 to 10μM with a quenching constant (Ksv) of 4.9×104 M-1. Most importantly, magnetic measurements showed that the Fe3O4@C@CdTe core/shell microspheres were superparamagnetic and they could be separated and collected easily using a commercial magnet in 10s。
5. Novel fluorescent composite nanofibrous films of rhodamine 6G/PAN and europium complexes/PAN are prepared by electrospinning. The optical properties of electruspun nanofibrous films are studied. For the rhodamine 6G/PAN fluorescent composite nanofibrous films, we have used casting films as reference material to compare the aggregation states of incorporation of Rh6G in electrospun nanofibrous films and casting films. The large specific surface area of the nanofibers and fast evaporation of the solvents in the electrospinning process reduced the aggregation of Rh6G. For the europium complexes/PAN fluorescent composite nanofibrous films, the thermal-stability, photo-stability and photoluminescence properties of these composite nanofibers are studied in comparison to that of the pure europium complexes in detail. The results indicate that, the PAN can provide a rigid environment for the europium complexes, so the thermal-stability and photo- stability of composite nanofibers are considerably improved. Most importantly, the luminescent quantum efficiency and luminescence lifetime of the composite nanofibers are of great improvement. The results demonstrate that the electrospun films are an ideal material for incorporation of fluorescent dyes and europium complexes.
6. The Mannich reaction was successfully used in modification of the electrospun films surfaces. Further modification of electrospun films with fluorescent molecules presents the possibility of practical sensing applications of the electrospun films.
引文
[1]何立芳,林丹丽,李耀群。同步荧光分析法的应用及其新进展化学进展,2004,16,879-885.
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