罗丹明、荧光素、尼罗红及尼罗兰衍生物的合成及应用
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摘要
本论文分别以罗丹明、荧光素、尼罗红和尼罗兰为母体,从改善罗丹明的荧光量子产率、大斯托克斯位移和引入活性基团方面对其结构进行修饰;从改善荧光素的荧光量子产率对pH值的敏感范围、对光敏感的基团、特异选择性和大斯托克斯位移方面对其结构进行修饰;从改善尼罗红和尼罗兰荧光量子产率和水溶性方面对其结构进行修饰。利用紫外-可见光谱和荧光光谱对这些衍生物进行性能检测,从中筛选出性能优异的荧光探针,并应用在荧光微球的制备、亚硝酸根离子的测定和细菌中聚羟基脂肪酸酯(PHAs)的检测方面。
设计合成了性能优异的烯丙基罗丹明B、烯丙基荧光素、烯丙基尼罗红、不对称罗丹明和吡咯烷基罗丹明S五种荧光探针,并通过分散共聚和吸附的方法制备了五种聚苯乙烯基质的荧光微球。通过环境扫描电子显微镜、激光扫描共聚焦显微镜、荧光分光光度计、傅立叶转换红外光谱仪等仪器对制备的五种荧光微球进行了表征,发现这五种荧光微球具有良好的分散性、高且稳定的荧光强度。研究了这三种共聚荧光微球在四氢呋喃中的光谱性质,发现聚合在微球中的荧光探针具有和自由荧光探针一致的性质。并对这五种荧光微球和相应的荧光探针在乙醇中不同的荧光光谱,作了理论探讨。此外,在共聚荧光微球的表面引入了氨基功能基团,并测定了氨基的含量。
设计合成了不对称结构的罗丹明衍生物,从中筛选出性能优异的荧光探针,它是N端刚化的7-羟基-1,2,3,4-四氢喹啉不对称罗丹明。在酸性介质中,发现它能和亚硝酸根离子进行反应,生成荧光强度低的产物,利用这种荧光淬灭的机理建立了测定亚硝酸根离子的方法。此方法简单,具有良好的重复性、高的灵敏度和选择性。使用此方法来检测水中痕量亚硝酸根离子,得到了满意的结果。
设计合成了两种具有活性基团的酰胺类荧光素衍生物,以期在生物分析方面得到应用。光学性能研究的结果表明,酰胺类荧光素衍生物能提供多种吸收和发射最大值,具有良好的特异选择性和光稳定性,大的斯托克斯位移,并适合在酸性、中性和碱性环境下对生物体进行标记。
设计合成了底环上有氯、溴和羧基的罗丹明衍生物,在此基础上能设计出含有活性基团、复杂结构和适合生物检测的罗丹明衍生物。合成了1-(5-荧光素)-2,4,6-三甲基吡啶鎓高氯酸盐,由于其结构中含有阳离子可与生物体内负电中心通过静电引力结合,有望通过进一步研究其荧光性能而在生物分析中得到应用。
设计合成了含有活性基-羧基、氨基、羟基的尼罗红和尼罗兰衍生物,用来标记生物分子。合成的水溶性尼罗红比文献报道的收率高,尼罗兰衍生物能用作酸碱指示剂来测定细胞中的pH值。此外,水溶性好的双羧基尼罗兰和尼罗红,用来对细菌中的聚羟基脂肪酸酯进行染色,并通过荧光显微镜来鉴定聚羟基脂肪酸酯的胶束,从而建立了简单、快速、高灵敏的染色方法。
Based on rhodamine, fluorescein, nile red and nile blue in this thesis, respectively, rhodamine derivatives were designed and synthesized in order to modificate their fluorescence quantum yield, the large Stokes shift and incorporate reactive groups. Fluorescein derivatives were designed and synthesized in order to modificate pH-sensitive range, light-sensitive group, binding specificity and the large Stokes shift. Nile red and nile blue derivatives were designed and synthesized in order to modificate fluorescence quantum yield and water solubility. Then fluorescence properities of these derivatives were investigated by UV-vis spectra and fluorescence spectra, and the better fluorescent probes were selected and applied in the preparation of fluorescent microspheres,the determination of nitrite in water and the detection of polyhydroxyalkanoates of bacteria.
Allyl rhodamine B, allyl fluorescein, allyl nile red, asymmetrical rhodafluor and pyrrolidinyl rhodamine S were designed and synthesized. And then they were used in the preparation of polystyrene-based fluorescent microspheres by the dispersion copolymerization and absorption method. These fluorescent microspheres were characterized by environmental scanning electron microscopy, laser scanning confocal microscopy, fluorescence spectrophotometry and fourier transform infrared spectrometer. They exhibited good dispersion and stable and high fluorescence intensity. Spectral properties of copolymerization fluorescent microspheres in tetrahydrofuran indicated these individual characteristics of labels should be maintained in the fluorescent microspheres. The differences of the fluorescent spectra between five fluorescent microspheres and their corresponding parent labels in ethanol had been investigated. Furthermore, copolymerization fluorescent microspheres were functionalized with amino groups, and the amount of amino groups was determined.
A series of asymmetrical rhodamine derivatives were prepared and selected the better fluorescent probes. They were N steeled asymmetrical rhodamine containing 7-hydroxy-1,2,3,4-tetrahydroquinoline, which had a high fluorescence quantum yield and large Stokes shift. They can react with nitrite in an acidic medium to form a nitroso product, which had much lower fluorescence. Therefore, the method for trace nitrites was developed, which was simple, sensitive and selective. This method was applied to the determination of nitrite in tap water and lake water with satisfactory results.
Two kinds of xanthamide fluorescein derivatives with active groups were prepared, which can be used in biological analysis. The results of their fluorescent properties showed that they can offer a wide variety of absorption and emission maximums. And they had excellent binding specificity and photostability and large Stokes shift. In addition, they can be employed as a biological fluorescence tag in acidic, neutral and alkaline environments.
Rhodamine derivatives with chlorine, bromine and carboxyl group on the bottom ring were prepared. On this basis, the complicated rhodamine derivatives with reactive group can be designed from them, which would be suitable for biological detection.
1-(Fluorescein-5-yl)-2,4,6-trimethylpyridinium perchlorate with positive charge was prepared, it can combine with biomolecules with negative charge through electrostatic attraction. It would be applied in biological applications by the fluorescence analysis.
Nile red and nile blue derivatives with carboxyl or amino or hydroxyl group were synthesized, which were used to tag biological molecules. The dicarboxylic acid nile red had the better yield than that was reported, nile blue derivatives were found to be clear pH-dependent and could be used as acid-base indicators to measure intracellular pH. In addition, the dicarboxylic acid nile red and nile blue with good solubility in aqueous media were used to develop a simple, quick, safe, highly sensitive staining method to detect polyhydroxyalkanoates of bacteria, which was confirmed by fluorescence images of polyhydroxyalkanoates granules of bacteria.
设计合成了性能优异的烯丙基罗丹明B、烯丙基荧光素、烯丙基尼罗红、不对称罗丹明和吡咯烷基罗丹明S五种荧光探针,并通过分散共聚和吸附的方法制备了五种聚苯乙烯基质的荧光微球。通过环境扫描电子显微镜、激光扫描共聚焦显微镜、荧光分光光度计、傅立叶转换红外光谱仪等仪器对制备的五种荧光微球进行了表征,发现这五种荧光微球具有良好的分散性、高且稳定的荧光强度。研究了这三种共聚荧光微球在四氢呋喃中的光谱性质,发现聚合在微球中的荧光探针具有和自由荧光探针一致的性质。并对这五种荧光微球和相应的荧光探针在乙醇中不同的荧光光谱,作了理论探讨。此外,在共聚荧光微球的表面引入了氨基功能基团,并测定了氨基的含量。
设计合成了不对称结构的罗丹明衍生物,从中筛选出性能优异的荧光探针,它是N端刚化的7-羟基-1,2,3,4-四氢喹啉不对称罗丹明。在酸性介质中,发现它能和亚硝酸根离子进行反应,生成荧光强度低的产物,利用这种荧光淬灭的机理建立了测定亚硝酸根离子的方法。此方法简单,具有良好的重复性、高的灵敏度和选择性。使用此方法来检测水中痕量亚硝酸根离子,得到了满意的结果。
设计合成了两种具有活性基团的酰胺类荧光素衍生物,以期在生物分析方面得到应用。光学性能研究的结果表明,酰胺类荧光素衍生物能提供多种吸收和发射最大值,具有良好的特异选择性和光稳定性,大的斯托克斯位移,并适合在酸性、中性和碱性环境下对生物体进行标记。
设计合成了底环上有氯、溴和羧基的罗丹明衍生物,在此基础上能设计出含有活性基团、复杂结构和适合生物检测的罗丹明衍生物。合成了1-(5-荧光素)-2,4,6-三甲基吡啶鎓高氯酸盐,由于其结构中含有阳离子可与生物体内负电中心通过静电引力结合,有望通过进一步研究其荧光性能而在生物分析中得到应用。
设计合成了含有活性基-羧基、氨基、羟基的尼罗红和尼罗兰衍生物,用来标记生物分子。合成的水溶性尼罗红比文献报道的收率高,尼罗兰衍生物能用作酸碱指示剂来测定细胞中的pH值。此外,水溶性好的双羧基尼罗兰和尼罗红,用来对细菌中的聚羟基脂肪酸酯进行染色,并通过荧光显微镜来鉴定聚羟基脂肪酸酯的胶束,从而建立了简单、快速、高灵敏的染色方法。
Based on rhodamine, fluorescein, nile red and nile blue in this thesis, respectively, rhodamine derivatives were designed and synthesized in order to modificate their fluorescence quantum yield, the large Stokes shift and incorporate reactive groups. Fluorescein derivatives were designed and synthesized in order to modificate pH-sensitive range, light-sensitive group, binding specificity and the large Stokes shift. Nile red and nile blue derivatives were designed and synthesized in order to modificate fluorescence quantum yield and water solubility. Then fluorescence properities of these derivatives were investigated by UV-vis spectra and fluorescence spectra, and the better fluorescent probes were selected and applied in the preparation of fluorescent microspheres,the determination of nitrite in water and the detection of polyhydroxyalkanoates of bacteria.
Allyl rhodamine B, allyl fluorescein, allyl nile red, asymmetrical rhodafluor and pyrrolidinyl rhodamine S were designed and synthesized. And then they were used in the preparation of polystyrene-based fluorescent microspheres by the dispersion copolymerization and absorption method. These fluorescent microspheres were characterized by environmental scanning electron microscopy, laser scanning confocal microscopy, fluorescence spectrophotometry and fourier transform infrared spectrometer. They exhibited good dispersion and stable and high fluorescence intensity. Spectral properties of copolymerization fluorescent microspheres in tetrahydrofuran indicated these individual characteristics of labels should be maintained in the fluorescent microspheres. The differences of the fluorescent spectra between five fluorescent microspheres and their corresponding parent labels in ethanol had been investigated. Furthermore, copolymerization fluorescent microspheres were functionalized with amino groups, and the amount of amino groups was determined.
A series of asymmetrical rhodamine derivatives were prepared and selected the better fluorescent probes. They were N steeled asymmetrical rhodamine containing 7-hydroxy-1,2,3,4-tetrahydroquinoline, which had a high fluorescence quantum yield and large Stokes shift. They can react with nitrite in an acidic medium to form a nitroso product, which had much lower fluorescence. Therefore, the method for trace nitrites was developed, which was simple, sensitive and selective. This method was applied to the determination of nitrite in tap water and lake water with satisfactory results.
Two kinds of xanthamide fluorescein derivatives with active groups were prepared, which can be used in biological analysis. The results of their fluorescent properties showed that they can offer a wide variety of absorption and emission maximums. And they had excellent binding specificity and photostability and large Stokes shift. In addition, they can be employed as a biological fluorescence tag in acidic, neutral and alkaline environments.
Rhodamine derivatives with chlorine, bromine and carboxyl group on the bottom ring were prepared. On this basis, the complicated rhodamine derivatives with reactive group can be designed from them, which would be suitable for biological detection.
1-(Fluorescein-5-yl)-2,4,6-trimethylpyridinium perchlorate with positive charge was prepared, it can combine with biomolecules with negative charge through electrostatic attraction. It would be applied in biological applications by the fluorescence analysis.
Nile red and nile blue derivatives with carboxyl or amino or hydroxyl group were synthesized, which were used to tag biological molecules. The dicarboxylic acid nile red had the better yield than that was reported, nile blue derivatives were found to be clear pH-dependent and could be used as acid-base indicators to measure intracellular pH. In addition, the dicarboxylic acid nile red and nile blue with good solubility in aqueous media were used to develop a simple, quick, safe, highly sensitive staining method to detect polyhydroxyalkanoates of bacteria, which was confirmed by fluorescence images of polyhydroxyalkanoates granules of bacteria.
引文
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