基于罗丹明B的新型荧光探针的合成及性能研究
发布时间：2018-07-16 18:24
【摘要】：基于罗丹明的‘'OFF-ON"效应,本论文选取罗丹明B为荧光基团,通过与水合肼的取代反应,合成罗丹明B-酰肼作为反应原料,设计并合成出了4种罗丹明B衍生物,利用质谱、核磁对目标化合物的结构进行了确认。通过紫外吸收光谱和荧光光谱研究了不同识别基团的引入对罗丹明B衍生物离子识别性能的影响。主要内容如下：①R1是罗丹明B-酰肼与对溴苯甲醛直接相连,对金属阳离子没有识别能力。但对pH敏感,在酸碱条件下,出现开关环的显色反应,且具有快速、稳定、可逆的识别特点。②R2为直接引入对甲氧基苯甲醛,本身无色,无荧光,在加入Hg2+后荧光强度增加了15倍左右,并且颜色从无色变为紫红色。利用Job-Plot光度滴定法得到络合比为1：1,结合常数为1.43×105L/mol,最低检测限为12.5×10-mol/L,预测其可作为Hg2+荧光探针应用的可能性。③R3以邻苯二胺为识别基团,对Ag+和Cu2+都有一定的选择性,同时伴随着颜色从无色到粉色的变化,故在实际检测应用中两者会存在干扰。在单独对Ag+的识别实验中,所得体系的紫外最大吸光度和荧光发射强度都出现明显增强的现象,荧光强度增加了25倍荭右,得到络合比为1：1,结合常数为4.16×104 L/mol,最低检测限为4.3×10-6mol/L。④R4以2-氨基-5-巯基-1,3,4-噻二唑为识别基团,能对Cu2+专一选择识别,且不受其它离子十扰。作用时体系的的紫外最大吸光度出现明显增强的现象,并能够裸眼识别从无色到桃红色的变化。得到络合比为1：1,结合常数为4.45×1 04L/mol,最低检测限为8.4×10-6mol/L,预测其可作为Cu2+荧光分子探针,应用于环境检测的可能性。
[Abstract]:Based on the Rhodamine OFF-ON effect, four Rhodamine B derivatives were designed and synthesized by the substitution reaction of hydrazine hydrate with Rhodamine B as the fluorescence group. Four Rhodamine B derivatives were designed and synthesized by mass spectrometry. The structure of the target compound was confirmed by NMR. The effects of different recognition groups on the ion recognition properties of Rhodamine B derivatives were studied by UV and fluorescence spectra. The main contents are as follows: 1: 1R1 is a direct link between rhodamine B-hydrazide and p-bromobenzaldehyde and has no ability to recognize metal cations. But sensitive to pH, the color reaction of switch ring appears under the condition of acid and base, and it has fast, stable and reversible recognition characteristic. 2R2 is the direct introduction of p-methoxybenzaldehyde, which is colorless and fluorescence free. After adding Hg 2, the fluorescence intensity increased about 15 times, and the color changed from colorless to purplish red. By means of Job-Plot spectrophotometric titration, the complexation ratio is 1: 1, the binding constant is 1.43 脳 10 ~ (-5) L / mol, and the lowest detection limit is 12.5 脳 10 ~ (-mol / L). The possibility of its application as a fluorescent probe for Hg2 is predicted. At the same time, with the change of color from colorless to pink, there will be interference between them in practical application. In the recognition experiment of Ag alone, the UV maximum absorbance and fluorescence emission intensity of the obtained system were obviously enhanced, and the fluorescence intensity increased by 25 times to the right. The complexation ratio is 1: 1, the binding constant is 4.16 脳 10 ~ 4 L / mol, the lowest detection limit is 4.3 脳 10 ~ (-6) mol / L 路L ~ (4) R _ (4) with 2-amino-5-mercapto-3-thiadiazole as the recognition group, the Cu _ (2) can be specifically selected and recognized without the interference of other ions. The UV maximum absorbance of the system increases obviously and can recognize the change from colorless to peach red by naked eyes. The complexation ratio is 1: 1, the binding constant is 4.45 脳 10 ~ (-4) L / mol, and the lowest detection limit is 8.4 脳 10 ~ (-6) mol / L. It is predicted that it can be used as a fluorescent molecular probe of Cu _ 2 for environmental detection.
【学位授予单位】：上海应用技术大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O657.3
，
本文编号：2127253
[Abstract]:Based on the Rhodamine OFF-ON effect, four Rhodamine B derivatives were designed and synthesized by the substitution reaction of hydrazine hydrate with Rhodamine B as the fluorescence group. Four Rhodamine B derivatives were designed and synthesized by mass spectrometry. The structure of the target compound was confirmed by NMR. The effects of different recognition groups on the ion recognition properties of Rhodamine B derivatives were studied by UV and fluorescence spectra. The main contents are as follows: 1: 1R1 is a direct link between rhodamine B-hydrazide and p-bromobenzaldehyde and has no ability to recognize metal cations. But sensitive to pH, the color reaction of switch ring appears under the condition of acid and base, and it has fast, stable and reversible recognition characteristic. 2R2 is the direct introduction of p-methoxybenzaldehyde, which is colorless and fluorescence free. After adding Hg 2, the fluorescence intensity increased about 15 times, and the color changed from colorless to purplish red. By means of Job-Plot spectrophotometric titration, the complexation ratio is 1: 1, the binding constant is 1.43 脳 10 ~ (-5) L / mol, and the lowest detection limit is 12.5 脳 10 ~ (-mol / L). The possibility of its application as a fluorescent probe for Hg2 is predicted. At the same time, with the change of color from colorless to pink, there will be interference between them in practical application. In the recognition experiment of Ag alone, the UV maximum absorbance and fluorescence emission intensity of the obtained system were obviously enhanced, and the fluorescence intensity increased by 25 times to the right. The complexation ratio is 1: 1, the binding constant is 4.16 脳 10 ~ 4 L / mol, the lowest detection limit is 4.3 脳 10 ~ (-6) mol / L 路L ~ (4) R _ (4) with 2-amino-5-mercapto-3-thiadiazole as the recognition group, the Cu _ (2) can be specifically selected and recognized without the interference of other ions. The UV maximum absorbance of the system increases obviously and can recognize the change from colorless to peach red by naked eyes. The complexation ratio is 1: 1, the binding constant is 4.45 脳 10 ~ (-4) L / mol, and the lowest detection limit is 8.4 脳 10 ~ (-6) mol / L. It is predicted that it can be used as a fluorescent molecular probe of Cu _ 2 for environmental detection.
【学位授予单位】：上海应用技术大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O657.3
，
本文编号：2127253
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