苯并-1,3-唑类杂环荧光化合物的合成与荧光探针性能研究

发布时间：2019-04-09 08:27

【摘要】：近年来，电位敏感性探针化合物是研究较为广泛的荧光化合物，该类化合物在生物膜电位检测方面具有非常重要的意义。该类化合物因具有反应时间短、水溶性好、摩尔吸收系数大、可避开背景干扰及检测灵敏度高等优点而受到了人们的广泛关注，也逐渐成为人们的研究焦点之一。该类化合物因具有与菁类化合物类似的特殊的大π共轭体系，可使其具有良好的荧光性能。本文以2-甲基苯并噻唑、原甲酸三乙酯和3-羧甲基罗丹宁为原料，设计合成了一系列电位敏感性探针化合物及其衍生物，并对合成的化合物进行了核磁共振氢谱、红外光谱、质谱等结构表征。根据该类化合物的结构特点，我们发现其不仅具有良好的水溶性，而且具有能与金属离子配位的特殊结构。因此，该类化合物具有通过配位作用来检测金属离子的可能性。鉴于此推断，论文测定了该系列化合物的紫外光谱和荧光光谱性质，以及通过测定甲醇溶液或者水溶液中14种金属离子：Al3+，Ca2+，Cd2+，Co2+，Cu2+，Fe3+，Hg2+，K+，Mg2+，Mn2+，Na+，Sn2+，Sn4+，Zn2+对目标化合物荧光强度的影响，发现Sn2+对化合物C、D、G和H有很好的荧光淬灭作用。这四种化合物的发射波长均在570nm左右，可以有效的避开生物自荧光干扰，提高信噪比；水溶性好，降低该系列化合物在水中的自聚集程度，从而使其在水溶液中有较好的荧光强度。因此，该系列化合物可作为Sn2+的荧光探针传感器开展进一步的研究。由于3-羧甲基罗丹宁的引入对以上化合物的水溶性有一定的提高作用，因此，在本实验室前期研究的基础上，，以2-（2’-羟基苯基）苯并咪唑为基本结构，合成了一系列溶解性好、荧光强度大、激发波长红移的新型化合物。并测定了该系列化合物与上述14种金属离子作用后的荧光变化，发现化合物I对Co2+有一定的选择性，而化合物J则Fe3+对有较强的选择性，它们可作为相应离子的荧光探针传感器开展进一步的探究。
[Abstract]:In recent years, potential-sensitive probe compounds are widely studied as fluorescent compounds. These compounds are of great significance in biomembrane potential detection. Because of their short reaction time, good water solubility, large molar absorption coefficient, avoiding background interference and high detection sensitivity, these compounds have been paid more and more attention and become one of the focus of research. These compounds have good fluorescence properties due to their special large 蟺 conjugate systems similar to those of cyanine compounds. A series of potential sensitive probe compounds and their derivatives were designed and synthesized by using 2-methylbenzothiazole, triethyl orthoformate and 3-carboxymethyl rhodanine as raw materials. The structure was characterized by IR, MS and so on. According to the structural characteristics of these compounds, we found that they not only have good water solubility, but also have a special structure which can coordinate with metal ions. Therefore, these compounds have the possibility to detect metal ions by coordination. In view of this conclusion, the UV and fluorescence spectra of these compounds were determined, and 14 kinds of metal ions in methanol solution or aqueous solution were determined: Al3, Ca2, Cd2, Co2, Cu2, Fe3, Hg2, K, Mg2, Mn2, Na, Sn2. The effects of Sn4 and Zn2 on the fluorescence intensity of the target compounds were studied. It was found that Sn2 had a good fluorescence quenching effect on compounds C, D, G and H. The emission wavelengths of these four compounds are all about 570nm, which can effectively avoid the interference of biological self-fluorescence and improve the signal-to-noise ratio (SNR). Water solubility is good, and the degree of self-aggregation of these compounds in water is reduced, so that they have better fluorescence intensity in aqueous solution. Therefore, these compounds can be used as fluorescent probe sensors of Sn2 for further research. Since the introduction of 3-carboxymethyl rhodanin can improve the water solubility of the above compounds to a certain extent, on the basis of previous studies in our laboratory, 2-(2-hydroxyphenyl) benzimidazole was used as the basic structure. A series of novel compounds with good solubility, high fluorescence intensity and red shift of excitation wavelength were synthesized. The fluorescence changes of these compounds with the above 14 metal ions have been determined. It is found that compound I has a certain selectivity to Co2, while compound J has a strong selectivity to Fe3. They can be used as fluorescence probe sensors of corresponding ions for further exploration.
【学位授予单位】：天津理工大学
【学位级别】：硕士
【学位授予年份】：2014
【分类号】：R914.5

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