【摘要】：近年來，電位敏感性探針化合物是研究較為廣泛的熒光化合物，該類化合物在生物膜電位檢測方面具有非常重要的意義。該類化合物因具有反應(yīng)時間短、水溶性好、摩爾吸收系數(shù)大、可避開背景干擾及檢測靈敏度高等優(yōu)點(diǎn)而受到了人們的廣泛關(guān)注，也逐漸成為人們的研究焦點(diǎn)之一。該類化合物因具有與菁類化合物類似的特殊的大π共軛體系，可使其具有良好的熒光性能。 本文以2-甲基苯并噻唑、原甲酸三乙酯和3-羧甲基羅丹寧為原料，設(shè)計(jì)合成了一系列電位敏感性探針化合物及其衍生物，并對合成的化合物進(jìn)行了核磁共振氫譜、紅外光譜、質(zhì)譜等結(jié)構(gòu)表征。 根據(jù)該類化合物的結(jié)構(gòu)特點(diǎn)，我們發(fā)現(xiàn)其不僅具有良好的水溶性，而且具有能與金屬離子配位的特殊結(jié)構(gòu)。因此，該類化合物具有通過配位作用來檢測金屬離子的可能性。鑒于此推斷，論文測定了該系列化合物的紫外光譜和熒光光譜性質(zhì)，以及通過測定甲醇溶液或者水溶液中14種金屬離子：Al3+，Ca2+，Cd2+，Co2+，Cu2+，F(xiàn)e3+，Hg2+，K+，Mg2+，Mn2+，Na+，Sn2+，Sn4+，Zn2+對目標(biāo)化合物熒光強(qiáng)度的影響，發(fā)現(xiàn)Sn2+對化合物C、D、G和H有很好的熒光淬滅作用。這四種化合物的發(fā)射波長均在570nm左右，可以有效的避開生物自熒光干擾，提高信噪比；水溶性好，降低該系列化合物在水中的自聚集程度，從而使其在水溶液中有較好的熒光強(qiáng)度。因此，該系列化合物可作為Sn2+的熒光探針傳感器開展進(jìn)一步的研究。 由于3-羧甲基羅丹寧的引入對以上化合物的水溶性有一定的提高作用，因此，在本實(shí)驗(yàn)室前期研究的基礎(chǔ)上，，以2-（2’-羥基苯基）苯并咪唑?yàn)榛窘Y(jié)構(gòu)，合成了一系列溶解性好、熒光強(qiáng)度大、激發(fā)波長紅移的新型化合物。并測定了該系列化合物與上述14種金屬離子作用后的熒光變化，發(fā)現(xiàn)化合物I對Co2+有一定的選擇性，而化合物J則Fe3+對有較強(qiáng)的選擇性，它們可作為相應(yīng)離子的熒光探針傳感器開展進(jìn)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.
【學(xué)位授予單位】：天津理工大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2014
【分類號】：R914.5

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