含氮芳香杂环化合物荧光探针的合成及离子识别

发布时间：2018-07-03 00:50

本文选题：荧光探针 + 锌离子　；参考：《渤海大学》2017年硕士论文

【摘要】：分子识别,作为超分子化学方向的重点研究内容,在化学、环境及生命科学等领域具有重要的作用。一些含氮杂环化合物如咪唑并吡啶、苯并咪唑以及8-氨基喹啉等,因为其具有良好的发光性能而被广泛地报道并应用在分子识别工作中。本文以这些化合物为底物设计合成了五种荧光探针,研究了它们的光谱性质以及识别性能,具体的结果如下:1.以咪唑并吡啶类衍生物为荧光主体设计合成一种新型的荧光探针L1,该探针在乙腈/Tris 1:1(9:1,v/v,Tris-HCl 10 m M,pH=7.4)溶液中对Zn2+有选择性识别,其饱和倍数为15倍,受体与Zn2+为1:1结合,检测限为2.7×10-6 M,L1在pH 6-10的区间内对锌离子有较好的识别。2.以苯并咪唑衍生物为主体设计合成了一种氨基酸荧光探针L2。测试体系为HEPES/乙醇(9:1,v/v,HEPES 10 mM,pH=7.4),探针L2识别Hcy和Cys的饱和倍数均为100倍,对Hcy和Cys的检测限分别为9.0×10-6 M和9.1×10-6 M。pH在6-8之间的识别效果较好。密度泛函理论计算结果表明,L2与Cys的产物具有激发态分子内质子转移(ESIPT)性质,与Hcy的产物不具有ESIPT效应。因此,通过调控ESIPT过程,实现了L2对Hcy和Cys的识别。3.以8-氨基喹啉为荧光主体设计并合成了两个席夫碱类荧光探针分子,即L3和L4。在DMSO-HEPES(1:1,v/v,10 m M,pH=7.4)体系中它们对锌离子具有选择性,饱和倍数为15倍,结合比为1:1。L3和L4对Zn2+的检测限分别为9.7×10-5 M和1.6×10-5 M,探针L3,L4对Zn2+具有良好的荧光识别作用。4.以苯并咪唑衍生物为底物设计合成了一种银离子荧光探针L5,探针在HEPES的体系中可识别Ag~(+),饱和倍数为10倍,结合比为1:1,检测限为5×10-6 M,表明探针L5对Ag~(+)具有良好的识别效果。
[Abstract]:Molecular recognition, as the key research content of supramolecular chemical direction, plays an important role in the fields of chemistry, environment and life science. Some nitrogenous heterocyclic compounds, such as imidazole and pyridine, benzimidazole, and 8- amino quinoline, have been widely reported and used in molecular recognition because of their good luminescence properties. In this paper, five fluorescent probes are designed and synthesized with these compounds as substrates. Their spectral properties and recognition properties are studied. The specific results are as follows: 1. a novel fluorescent probe L1 is designed and synthesized using imidazolidic pyridine derivatives as the fluorescent body. The probe is used for Z in acetonitrile / Tris 1:1 (9:1, v/v, Tris-HCl 10 m M, pH=7.4) solution. N2+ has a selective recognition, its saturation multiple is 15 times, the receptor and Zn2+ are combined with 1:1, the detection limit is 2.7 x 10-6 M, and L1 has a better identification of zinc ions in the range of pH 6-10. A benzimidazole derivative is designed and synthesized to synthesize an amino acid fluorescent probe L2. test system for HEPES/ ethanol (9:1, v/v, HEPES 10, 10). The saturation multiple of Hcy and Cys is 100 times, and the detection limits for Hcy and Cys are 9 x 10-6 M and 9.1 x 10-6 M.pH respectively. The density functional theory results show that the products of L2 and Cys have the properties of the excited state intramolecular transfer (ESIPT) and do not have the ESIPT effect with the products of Hcy. Therefore, the ESIPT is regulated by the ESIPT. The process, realized the identification of Hcy and Cys by L2, and designed and synthesized two Schiff base fluorescent probes with 8- amino quinoline as the subject of fluorescence. That is, L3 and L4. have selectivity to zinc ions in DMSO-HEPES (1:1, v/v, 10 m M) system, and the saturation multiple is 15 times, and the detection limit of binding ratio is 9.7 x respectively. 5 M and 1.6 x 10-5 M, probe L3, L4 have good fluorescence recognition to Zn2+,.4. based on benzimidazole derivative as substrate, a silver ion fluorescent probe L5 is designed. The probe can identify Ag~ (+) in HEPES system, the saturation multiplier is 10 times, the binding ratio is 1:1, and the detection limit is 5 * 10-6 M. Fruit.
【学位授予单位】：渤海大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O657.3

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