含2-苯基1,2,3-三唑骨架衍生物的合成及荧光性质的研究

发布时间：2018-04-09 23:44

本文选题：荧光探针　切入点：CN-　出处：《新疆大学》2017年硕士论文

【摘要】：课题组在前期的研究中发现含2-苯基-1,2,3三唑骨架的化合物有很好的光学性质,本论文通过官能团修饰,制得新型的含2-苯基-1,2,3-三唑骨架的有机小分子,并对所合成化合物的光学性质进行初步的研究,研究内容如下:1.利用Suzuki反应,2-对溴苯基-2H-1,2,3三唑-4-甲醛分别与1-萘硼酸、(4-(二苯基氨基)苯基)硼酸、9-蒽硼酸、(9-苯基-9H-咔唑-3-基)硼酸和芴硼酸反应,得到化合物Q1,Q2,M2,Q4,Q5。然后Q1和M2与丙二腈通过knoevenagel缩合反应得到化合物M1,M3,并对所合成的化合物用~1H NMR,~(13)C NMR和TOF-MS,X射线衍射进行了表征。2.设计合成的M1荧光探针,通过紫外可见光谱和荧光光谱发现M1有分子内电荷转移(ICT)和聚集态荧光增强特性(AIEE)。研究发现M1提供了一种新的检测CN-的方法,M1对CN-有很好的选择性和高灵敏度,检出限为3.91×10~(-8) M。并通过1H NMR滴定实验和HR-MS来研究M1和CN-作用机理。3.研究发现探针M2具有聚集态荧光增强(AIEE)的特性。M2在纯CH_3CN有较弱的荧光,但是在M2体系中加入水,并当水的比例大于70%时,M2荧光强度有明显的增强。当fw=99%时,荧光强度达到最大数值,其荧光强度是纯CH_3CN溶液里荧光强度的48.5倍。当fw=99%时,M2的荧光量子产率为7.22%。经进一步的研究发现,M2对高半胱氨酸(Hcy)表现出了良好的选择性。对Hcy检出限为3.262×10-6 M,并通过HR-MS来研究M2和Hcy之间的作用机理。4.针对M3的荧光性能研究中,发现M3可作为一种检测H2S的荧光比色化学传感器。当H2S加入到M3的CH_3CN/H2O(v/v=6:4)溶液中,可使M3溶液颜色由黄色变为无色,而其他离子没有颜色变化,用裸眼便可识别H2S。M3对H_2S有识别专一性,检出限为2.6×10~(-7) M。
[Abstract]:In our previous studies, we found that the compounds containing 2-phenyl-1-triazole skeleton have very good optical properties. In this paper, a novel organic small molecule containing 2-phenyl -1H _ 2N _ 2O _ 3-triazole skeleton was prepared by modification of functional groups.The optical properties of the synthesized compounds are studied as follows: 1. 1.The compound Q1Q _ 2H _ 2H _ 2N _ 4Q _ (5) was synthesized by the Suzuki reaction of 2-bromophenyl-2H-1-triazole-3-triazole-4-formaldehyde with 1-naphthylborate 4-( diphenylamino) phenyl) borate 9-phenyl-9H-carbazole-3-yl) boric acid and fluorene boric acid, respectively.The compound M _ 1N _ 3 was obtained by knoevenagel condensation of Q1 and M2 with malonitrile. The synthesized compounds were characterized by ~ (13) C NMR and TOF-MS ~ (2) X-ray diffraction.The M1 fluorescence probe was designed and synthesized. It was found by UV-Vis and fluorescence spectra that M1 had intramolecular charge transfer (ICTI) and agglomerated fluorescence enhancement characteristics.It is found that M1 provides a new method for the detection of CN- with a high sensitivity and selectivity to CN-, and the detection limit is 3.91 脳 10 ~ (-1) -8) M.The mechanism of M1 and CN-interaction was studied by 1H NMR titration and HR-MS.It is found that the probe M2 has the characteristic of aggregated fluorescence enhancement. M2 has weak fluorescence in pure CH_3CN, but water is added to M2 system, and the fluorescence intensity of M2 increases obviously when the ratio of water is more than 70.When fw = 99, the fluorescence intensity reaches the maximum value, and the fluorescence intensity is 48.5 times higher than that in pure CH_3CN solution.The fluorescence quantum yield of M 2 is 7.22 when fw = 99.After further study, it was found that M 2 showed a good selectivity to Hcyine.The detection limit of Hcy is 3.262 脳 10 ~ (-6) M, and the interaction mechanism between M2 and Hcy is studied by HR-MS.It is found that M _ 3 can be used as a fluorescence colorimetric chemical sensor for detecting H _ 2S.
【学位授予单位】：新疆大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626.26;O657.3

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