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摘要：罗丹明类荧光探针具有优异的光物理和光化学性能，如光稳定性好、摩尔消光系数高、激发波长和发射波长较长以及荧光量子产率高等优点，成为应用最为广泛的一类荧光探针。本课题根据罗丹明的“OFF-ON”机理，以罗丹明B和不同的取代芳酯为原料，经肼解，酰化反应，合成了两种新型罗丹明衍生物，经过1H NHR结构鉴定，与目标化合物结构一致。以终产物RH1为例，利用单因素优化法对合成工艺进行优化，得到了较佳的工艺条件：反应物摩尔比为3：5，反应温度为80℃，反应时间为8h。此研究结果可为含1,3,4-噁二唑的罗丹明类衍生物的进一步研发提供有价值的理论依据。35178
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毕业论文关键词：罗丹明、1,3,4-噁二唑、荧光探针、合成
Synthesis of Rhodamine-based Fluorescent Probes Containing 1,3,4-oxadiazole
Abstract: Rhodamine-based fluorescent probes have excellent photophysical and photochemical properties such as high stability against light and chemical reactions, high molar extinction coefficient，long absorption and emission wavelength，and high fluorescence quantum yields, etc. Therefore, they have become one of the most widely applied fluorescent probes. According to rhodamine's "OFF-ON" mechanism, two novel rhodamine derivatives were synthesized by using rhodamine B and different substituted aromatic esters as raw materials via hydrazinolysis and acylation reaction. The products were characterized structurally by 1H NMR and the results showed that their structures were accord with the target compounds. By selecting the synthesis of final product RH1 as the model reaction, we used single factor optimization method to optimize the synthesis process, and got the optimum conditions for the process are as follows: the molar ratio of reactants is 3:5, the reaction temperature is 80℃, the reaction time is 8h. The research may provides valuable theoretical basis for the further development of rhodamine-based fluorescent probes containing 1,3,4-oxadiazole.
Keywords: rhodamine, 1,3,4-oxadiazole, fluorescent probe, synthesis
目录
1.绪论 1
1.1引言 1
1.2 荧光探针简介 1
1.2.1 荧光产生的原理 1
1.2.2 荧光探针的概述 2
1.2.3 荧光探针的研究应用 3
1.3 罗丹明类荧光探针简介 3
1.3.1 罗丹明类荧光探针的概述 3
1.3.2 罗丹明荧光探针的合成及应用 5
1.4 1,3,4-噁二唑衍生物 10
1.4.1 1,3,4-噁二唑衍生物的合成方法 11
1.4.2 1,3,4-噁二唑衍生物的研究进展 12
1.5 研究目的和意义 14
1.5.1 研究意义 14
1.5.2 研究方案 14
2.实验部分 15
2.1 实验试剂与药品 15
2.2 仪器装置 16
2.2.1反应装置 16
2.2.2过滤装置 16
2.2.3检测装置 16
2.2.4附属设备 16
2.3 化合物的合成反应 16
2.3.1苯甲酰肼的合成 16
2.3.2.对甲基苯甲酰肼的合成 17
2.3.3 2-苯基-5-巯基-1,3,4-噁二唑的合成 17
2.3.4 2-对甲苯基-5-巯基-1,3,4-噁二唑的合成 17
2.3.5罗丹明B-酰肼的合成 18
2.3.6 RB的合成 18
2.3.7目标产物RH1的合成 18
2.3.8目标产物RH2的合成 19
3. 实验结果及优化 19
3.1 RB的合成优化 19
3.1.1反应物摩尔比的优化 19