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摘要:阴离子在自然界和生物体内广泛存在，在许多生物和化学过程中都起着基础而重要的作用。但是阴离子的过量存在又会对环境造成污染、对生命体造成危害。CN对环境、人体健康存在巨大的潜在威胁，CN一旦进入人体，对人有致命的危险。目前对CN识别检测的方法中，荧光探针因其识别快速、灵敏度高、选择性好而被广泛研究。探针与CN的识别作用机理主要分为C-C键的形成、质子转移、C-B键的形成、电子转移等。本课题在已有文献的基础上，设计了基于C-C键形成的荧光探针。该荧光探针以1,8-萘酰亚胺为荧光发色团，以苯乙炔为连接体，以醛基为结合CN的接受体。因所设计化合物的分子内的电子排布以及结构特性，在与CN作用后，其光谱数据会发生显著变化，进而达到识别检测CN的目的。31493
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毕业论文关键词： 阴离子识别；氢键；萘酐；苯炔；荧光探针
Naphthalimide fluorescent receptors based o-n remote control of hydrogen bond: Design, synthesis and anion recognition
Abstract: Anion exists widely in nature and organism, which play an important role in many biological and chemical processes. However, the excess anions can pollute the environment and do harm to the living organisms. CN, one of the anions, is a huge potential threat to the environment and human health. Once CN enters the human body, it can be fatal for human life. Among the current recognition and detection method of CN, the fluorescent probe has been extensively studied because of its advantages of fast recognition, high sensitivity and high selectivity. Recognition mechanism of the probe to CN are mainly pided into the formation of C-C bond, the transformation of the proton, the formation of C-B bond, the transformation of the electron and so on. Based on the previous document, we design a fluorescent probe, which is based on the formation of C-C bond by remote control of intramolecular hydrogen bond. The fluorescent probe based on 1,8-naphthalimide derivatives, using the benzene acetylene as the connector, and aldehyde group as a binding site to recognize CN. According to the configuration of the electron and the structural characteristics of the molecular compounds, after the probe binding with CN, its spectrum data has remarkable changes, and be achieved to the purpose of identifying and detecting CN.
Key Words: Anion Recognition; Fluorescent Probe; CN; Hydrogen Bonds
目录
1前言 1
1.1课题来源及背景、研究目的 1
1.2理论意义和实际应用价值 2
2文献综述与方案论证 4
2.1文献综述 4
2.1.1基于C-C形成的CN-识别探针 4
2.1.2基于质子转移作用的探针 7
2.1.3基于C-B键形成的反应 7
2.1.4基于电子转移的反应 9
2.2方案论证 9
3实验部分 11
3.1试剂及仪器 11
3.1.1试剂 11
3.1.2仪器 12
3.2实验方法 12
3.2.16-溴-2-丁基-1H-苯并〔脱〕异喹啉-1,3（2H）-二酮的合成 12
3.2.2N-正丁基-3-硝基-4-溴-1,8-萘酰亚胺的合成 13
3.2.3N-正丁基-3-氨基-4-溴-1,8-萘酰亚胺的合成 14
3.2.4 N-丁基-4-溴 - 3-乙酰基-1,8-萘二甲酰亚胺的合成 15
3.2.52-（（三甲基甲硅烷基）乙炔基）苯甲醛的合成 15
3.2.62-乙炔基苯甲醛的合成 16
3.2.7 N-（2-丁基-6 -（（2-甲酰基苯基）乙炔基）-1,3-二氧代-2,3-二氢-1H-苯并〔脱〕异喹啉-5-基）乙酰胺的合成 17
3.3探针分子9的阴离子识别性能研究 19