摘要：在自然界和生物体内，阴离子广泛存在，并且在许多生物和化学过程中，都扮演着重要的作用。但同时，阴离子的过量存在，不仅会对环境造成污染，而且也会对生命体造成危害。CN—是阴离子中对环境、人体健康存在巨大的潜在威胁的一种，一旦CN—进入人体，对人有着致命的危险。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。识别CN—的荧光探针的设计机理主要分为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，利用CN—对不饱和双键的加成反应，设计了含硝基取代的邻醛基苯炔共轭延伸的萘酰亚胺荧光探针（3a及3b）。通过N-丁基-4-溴-3-硝基-1，8-萘酰亚胺（1a）及N-丁基-4-溴-5-硝基-1，8-萘酰亚胺（1b）与邻炔基苯甲醛(2)发生Sonogashira偶联反应合成了目标分子（3a及3b），其结构通过1H NMR表征。进一步，通过紫外光谱及荧光光谱实验，分别探讨了目标分子（3a及3b）对CN—的光谱滴定、选择性及竞争实验。57603

毕业论文关键词：  阴离子识别；荧光探针；CN—；不饱和双键

Nitro naphthalimide anion receptors synthesis control

Abstract:Anion exists widely in nature and organism, play a 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— enter 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.The issue on the basis of the existing literature on the use of CN— addition reaction of an unsaturated double bond, designed nitro-containing ortho-substituted phenyl propargyl aldehyde conjugated extending naphthalimide fluorescent probe (3a and 3b ). By N- buty-l,4-bromo-3-nitro-1,8-naphthalimide (1a) and N- buty-l,4-bromo-5-nitro-1,8-naphthalimide (1b) with o-yn-benzaldehyde (2) occurs Sonogashira coupling reaction of the target molecule (3a and 3b), its structure by 1H NMR characterization. Further, by UV spectroscopy and fluorescence spectroscopy experiments were discussed target molecule (3a and 3b) of CN— spectral titration, selectivity and competition experiments.

Key Words :  Anion Sensor; Fluorescent Probe; CN—; Unsaturated Double Bond

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 1

2文献综述与方案论证 3

  2.1  文献综述 3

    2.1.1  基于C-C形成的CN识别探针 3

    2.1.2  基于质子转移作用的探针 6

    2.1.3  基于C-B键形成的反应 6

    2.1.4  基于电子转移的反应 7

  2.2  方案论证 9

3合成部分 11

  3.1  试剂及仪器 11

    3.1.1  试剂