摘要：阴离子在生物体和自然界中都普遍存在，在生物过程和化学反应中起到重要的作用，但是某些阴离子的存在也会对环境和生命安全存在着威胁，氰根离子就对环境和人类的生命存在着潜在的威胁。氰根离子一旦进入人体，便会抑制细胞呼吸，对人体造成危害。近几年来，寻找能够有效识别氰根离子的探针逐渐成为超分子化学领域的一个研究热点。因为荧光探针具有灵敏度高，识别快速，选择性好等特点，所以发展识别氰根离子的荧光探针便成为化学领域重要的研究部分。72178

氰根离子的荧光探针识别作用机理主要为分子内氢键、C-B键的形成、C-C键的形成、质子转移、电子转移等。本课题在已有文献的基础上，通过吡啶-2-乙腈和4-溴-3-硝基-1,8-萘酰亚胺发生取代反应，进而经氯化亚锡还原硝基的同时发生分子内氢重排反应，设计并合成了一种新颖的含分子内NH…NH2氢键的萘酰亚胺荧光探针，所得中间体及目标产物经过NMR及HRMS谱图进行鉴定。

毕业论文关键词：氰根离子；荧光探针；分子内氢键；萘酰亚胺；重排反应

Design and Synthesis of 1,8-Naphthalimide Receptor Based on intramolecular NH。。。NH2 Hydrogen Bonding

Abstract: Cyanide ions are widely present in nature and industrial production and play an important role in many biological and chemical processes。 But cyanide ions are a huge threat to the environment and human health。 Once the cyanide ions into the human body, it will inhibit cell respiration, causing harm to the human body。 In recent years, it has become a research interest in the field of supramolecular chemistry to develop a fluorescent probe that can effectively recognize cyanide ions。 Because fluorescent probes have the characteristics of high sensitivity, fast identification and good selectivity, so the development of fluorescent probes for sensing of cyanide ions has become an important research field in recent years。

The mechanism of fluorescence probe for sensing of cyanide ion is mainly C-B bond formation, C-C bond formation, proton transfer, electron transfer and so on。 In this paper, the substitution reaction of pyridine-2-acetonitrile and 4-bromo-3-nitro-1,8-naphthalimide was performed based on the previous work, and followed by reduction of nitro group to afford a novel naphthalimide derivative, which was designed and synthesized as novel fluorescent probe containing NH…NH2 hydrogen bonds。 The corresponding intermediates and the target products were identified by NMR and HRMS spectra。

Key words: Cyanide ion; Fluorescent probe; intramolecular hydrogen bond; Naphthalimide; Rearrangement reaction

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 4

  2。1  文献综述 4

  2。1。1 识别氰根离子的方法 4

  2。1。2 氢键的类型 7

  2。1。3 关于1,8-萘酰亚胺的研究 7

  2。1。4 化学反应机理 10

  2。2  方案论证 10

3合成部分 12

  3。1  试剂及仪器 12

  3。1。1  试剂 12

  3。1。2  仪器