摘要目前，在阴离子识别领域内,发展一种对阴离子具有高选择性、高灵敏度的人工合成受体是超分子化学研究的热点。1,8-萘酰亚胺荧光团因平面共轭刚性结构、强的推拉体系、强的光稳定性以及较高的量子产率等优良性能，被广泛用于识别受体的荧光团或发色团。本论文基于前期设计的4位吡啶二乙腈1,8-萘酰亚胺受体,期望通过在原受体的5位引入苄氨基，以其稳定潜在的阴离子氢键复合物而观测到较好的光学信号。实验从起始原料苊出发，经溴化、硝化、氧化、酰胺化等4步经典反应,取得重要中间体,即4-溴-5-硝基-1,8-萘酰亚胺。同时完成了苄胺取代硝基反应,制备得到4-溴-5-苄氨基-1,8-萘酰亚胺中间体（2.6g）并对其结构进行了鉴定,为后续合成目标化合物奠定了一定的研究基础。24199
毕业论文关键词:1,8-萘酰亚胺，氟离子,合成，阴离子识别
Abstract
Nowadays，in the anion recognition field, the development of artificial anion receptors of high selectivity as well as high sensitivity have attracted much attention in supramolecular chemistry. The fluorophore/chromophore containing 1,8-naphthalimide was widely used as signal unit of receptors in viewing to its rigid and conjugated system, strongly pull draw system, higher light stability and high quantum yield. Based on the previous reported receptor 4-pyridine acetonitrile 1,8-naphthalimide, in this thesis, benzyl amino group was introduced to the 5-position of 1,8-naphthalimide, which might be helpful for stable potential complex of anion with receptor so as to obtain more distinctive optical output signal. The key intermediate of 4-bromo-5-nitro-1,8-naphthalimide was obtained from the starting material acenaphthene, goes through a series of bromination, nitration, oxidation and amidation. Furthermore, 4-bromo-5-benzylamino-1,8-naphthalimide (2.6g) was obtained by substitution of benzylamino with above-mentioned key intermediate, and the product was confirmed by 1H-NMR analysis, which is helpful for us to synthesis of target compounds in future.
Keywords: 1,8-naphthalimide, fluoride ion, synthesis, anion recognition
目录
1.前言 1
1.1研究背景 1
1.1.1阴离子识别的研究意义 1
1.1.2阴离子受体识别机理 1
1.2光学检测机理 4
1.3反应型氟离子探针 5
1.3.1. F–诱导SI-O，SI-C断裂 5
1.3.2. 氟离子引发分子内氢转移 6
1.3.3. 氟离子引发CHCN基氧化脱氰基反应 6
2.文献综述与方案论证 9
2.1 文献综述 9
2.1.1 4-溴-5-硝基萘酰亚胺 9
2.1.2结构特性和荧光性能 10
2.2实验机理 10
2.2.1. NBS溴化反应 10
2.2.2. 硝化反应 11
2.2.3. 酰胺化反应 12
2.2.4. 取代反应 12
2.2方案论证 13
2.2.1实验方案确定 13
2.2.2实验路线 13
3.实验材料 14
3.1主要仪器 14
3.2主要试剂 15
4.实验部分 16
4.1 5-溴苊的合成 16
4.1.1实验步骤 16
4.2 5-溴-6-硝基苊的合成 17
4.2.1实验步骤 17
4.3 K4的合成 17
4.3.1实验步骤 17
4.4 P1的合成 18
4.4.1实验步骤 18
4.5目标物的合成 19
4.5.1实验步骤 19
5.结果和讨论 21
5.1分析方法 21 4-溴-5-苄胺基-1,8-萘酰亚胺衍生物的合成研究:http://www.751com.cn/yixue/lunwen_17593.html