论文总字数：18032字

摘 要

有机光致变色材料在光信息存储、光滤波器、防伪、光致变色涂层等领域均具有广泛的应用前景。尤其是在光信息存贮领域的应用研究，成为目前科学家研究的焦点。有机光致变色材料被公认是最有应用前景的功能材料。目前应用十分广泛，如军事领域上光信息存储材料、光致变色伪装材料、强闪光防护、宇宙线的防护、辐射计量计等方面；民用品如光致变色涂料、光致变色纺织品、光致变色镀膜玻璃或夹层玻璃方面、墙体涂料、建筑物标示等都离不开变色材料。

本文以1,10-邻菲啰啉为原料，在强酸氧化剂的作用下首先合成1,10-菲啰啉-5,6-二酮，进行第二步反应1,10-菲啰啉-5,6-二酮与盐酸羟胺反应生成5-亚硝基-6-羟基-1,10-菲啰啉的中间体，再进行第三部反应将5-亚硝基-6-羟基-1,10-菲啰啉与1,3,3-三甲基-2-亚甲基吲哚林通过缩合反应得到螺噁嗪化合物，即1,3,3-三甲基-螺[吲哚-菲啰啉并噁嗪]。通过核磁共振的方法对目标产物进行验证，可得目标产物与预期结构相符。

通过紫外光谱的方法对目标化合物进行光致变色性能测试研究，螺噁嗪类化合物的紫外吸收光谱的最大吸收波长随溶剂极性的增大而增大，出现红移；在螺噁嗪吲哚林环上引入供电子基团后，其开环体最大吸收波长红移；在螺噁嗪吲哚林环引入吸电子基团后，其开环体最大吸收波长蓝移。

螺噁嗪化合物是一种非常重要的化合物，具有较高的化学稳定性、光敏性和抗光疲劳性，在光信息记录、非银盐成像、非线性光电子器件、光过滤器、防伪印刷、装饰等领域中应用有很多价值。

关键词：光致变色 螺噁嗪 合成

photochromic compounds synthesis and performance research

Abstract

Organic photochromic materials in optical information storage, optical filter, anti-counterfeiting, photochromic coating, and other fields have broad application prospects.Especially in the application research in the field of optical information storage, become the focus of current research scientists.Organic photochromic materials are known to be the most application prospect of functional materials.They are widely used at present, such as military field glazing information storage materials, photochromic camouflage materials, strong flash protection, cosmic ray radiation protection, measurement meter etc. ^[1];Civilian products such as photochromic paint, photochromic textiles, photochromic coated glass or laminated glass, wall coatings, such as building marked cannot leave the color material.

Based on 1, 10 - phenanthroline as raw material, under the action of strong oxidant, first the synthesis of 1, 10 - phenanthroline 5, 6 - diketone, for the second step reaction 1, 10 - phenanthroline 5 or 6 - diketone and hydroxylamine hydrochloride reaction of 5 - nitroso - 6 - hydroxy - 1, 10 - phenanthroline intermediates, and then to the third reaction will be 5 - nitroso - 6 - hydroxy - 1, 10 phenanthroline and 1 filling - trimethyl - 2 - methylene indole forest screw oxazine compound is obtained by condensation reaction, namely 1 filling - trimethyl - screw [indole - Philippines then Lin and oxazine].Validation of target product by using the method of nuclear magnetic resonance (NMR), can get the target product is consistent with the expected structure.

Of target compounds by using the method of ultraviolet spectrum photochromic performance test research, screw oxazine compounds the maximum absorption wavelength of ultraviolet absorption spectrum increases with increase of polarity of the solvent, a red shift;The screw oxazine indole Lin Huan for electronics group, is introduced in its maximum absorption wavelength redshift open loop body;The screw oxazine indole Lin Huan electron-withdrawing groups are introduced to the poor maximum absorption wavelength of the blue shift.

Screw oxazine compounds is a very important and has high chemical stability, photosensitivity and light fatigue resistance, in silver halide imaging, nonlinear optical information recording, optoelectronic devices, optical filters, anti-counterfeiting printing, decoration and other fields of application there are a lot of value.

Keywords:photochromic;Screw oxazine;synthesis

目录

摘要 I

Abstract II

第一章　文献综述 1

1.1 引言 1

1.2 有机光致变色化合物的概述 1

1.2.1 光致变色的定义 1

1.3 有机光致变色材料的种类 2

1.3.1 螺吡喃光致变色体系 2

1.3.2 六苯基双咪唑光致变色体系 3

1.3.3 水杨醛缩苯胺类希夫碱 3

1.3.4 偶氮苯类化合物 4

1.3.5 萘并吡喃类化合物 4

1.3.6 二芳基乙烯类化合物 4

1.3.7 俘精酸酐光致变色体系 5

1.4 光致变色材料的应用前景 5

1.5 本文的研究目的和意义 6

第二章 螺噁嗪类化合物的合成与表征 7

2.1 前言 7

2.2 螺噁嗪光致变色机理 7

2.3 螺噁嗪的合成路线 8

2.4 1,10-菲啰啉-5,6-二酮的合成 8

2.4.1 仪器 8

2.4.2 试剂 8

2.4.3 实验过程 9

2.4.4 结果与讨论 9

2.5 5-亚硝基-6-羟基-1,10-菲啰啉的合成 11

2.5.1 仪器 11

2.5.2 试剂 12

2.5.3 实验过程 12

2.5.4 结果与讨论 12

2.6 1,3,3-三甲基-螺[吲哚-菲啰啉并噁嗪]的合成 13

2.6.1 仪器 13

2.6.2 试剂 13

2.6.3 实验过程 13

2.6.4 结果与讨论 14

第三章 螺噁嗪光致变色性能研究 15

3.1 螺噁嗪化合物溶剂化效应 15

第四章　结论与展望 16

4.1 结论 16

4.2 展望 16

参考文献 17

附图 19

致谢 20

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