论文总字数：22592字

摘 要

有机光致变色材料在光滤波器、光信息存储、光致变色涂层、防伪等领域均具有广泛的应用前景。有机光致变色材料主要包括螺吡喃类、螺噁嗪类、二芳基乙烯类、偶氮苯类、萘并吡喃类以及俘精酸酐类等。其中二芳基乙烯类光致变色材料因具有良好的热稳定性，抗疲劳性，及响应时间短等优点，而成为有机光致变色材料研究的热点；而双光能团光致变色材料因为具有两个光致变色单元，当两个光致变色单元属于不同类型时即可在不同波长的光下产生多个稳定态，其应用前景更为广泛。

在本文中，首先以碘苯、苯乙炔、N-碘代丁二酰亚胺（NIS）、2-甲基-噻吩等为原料合成了两种中间体化合物2a，2b；其次将对苯二甲醛、间苯二甲醛和中间体化合物2a、2b发生羰氨缩合成环反应，得到目标化合物3a，3b，3c，3d；再次对合成的中间体和目标化合物均经过熔点(Mp)、核磁共振氢谱(HNMR)表征，与预期结构相符；然后研究目标化合物3a-3c乙腈溶液的紫外可见吸收光谱(UV)，分别在358 nm，357 nm，310 nm处有最大吸收峰，3c较3b有明显蓝移；最后探讨了了3d的光响应性能和溶剂化效应，发现3d的乙腈溶液随着紫外照射时间的增加，紫外吸收峰有明显变化，可见光区出现新的吸收峰，溶液颜色由无色变为粉红色；研究了3d在不同极性溶剂中的紫外和荧光光谱，结果表明随溶剂极性增大，紫外和荧光光谱都有一定程度蓝移，说明化合物3d有负溶剂化效应，意味着该化合物的激发态极性比基态的低。

关键字：光致变色 二芳基乙烯 双官能团

ABSTRACT

Organic photochromic materials have broad application prospects in optical information storage, optical filter, anti-counterfeiting, photochromic coating, and other fields. Organic photochromic materials mainly include spiropyrane, spirooxazine, diarylethene, azobenzol, naphthopyran, fulgide, etc. Among them, the diarylethene type photochromic materials have been a research hotspot in the study of organic photochromic materials, owing to their good thermal stability, fatigue resistance, and the short response time, etc. Having two different types of photochromic unit of dual energy group photochromic compounds can produce multiple steady states at different wavelengths of light, and their application prospect can be more widely.

In this paper，firstly, two intermediate compounds 2a and 2b were synthesized as iodobenzene， phenylacetylene， N- iodosuccinimide (NIS)， 2- methyl – thiophene and others raw materials. Secondly, as terephthalaldehyde and isophthalaldehyde raw materials with 2a and 2b occurrenced carbonyl amino condensed ring reaction, target compounds 3a， 3b， 3c， 3d were synthesized. Thirdly, synthesized intermediates and target compounds were characterized by melting point (Mp), nuclear magnetic resonance hydrogen spectrum (HNMR) characterization, and they are consistent with the expected structure. Then the acetonitrile solution of target compounds 3a-3c were tested with uv-visible absorption spectrum (UV), respectively showing that in 358 nm, 357 nm and 310 nm has maximum absorption peak. The 3c has obvious blue shift compare with 3b. Finally the light response performance and solvation effects of the 3d were discussed, finding that, the acetonitrile solution of 3d ultraviolet absorption peaks have obvious changed with the increase of ultraviolet rradiation time, a new absorption peak appears in visible light region, and the solution is colorless color into pink. The uv and fluorescence spectrum of 3d in different polar solvent study shows that the uv and fluorescence spectrum both have a blue shift with the increasing of solvent polarity. So we found that compound of 3d has a negative effect of the solvent, what it means that the polarity of the excited state is lower than that of the ground state.

KEYWORDS：photochromic, diarylethene, bifunctional

目录

摘要 I

ABSTRACT II

目录 I

第一章 文献综述 1

1.1 引言 1

1.2 光致变色材料应用 1

1.2.1纺织印染方面 1

1.2.2 在建筑材料方面 2

1.2.3光信息处理方面 4

1.3 二芳基乙烯类双光能团光致变色材料 5

1.4 结语 7

第二章 中间体化合物的合成 8

2.1 中间体化合物苯偶酰（2a）的合成 8

2.1.1 实验药品 8

2.1.2 仪器设备 8

2.1.3 实验步骤 9

2.2 中间体化合物1, 2- 双-（2-氯-5-甲基-噻吩-3- 基）乙二酮（2b）的合成 9

2.2.1 实验药品 10

2.2.1 仪器设备 10

2.2.3 实验步骤 10

2.3 小结 11

第三章 目标化合物的合成 12

3.1 目标化合物4- (4, 5- 二苯- 1氢- 咪唑- 2- 基)苯甲醛(3a)的合成 12

3.1.1 实验药品 12

3.1.2 仪器设备 12

3.1.3 实验步骤 13

3.2 化合物1, 4- 双(4, 5- 二苯- 1氢- 咪唑- 2- 基)苯(3b)的合成 13

3.2.1 实验药品 14

3.2.2 仪器设备 14

3.2.3 实验步骤 14

3.3 化合物1, 3- 双(4, 5- 二苯- 1氢- 咪唑- 2- 基)苯(3c)的合成 14

3.3.1 实验药品 15

3.3.2 仪器设备 15

3.3.3 实验步骤 15

3.4化合物2- (4- (4, 5- 双( 5- 氯- 2- 甲基- 噻吩- 3- 基)- 1氢- 咪唑- 2- 基) 苯) -4, 5- 二苯- 1氢- 咪唑(3d)的合成 16

3.4.1 实验药品 16

3.4.2 仪器设备 16

3.4.3 实验步骤 16

3.5 小结 17

第四章 性能研究 19

4.1前言 19

4.2实验部分 19

4.2.1主要试剂与设备 19

4.2.2实验步骤 19

4.2.3结果与讨论 20

4.2 小结 22

第五章 结论与展望 23

5.1 结论 23

5.2 展望 23

参考文献 24

附录 26

致谢 30

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