9,10-二苯乙烯基蒽衍生物的合成及其压致、热致变色性能研究

发布时间：2018-03-31 22:11

本文选题：聚集诱导发光　切入点：压致变色　出处：《天津大学》2015年硕士论文

【摘要】：自聚集诱导发光(AIE)现象发现以来,具有AIE性质的有机发光材料在高科技领域的应用前景日益凸显。最近的研究结果表明已报道的AIE有机化合物大多数具有明显的敏感变色性能,极大促进了它们在信息存储、化学传感等领域的发展与应用。9,10-二苯乙烯基蒽类衍生物因其扭曲的骨架结构常被报道具有AIE效应及敏感变色性能,已成为有机敏感变色材料的研究热点。为此,本文合成了一系列烷氧基取代的9,10-二苯乙烯基蒽类衍生物,探究其AIE效应、压致变色及热致变色性能,并深入探讨结构与发光性质之间的关系,主要内容和成果如下:(1)设计合成了分别在苯环邻位和对位丁氧基(包括正丁氧基,异丁氧基,叔丁氧基)取代的9,10-二苯乙烯基蒽类小分子(DSA4),并成功培养了其中DSA-pn4,DSA-pt4,DSA-oi4三个化合物的单晶。通过荧光发射光谱等测试,发现5个DSA4化合物均具有明显的AIE性能,其中DSA-pt4,DSA-on4,DSA-oi4受压后发生由黄绿色到黄色显著的荧光颜色变化,表明其具有显著的压致变色新性能。通过DSC、广角X射线衍射和单晶X-射线衍射的表征,研究了DSA4光学性质与晶体结构之间的关系,提出了DSA4压致变色机理,揭示了烷基的异构化能有效得调控DSA4的聚集模式,从而对其光学性质以及压致变色性能产生影响,为设计新型PAIE材料提供了新思路。(2)设计合成了一系列苯环对位直链烷基(包括正丁基,正辛基,正十六烷基)取代的9,10-二苯乙烯基蒽类小分子(DSA-pnn,n=4,8,16),成功培养了它们的单晶。通过荧光发射光谱等测试,3个DSA-pnn化合物均表现出明显的AIE现象和良好的热致变色性能,是一类极具应用前景的热致变色材料。通过DSC、广角X射线衍射和单晶X-射线衍射测试,我们探讨了其光学性质与晶体结构之间的关系,提出了DSA-pnn热致变色机理并解释了外缘烷基链长对其光学性质及其热致变色性能的影响,为以后的相关研究提供了参考。
[Abstract]:Since the discovery of agglomeration induced luminescence (AIEI) phenomenon, the applications of organic luminescent materials with AIE properties have become increasingly prominent in high-tech fields. Recent research results show that most of the reported organic compounds of AIE have obvious sensitive discoloration properties. It has greatly promoted their development and application in the fields of information storage, chemical sensing and so on. The derivatives of diphenylvinyl anthracene have been reported to have AIE effect and sensitive discoloration due to their distorted skeleton structure. In this paper, a series of alkoxy substituted 9 ~ (10) -diphenyl vinyl anthracene derivatives were synthesized, and their AIE effect, pressure-chromic and thermochromic properties were investigated. The relationship between structure and luminescent properties is discussed. The main contents and results are as follows: 1) Design and synthesis of p-butanoxy (including n-butanoxy, isobutoxy) in benzene ring. The monocrystalline of DSA-pn4- DSA-pt4- DSA-oi4 was successfully cultured. The results of fluorescence emission spectra showed that all of the five DSA4 compounds had obvious AIE properties. Among them, DSA-pt4N4 DSA-oi4 shows a significant change of fluorescence color from yellowish green to yellow after compression, which indicates that DSA-pt4 has a new characteristic of pressure-induced chromotropic. It is characterized by DSC-wide angle X-ray diffraction and single crystal X-ray diffraction. The relationship between the optical properties and crystal structure of DSA4 was studied, and the mechanism of DSA4 pressure-chromism was proposed. It was revealed that the aggregation mode of DSA4 could be effectively regulated by the isomerization of alkyl, which had an effect on the optical properties and the photochromic properties of DSA4. A series of p-position alkyl groups of benzene ring (including normal Ding Ji, n-octyl) were designed and synthesized for the design of novel PAIE materials. The monocrystalline of DSA-pnnnnnnnnnnnnnnion (DSA-pnnnnnnnion) substituted by n-hexadecyl) was successfully grown. The results of fluorescence emission spectra showed that all of the three DSA-pnn compounds showed obvious AIE phenomenon and good thermochromic properties. It is a kind of thermochromic materials with great application prospect. By means of DSC, wide-angle X-ray diffraction and single crystal X-ray diffraction, we have discussed the relationship between their optical properties and crystal structure. The thermochromic mechanism of DSA-pnn and the effect of alkyl chain length on its optical properties and thermochromic properties are proposed.
【学位授予单位】：天津大学
【学位级别】：硕士
【学位授予年份】：2015
【分类号】：TB34

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