基于偶氮苯的酯类化合物的合成及其光电性能研究
发布时间：2018-11-11 08:51
【摘要】：基于偶氮苯的光刺激响应性材料是材料领域的研究热点。本文合成了系列含酯类的偶氮苯化合物,并对其结构进行了表征,研究了它们的电致变色性能和光响应性能。具体研究内容如下：第一章对变色材料的种类、作用进行概述,介绍了几种不同的变色材料与实际生活的关系,总结了电致变色材料的研究进展和在生活中的应用,简述了电致变色器件的结构和制备方法。对电致变色材料的分类进行了概述。含有酯类的有机物的电致变色材料的研究现状进行了综述,最后提出本文的研究目的和意义。第二章以4-硝基苯甲酸、4-甲氧基苯甲醇、4-三氟甲基苯甲醇等为原料,通过还原偶联、酯化反应合成了六种4,4’-两个酯基官能团的偶氮苯类化合物ADDEDs,通过1H NMR、13C NMR、LC-MS等确认了它们的结构。研究了化合物ADDEDs的电致变色性能,结果表明,该类化合物有较快的响应时间和良好的循环稳定性；讨论了不同取代基结构对电致变色性能的影响；考察了ADDEDs分别在DMF溶液中和电致变色条件下的光致异构化现象。结果表明,化合物ADDEDs具有良好的电致变色性能和光响应性能。第三章以3-硝基苯甲酸、4-甲氧基苯甲醇、4-三氟甲基等为原料,通过还原偶联、酯化反应合成了六种3,3'-两个酯基官能团的偶氮苯类化合物ADADEs,通过1H NMR、13C NMR、LC-MS等表征了它们的结构。研究了六种化合物ADADEs的电致变色性能,讨论了不同取代基对电致变色性能的影响,与第二章中的化合物ADDEDs的电致变色性能进行了比较,结果表明,化合物ADDEDs的电致变色性能更优,可能的原因是,发生氧化还原形成阴离子自由基时,化合物ADDEDs具有更高的电荷密度；研究了六种化合物ADADEs在DMF中和电致变色条件下的光致异构化现象,结果表明,化合物ADADEs在两种条件下都具有良好的光响应性能。第四章以3,5-二硝基苯甲酸、4-甲氧基苯甲醇、4-三氟甲基等为原料,通过还原偶联、酯化反应合成了六种3,3’,5,5’-四个酯基官能团的偶氮苯类化合物ATFAEDs,通过1H NMR、13C NMR、LC-MS等表征了它们的结构。研究了化合物ATFAEDs的电致变色性能,讨论了不同取代基对电致变色性能的影响,分别与化合物ADDEDs和ADADEs的电致变色性能进行了比较,结果表明,化合物ADDEDs的电致变色性能最优,其次是化合物ATFAEDs,化合物ADADEs较差；研究了六种ATFAEDs在DMF中和电致变色条件下的光致异构化现象,结果表明,化合物ATAFAEDs在两种条件下都具有良好的光响应性能。第五章以4-氨基吡啶、苯酚、甲基丙烯酸、4-三氟甲基苯甲酸等为原料,通过重氮化、偶联、酯化反应合成了四种4,4'-酯基和毗啶盐的化合物EAZOPs,通过1H NMR、13C NMR、LC-MS等表征了它们的结构。研究了四种不同取代基的EAZOPs的电致变色性能,讨论了不同取代基对电致变色性能的影响,分别与合成的化合物ADDEDs、ADADEs和ATFAEDs的电致变色性能进行了比较,结果表明,化合物EAZOPs的电致变色性能并没有很大提高。第六章以4-氨基吡啶、溴化苄、双草酸基硼酸锂、六氟磷酸铵等为原料,通过氧化偶联和阴离子交换反应合成了四种含有不同阴离子的偶氮吡啶盐化合物AZOPs,通过'H NMR、13C NMR、LC-MS等表征了它的结构。研究了四种不同阴离子的AZOPs的电致变色性能,讨论了不同的阴离子取代基对电致变色性能的影响,结果表明,当化合物中含有不同的阴离子时,化合物AZOPs具有不同的电致变色性能：与化合物EAZOPs相比,稳定性有明显的提高。第七章总结了全文内容,并对该研究方向在未来的发展进行了展望。
[Abstract]:The photostimulation responsive material based on azobenzene is a hot spot in the field of materials. In this paper, a series of ester-containing azobenzene compounds were synthesized and their structure was characterized, and their electrochromic properties and optical response properties were studied. The specific research contents are as follows: The first chapter gives an overview of the type and function of the color-changing material, introduces the relationship between the different color-changing materials and the real life, summarizes the research progress of the electro-chromic material and the application in life, and briefly describes the structure and the preparation method of the electro-chromic device. The classification of electrochromism materials is summarized. The research status of electro-chromic materials of organic compounds containing esters is reviewed, and the purpose and significance of this paper are put forward. The second chapter uses 4-nitrobenzoic acid, 4-methoxybenzyl alcohol, 4-trifluoromethylbenzyl alcohol and the like as raw materials, The structure was confirmed by 1H NMR, 13C NMR, LC-MS and so on. The electrochromism of the compound ADDEDs is studied. The results show that the compound has fast response time and good cycle stability, and the effect of different substituent structures on the electrochromism performance is discussed. The photo-induced isomerization of ADDEDs in DMF solution and electrochromism was investigated. The results showed that the compound ADDEDs had good electrochromism and optical response. The third chapter uses 3-nitrobenzoic acid, 4-methoxybenzyl alcohol, 4-trifluoromethyl and the like as raw materials, and the six kinds of 3, 3 'are synthesized by reductive coupling and esterification reaction. The structures of the azobenzene compound ADADEs of the two ester-based functional groups were characterized by 1H NMR, 13C NMR, LC-MS, and the like. The electrochromic properties of the ADADEs in the six compounds were studied. The effect of different substituents on the electrochromic properties of ADDEDs was discussed, and the electrochromic properties of the compound ADDEDs in the second chapter were compared. The results showed that the electrochromism of the compound ADDEDs was better and the possible cause was, The compound ADDEDs have higher charge density when the oxidation-reduction forms the anionic free radical. The photo-induced isomerization of the ADADEs in DMF and electrochromism is studied. The results show that the compound ADADEs has good optical response under both conditions. The fourth chapter uses 3,5-dinitrobenzoic acid, 4-methoxybenzyl alcohol, 4-trifluoromethyl and the like as raw materials, and the six kinds of 3, 3', 5, 5 are synthesized by reductive coupling and esterification reaction. The structure of the azobenzene compound ATFAEDs of '-four ester group functional groups is characterized by 1H NMR, 13C NMR, LC-MS and the like. The electrochromic properties of the compound ATFAEDs were studied. The effects of different substituents on the electrochromic properties of the compounds were discussed. The electrochromic properties of the compounds ADDEDs and ADADEs were compared. The results showed that the electrochromic properties of the compound ADDEDs were the best, followed by the low compound ATFAEDs and the ADEs of the compound. The photoinduced isomerization of six ATFAEDs in DMF and electrochromism is studied. The results show that the compound ATAFAEDs has good optical response under both conditions. In the fifth chapter, four kinds of 4, 4' were synthesized by diazotization, coupling and esterification with 4-aminophenylbenzene, phenol, methacrylic acid, 4-trifluoromethylbenzoic acid and the like as raw materials. The structure of the compound EAZOPs of the ester group and the salt-based salt was characterized by 1H NMR, 13C NMR, LC-MS, and the like. The electrochromic properties of EAZOPs with four different substituents were studied. The effects of different substituents on the electrochromism were discussed, and the electrochromic properties of the synthesized compounds ADDEDs, ADADEs and ATFAEDs were compared. The results showed that the electrochromism of the compound EAZOPs was not greatly improved. In the sixth chapter, four kinds of AZOPs with different anions were synthesized by oxidative coupling and anion exchange reaction using 4-aminophenylbenzene, bromitization, dioxalate, lithium hexafluorophosphate and the like as raw materials. The structure was characterized by 'H NMR, 13C NMR, LC-MS, etc. The effects of different anion substituents on the electrochromism of AZOPs with different anions were studied. The results show that the compound AZOPs has different electrochromic properties when different anions are contained in the compound: compared with the compound EAZOPs, and the stability is obviously improved. Chapter 7 summarizes the content of the whole text, and looks forward to the future development of the research direction.
【学位授予单位】：西南大学
【学位级别】：硕士
【学位授予年份】：2015
【分类号】：O621;TB34
本文编号：2324363
[Abstract]:The photostimulation responsive material based on azobenzene is a hot spot in the field of materials. In this paper, a series of ester-containing azobenzene compounds were synthesized and their structure was characterized, and their electrochromic properties and optical response properties were studied. The specific research contents are as follows: The first chapter gives an overview of the type and function of the color-changing material, introduces the relationship between the different color-changing materials and the real life, summarizes the research progress of the electro-chromic material and the application in life, and briefly describes the structure and the preparation method of the electro-chromic device. The classification of electrochromism materials is summarized. The research status of electro-chromic materials of organic compounds containing esters is reviewed, and the purpose and significance of this paper are put forward. The second chapter uses 4-nitrobenzoic acid, 4-methoxybenzyl alcohol, 4-trifluoromethylbenzyl alcohol and the like as raw materials, The structure was confirmed by 1H NMR, 13C NMR, LC-MS and so on. The electrochromism of the compound ADDEDs is studied. The results show that the compound has fast response time and good cycle stability, and the effect of different substituent structures on the electrochromism performance is discussed. The photo-induced isomerization of ADDEDs in DMF solution and electrochromism was investigated. The results showed that the compound ADDEDs had good electrochromism and optical response. The third chapter uses 3-nitrobenzoic acid, 4-methoxybenzyl alcohol, 4-trifluoromethyl and the like as raw materials, and the six kinds of 3, 3 'are synthesized by reductive coupling and esterification reaction. The structures of the azobenzene compound ADADEs of the two ester-based functional groups were characterized by 1H NMR, 13C NMR, LC-MS, and the like. The electrochromic properties of the ADADEs in the six compounds were studied. The effect of different substituents on the electrochromic properties of ADDEDs was discussed, and the electrochromic properties of the compound ADDEDs in the second chapter were compared. The results showed that the electrochromism of the compound ADDEDs was better and the possible cause was, The compound ADDEDs have higher charge density when the oxidation-reduction forms the anionic free radical. The photo-induced isomerization of the ADADEs in DMF and electrochromism is studied. The results show that the compound ADADEs has good optical response under both conditions. The fourth chapter uses 3,5-dinitrobenzoic acid, 4-methoxybenzyl alcohol, 4-trifluoromethyl and the like as raw materials, and the six kinds of 3, 3', 5, 5 are synthesized by reductive coupling and esterification reaction. The structure of the azobenzene compound ATFAEDs of '-four ester group functional groups is characterized by 1H NMR, 13C NMR, LC-MS and the like. The electrochromic properties of the compound ATFAEDs were studied. The effects of different substituents on the electrochromic properties of the compounds were discussed. The electrochromic properties of the compounds ADDEDs and ADADEs were compared. The results showed that the electrochromic properties of the compound ADDEDs were the best, followed by the low compound ATFAEDs and the ADEs of the compound. The photoinduced isomerization of six ATFAEDs in DMF and electrochromism is studied. The results show that the compound ATAFAEDs has good optical response under both conditions. In the fifth chapter, four kinds of 4, 4' were synthesized by diazotization, coupling and esterification with 4-aminophenylbenzene, phenol, methacrylic acid, 4-trifluoromethylbenzoic acid and the like as raw materials. The structure of the compound EAZOPs of the ester group and the salt-based salt was characterized by 1H NMR, 13C NMR, LC-MS, and the like. The electrochromic properties of EAZOPs with four different substituents were studied. The effects of different substituents on the electrochromism were discussed, and the electrochromic properties of the synthesized compounds ADDEDs, ADADEs and ATFAEDs were compared. The results showed that the electrochromism of the compound EAZOPs was not greatly improved. In the sixth chapter, four kinds of AZOPs with different anions were synthesized by oxidative coupling and anion exchange reaction using 4-aminophenylbenzene, bromitization, dioxalate, lithium hexafluorophosphate and the like as raw materials. The structure was characterized by 'H NMR, 13C NMR, LC-MS, etc. The effects of different anion substituents on the electrochromism of AZOPs with different anions were studied. The results show that the compound AZOPs has different electrochromic properties when different anions are contained in the compound: compared with the compound EAZOPs, and the stability is obviously improved. Chapter 7 summarizes the content of the whole text, and looks forward to the future development of the research direction.
【学位授予单位】：西南大学
【学位级别】：硕士
【学位授予年份】：2015
【分类号】：O621;TB34
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