【摘要】：基于偶氮苯的光刺激響應(yīng)性材料是材料領(lǐng)域的研究熱點(diǎn)。本文合成了系列含酯類的偶氮苯化合物,并對(duì)其結(jié)構(gòu)進(jìn)行了表征,研究了它們的電致變色性能和光響應(yīng)性能。具體研究內(nèi)容如下：第一章對(duì)變色材料的種類、作用進(jìn)行概述,介紹了幾種不同的變色材料與實(shí)際生活的關(guān)系,總結(jié)了電致變色材料的研究進(jìn)展和在生活中的應(yīng)用,簡述了電致變色器件的結(jié)構(gòu)和制備方法。對(duì)電致變色材料的分類進(jìn)行了概述。含有酯類的有機(jī)物的電致變色材料的研究現(xiàn)狀進(jìn)行了綜述,最后提出本文的研究目的和意義。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為原料,通過還原偶聯(lián)、酯化反應(yīng)合成了六種4,4’-兩個(gè)酯基官能團(tuán)的偶氮苯類化合物ADDEDs,通過1H NMR、13C NMR、LC-MS等確認(rèn)了它們的結(jié)構(gòu)。研究了化合物ADDEDs的電致變色性能,結(jié)果表明,該類化合物有較快的響應(yīng)時(shí)間和良好的循環(huán)穩(wěn)定性；討論了不同取代基結(jié)構(gòu)對(duì)電致變色性能的影響；考察了ADDEDs分別在DMF溶液中和電致變色條件下的光致異構(gòu)化現(xiàn)象。結(jié)果表明,化合物ADDEDs具有良好的電致變色性能和光響應(yīng)性能。第三章以3-硝基苯甲酸、4-甲氧基苯甲醇、4-三氟甲基等為原料,通過還原偶聯(lián)、酯化反應(yīng)合成了六種3,3'-兩個(gè)酯基官能團(tuán)的偶氮苯類化合物ADADEs,通過1H NMR、13C NMR、LC-MS等表征了它們的結(jié)構(gòu)。研究了六種化合物ADADEs的電致變色性能,討論了不同取代基對(duì)電致變色性能的影響,與第二章中的化合物ADDEDs的電致變色性能進(jìn)行了比較,結(jié)果表明,化合物ADDEDs的電致變色性能更優(yōu),可能的原因是,發(fā)生氧化還原形成陰離子自由基時(shí),化合物ADDEDs具有更高的電荷密度；研究了六種化合物ADADEs在DMF中和電致變色條件下的光致異構(gòu)化現(xiàn)象,結(jié)果表明,化合物ADADEs在兩種條件下都具有良好的光響應(yīng)性能。第四章以3,5-二硝基苯甲酸、4-甲氧基苯甲醇、4-三氟甲基等為原料,通過還原偶聯(lián)、酯化反應(yīng)合成了六種3,3’,5,5’-四個(gè)酯基官能團(tuán)的偶氮苯類化合物ATFAEDs,通過1H NMR、13C NMR、LC-MS等表征了它們的結(jié)構(gòu)。研究了化合物ATFAEDs的電致變色性能,討論了不同取代基對(duì)電致變色性能的影響,分別與化合物ADDEDs和ADADEs的電致變色性能進(jìn)行了比較,結(jié)果表明,化合物ADDEDs的電致變色性能最優(yōu),其次是化合物ATFAEDs,化合物ADADEs較差；研究了六種ATFAEDs在DMF中和電致變色條件下的光致異構(gòu)化現(xiàn)象,結(jié)果表明,化合物ATAFAEDs在兩種條件下都具有良好的光響應(yīng)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為原料,通過重氮化、偶聯(lián)、酯化反應(yīng)合成了四種4,4'-酯基和毗啶鹽的化合物EAZOPs,通過1H NMR、13C NMR、LC-MS等表征了它們的結(jié)構(gòu)。研究了四種不同取代基的EAZOPs的電致變色性能,討論了不同取代基對(duì)電致變色性能的影響,分別與合成的化合物ADDEDs、ADADEs和ATFAEDs的電致變色性能進(jìn)行了比較,結(jié)果表明,化合物EAZOPs的電致變色性能并沒有很大提高。第六章以4-氨基吡啶、溴化芐、雙草酸基硼酸鋰、六氟磷酸銨等為原料,通過氧化偶聯(lián)和陰離子交換反應(yīng)合成了四種含有不同陰離子的偶氮吡啶鹽化合物AZOPs,通過'H NMR、13C NMR、LC-MS等表征了它的結(jié)構(gòu)。研究了四種不同陰離子的AZOPs的電致變色性能,討論了不同的陰離子取代基對(duì)電致變色性能的影響,結(jié)果表明,當(dāng)化合物中含有不同的陰離子時(shí),化合物AZOPs具有不同的電致變色性能：與化合物EAZOPs相比,穩(wěn)定性有明顯的提高。第七章總結(jié)了全文內(nèi)容,并對(duì)該研究方向在未來的發(fā)展進(jìn)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.
【學(xué)位授予單位】：西南大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2015
【分類號(hào)】：O621;TB34

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本文編號(hào)：2324363