本文選題：合成 + 扭曲�。� 參考：《河北大學(xué)》2017年碩士論文

【摘要】：多并苯分子是一類線型芳香環(huán)類碳?xì)浠衔?目前并苯分子作為關(guān)鍵功能層在有機(jī)電子學(xué)中已經(jīng)被廣泛研究,主要包括有機(jī)發(fā)光二極管,有機(jī)太陽(yáng)能電池,有機(jī)場(chǎng)效應(yīng)晶體管,非線性光學(xué)器件等。然而,這類分子穩(wěn)定性較差,對(duì)光、氧氣非常敏感,易發(fā)生分子間聚合,因此在本部分將雜原子摻雜到并苯分子主體骨架之中形成雜并苯分子,不但能夠提高穩(wěn)定性和抗氧化性,還能實(shí)現(xiàn)分子的n-型材料到p-型材料的自由切換。為此,我們將氧原子摻雜到并苯類分子主體骨架之中,得到系列雜并苯分子,測(cè)試了分子光、電、熱學(xué)性能,并將所得分子作為功能層制備了有機(jī)電子器件,測(cè)試其相關(guān)性能。研究?jī)?nèi)容主要分為以下幾個(gè)部分:(1)本文通過(guò)親核取代反應(yīng)合成了以芘為末端的十二環(huán)扭曲并苯分子DPyN和以菲為末端的功能化的十并苯扭曲分子CTNA、NTNA,并通過(guò)1H NMR、13C NMR和MALDI-TOF證明分子結(jié)構(gòu)正確。分子DPyN在有機(jī)溶劑中發(fā)出紅色熒光,具有良好的熱穩(wěn)定性,以DPyN作為功能層制備的存儲(chǔ)器件顯示出良好的存儲(chǔ)性能。CTNA和NTNA顯示出較好的熱穩(wěn)定性。(2)通過(guò)二氯吡嗪,二氯喹喔啉分別與鄰二芳酚衍生物偶聯(lián)合成了氧雜并苯分子ADOP、ADOQ,通過(guò)1H NMR、13C NMR和MALDI-TOF確定了分子結(jié)構(gòu)。X-單晶衍射分析得到,其在固體狀態(tài)下的分子結(jié)構(gòu)與空間排列,ADOP是扭曲拓?fù)浣Y(jié)構(gòu),ADOQ表現(xiàn)出躺椅式構(gòu)型。所得分子在有機(jī)溶劑中發(fā)出藍(lán)色熒光,具有良好的熱穩(wěn)定性,TGA顯示ADOP和ADOQ失重5%的分解溫度分別為444oC和446oC。通過(guò)再沉淀法,ADOP和ADOQ分別組裝形成納米帶和納米線。(3)應(yīng)用經(jīng)典的有機(jī)化學(xué)反應(yīng)合成了十三環(huán)雜并苯分子12,通過(guò)1H NMR、13C NMR和MALDI-TOF確定了分子結(jié)構(gòu),其是供體-受體-供體型雙極材料分子,可以作為良好的有機(jī)半導(dǎo)體材料。此分子顯示良好的熱穩(wěn)定性能;具有寬吸收帶,集中在565/613 nm處;固體狀態(tài)下是墨綠色固體,發(fā)出紅色熒光。(4)設(shè)計(jì)合成了十一環(huán)并苯分子29,通過(guò)1H NMR和MALDI-TOF確定了分子結(jié)構(gòu),其是供體-受體-供體型雙極材料分子,應(yīng)用紫外可見光譜和熱重分析對(duì)化合物進(jìn)行了光學(xué)和熱學(xué)性能的測(cè)定,其可以作為良好的有機(jī)半導(dǎo)體材料。
[Abstract]:Polybenzenes are a kind of linear aromatic ring hydrocarbons. At present, benzenes, as key functional layers, have been widely studied in organic electronics, including organic light-emitting diodes, organic solar cells, and airfield effect transistors. Nonlinear optical devices, etc. However, these molecules have poor stability, are sensitive to light and oxygen, and are prone to intermolecular polymerization. Therefore, in this part, hetero atoms are doped into the framework of benzenes molecules to form heterobenzene molecules. It can not only improve the stability and oxidation resistance, but also realize the free switching from n-type material to p-type material. Therefore, a series of heterobenzene molecules were obtained by doping oxygen atoms into the host skeleton of benzenes. The molecular optical, electrical and thermal properties were tested. The organic electronic devices were prepared by using the resulting molecules as functional layers and their related properties were tested. The main contents of this study are as follows: (1) in this paper, we synthesized DPyN with pyrene end and CTNAN NTNAA with phenanthrene terminal by nucleophilic substitution reaction. MALDI-TOF proves that the molecular structure is correct. Molecular DPyN gives off red fluorescence in organic solvents and has good thermal stability. The memory devices prepared with DPyN as the functional layer show good storage performance. CTNA and NTNA show good thermal stability through dichloropyrazine. Dichloroquinoxaline was coupled with o-diarophenol derivatives to form oxa-heterobenzene molecule ADOPOQ. The molecular structure was determined by 1H NMR-13C NMR and MALDI-TOF. The molecular structure and spatial arrangement of ADOP in solid state are twisted topological structure and ADOQ shows a lie chair configuration. The obtained molecules emit blue fluorescence in organic solvents and have good thermal stability. TGA shows that the decomposition temperature of 5% weight loss of ADOP and ADOQ is 444oC and 446oC, respectively. Nanobelts and nanowires were assembled into nanobelts and nanowires by reprecipitation method.) Tridecyclic heterobenzene 12 was synthesized by classical organic chemical reaction. The molecular structure was determined by 1H NMR-13C NMR and MALDI-TOF. It is a donor-acceptor-donor bipolar material molecule and can be used as a good organic semiconductor material. The molecule shows good thermal stability; it has a wide absorption band, concentrated at 565 / 613nm; the solid state is a dark green solid, emitting red fluorescence. (4) an undecyclic benzene-containing molecule 29 was designed and synthesized. The molecular structure was determined by 1H NMR and MALDI-TOF. It is a donor-receptor-donor bipolar material molecule. The optical and thermal properties of the compound have been determined by UV-Vis spectroscopy and thermogravimetric analysis. It can be used as a good organic semiconductor material.
【學(xué)位授予單位】：河北大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2017
【分類號(hào)】：O649.5

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