氧杂并苯分子的制备、光电性质及应用

发布时间：2018-05-28 06:33

本文选题：合成 + 扭曲　；参考：《河北大学》2017年硕士论文

【摘要】：多并苯分子是一类线型芳香环类碳氢化合物,目前并苯分子作为关键功能层在有机电子学中已经被广泛研究,主要包括有机发光二极管,有机太阳能电池,有机场效应晶体管,非线性光学器件等。然而,这类分子稳定性较差,对光、氧气非常敏感,易发生分子间聚合,因此在本部分将杂原子掺杂到并苯分子主体骨架之中形成杂并苯分子,不但能够提高稳定性和抗氧化性,还能实现分子的n-型材料到p-型材料的自由切换。为此,我们将氧原子掺杂到并苯类分子主体骨架之中,得到系列杂并苯分子,测试了分子光、电、热学性能,并将所得分子作为功能层制备了有机电子器件,测试其相关性能。研究内容主要分为以下几个部分:(1)本文通过亲核取代反应合成了以芘为末端的十二环扭曲并苯分子DPyN和以菲为末端的功能化的十并苯扭曲分子CTNA、NTNA,并通过1H NMR、13C NMR和MALDI-TOF证明分子结构正确。分子DPyN在有机溶剂中发出红色荧光,具有良好的热稳定性,以DPyN作为功能层制备的存储器件显示出良好的存储性能。CTNA和NTNA显示出较好的热稳定性。(2)通过二氯吡嗪,二氯喹喔啉分别与邻二芳酚衍生物偶联合成了氧杂并苯分子ADOP、ADOQ,通过1H NMR、13C NMR和MALDI-TOF确定了分子结构。X-单晶衍射分析得到,其在固体状态下的分子结构与空间排列,ADOP是扭曲拓扑结构,ADOQ表现出躺椅式构型。所得分子在有机溶剂中发出蓝色荧光,具有良好的热稳定性,TGA显示ADOP和ADOQ失重5%的分解温度分别为444oC和446oC。通过再沉淀法,ADOP和ADOQ分别组装形成纳米带和纳米线。(3)应用经典的有机化学反应合成了十三环杂并苯分子12,通过1H NMR、13C NMR和MALDI-TOF确定了分子结构,其是供体-受体-供体型双极材料分子,可以作为良好的有机半导体材料。此分子显示良好的热稳定性能;具有宽吸收带,集中在565/613 nm处;固体状态下是墨绿色固体,发出红色荧光。(4)设计合成了十一环并苯分子29,通过1H NMR和MALDI-TOF确定了分子结构,其是供体-受体-供体型双极材料分子,应用紫外可见光谱和热重分析对化合物进行了光学和热学性能的测定,其可以作为良好的有机半导体材料。
[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.
【学位授予单位】：河北大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O649.5

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