荧光新材料的合成及性能研究

发布时间：2018-11-19 16:45

【摘要】：本文为了寻找荧光性能优良的有机发光材料,设计合成了一系列二苯乙烯类化合物,并对影响其荧光性能的因素做了系列探讨以获得较佳荧光结构的化合物。本论文的主要内容如下：1.本文通过Michaelis-Arbuzov反应和Wittig-Homer反应合成了50个二苯乙烯类化合物,其中14个化合物未见文献报道。所合成化合物经过红外光谱、核磁共振等表征手段确定了其结构,同时测定了它们的紫外-可见光谱和荧光发射光谱。2.通过Wittig-Horner反应构建的乙烯双键具有高度的立体专一性,所得产物均为反式构型。3.通过对Wittig-Horner反应机理和实验结果的分析,探讨了不同取代苄基膦酸酯对反应条件的影响,优化了二苯乙烯类化合物的合成工艺。4.培养得到了9个二苯乙烯类化合物的单晶,并分析了这些化合物的平面刚性结构对其荧光的影响。单晶数据显示化合物8h、9a、9d、10d、10g、10i、11d、14o、14p分子中乙烯桥两端芳香环之间的二面角分别为3.41°、2.10°、4.82°、25.27°、26.24°、2.74°、30.54°、0.91°、28.25°,这表明并非所有化合物均有较好的共平面性。荧光分析表明提高化合物的共平面性能够显著增强化合物的荧光性能,反之,则降低荧光性能。5.分析目标化合物的荧光发射光谱,探索了不同取代基团和不同芳香环对二苯乙烯类化合物荧光性能的影响,并得出(E)-2-甲氧基-6-(苯乙烯基)萘(15r)的荧光量子产率最大为0.388,(E)-4-乙氧基-4'-硝基二苯乙烯(13d)的最大荧光发射波长最长达到566nm。我们亦可做出推论,即在苯环上对位引入甲氧基,将萘环上2-甲氧基置换为2-硝基,得到的化合物(E)-2-硝基-6-(4’-甲氧基苯乙烯基)萘其最大荧光发射波长将变得更长、荧光量子产率更大,应用于有机荧光材料前景较好。
[Abstract]:In order to search for organic luminescent materials with excellent fluorescence properties, a series of stilbene compounds were designed and synthesized, and the factors affecting their fluorescence properties were discussed to obtain better fluorescent compounds. The main contents of this thesis are as follows: 1. In this paper, 50 stilbene compounds were synthesized by Michaelis-Arbuzov reaction and Wittig-Homer reaction, of which 14 compounds were not reported in literature. The synthesized compounds were characterized by IR and NMR, and their UV-Vis and fluorescence emission spectra were determined. 2. 2. The ethylene double bond prepared by Wittig-Horner reaction has a high stereospecific property and the products are all trans configuration. Based on the analysis of Wittig-Horner reaction mechanism and experimental results, the effects of different substituted benzyl phosphonate on the reaction conditions were discussed, and the synthesis process of stilbene compounds was optimized. 4. Nine single crystals of stilbene compounds were obtained and the effects of the planar rigid structure of these compounds on their fluorescence were analyzed. The single crystal data show that the dihedral angles between the aromatic rings at the two ends of the ethylene bridge are 3.41 掳, 2.10 掳, 4.82 掳, 25.27 掳, 26.24 掳, 2.74 掳, 30.54 掳, respectively. 0.91 掳, 28.25 掳, which indicates that not all compounds have good coplanarity. Fluorescence analysis showed that the fluorescence properties of the compounds could be significantly enhanced by increasing the coplanarity of the compounds, whereas the fluorescence properties of the compounds were decreased by 5. 5%. The fluorescence emission spectra of the target compounds were analyzed. The effects of different substituents and aromatic rings on the fluorescence properties of stilbenes were investigated. The maximum fluorescence quantum yield of (E) 2-methoxy-6- (styrene-naphthalene) (15r) is 0.388, and the maximum fluorescence emission wavelength of (E) -4-ethoxy-4N-nitrostilbene (13d) is 566nmm. We can also infer that the methoxy group is introduced to the benzene ring, and the 2-methoxy group in the naphthalene ring is replaced with 2-nitro-group. The maximum fluorescence emission wavelength and fluorescence quantum yield of the compound (E) _ 2-nitro-6- (4H-methoxystyrene-yl) naphthalene will become longer, and its application in organic fluorescent materials will be better.
【学位授予单位】：东南大学
【学位级别】：硕士
【学位授予年份】：2015
【分类号】：TB34;O621.22

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