具有腙式结构的化合物的合成及其聚集诱导发光性能的研究

发布时间：2019-02-27 18:01

【摘要】：本文设计合成一系列腙类衍生物,包括以砜式结构为中心的V型D-π-A-π-D结构的两个系列八种腙类衍生物以及以三苯胺为中心的三种腙类衍生物,并使用元素分析,红外,核磁等方法其表征。随后,我们对它们的聚集诱导发光性能进行了测试,并对其应用进行了研究。聚集诱导发光性能测试揭示了这几种腙类衍生物在聚集态下的荧光增强及其较高的荧光量子产率。同时,荧光显微镜测试直观展示了这些腙类衍生物在聚集态下的强荧光。我们还使用了扫描电子显微镜对BAHDS衍生物以及DHS衍生物进行了研究,揭示了聚集态这两种腙类衍生物的纳米级形貌特点。本文还从分子动力学计算的角度对BAHDS衍生物以及DHS衍生物的高聚集荧光进行了解释。计算结果介绍了这两种以砜式结构为中心的腙类衍生物的几种堆积方式,氢键效应,特殊的分子间作用力等原因阻碍了其分子内旋转,从而增强了其聚集荧光。我们还发现三种TPAS衍生物无论在纯THF溶剂下还是在THF/水混合溶剂下都有极高的荧光量子产率,其中聚集态下的TPAS-3在THF/水混合溶剂中,当水含量较高时出现较大的荧光红移,揭示了TPAS-3在水中较强的溶剂化效应。同时,我们对BAHDS衍生物以及DHS衍生物进行了一系列活细胞成像实验,实验证明了这两种腙类衍生物具有良好的细胞穿透性以及较低的循环毒性,在生物学领域的具有较高的应用价值。
[Abstract]:In this paper, a series of Hydrazone derivatives are designed and synthesized, including two series of eight Hydrazone derivatives with V-type D-蟺-A-蟺-D structure centered on sulfone structure and three Hydrazone derivatives centered on triphenylamine. It was characterized by IR, NMR, etc. Then, we tested their aggregation-induced luminescence properties and studied their application. The fluorescence enhancement of these Hydrazone derivatives in the aggregated state and their high fluorescence quantum yields were revealed by the aggregation-induced luminescence performance test. At the same time, fluorescence microscope test showed the strong fluorescence of these Hydrazone derivatives in aggregation state. BAHDS derivatives and DHS derivatives were also studied by scanning electron microscopy (SEM). The nano-morphology characteristics of the two Hydrazone derivatives were revealed. The high aggregation fluorescence of BAHDS derivatives and DHS derivatives is also explained from the point of view of molecular dynamics calculation. The calculation results show that several stacking methods, hydrogen bonding effect and special intermolecular force hinder the intramolecular rotation of the two Hydrazone derivatives with sulfone structure as the center, and thus enhance the aggregation fluorescence of Hydrazone derivatives. We also found that three TPAS derivatives have very high fluorescence quantum yields both in pure THF solvent and in THF/ water mixed solvent, in which TPAS-3 in aggregated state is in THF/ water mixed solvent. When the content of water is high, there is a large red shift of fluorescence, which indicates the strong solvation effect of TPAS-3 in water. At the same time, we carried out a series of living cell imaging experiments on BAHDS derivatives and DHS derivatives. The results showed that the two Hydrazone derivatives had good cell penetration and low circulatory toxicity. It has high application value in the field of biology.
【学位授予单位】：苏州大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O621.22

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