BODIPY衍生物与TPE冠醚主客体作用研究

发布时间：2018-05-05 16:14

本文选题：氟硼二吡咯 + 四苯乙烯　；参考：《南京理工大学》2017年硕士论文

【摘要】：超分子化学,它是一门涵盖化学,生物学、材料学、物理学、信息科学等多学科交叉的学科。由超分子化学衍生出来很多相关学科,如超分子光学材料、超分子化学材料、超分子纳米材料等。超分子化学可以用于,控制超分子纳米粒子的聚集与分散,光电信号的处理、分子机械与器件的构造、刺激响应型超分子材料构建以及生理体内药物的运载和控释等方面。本论文中,我们设计并合成了通过醚键将四苯乙烯(TPE)和二苯并-24-冠-8(DB24C8)连接在一起,构建一种对称的具有聚集诱导发光性能的主体分子M1。同时我们设计并合成了以氟硼二吡咯(BODIPY)为母体结构的亚胺类BODIPY衍生物作为荧光客体分子M2。合成的所有分子都经过1H-NMR,13C-NMR和MS等表征手段确定其结构。主体分子M1结构当中包含一个四苯乙烯结构,而具有该结构的化合物一般都有聚集诱导发光效应,两个冠醚空穴为客体分子的进入创造了较大的可能性。客体分子M2具有BODIPY母体结构,而BODIPY类化合物在有机溶液中具有优良的荧光性能。本文中客体分子M2带有较长侧链除了能够更好的与冠醚空穴作用,另外一个性能是在水溶液中不会出现荧光猝灭效应。然后,我们研究了主体分子M1和客体分子M2在THF/H20= 1:9(V/V)的溶液中主客体相互作用行为。研究发现主体分子M1与客体分子M2之间存在荧光共振能量转移现象,并且是从聚集诱导发光向非聚集诱导发光进行能量转移。通过荧光滴定和核磁滴定实验进一步确定了其主体分子M1与客体分子M2在中性,酸性和碱性条件下主客体作用的可能性,研究表明,该主客体系统的荧光共振能量转移效率受酸碱度影响很小。该高pH稳定性的荧光共振能量转移体系的发现对于荧光分子开关、荧光探针、太阳能电池吸光材料的设计与开发具有十分重要意义。
[Abstract]:Supramolecular chemistry, it is a multidisciplinary subject covering chemistry, biology, materials science, physics, information science and so on. Many related subjects are derived from supramolecular chemistry, such as supramolecular optical materials, supramolecular chemical materials, supramolecular nanomaterials and so on. Supramolecular chemistry can be used to control the aggregation and dispersion of supramolecular nanoparticles, the processing of photoelectric signals, the construction of molecular machinery and devices, the construction of stimulative supramolecular materials and the delivery and controlled release of drugs in vivo. In this thesis, we have designed and synthesized a symmetric host molecule M1 with aggregation induced luminescence by binding tetrastyrene (TPE) with dibenzo-24-crown-8 (DB24C8) by ether bond. At the same time, we have designed and synthesized imines BODIPY derivatives with fluoroborate dipyrrolidine (BODIPY) as the fluorescent guest molecule M2. All the synthesized molecules were characterized by 1H-NMR-13C-NMR and Ms. The structure of the host molecule M1 contains a tetrastyrene structure, and the compounds with this structure generally have aggregation induced luminescence effect. Two crown ether holes create a great possibility for the entry of the guest molecule. The guest molecule M2 has the BODIPY matrix structure, while the BODIPY class compounds have excellent fluorescence properties in organic solution. In this paper, the guest molecule M2 has a long side chain which can interact with crown ether hole better, and another property is that there is no fluorescence quenching effect in aqueous solution. Then, we study the host-guest interaction between host molecule M1 and guest molecule M2 in THF / H20 = 1: 9 V / V) solution. It is found that there is a phenomenon of fluorescence resonance energy transfer between host molecule M1 and guest molecule M2, and the energy transfer is from agglomeration induced luminescence to nonaggregation induced luminescence. The possibility of host and guest interaction between host molecule M1 and guest molecule M2 in neutral, acidic and alkaline conditions was further determined by fluorescence titration and nuclear magnetic titration. The fluorescence resonance energy transfer efficiency of the host and guest system is very little affected by pH. The discovery of the fluorescence resonance energy transfer system with high pH stability is of great significance for the design and development of fluorescent molecular switches, fluorescent probes and absorbent materials for solar cells.
【学位授予单位】：南京理工大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O641.3

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