丁二炔连接的BODIPY低聚物的合成及光谱性能研究

发布时间：2018-06-02 14:13

本文选题：丁二炔 + BODIPY低聚物　；参考：《安徽师范大学》2017年硕士论文

【摘要】：近几年,π-共轭功能性有机体系在分子电子学和纳米技术等新兴领域有着潜在的应用,所以备受人们的关注。基于BODIPY骨架的荧光低聚物具有大的共轭面和良好的光电特性,还可以进一步的进行修饰,因此具有很好的潜在应用价值。本论文展示了2,6-二三甲基硅基乙炔-BODIPYs通过自身偶联一锅法合成具有可溶性、线性的丁二炔相连的BODIPY低聚物,反应条件温和,可以达到四个BODIPY相连。这一系列丁二炔相连的BODIPY显示了紫外吸收和荧光发射波长的红移。通过对比光谱性质,我们发现它们的电子是沿着骨架离域的。这些低聚物的末端可以进一步的修饰,进而可以合成更好的分子线或更具有吸引力的荧光探针。其中,我们发展了一种具有水溶性的BODIPY二聚物,其荧光进一步的红移,可以作为比率粘度探针。这种类型分子转子的工作原理是基于这种二聚物存在两种荧光构象,相对于BODIPY母核,一种是相互扭曲另一种是共平面,相互转化的速度依赖于粘度的大小。在甲醇或乙醇这种粘度低的介质内,化合物15以共平面为主,其最大发射波长为624 nm,在丙三醇这种粘度大的介质内,两个BODIPY单元绕丁二炔旋转的速度变慢,主要以相互扭曲的构象存在,最大发射波长降为593 nm。在乙醇含有10%,丙三醇含有90%体积比的混合介质内,发现二聚物15随着温度发生变化,当温度升高时,共平面的构象在增加,相互扭曲的构象在减少。因此,这个二聚物15可以作为检测介质粘度的比率粘度探针。
[Abstract]:In recent years, 蟺-conjugated functional organic systems have potential applications in molecular electronics and nanotechnology. Fluorescent oligomers based on BODIPY skeleton have large conjugate surface, good photoelectric properties and can be further modified, so they have good potential application value. In this paper, it is shown that BODIPY oligomers with soluble and linear butylene are synthesized by self-coupling one-pot method. The reaction conditions are mild and four BODIPY can be linked to each other by the method of 2-dimethylsilyl acetylen-BODIPYs. This series of butylene linked BODIPY shows the red shift of UV absorption and fluorescence emission wavelengths. By comparing the spectral properties, we find that their electrons are delocalized along the skeleton. The ends of these oligomers can be further modified to produce better molecular lines or more attractive fluorescent probes. Among them, we have developed a water-soluble BODIPY dimer, its fluorescence further red shift, can be used as a ratio viscosity probe. The working principle of this type of molecular rotor is based on the existence of two fluorescent conformations of the dimer, one distorts each other and the other is coplanar, and the rate of conversion depends on the viscosity of the dimer. In a medium with low viscosity such as methanol or ethanol, compound 15 is mainly coplanar, and its maximum emission wavelength is 624 nm. In a medium with high viscosity, two BODIPY units rotate slowly around butadiene. The maximum emission wavelength is reduced to 593 nm. In the mixture medium containing 10% ethanol and 90% volume ratio of glycerol, it is found that the dimer 15 changes with the temperature. When the temperature increases, the conformation of coplanar is increasing and the conformation of mutual distortion is decreasing. Therefore, the dimer 15 can be used as a ratio viscosity probe for medium viscosity detection.
【学位授予单位】：安徽师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O631.24

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