2,3-位苯并BODIPY的合成及荧光性质研究

摘要BODIPY（4,4-difluoro-4-bora-3a,4a-diazas-indacene）是近些年来人们发现的一类新型的有机荧光化合物。由于其具有良好的光物理性质和光化学性质，近些年得到了广大学者的研究。BODIPY易于官能化，在其各个取代位引入不同的取代基就可以得到不同的衍生物，只要对其进行合理官能化，便可以作为一种高效的光敏剂用于光动力疗法。为了满足对实际需求，我们对实验的进行了不断修改和改进，使衍生物的吸收峰和发射峰红移不但可以减小衍生物在接近红外光的传播过程中所受到的干扰而且还对物质有极好的通透性。所以其在生物科学、材料科学和固态发光方面会有很好的应用。本文以苯甲醛和2,4-二甲基吡咯为原料合成硼二吡咯亚甲基化合物1，之后合成其2位单碘取代化合物2，再与2-醛基苯硼酸偶联反应，生成含有醛基的BODIPY3，之后利用分子内缩合反应，合成目标分子BODIPY4，通过核磁共振与质谱检测来确定最终产物及表征其结构。紫外和荧光光谱研究发现，其紫外和荧光光谱较2,3-位没有修饰的BODIPY1分别红移51nm和66nm。证明这种稠合是一种有效的红移BODIPY吸收和发光的手段。84902

毕业论文关键词：BODIPY 、荧光染料、红移、偶联反应、缩合反应

Abstract BODIPY (4,4-difluoro-4-bora-3a, 4a-diazas-indacene) is a new kind of organic fluorescent compounds found by people in recent years。 Because of its photophysical and photochemical properties of the。BODIPY research in recent years has been the majority of scholars easy functionalization, replaced the introduction of different substituents can get different derivatives at all, as long as reasonable functionalization of the can as an effective photosensitizer for photodynamic therapy。 In order to meet the actual demand, we are constantly revised and improved on the experiment, the interference derivative absorption peak and emission peak redshift can not only reduce the derivatives in the communication process in the near infrared light but also excellent permeability of material。 So in biological science, materials science and solid-state lighting will have a good application in this paper。 Benzaldehyde and 2,4 dimethyl pyrrole as raw material to synthesize boron Dipyrrole methylene compounds 1, synthetic 2 and 2,6 bit single iodine compounds 2, again with 2 aldehyde phenyl boronic acid coupling and intramolecular fused ring reaction, generated containing BODIPY3 aldehyde group and by intramolecular condensation reaction, the synthesis of target molecules BODIPY4, do nuclear magnetic resonance (NMR) and mass spectrometric detection, used to determine the final product and its structure was characterized。 UV and fluorescence spectra, it can be found that, the UV Vis and fluorescence spectra than 2,3 position no modification of the BODIPY1 respectively redshift 51nm and 66nm。 prove this kind of fused is a means of effective redshift BODIPY absorption and luminescence。

Key words: BODIPY, fluorescent dyes, red shift, coupling reaction, condensation reaction

摘要 I

Abstract II

第一章绪论 5

1 。1 BODIPY简介 5

1。2 BODIPY的应用 7

1。2。1 BODIPY用于细胞乏氧检测 7

1。2。2 在医学方面的应用（美白牙齿） 8

1。3 调谐大分子量BODIPY衍生物的固态发光 9

1。4 对BODIPY及其衍生物的研究进展 15

1。5近红外光谱技术特点及应用 2,3-位苯并BODIPY的合成及荧光性质研究:http://www.youerw.com/huaxue/lunwen_101147.html