基于交叉脱氢偶联的氟硼二吡咯区域选择性的衍生和应用

发布时间：2018-03-29 22:38

本文选题：BODIPY　切入点：合成　出处：《安徽师范大学》2017年硕士论文

【摘要】：氟硼二吡咯(Boron dipyrromethene,简称BODIPY)是一类非常有价值的荧光染料,是近几年荧光染料研究的热门。BODIPY具有很突出的理化性能,并且由于这些优异的性能使得BODIPY在各个领域有着广泛的应用。BODIPY可以通过官能团的修饰衍生来改变相应的光学性质,从而增加BODIPY的应用价值。因此对BODIPY进行官能化修饰对于研究BODIPY的实际应用具有重要意义。本论文分为两部分内容:一、此部分通过利用BODIPY染料与烯烃(醚)在叔丁基过氧化氢的氧化下,加入四丁基碘化铵成功开发了一种交叉脱氢偶联(CDC)反应。此反应是一个用于在BODIPY染料的α位区域高度选择性的官能化的一种方法。并且对于这个新颖BODIPYα-烯烃(醚)化的反应提出了自由基反应历程的机理。最后研究了合成化合物的光学性质。二、利用上述氟硼二吡咯的CDC反应,开发了一锅法3,5位BODIPY上醛(酰基)的反应。通过使用1,3-二氧戊环类化合物进行α位区域官能化,随后用一锅法进行水解合成了一系列3,5位醛(酰基)化的BODIPY衍生物,此反应提供了一个直接合成3,5位醛(酰基)化的BODIPY的方法。同时利用相应的酰氯在BF3·Et2O的作用下合成了一系列β位酰基化的BODIPY衍生物。对部分3,5位醛(酰基)化的BODIPY进行了单晶X-射线衍射表征并研究了所合成的化合物的光谱性质。
[Abstract]:Fluorine boron two pyrrole (Boron dipyrromethene, referred to as BODIPY) is a kind of very valuable fluorescent dyes,.BODIPY dyes is a hot research in recent years has fluorescent physicochemical properties is very prominent, and because of these excellent properties make BODIPY are widely used in various fields of.BODIPY can be derived by functional group modification change the corresponding optical properties, thus increasing the application value of BODIPY. So it has important significance for practical applications of functionalized modification of BODIPY for BODIPY. This thesis is divided into two parts: first, this part through the use of BODIPY dyes and olefin (ether) in the oxidation of tert butyl hydroperoxide, adding four Butyl Ammonium Iodide the successful development of a cross dehydrogenative coupling (CDC) reaction. This reaction is a method used in a BODIPY dye alpha region highly selective functionalization and for this. A novel BODIPY alpha olefin (ether) of the reaction mechanism was proposed. Finally, a free radical process of optical properties of compounds by CDC reaction. Two, the fluorine boron two pyrrole, developed one pot 3,5 BODIPY aldehyde (Xian Ji) reaction. Through the use of 1,3- two dioxolane compound alpha region functionalized, followed by one pot method for a series of 3,5 aldehyde synthesis hydrolysis (Xian Ji) BODIPY derivatives, this reaction provides a direct synthesis of 3,5 aldehyde (Xian Ji) method of BODIPY. At the same time using the corresponding chloride derivatives of BODIPY a series of beta Xian Ji in the synthesis of BF3 under the effect of Et2O on the part of 3,5 aldehyde (Xian Ji) of the BODIPY of single crystal X- ray diffraction characterization and spectroscopic properties of compounds were studied.

【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】：O657.3

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