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首页> 外文期刊>Chemistry: A European journal >Functionalization of Boron Dipyrrin (BODIPY) Dyes through Iridium and Rhodium Catalysis: A Complementary Approach to alpha- and beta-Substituted BODIPYs
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Functionalization of Boron Dipyrrin (BODIPY) Dyes through Iridium and Rhodium Catalysis: A Complementary Approach to alpha- and beta-Substituted BODIPYs

机译：硼双吡啶（BODIPY）染料通过铱和铑催化的功能化：α和β取代BODIPY的一种补充方法

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摘要

Iridium-catalyzed direct borylation has been applied to meso-substituted dipyrromethane and boron dipyrrin (BODIPY) dyes. Borylation is highly regioselective and complementary: it occurs exclusively at the alpha position for meso-mesityldipyrromethane and at the beta positions for meso-mesityl BODIPY dye. This regioselective borylation enables a variety of alpha- and beta-substituted BODIPY dyes to be synthesized. Introduction of alpha,beta-enoate and alpha,beta,gamma,delta-dienoate functions into BODIPY dyes at the alpha or beta positions was achieved by rhodium-catalyzed Heck-type addition of the borylated compounds to acrylate and 2,4-pentadienoate esters. This functionalization has a significant effect on the electronic properties of BODIPY dyes, as seen in substantial redshift of the absorption and emission spectra. Comparative studies showed that the alpha- and beta-substituted series of BODIPY dyes show substantially different photophysical properties, and thus the importance of the position to be functionalized is highlighted.
机译：铱催化的直接硼化已应用于介孔取代的二吡咯甲烷和硼二吡咯啉（BODIPY）染料。硼化具有高度的区域选择性和互补性：它仅在中消旋间苯二甲酰甲烷的α位和在中消旋间苯二酚染料的β位发生。这种区域选择性的硼酸酯化使得能够合成多种被α和β取代的BODIPY染料。通过铑催化将硼酸化的化合物添加到丙烯酸酯和2,4-戊二烯酸酯中，将α，β-烯酸酯和α，β，γ，δ-二烯酸酯功能引入α或β位的BODIPY染料中。如吸收和发射光谱的大量红移所示，这种官能化对BODIPY染料的电子性能具有重大影响。比较研究表明，BODIPY染料的α-和β-取代系列显示出显着不同的光物理性质，因此突出了要进行功能化的位置的重要性。

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