α-/β-Formylated Boron-Dipyrrin (BODIPY) Dyes: Regioselective Syntheses and Photophysical Properties
α-/β-Formylated Boron-Dipyrrin (BODIPY) Dyes: Regioselective Syntheses and Photophysical Properties
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DOI：
10.1002/ejoc.201100736
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发表时间：
2011-10-01
影响因子：
2.8
通讯作者：
Hao, Erhong
中科院分区：
文献类型：
--
作者：
Yu, Changjiang;Jiao, Lijuan;Hao, Erhong
基于Vilsmeier-Haack反应，对吡咯未取代的二吡咯甲烷1和硼-二吡咯（BODIPY）染料4进行了甲酰化。它是高度区域选择性和互补性的，并且对于吡咯未取代的二吡咯甲烷1和BODIPY染料4分别仅发生在α-和β-位置。这种区域选择性的取代使得能够合成各种α-和β-取代的BODIPY染料。甲酰基的安装影响的BODIPY发色团的电子性质，导致在红色和蓝色的吸收和发射最大值，分别为α-和β-甲酰化的BODIPY 3和5。
Formylation has been performed on pyrrole-unsubstituted dipyrromethanes 1 and boron-dipyrrin (BODIPY) dyes 4 based on a Vilsmeier-Haack reaction. It is highly regioselective and complementary and occurs exclusively at the alpha- and beta-position, respectively, for pyrrole-unsubstituted dipyrromethanes 1 and BODIPY dyes 4. This regioselective formylation enables the syntheses of a variety of alpha- and beta-substituted BODIPY dyes. The installation of formyl groups affects the electronic properties of the BODIPY chromophore, resulting in red-and blueshifts of the absorption and emission maxima, respectively, for the alpha- and beta-formylated BODIPYs 3 and 5.