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首页> 外文期刊>RSC Advances >Synthesis, structure, photophysical, electrochemical properties and antibacterial activity of brominated BODIPYs
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Synthesis, structure, photophysical, electrochemical properties and antibacterial activity of brominated BODIPYs

机译：溴化BODIPY的合成，结构，光物理，电化学性质和抗菌活性

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摘要

A series of mono- and di-brominated BODIPYs (1-5) was synthesized and characterized with a view to study the performance of dyes towards antibacterial activity. Regioselective bromination at the 2- and 2,6-positions of the BODIPY core was achieved with quantitative yield. The bromination of meso-(4-hydroxyphenyl) BODIPY (5) yielded an unexpected dibromo derivative, where the bromine groups were installed at the 3,5-positions of the phenyl ring rather than the 2,6-positions of the BODIPY core, which is confirmed and supported by UV-visible, fluorescence, and H-1 NMR spectroscopic analyses, electrochemical studies, and also by single crystal X-ray crystallography. We observed a red shift of similar to 16 nm in the absorption and 20-29 nm in the emission spectra in CH2Cl2 for the installation of each bromine group at the BODIPY core. The small difference between the first reduction potentials of the parent and dibromo derivative (5 and 5b) reveal that dibromination does not occur on the pyrrolic moiety. The intermolecular interactions involving C center dot center dot center dot H, F center dot center dot center dot H, H center dot center dot center dot H, and Br center dot center dot center dot H are the key factors in stabilizing the molecular crystal packing. The antibacterial properties of these dyes were investigated and the brominated derivatives showed better antibacterial effects than their corresponding parent BODIPYs, particularly the unusual dibromo derivative, 5b.
机译：合成并表征了一系列单溴和二溴BODIPYs（1-5），以研究染料对抗菌活性的性能。 BODIPY核心的2和2，6-位区域选择性溴化以定量收率实现。内消旋-（4-羟苯基）BODIPY（5）的溴化反应产生了意想不到的二溴衍生物，其中溴基团安装在苯环的3,5-位而不是BODIPY核的2,6-位，通过紫外可见光，荧光和H-1 NMR光谱分析，电化学研究以及单晶X射线晶体学得到证实和支持。对于在BODIPY核心处安装每个溴基团，我们观察到CH2Cl2的吸收光谱中的红移接近16 nm，发射光谱中的红移约20-29 nm。母体和二溴衍生物的第一还原电位之间的微小差异（5和5b）表明，在溴部分上不发生二溴化作用。涉及C中心点中心点中心点H，F中心点中心点中心点H，H中心点中心点中心点H和Br中心点中心点中心点H的分子间相互作用是稳定分子晶体堆积的关键因素。 。对这些染料的抗菌性能进行了研究，溴化衍生物显示出比其相应的母体BODIPY更好的抗菌效果，尤其是不寻常的二溴衍生物5b。

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