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Synthesis of 510-bis(Trifluoromethyl) Substituted β-Octamethylporphyrins and Central-Metal-Dependent Solvolysis of Their meso-Trifluoromethyl Groups

机译:510-双(三氟甲基)取代的β-八甲基卟啉的合成及其中三氟甲基的中心金属依赖性溶剂解

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摘要

5,10-Bistrifluoromethyl substituted β-octamethylporphyrins were synthesized via a scrambling side reaction of a dipyrromethane precursor in the presence of a large excess of trifluoroacetic acid. Compared with the trans-analogs, the cis-analogs of meso-trifluoromethyl β-octaalkylporphyrin showed more red-shifted absorption bands. These meso-trifluoromethyl derivatives of β-octaalkylporphyrins underwent smooth metalation, similar to other common porphyrins, however, the corresponding zinc complexes underwent a type of solvolysis, whereby the trifluoromethyl groups were converted into methoxycarbonyl groups by the methanol used as solvent. UV-visible absorption spectra and X-ray crystal structure analyses revealed that the presence of a methoxycarbonyl substituent did not influence the deformation of the molecular framework and its absorption properties; this is because the methoxycarbonyl has a planar and perpendicular geometry, as opposed to the relatively bulky trifluoromethyl substituent.
机译:在大量过量的三氟乙酸存在下,通过二吡咯甲烷前体的加扰副反应,合成了5,10-二氟甲基取代的β-八甲基卟啉。与反式类似物相比,内三氟甲基β-八烷基卟啉的顺式类似物显示出更多的红移吸收带。与其他普通的卟啉类似,这些β-八烷基卟啉的内消旋三氟甲基衍生物经历了平滑的金属化,但是,相应的锌配合物经历了一种溶剂分解,由此三氟甲基被用作溶剂的甲醇转化为甲氧基羰基。紫外可见吸收光谱和X射线晶体结构分析表明,甲氧羰基取代基的存在不影响分子骨架的变形及其吸收性能;这是因为与相对庞大的三氟甲基取代基相反,甲氧羰基具有平面和垂直的几何形状。

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