A new one-pot synthesis of mu-oxo dimeric iron(III) porphyrins from meso-tetraarylporphyrins

作者:Liu, Qiang; Gong, Yan Zhi; Gong, Chang Jun; Li, Qing Hong; Guo, Can Cheng*
来源:Journal of Porphyrins and Phthalocyanines, 2009, 13(8-9): 854-858.
DOI:10.1142/S1088424609000024

摘要

A new synthesis of mu-oxo dimeric iron(III) porphyrins from meso-tetraarylporphyrins in one-pot procedure is reported. mu-oxo dimeric iron(III) porphyrin was obtained in high yield (up to 93%) from the reaction of meso-tetraarylporphyrin with ferrous chloride in DMF at pH 8-11. Compared with other synthetic methods of mu-oxo dimeric iron(III) porphyrin from meso-tetraarylporphyrins, the one-pot procedure has higher yields of mu-oxo dimeric iron(III) porphyrins and is a simpler and more convenient procedure. In order to evaluate the range of applicability of this method, mu-oxo dimeric iron(III) porphyrins with different substituents were prepared by the reaction of the corresponding meso-tetraarylporphyrins with ferrous chloride. The results showed that it was possible to apply this one-pot procedure to the synthesis of other mu-oxo dimeric iron porphyrins in excellent yields. A mechanism for the formation of mu-oxo dimeric iron porphyrins was proposed based on the reaction intermediates characterized by HPLC and UV-vis methods.