Studies on selective β/β′ bromination of π-extended porphyrins and subsequent coupling reactions
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Monobromination of β, β′-π-extended porphyrins was found to selectively occur at the β or β′ position of the porphyrins which is antipodal to the fused aromatic ring. Subsequent Sonogashira or Heck coupling of the resultant bromoporphyrin introduced a carboxylphenylethynyl group or an acrylic acid group to the π-extended porphyrin. The optimal reaction conditions were found for the Sonogashira and Heck coupling reaction. All of the coupling products have shown a broadening and red-shift of the Soret band and Q bands in the UV–Vis absorption spectra compared with the π-extended porphyrin starting materials and the original unmodified porphyrins.
KeywordsLarge π-aromatic Porphyrin Bromination Selectivity Sonogashira Heck
This work is supported by National Natural Science Foundation of China (No. 21076147), Natural Science Foundation of Tianjin (No. 10JCZDJC23700), China International Science and Technology Project (No 2012DFG41980) and Seed Foundation of Tianjin University (Bao Zhang).