A convenient preparation of thioether functionalized porphyrins |
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Authors: | Michael M. Pollard |
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Affiliation: | Department of Chemistry, University of Alberta, Edmonton, Alberta, Canada T6G 2G2 |
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Abstract: | This paper describes a convenient and high yielding three-step approach for the synthesis of trans-tetraphenylporphyrins possessing two thioethers in the ortho positions, which will facilitate the synthesis of more elaborate and complex porphyrin architectures. Their synthesis is realized by a double nucleophilic aromatic substitution of 2 equiv of a thiolate on 2,6-dichlorobenzaldehyde to generate a bis-thioether substituted benzaldehyde. This aldehyde is then condensed with 2 equiv of pyrrole to give a dipyrromethane, which in the final step reacts with an aromatic aldehyde to give a series of thioether-substituted trans-tetraphenylporphyrins. |
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Keywords: | trans-Porphyrins Thioethers Synthesis Dipyrromethanes 2,6-Disubstituted aldehydes |
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