Four-atom-linked capped porphyrins: Synthesis and characterization

Martin R. Johnson, Won K. Seok, Wuping Ma, Carla Slebodnick, Keith M. Wilcoxen, James A Ibers*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

Three new capped porphyrins, H2(OC2OPor) (7), H2(OC(CO)NPor) (13), and H2(OC2NPor) (14), to be used as heme model compounds, have been synthesized and characterized. These compounds have the shortest linkages between cap and porphyrin plane of any four-arm capped porphyrins synthesized to date. The general synthetic procedure for H2(OC2OPor) involves the reaction of a tetraaldehyde "cap" with pyrrole to form the capped porphyrin. In the synthesis of the tetraamide-capped porphyrin, H2(OC(CO)NPor), a tetraacid chloride cap is reacted with meso-α,α,α,α-tetra-(o-aminophenyl)porphyrin. The amide groups may be reduced to form H2(OC2NPor). With the use of FeBr2, Fe2+ may be inserted in high yield into H2(OC2OPor) and H2(OC(CO)NPor). The crystal structures of H2(OC2NPor), Fe(OC2OPor)(OMe), and [Fe(OC2OPor)]2(μ-O) provide details on the types and amounts of cap expansion necessary to accommodate small ligands of biological interest, such as O2 and CO.

Original languageEnglish (US)
Pages (from-to)3298-3303
Number of pages6
JournalJournal of Organic Chemistry
Volume61
Issue number10
DOIs
StatePublished - May 17 1996

ASJC Scopus subject areas

  • Organic Chemistry

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