Synthesis and characterization of the new 22‐π aromatic furan‐containing macrocycle, “ozaphyrin”

Douglas C. Miller*, Martin R. Johnson, John J. Becker, James A Ibers

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

The new 22‐π, aromatic “pentaplanar” macrocycle, ozaphyrin (6), has been synthesized by a McMurry coupling of 5,5′‐diformyl‐4,4′‐dipropyl‐2,2′‐bipyrrole (1) with 2,5‐bis(5‐formyl‐4‐propyl‐2‐pyrrolyl)furan (5). This synthetic pathway to ozaphyrin and its characterization by 1H nmr spectroscopy, uv‐visible spectroscopy, cyclic voltammetry, and X‐ray crystallography are described. The structure consists of layers of planar, staggered macrocycles stacked perpendicular to the α‐axis. Ozaphyrin crystallizes with four formula units in the monoclinic space group C52h‐P21/n in a cell of dimensions a = 10.481(7) Å, b = 17.353(17) Å, c = 18.726(12) Å, and β = 102.84(5)° (108 K). The structure has been refined on F2 (5171 unique reflections, 411 variables) to Rw(Fo2) = 0.165. The conventional agreement index R(F) is 0.074 for the 3289 reflections have Fo2>2o(Fo2).

Original languageEnglish (US)
Pages (from-to)1485-1490
Number of pages6
JournalJournal of Heterocyclic Chemistry
Volume30
Issue number6
DOIs
StatePublished - Jan 1 1993

ASJC Scopus subject areas

  • Organic Chemistry

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