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Synthesis and characterization of the new 22‐π aromatic furan‐containing macrocycle, “ozaphyrin”
Author(s) -
Miller Douglas C.,
Johnson Martin R.,
Becker John J.,
Ibers James A.
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300604
Subject(s) - monoclinic crystal system , chemistry , furan , cyclic voltammetry , crystallography , spectroscopy , nuclear magnetic resonance spectroscopy , characterization (materials science) , stereochemistry , crystal structure , organic chemistry , nanotechnology , electrochemistry , materials science , physics , electrode , quantum mechanics
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 1 H 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 C 5 2h ‐P2 1 / 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 F 2 (5171 unique reflections, 411 variables) to R w (F o 2 ) = 0.165. The conventional agreement index R(F) is 0.074 for the 3289 reflections have F o 2 >2 o (F o 2 ).