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A meso ‐Tetraaryl‐21‐carbaporphyrin: Incorporation of a Cyclopentadiene Unit into a Porphyrin Architecture
Author(s) -
Garbicz Mateusz,
LatosGrażyński Lechosław
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201901808
Subject(s) - synthon , cyclopentadiene , porphyrin , moiety , steric effects , chemistry , ferrocene , dendrimer , protonation , rational design , aryl , stereochemistry , crystallography , polymer chemistry , photochemistry , materials science , nanotechnology , organic chemistry , ion , electrode , electrochemistry , catalysis , alkyl
Incorporation of a cyclopentadiene moiety into the meso ‐tetraarylporphyrin framework, using 1,3‐bis(arylhydroxymethyl)ferrocene as a synthon, resulted in the rational synthesis of a meso ‐tetraaryl‐21‐carbaporphyrin. The molecular design preserves all essential virtues of the original tetrapyrrolic architecture of meso ‐tetraarylporphyrin, including the perfect match between the ionic radii of an inserted metal and the size of the macrocyclic (CNNN) core, and steric protection provided by thoughtfully chosen meso ‐aryl substituents. Its protonation of the inner core reveal an adjustable (trigonal versus tetrahedral) geometry.