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Tetraphenylbenziporphyrin—A Ligand for Organometallic Chemistry
Author(s) -
Stępień Marcin,
LatosGrażyński Lechosław
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20011203)7:23<5113::aid-chem5113>3.0.co;2-v
Subject(s) - chemistry , pyrrole , benzaldehyde , palladium , tetraphenylporphyrin , benzene , ring (chemistry) , yield (engineering) , medicinal chemistry , platinum , ligand (biochemistry) , methanol , carbon atom , molecule , organometallic chemistry , metal , polymer chemistry , inorganic chemistry , photochemistry , organic chemistry , catalysis , porphyrin , biochemistry , materials science , receptor , metallurgy
6,11,16,21‐Tetraphenylbenziporphyrin (TPBPH)H, an analogue of tetraphenylporphyrin with one of the pyrrole groups replaced by a benzene ring, is formed in good yield in the condensation of the appropriate precursor with pyrrole and benzaldehyde. (TPBPH)H gives organometallic complexes with palladium( II ) and platinum( II ), [(TPBP)Pd II ] and [(TPBP)Pt II ], in which the metal ion is bound in the macrocyclic cavity by three pyrrolic nitrogen atoms and a carbon atom of the benzene ring. In the reaction with silver( I ) acetate benziporphyrin does not yield a stable complex but undergoes selective acetoxylation at the internal carbon atom. (TPBPH)H is reversibly reduced to 6‐benziphlorin and reacts with a water or methanol molecule to give 6‐hydroxy‐ or 6‐methoxy‐6‐benziphlorin, respectively.