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Efficient Regiospecific Conjugated Ring Fusion in N‐Confused Porphyrin
Author(s) -
Chmielewski Piotr J.,
Maciołek Justyna,
Szterenberg Ludmiła
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900338
Subject(s) - chemistry , porphyrin , ring (chemistry) , conjugated system , pyrrole , protonation , cyclic voltammetry , dimer , aromaticity , aryl , carbon atom , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , electrochemistry , molecule , ion , alkyl , electrode , polymer
Acid‐catalyzed exocyclic ring formation in meso ‐tetrakis(3′,5′‐dimethoxyphenyl)‐2‐aza‐21‐carbaporphyrin takes place regioselectively between the external carbon atom of the confused pyrrole and the ortho ‐carbon atom of the adjacent meso ‐aryl group. The ring fusion strongly alters the spectroscopic properties of the macrocycle, but its aromaticity is preserved, as shown by NMR spectroscopy as well as DFT calculations. A tendency to self‐associate is observed for partially protonated and nickel(II)‐metalated systems. A novel silver(I)‐bridged dimer is formed in the reaction of the fused carbaporphyrin with AgBF 4 . Cyclic voltammetry studies of this system indicate an interaction between the subunits. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)