Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 23, Pages 3930-3939Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900338
Keywords
Porphyrinoids; Aromaticity; Macrocycles; Fused ring systems
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Funding
- Ministry of Science and Higher Education [PBZ-KBN-118/T09/2004]
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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 AgBF4. Cyclic voltammetry studies of this system indicate an interaction between the subunits. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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