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Porphocyanines: Expanded aromatic tetrapyrrolic macrocycles

TitlePorphocyanines: Expanded aromatic tetrapyrrolic macrocycles
Publication TypeJournal Article
Year of Publication1996
AuthorsXie, LY, Boyle, RW, Dolphin, D
JournalJournal of the American Chemical Society
Date PublishedMay
Type of ArticleArticle
ISBN Number0002-7863
KeywordsCOMPLEX, porphyrins

Porphocyanines are tetrapyrrolic macrocycles containing two dipyrromethene units linked together by two C=N-C bridges. The syntheses of 2,3,7,8,14,15,19,20-octaethylporphocyanine 5,17-diphenylporphocyanine, 2,3,7,8-tetraethyl-17-phenylporphocyanine and other meso-aryl and beta-alkyl, including a tetra-beta-propionate, derivatives and metal complexes are described. The physical and chemical properties of porphocyanines show them to be aromatic. The aromaticity is reflected in the large deshielding of the outer beta-protons and shielding of the inner pyrrolic protons in their NMR spectra. The optical spectra of these compounds exhibit Soret and Q bands similar to porphyrins but all significantly bathochromically shifted. The ability of porphocyanines to act as catalysts for the generation of singlet molecular oxygen was investigated using a cholesterol oxidation assay.

URL<Go to ISI>://A1996UM41600015