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Issue 81, 2012
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Synthesis of π-extended porphyrins via intramolecular oxidative coupling

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Abstract

Porphyrins fused with other aromatic units at the meso- and β-positions have recently emerged as a hot topic of research. Their synthesis typically starts with preparation of precursors via either Suzuki coupling of a meso-bromoporphyrin or mixed-aldehyde condensation, and is followed by oxidative aromatic coupling, often using high-valent metal reagents (DDQ/Sc(OTf)3 and Fe(III) salts are among the most popular). In recent years, porphyrins were oxidatively coupled not only with well-known aromatic hydrocarbons such as naphthalene and pyrene, but also with more complex heterocyclic fragments, including indole, phenanthro[1,10,9,8-cdefg]carbazole and BODIPY. A subtle relationship exists between the output of intramolecular oxidative coupling and the nature of the second aromatic moiety, cation in the porphyrin cavity, oxidant, and type of remaining meso-substituent. The extension of the porphyrin chromophore leads to significant change in linear and non-linear optical properties. Very strong bathochromic shifts of absorption (λmax reaching 1.5–2 microns in some cases) and increases in two-photon absorption cross-sections are typical for these functional dyes.

Graphical abstract: Synthesis of π-extended porphyrins via intramolecular oxidative coupling

  • This article is part of the themed collection: Aromaticity
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Publication details

The article was received on 20 Feb 2012, accepted on 01 May 2012 and first published on 01 May 2012


Article type: Feature Article
DOI: 10.1039/C2CC31279D
Citation: Chem. Commun., 2012,48, 10069-10086
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    Synthesis of π-extended porphyrins via intramolecular oxidative coupling

    J. P. Lewtak and D. T. Gryko, Chem. Commun., 2012, 48, 10069
    DOI: 10.1039/C2CC31279D

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