Issue 81, 2012

Synthesis of π-extended porphyrinsvia intramolecular oxidative coupling

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

Article information

Article type
Feature Article
Submitted
20 Feb 2012
Accepted
01 Mei 2012
First published
01 Mei 2012

Chem. Commun., 2012,48, 10069-10086

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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