Functional Porphyrinoids from a Biomimetically Decorated Bipyrrole

✍ Scribed by Martin Bröring; Frédérique Brégier; Robin Krüger; Christian Kleeberg

• Book ID: 102168863
• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 319 KB
• Volume: 2008
• Category: Article
• ISSN: 1434-1948
• DOI: 10.1002/ejic.200800946

✦ Synopsis

Abstract

The known 5,5′‐diformyl‐3,3′‐bis(methoxycarbonylethyl)‐4,4′‐dimethyl‐2,2′‐bipyrrole was employed in the preparation of biomimetic functional porphyrinoids. Tetrapyrrolic 2,2′‐bidipyrrins could be obtained from condensations with two equivalents of 3,4‐dialkyl‐2‐methylpyrroles. From these compounds, a manganese(III) corrole as well as a boron‐containing bis(bodipy) fluorophor are accessible as functional species in one‐step reactions. Both products were investigated by means of X‐ray crystallography. Attempts to hydrolyze the methyl ester moieties were successful only for the manganese corrole and yielded a buffer–soluble, heme‐analogous corrole complex. The dinuclear BF~2~ chelate [bis(bodipy)], on the other hand, decomposes unselectively under the applied conditions. A rationale for this decomposition was derived from crystallographic work on a related hydrolysis product with a F–B–O–B–F moiety. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)