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Synthesis 2010(5): 741-748  
DOI: 10.1055/s-0029-1218602
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Highly Versatile Octasubstituted Phthalocyanine Scaffold for ex post Chemical Diversification

Herwig J. Bertholda, Theo Schotten*b, Frank Hoffmanna, Joachim Thiema
a University of Hamburg, Department of Chemistry, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
b CAN GmbH, Grindelallee 117, 20146 Hamburg, Germany
Fax: +49(40)428385797; e-Mail: schotten@can-hamburg.de;
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Publikationsverlauf

Received 11 September 2009
Publikationsdatum:
11. Dezember 2009 (online)

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Abstract

The TBDPS protecting group was conveniently employed for the convergent synthesis of a highly soluble, fully protected octa-peripheral (op) substituted phthalocyanine (Pc). After facile deprotection, ex post modification of this full-fledged Pc scaffold by various linkers was successfully achieved. This strategy overcomes the downsides of widely established linear convergent approaches under harsh conditions, which are not only destructive to chemically sensitive substituents, but also detrimental to rapid diversification towards Pc libraries.

Key words

heterocycles - dendrimers - protecting groups - phthalocyanine - ex post diversification - divergent strategy

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13

Alternatively, the axial ligand of 12 might be interpreted as H2O. However, there are two indications that the axial ligand is NH3: 1. The distance is in accordance with a typical Zn-N bond in such compounds, 2. calculation of both structural models resulted in the smaller R value for NH3.