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Synlett 2006(19): 3231-3236  
DOI: 10.1055/s-2006-951547
LETTER
© Georg Thieme Verlag Stuttgart · New York

First Synthesis of Symmetrical and Unsymmetrical Conjugated Trinuclear Phthalocyanines Covalently Linked by Ethynyl Bridges

Eva M. García-Frutos, David D. Díaz, Purificación Vázquez*, Tomás Torres*
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco 28049 Madrid, Spain
Fax: +34(91)3973966; e-Mail: tomas.torres@uam.es;
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Publication History

Received 28 August 2006
Publication Date:
23 November 2006 (online)

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Abstract

For the first time, symmetrical and unsymmetrical π-electron-conjugated trinuclear phthalocyanines (Pcs) were syn­thesized with the Pc units connected directly by ethynyl linkages. Symmetrically alkoxy-substituted bridged ethynylphthalocyaninatozinc(II) triad was prepared by direct Sonogashira cross-coupling reaction between suitable diiodo Pc and alkynyl Pc derivatives. Nevertheless, the synthesis of the Pc-based triad having a donor-­acceptor electron character was carried out by means of co-cyclo­tetramerization of two different phthalonitriles, namely 4,5-bis(propylsulfonyl)phthalonitrile and 4,5-[hexa(butoxy)ethynylphthalo-cyaninatozinc(II)]phthalonitrile in the presence of a cobalt(II) salt.

Key words

phthalocyanines - triad - ethynyl - Sonogashira reaction