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Synthesis 2009(12): 1975-1978  
DOI: 10.1055/s-0029-1216809
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2,3,9,10,16,17,23,24-Octasubstituted Phthalocyaninatozinc(II) Complexes Mediated by Reductive Agents

Gabriela A. Gauna, Ana Clara Monsalvo, Josefina Awruch*
Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina
Fax: 54(11)45083645; e-Mail: jawruch@ffyb.uba.ar;
Further Information

Publication History

Received 7 January 2009
Publication Date:
12 May 2009 (online)

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Abstract

N-Butyl-N-(4,5-dicyano-2-methylbenzyl)butanamide (6) was synthesized in 69% yield from the corresponding 4,5-dibromo derivative 5. Treatment of 6 with zinc acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gave the octasubstituted zinc(II) phthalocyanine 7, which was reduced with diborane to the give phthalocyanine­ 8. Quaternization of 8 with iodomethane gave the cationic dye 9.

Key words

octasubstituted phthalocyaninatozinc - reduction - nucleophilic aromatic substitution - phthalocyanine - zinc complexes

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