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This study presents the preparation of a novel tetra-substituted phthalonitrile (1) namely 3,6-bis(hexyloxy)-4,5-bis(4-(trifluoromethoxy)phenoxy)phthalonitrile (1) and its metal-free (2)/metal {M= Zn (3), Cu (4), Co (5), Lu(CH3COO) (6), Lu (7)} phthalocyanines....

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A new route to the synthesis of 4-chloro-5-alkyl-phthalonitrile derivatives was shown by the displacement reaction of 4,5-dichloro-phthalonitrile and diethylmalonate, a CH -acidic precursor, in the presence of K 2 CO 3. Cyclotetramerization of 1-chloro-3,4-dicyano-6-(1,1-dicarbethoxy-methyl)benzene and the metal salt without any solvent gave the corresponding metallophthalocyanines ( M = Co , Cu or Pd ). Transesterification occurred when the reaction was carried out in hexanol in the presence of DBU to obtain the metal-free derivative. Treatment of 1-chloro-3,4-dicyano-6-(1,1-dicarbethoxy-methyl)benzene with sodium ethoxide at ambient temperature and further acidification resulted in 2,9,16,23-tetra(carboxymethyl)-3,10,17,24-tetrachloro-phthalocyaninatopalladium(II) with partial decarboxylation. Its electronic spectrum in aqueous solution indicated no appreciable change over a pH range from 7 to 12.

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