In this study, the preparation of novel 7-hydroxy-3-(2-chloro-4-fluorophenyl)coumarin (
1), the ligand, 7-(3,4-dicyanophenoxy)-3-(2-chloro-4-fluorophenyl)coumarin (
2), metal-free phthalocyanine
3 and metallophthalocyanine complexes
4 and
5 (MPcs, M = Co, Zn), β-substituted with 7-oxo-3-(2-chloro-4-fluorophenyl)coumarin functional group was achieved. By the reaction of 7-hydroxy-3-(2-chloro-4-fluorophenyl)coumarin (
1) with 1,2-dicyano-4-nitrobenzen in dry DMF as the solvent in the presence of K
2CO
3 as the base, the 7-(3,4-dicyanophenoxy)-3-(2-chloro-4-fluorophenyl)coumarin (
2) was synthesized. Compound
2 reacted with Co(CH
3COO)
2·4H
2O in 2-
N,
N-dimethylaminoethanol to furnish a novel coumarin containing cobalt(II) phthalocyanine
4. The cyclotetramerization of
2 with Zn(CH
3COO)
2·2H
2O in 2-
N,
N-dimethylaminoethanol gave the novel coumarin containing Zn(II)phthalocyanine
5; while tetramerization without any metal salts in 2-
N,
N-dimethylaminoethanol gave the metal-free phthalocyanine
3. The structures of obtained compounds were confirmed by elemental analysis, UV–Vis, IR, MALDI-TOF mass and
1H NMR spectra. The cyclic and differential pulse voltammetry, and
in situ spectroelectrochemistry of 7-oxo-3-(2-chloro-4-fuorophenyl)coumarin substituted phthalocyanines
3,
4 and
5 allowed us to identify metal- and phthalocyanine ring-based redox processes of the complexes.
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