Synthesis, characterization, photophysical and photochemical properties of zinc and indium phthalocyanines bearing a vanillylacetone moiety known as an anticarcinogenic agent

The synthesis of novel peripherally/non-peripherally tetra and octa vanillylacetone-substituted zinc and indium phthalocyanines was performed by cyclotetramerization of 4-[2-methoxy-4-(3-oxobutyl)phenoxy]phthalonitrile (1)/3-[2-methoxy-4-(3-oxobutyl)phenoxy]phthalonitrile (2) and 4,5-bis[2-methoxy-4-(3-oxobutyl)phenoxy]phthalonitrile (3). The novel chromogenic compounds were characterized by elemental analysis, 1H NMR, mass spectra, FT-IR and UV–Vis spectral data. The effects of the zingerone units on the zinc and indium phthalocyanine complexes (4–9) were also investigated.

Graphical abstractThe synthesis of novel peripherally / non-peripherally tetra, and octa vanillylacetone-substituted zinc and indium phthalocyanines was performed by cyclotetramerization of 4-[2-methoxy-4-(3-oxobutyl)phenoxy]phthalonitrile (1) / 3-[2-methoxy-4-(3-oxobutyl)phenoxy]phthalonitrile (2) and 4,5-bis[2-methoxy-4-(3-oxobutyl)phenoxy] phthalonitrile (3). The novel chromogenic compounds were characterized by elementel analysis, 1H-NMR, Mass spectra, FT-IR and UV-vis spectral data. The effects of the zingerone units on the zinc and indium phthalocyanine complexes (4-9) were also investigated.Figure optionsDownload full-size imageDownload as PowerPoint slide