Synthesis and characterization of metallo phthalocyanines bearing 7-oxy-3-(4-pyridyl)coumarin substituents and their supramolecular structures with vanadyl bis(acetylacetonate)

The synthesis of novel zinc and cobalt metallo phthalocyanines with four 7-oxy-3-(4-pyridyl)coumarin dye groups on the periphery/non-periphery were prepared by cyclotetramerization of 7-(3,4-dicyanophenoxy)-3-(4-pyridyl)coumarin (1)/7-(2,3-dicyanophenoxy)-3-(4-pyridyl)coumarin (2) and also a phthalocyanine based on supramolecular structures have been prepared by the ready coordination of pyridine donor sites in 2,9(10),16(17),23(24)-tetrakis[7-oxo-3-(4-pyridyl)coumarin]-phthalocyaninatozinc (1a)/1,8(11),15(18),22(25)-tetrakis[7-oxo-3-(4-pyridyl)coumarin]-phthalocyaninatozinc (2a) with vanadyl bis(acetylacetonate). The novel chromogenic compounds were characterized by elemental analysis, 1H NMR, Mass spectra, FT-IR and UV–Vis spectral data. The IR-spectra of prepared compounds showed two characteristic intense bands at 1728–1719 cm−1 for lactone carbonyl and at 1592 cm−1 for the α, β unsaturated doubled bond.

The synthesis of novel zinc and cobalt metallo phthalocyanines with four 7-oxy-3-(4-pyridyl)coumarin dye groups on the periphery/non-periphery were prepared by cyclotetramerization of 7-(3,4-dicyanophenoxy)-3-(4-pyridyl)coumarin (1)/7-(2,3-dicyanophenoxy)-3-(4-pyridyl)coumarin (2) and also a phthalocyanine based on supramolecular structures have been prepared by the ready coordination of pyridine donor sites in 2,9(10),16(17),23(24)-tetrakis[7-oxo-3-(4-pyridyl)coumarin]-phthalocyaninatozinc (1a)/1,8(11),15(18),22(25)-tetrakis[7-oxo-3-(4-pyridyl)coumarin]-phthalocyaninatozinc (2a) with vanadyl bis(acetylacetonate). The novel chromogenic compounds were characterized by elemental analysis, 1H NMR, Mass spectra, FT-IR and UV–Vis spectral data. The IR-spectra of prepared compounds showed two characteristic intense bands at 1728–1719 cm−1 for lactone carbonyl and at 1592 cm−1 for the α, β unsaturated doubled bond.Figure optionsDownload as PowerPoint slideHighlights
► Supramolecular structures.
► Pyridylcoumarin.
► Vanadyl phthalocyanines.