Synthesis and characterization of novel phthalocyanines bearing quaternizable coumarin

The synthesis of novel metal-free and zinc phthalocyanines with four 3-[(2-diethylamino)ethyl]-7-oxo-4-methylcoumarin dye groups on the periphery were prepared by cyclotetramerization of a novel 3-[(2-diethylamino)ethyl]-7-[(3,4-dicyanophenoxy)]-4-methylcoumarin. The novel chromogenic compounds were characterized by elemental analysis, 1H NMR, 13C NMR, MALDI-TOF, IR and UV–Vis spectral data. The electronic spectra exhibit bands of coumarin identity along with characteristic Q and B bands of the phthalocyanine (Pc) core. The IR spectra of all the Pcs showed three characteristic intense bands, at 1704 cm−1 for the lactone carbonyl and two bands at 1489–1604 cm−1 for the conjugated olefinic system.

Graphical abstractThe synthesis of novel metal-free and zinc phthalocyanines with four 3-[(2-diethylamino)ethyl]-7-oxo-4-methylcoumarin dye groups on the periphery were prepared by cyclotetramerization of the novel 3-[(2-diethylamino)ethyl]-7-[(3,4-dicyanophenoxy)]-4-methylcoumarin. The novel chromogenic compounds were characterized by elementel analysis, 1H NMR, 13C NMR, MALDI-TOF, IR and UV–Vis spectral data. The electronic spectra exhibit bands of coumarin identity along with characteristic Q and B bands of the phthalocyanine (Pc) core. The IR spectra of all the Pcs showed three characteristic intense bands, at 1704 cm−1 for the lactone carbonyl and two bands at 1489–1604 cm−1 for the conjugated olefinic system.Figure optionsDownload full-size imageDownload as PowerPoint slide