Functional chalcone-substituted tetrakis-metallophthalocyanines: Synthesis and spectroscopic characterization

In this study, a new phthalonitrile derivative, (E)-4-(3-(3-(3-methoxyphenyl)acryloyl)phenoxy)phthalonitrile, and four peripherally (E)-4-(3-(3-(3-methoxyphenyl)acryloyl)phenoxy) tetrasubstituted new Ni(II), Zn(II), Co(II), and Cu(II) phthalocyanine derivatives are synthesized and characterized. (E)-4-(3-(3-(3-Methoxyphenyl)acryloyl)phenoxy)phthalonitrile is synthesized by heating (E)-1-(3-hydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one and 4-nitrophthalonitrile in the presence of K2CO3 in dry DMF at 60°C for 96 h. The metallophthalocyanines are prepared by cyclotetramerization of (E)-4-(3-(3-(3-methoxyphenyl)acryloyl)phenoxy)phthalonitrile with NiCl2, Zn(CH3COO)2, CoCl2, and CuCl2 in n-pentanol in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. Characterization of the new compounds is performed by means of IR, 1H NMR, 13C NMR, and mass and UV-Vis spectroscopy techniques.