Synthesis and characterization of a new organo-soluble metal-free and metallophthalocyanines bearing flexible moieties

This paper describes a new symmetric metal-free phthalocyanine and its transition metal complexes which were prepared by a condensation of 1,2-dihydroacenaphthylen-1-ol 1 and 4-nitro phthalonitrile 2 with Co(II), Ni(II), Cu(II), and Zn(II) salts in 2-(dimethylamino)ethanol, respectively. The novel phthalocyanines bearing oxygen donor atoms on peripheral position have been characterized by IR, UV–Vis, 1H NMR, 13C NMR, Mass spectra and elemental analysis. The thermal behaviours of 4–8 were investigated by TG/DTA.

Graphical abstractThis paper describes a new symmetric metal-free phthalocyanine and its transition metal complexes which were prepared by a condensation of 1,2-dihydroacenaphthylen-1-ol 1 and 4-nitro phthalonitrile 2 with Co(II), Ni(II), Cu(II), and Zn(II) salts in 2-(dimethylamino)ethanol, respectively. The novel phthalocyanines bearing oxygen donor atoms on peripheral position have been characterized by IR, UV–Vis, 1H NMR, 13C NMR, mass spectra and elemental analysis. The thermal behaviours of 4–8 were investigated by TG/DTA.Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights► The synthesis of 4-(1,2-dihydroacenaphthylen-1-yloxy)phthalonitrile (3) was obtained by base-catalyzed nucleophilic aromatic nitro displacement of 4-nitrophthalonitrile (2) with the –OH function of 1,2-dihydroacenaphthylen-1-ol (1). ► In contrast to the analogous compounds the novel phthalocyanines (4–8) that synthesized are soluble in CHCl3, CH2Cl2, THF, DMF, DMSO and pyridine. ► The obtained novel phthalocyanines (4–8) were observed not to be stable above 260 °C.