Preparation of aldehyde substituted phthalocyanines with improved yield and their use for Schiff base metal complex formation

• Functional Schiff base groups substituted phthalocyanine compounds was described.
• Tri-nuclear Schiff base complex was obtained from the ligand ZnPc and ZnCl2.
• The complexion formed on two diagonal corners by using substituents and Zn(II) ions.
• Obtaining a new compound via substituents of Pc ring appears an effective method.

The context of this study is based on the synthesis of tetrakis[salicyoxy-salicyhydrazone] phthalocyaninato zinc(II) (4), with four salicylhydrazone ligating groups that are directly linked through oxygen bridges to the macrocyclic core, and its tri-nuclear Zn(II) Schiff base complex Bis[bis(salicyoxy-salicyhydrazone)zinc(II)]phthalocyaninato zinc(II) (5) starting from tetrakis(2-formylphenoxy)phthalocyaninato zinc(II) (3) which was obtained with an improved yield via de-protection of tetra acetal-substituted phthalocyanine tetrakis[2-(1,3-dioxolan-2-yl)phenoxy]phthalocyaninato]zinc(II) (2) in acetic acid/FeCl3 system. The substituted zinc phthalocyanine (2) was prepared by the tetramerization of 4-[2-(1,3-dioxolan-2-yl) phenoxy] phthalonitrile (1) in the presence of the related metal salts. Complexion on the periphery to obtain trinuclear complex (5) has been performed through the reaction of the Schiff base substituted phthalocyanine (4) with the related zinc (II) salt in basic conditions in DMF. FT-IR, 1H NMR, 13C NMR, UV–Vis, ICP-OES and MS spectra were applied to characterize the prepared compounds. The fluorescence properties and quantum yields of the prepared complexes were investigated. The aggregation properties of the target phthalocyanines were also examined.

This study, the synthesis of tetrakis[salicyoxy-salicyhydrazone] phthalocyaninato zinc(II) with four salicylhydrazone ligating groups linked through oxygen bridges to the macrocyclic core, and its Zn(II) Schiff base complex was discussed. The fluorescence properties and quantum yields of the prepared complexes were investigated. The aggregation properties of the phthalocyanines were also examined.Figure optionsDownload as PowerPoint slide