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ISSN 1998-9539

Synthesis and Acid-base Properties of Isomeric β-Tetrachlorooctabromo- and β-Tetrabromooctachlorotetraphenylporphyrins

Nugzar Zh. Mamardashvili,@ Yulia B. Ivanova, and Natalya V. Chizhova

G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 153045 Ivanovo, Russian Federation

@CorrespondingauthorE-mail: ngm@isc-ras.ru

 

DOI: 10.6060/mhc180900m

 

Reactions of the Co(II)-5,10,15,20-tetra-(4-bromophenyl)porphyrin chlorination with excess of the thionyl chloride and the Co(II)-5,10,15,20-tetra-(4-chlorophenyl)porphyrin bromination with N-bromosuccinimide were investigated. Co(II)-2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetra-(chlorophenyl)porphyrin and Co(II)-2,3,7,8,12,13,17,18-octachloro-5,10,15,20-tetra-(4-bromo-phenyl)-porphyrin were synthesized and identified by UV-Vis, 1H NMR spectroscopy and mass-spectrometry. When the halogensubstituted Co(II)-porphyrins were treated with a chloric and sulfuric acids mixture, corresponding porphyrin-ligands were obtained. The acid-base properties of the 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetra-(4-chlorophenyl)porphyrin and 2,3,7,8,12,13,17,18-octachloro-5,10,15,20-tetra-(4-bromophenyl)porphyrin in acetonitrile were studied. Acidity and basicity constants of the synthesized porphyrin ligands were determined and the concentration intervals for their ionized forms existence were established.