Synthesis and Acid-base Properties of Isomeric Tetrachlorooctabromo- and 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

Macroheterocycles 2019 12(1) 22-28

Reactions of Co(II)-5,10,15,20-tetra(4-bromophenyl)porphyrin chlorination with excess of the thionyl chloride and 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-bromophenyl)porphyrin were synthesized and identified by UV-Vis, ¹H NMR spectroscopy and mass-spectrometry. When the halogen substituted 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.

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

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