Synthesis, Spectral, Acid-Basic, and Coordination Properties of Bromine- and Methoxy-Substituted Tetraphenylporphyrins

• Published in: Russian journal of general chemistry Vol. 91; no. 6; pp. 1050 - 1056
• Main Authors: Puchovskaya, S. G., Ivanova, Yu. B., Chizhova, N. V., Syrbu, S. A.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-06-2021; Springer; Springer Nature B.V
• Subjects: Acetonitrile; Analysis; Bromine; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Coordination; Mass spectrometry; NMR spectroscopy; Porphyrins; Substitutes; Synthesis; bromo(methoxy)-substituted porphyrins; coordination properties; acid-base properties; spectral properties; metalloporphyrins
• ISSN: 1070-3632; 1608-3350
• DOI: 10.1134/S1070363221060104

The direct synthesis of symmetrically substituted porphyrins: 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetra(3,5-dibromophenyl) porphyrin and 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetra(3,4,5-trimethoxyphenyl) porphyrin – was proposed. The obtained compounds were identified by electron absorption,
1
H NMR spectroscopy and mass spectrometry. The acid-base and coordination properties of 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetra(3,5-dibromophenyl) porphine and 2,3,7,8,12,13,17,18-octabromo-5,10,15,20-tetra(3,4,5-trimethoxyphenyl) porphine with respect to Zn
2+
and Pd
2+
ions in acetonitrile at 298–328 K were studied. The effect of substituents in the β-positions and
meso
-phenyl fragments of the macrocycle on the spectral and coordination properties of the analyzed compounds was revealed. β-Unsubstituted analogs studied earlier were used as objects of comparison.