Methods for the bromination of porphyrins and their derivatives at the meso and β-positions are examined. The dependence of the course of the reactions on the conditions and on the structure of the initial compounds is discussed.

Bromination of palladium meso-tetraphenyl tetrabenzoporphyrin ( Pd Ph4TBP, 1) by Me4NBr3 or Me4NBr/Br2 was shown to proceed regioselectively to the benzo-rings annelated to main porphyrin macrocycle. Conditions for preferential mono- and octa-bromination have been established. The respective mono- and octa-bromide ( Pd Ph4TBP( Br ), 2 and Pd Ph4TBP( Br )8, 3) have been isolated and characterized by UV-vis, NMR and LDI-TOF spectroscopy. Changes of electrochemical properties of tetrabenzoporphyrins induced by Br atoms were found to follow the same trends as the changes in analogous non-extended porphyrins. Room temperature phosphorescence is not substantially influenced by the substitution.

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Organic chemistry Z 0200 Bromination of Porphyrins -[103 refs.]. -(CHUMAKOV*, D. E.; KHOROSHUTIN, A. V.; ANISIMOV, A. V.; KOBRAKOV, K. I.; Chem. Heterocycl. Compd. (N. Y.) 45 (2009) 3, 259-283; Kosygin Moscow State Text. Univ., Moscow 117918, Russia; Eng.) -H. Toeppel 43-230