The synthesis and metal binding chemistry of carbahemiporphyrazines with an electron withdrawing substituent

Abstract

Benziphthalocyanine (bzpc) and dicarbahemiporphyrazine (dchp) are phthalocyanine analogs where one and two of the isoindoline units have been replaced with benzene rings. In this report, we present dchp and bzpc analogs 1 and 2 where CF3 groups have been placed on the 5-position of the benzene rings. Compounds 1 and 2 have identical structural features as their unmodified parent macrocycles, but some differences are observed in their metal adducts. Complex 1Ag shows few differences with the analogous dchp complex, but compounds 1Cu and 2Co exhibit reductions in M – C bond lengths arising from the electron withdrawing nature of the CF3 unit.