Rational synthesis of imidazolyl-porphyrinic molecules

ORGN 933

Jayeeta Bhaumik, jbhaumi@unity.ncsu.edu and Jonathan S. Lindsey, jlindsey@ncsu.edu. Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204
Imidazole-substituted metalloporphyrinic compounds are valuable for studies of self-assembly and for applications where water solubility is required. Gaining rational access to imidazolyl-porphyrinic molecules required the development of new protecting group approaches for the polar, reactive imidazole unit. The imidazole was successfully masked by the use of (1) the 2-(trimethylsilyl)ethoxymethyl (SEM) group at the imidazole pyrrolic nitrogen, and (2) a dialkylboron motif bound to the pyrrole of the dipyrromethane and coordinated to the imidazole pyrrolenyl nitrogen. Alkylation of the resulting imidazolyl-porphyrins afforded water-soluble imidazolium-porphyrins.