Amide-containing macrocycles as platforms for oxygen activation and anion recognition

INOR 79

Ivan V. Korendovych, ivan.korendovych@tufts.edu1, Mimi Cho1, Olga Kryatova, okryat01@tufts.edu1, Richard J. Staples, staples@chemistry.harvard.edu2, William M. Reiff, w.reiff@neu.edu3, and Elena V. Rybak-Akimova, erybakak@tufts.edu1. (1) Department of Chemistry, Tufts University, 62 Talbot Ave., Medford, MA 02155, (2) Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, (3) Department of Chemistry, Northeastern University, 360 Huntington Ave, Boston, MA 02115
Our approach to designing functional models of natural systems capable of selective stereospecific oxidation of substrates is based on iron complexes with macrocyclic ligands. Synthetic modification of the ligands (family I) allowed us to fine tune oxygen reactivity of the iron(II) complexes and change the reaction pathway. Several intermediates of biological relevance were characterized spectroscopically. The new amidopyridine macrocycles can be considered as new “expanded porphyrin analogs” providing control over the spin state and availability of protons as well as allowing for easy modifications, paving the way to new versatile metal complexes. Macrocycles of the general structure II possess small molecule- and anion-binding properties, as it was shown by NMR and X-ray diffraction studies. Macrocycle II (R=H) can selectively bind dicarboxylates of certain chain length. These properties of the amide containing macrocycles allow for design of systems having a metal “active” site and a recognition site.

 

Young Investigator Symposium
1:30 PM-5:30 PM, Sunday, August 19, 2007 BCEC -- 206 A/B, Oral

Division of Inorganic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007