2007 Student Research Conference:
20th Annual Student Research Conference


The Synthesis of [16-(2-Hydroxy-benzoyl)-2,3,11,12-tetramethyl-5,14-dihydro-5,9,14,18-tetraaza-dibenzo[a,h]cyclotetradecene-7-yl]-(2-hydroxy-phenyl)-methanone and its metal complexes
Paul A. Goodman*, Sarah Moser, and Robert Miller
Dr. John O'Brien, Faculty Mentor

Synthetic dioxygen carriers have a range of possible uses. The first steps toward developing a useful dioxygen carrier are synthesis and characterization of the molecule. Tetraazadibenzo[14]annulene has characteristics which are very similar to porphyrin and by extension very similar to the biological heme group found in hemoglobin. This makes the molecule an interesting candidate for a mimic, and a derivative of this macrocycle is the focus of this study. The macrocycle [16-(2-Hydroxy-benzoyl)-2,3,11,12-tetramethyl-5,14-dihydro-5,9,14,18-tetraaza-dibenzo[a,h]cyclotetradecene-7-yl]-(2-hydroxy-phenyl)-methanone has been prepared first by synthesizing 4-Oxo-4H-chromene-3-carbaldehyde and reacting with 4,5-dimethyl-1,2-phenylenediamine. This synthesis has been preformed in greater than 90% yield. Further synthesis incorporated metals in the +2 oxidation state into the center of the macrocycle. Potentially, with the insertion of the proper metal ion, this macrocycle may be a useful carrier of dioxygen.

Keywords: macrocycle


Presentation Type: Poster

Session: 8-7
Location: OP Lobby
Time: 4:15 pm

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