Dipyrrinones as anion receptors

CHED 383

Lyndsay Munro, lbm4@students.uwf.edu, Chris Musto, chemrocks72@yahoo.com, and Michael T. Huggins, mhuggins@uwf.edu. Department of Chemistry, University of West Florida, 11000 University Parkway, Pensacola, FL 32514
Anion binding is a relatively new area of molecular recognition chemistry that has potential applications in the chemical and biological worlds for extraction of pollutants, sensor development, medical applications, and various other fields. Dipyrrinones are well-known to be avid participants in hydrogen bonding. There are many examples of dipyrrinone interactions with carboxylic acids, amides, and even with itself via a network of intermolecular hydrogen bonds. In fact, it has been shown that dipyrrinone 1 exists predominately as the hydrogen-bonded dimer, both in the solid state and in solution. In the presence of various anions (Br-, Cl-, HSO4-, NO3-, etc), the hydrogen-bonded dimer is destroyed due to the formation of a 1-to-1 host:guest complex. The tetra-n-butylammonium hydrogen sulfate dipyyrinone 1 complex was characterized by x-ray crystal structure analysis and shown as such. The results of our studies in this area will be presented.