Using CPL for Enantioselective Recognition of Amino Acids

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The work described in this proposal is intended to serve as a starting point aimed at demonstrating that circularly polarized luminescence (CPL) spectroscopy would be an attractive complementary and/or alternative method to current techniques used as specific structural probes of chiral molecules. The initial efforts in this project will be to develop a technique to determine the absolute stereochemistry of simple chiral organic molecules such as amino acids. The emphasis here is the design of experiments aimed at understanding, improving, and maximizing the major non-covalent interactions governing the chiral discrimination between racemic lanthanide(lll) complexes and chiral organic molecules. Several aims will form the bulk of this proposal: (i) the ability to identify "ideal" racemic lanthanide complexes by designing and synthesizing appropriate ligands, (ii) the addition of chirality into our complex systems will improve the selectivity toward simple chiral molecules, (iii) a judicious change in the selected transition used for circular polarization excitation would overcome the limitation of the low intensity of the currently allowed-magnetic dipole chosen for CPL measurement, but will also considerably enhance the structural information gained from the Eu(lll) systems of interest, and (iv) the investigation of the importance of the various non-covalent chiral discriminatory interactions. The ultimate goal of this work is to be able to develop CPL spectroscopy as an important tool for biological applications.