Browsing by Author "Tsenkova, Boryana Krasimirova"
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- Synthesis and characterization of ionic co-crystals of enantiopure and racemic prolinePublication . Tsenkova, Boryana Krasimirova; Cavaco, Isabel; Duarte, TeresaAn ionic co-crystal (ICC) is a multicomponent solid formed by at least an organic molecule and an inorganic salt in a defined stoichiometric ratio. ICCs have the potential to alter physicochemical properties (such as solubility and thermal stability) of a pure organic material of interest, and recent research has also highlighted the possibility of chiral resolution through ICC formation. The purpose of the current work was to synthesize and characterize novel ionic co-crystals of racemic proline with lithium halides using mechanochemical and solution techniques, and to investigate the solid-state chiral resolution ability of lithium. The synthesis of molecular and ionic co-crystals of enantiopure and racemic proline with different inorganic salts and organic co-formers was attempted in order to obtain novel compounds with modified properties. Powder and Single Crystal X-ray diffraction, TGA and DSC were the main techniques used for the characterization of the novel compounds. The results obtained confirm the potential for chiral resolution through ICC formation as conglomerate and racemate ICCs were obtained. In the racemate ICCs, at least in the 1:1 stoichiometry amino acid to lithium halide, a very consistent pattern was observed - the homochiral preference of Lithium resulted in the formation of homochiral columns. Previously described in the literature ICC of (DL-Proline)2•ZnCl2 with homochiral columns spiked our interest and a different synthesis procedure was followed, resulting in the formation of a (DL-Proline)2•ZnCl2 polymorph without the homochiral columns. These results encourage further studying the factors that promote homochiral column formation in the crystal packing - a possible precursor to conglomerate formation. Narrowing down these factors could allow us in the future to fine-tune the co-crystallization of chiral compounds as a conglomerate or a racemate ICC and pave the road towards novel methods for chiral resolution.