Macrocyclic ionophores have recently gained attention and recognition in their ability to form sandwich complexes in solution with various anions by using their inward-projecting C-H bond donors. Through electrostatically binding with anions, these macrocycles effectively isolate the anions from solution. A retro-Claisen reaction has been observed to decompose fluorinated beta-diketones such as 1,1,1,5,5,5-hexafluoroacetylacetonate (hfac) into more water soluble trifluoroacetate (tfa). We will investigate the conditions required for fluorinated anions to undergo retro-Claisen and possibly other modes of decomposition. We will accomplish this by studying the effect of certain solvents such as chloroform on decomposition processes compared to the less acidic methylene chloride as well as the effect of solvation using methanol. In addition, we will explore if macrocycles can assist in building up lipophilic ß-diketonates to form anions that enhance size matching. These studies will be conducted using 1H and 19F NMR spectroscopy. From these findings, we can determine how cyanostar binds fluorinated organic anions and what conditions may facilitate retro-Claisen or other decomposition processes.

Investigation of the effect of solvent on fluorinated anions encapsulated by cyanostar

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