Perfluoroalkyl- vs alkyl substituted malonamides: Supramolecular effects and consequences for extraction of metals

Substitution of extracting molecules with a long perfluoroalkyl chain was performed in order to modulate the weak intermolecular interactions and the supramolecular ordering of an organic system employed to recover metals of interest during liquid-liquid extraction processes.

(Equipe LHYS et LTSM)

The fluorous compounds were compared to their hydrocarbon counterparts: both molecules present a hydrophilic moiety, responsible for metal chelation, and a hydrophobic chain, which enables solubility into organic media. But this chain is also oleophobic in the case of the fluorous compound. We observed that the oleophobic character the fluorous chain prevails over the tendency of hydrophilic moieties to self-assemble: in the organic phase, fluorous compounds lead to direct aggregates with a fluorous core, whereas hydrocarbon compounds lead to reverse aggregates with a hydrophilic core. 

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Dul MC., Braibant B., Dourdain S., Pellet-Rostaing S., Bourgeois D. and Meyer, D Journal of Fluorine Chemistry 200, 59 (2017)