Fluorocarbons are known to extract targets through noncovalent interactions with embedded fluorinated receptors. The strength of noncovalent interactions in fluorocarbons is significant in the few published studies, however, the knowledge of the related thermodynamics is very limited. In this study, ITC was employed to investigate quinazoline and pyridine (separately) with perfluorodecanoic acid (PFDA). ?G0 for the dissociation of (PFDA)2 in HFE-7500 (a semifluorous solvent) is 11.9�0.1 kJ/mol. The enthalpy for this reaction involving the breakdown of two hydrogen bonds is 32.3�1.3 kJ/mol. Quinazoline interacts with PFDA with ~1:1 stoichiometry, while pyridine interacts favorably with more than two equivalents of PFDA. The data associated with the pyridine/PFDA is complex, and can be best fit by a sequential binding analysis. Independently, we have developed fluorous nanoparticle composite films to act as a matrix for selective extractions based on molecular recognition. The ultimate goal is to develop extraction-based separation techniques and sensors.

Thermodynamics of molecular recognition in fluorous media using isothermal titration calorimetry (ITC)

244th National Meeting (2012)

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