Issue 10, 2018

A rationally designed perfluorinated host for the extraction of PFOA from water utilising non-covalent interactions

Abstract

Perfluorooctanoic acid (PFOA) is a persistent organic pollutant and widespread in the environment. Three hosts have been synthesized based upon the formation of a fluorous cavity and hydrogen bonding receptors with the aim of extracting PFOA from water into organic solvents. The hosts based upon a calix[4]arene functionalized at the lower rim with amide groups and fluorous ponytails are effective for the quantitative removal of PFOA. Modification to a partial cone or a trisaminoamine framework reduces the conformational rigidity and lowers the extraction efficiency. A comprehensive NMR spectroscopic analysis both in solution and the solid state, along with other characterization techniques, has elucidated the stoichiometry of the host:guest species and the binding constants have been measured. A computational study has given further insight into the binding modes and corroborated the spectroscopic measurements.

Graphical abstract: A rationally designed perfluorinated host for the extraction of PFOA from water utilising non-covalent interactions

Supplementary files

Article information

Article type
Paper
Submitted
14 Aug 2017
Accepted
15 Nov 2017
First published
15 Nov 2017

New J. Chem., 2018,42, 7956-7968

A rationally designed perfluorinated host for the extraction of PFOA from water utilising non-covalent interactions

H. Omorodion, M. Palenzuela, M. Ruether, B. Twamley, J. A. Platts and R. J. Baker, New J. Chem., 2018, 42, 7956 DOI: 10.1039/C7NJ03026F

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