Rim‐Based Binding of Perfluorinated Acids to Pillararenes Purifies Water

Author:

Gao Tu‐Nan12ORCID,Huang Si13ORCID,Nooijen Rick1ORCID,Zhu Yumei4ORCID,Kociok‐Köhn Gabriele5ORCID,Stuerzer Tobias6ORCID,Li Guanna12ORCID,Bitter Johannes H.2ORCID,Salentijn Gert I. J.17ORCID,Chen Bo3ORCID,Miloserdov Fedor M.1ORCID,Zuilhof Han148ORCID

Affiliation:

1. Laboratory of Organic Chemistry Wageningen University Stippeneng 4 6708WE Wageningen The Netherlands

2. Biobased Chemistry and Technology Wageningen University Bornse Weilanden 9 6708WG Wageningen The Netherlands

3. Key Laboratory of Phytochemical R&D of Hunan Province and Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research of Ministry of Education Hunan Normal University 410081 Changsha China

4. School of Pharmaceutical Science and Technology Tianjin University 92 Weijin Road Tianjin 300072 China

5. Materials and Chemical Characterisation Facility (MC2) University of Bath Claverton Down BA2 7AY Bath United Kingdom

6. Bruker AXS GmbH Östliche Rheinbrückenstraße 49 76187 Karlsruhe Germany

7. Wageningen Food Safety Research (WFSR) Wageningen University & Research 6700AE Wageningen The Netherlands

8. China-Australia Institute for Advanced Materials and Manufacturing Jiaxing University 314001 Jiaxing China

Abstract

AbstractPer‐ and polyfluoroalkyl substances (PFAS) pose a rapidly increasing global problem as their widespread use and high stability lead worldwide to water contamination, with significant detrimental health effects.[1] Supramolecular chemistry has been invoked to develop materials geared towards the specific capture of PFAS from water,[2] to reduce the concentration below advisory safety limits (e.g., 70 ng/L for the sum of perfluorooctane sulfonic acid, PFOS and perfluorooctanoic acid, PFOA). Scale‐up and use in natural waters with high PFAS concentrations has hitherto posed a problem. Here we report a new type of host–guest interaction between deca‐ammonium‐functionalized pillar[5]arenes (DAF−P5s) and perfluoroalkyl acids. DAF−P5 complexes show an unprecedented 1 : 10 stoichiometry, as confirmed by isothermal calorimetry and X‐ray crystallographic studies, and high binding constants (up to 106 M−1) to various polyfluoroalkyl acids. In addition, non‐fluorinated acids do not hamper this process significantly. Immobilization of DAF−P5s allows a simple single‐time filtration of PFAS‐contaminated water to reduce the PFOS/PFOA concentration 106 times to 15–50 ng/L level. The effective and fast (<5 min) orthogonal binding to organic molecules without involvement of fluorinated supramolecular hosts, high breakthrough capacity (90 mg/g), and robust performance (>10 regeneration cycles without decrease in performance) set a new benchmark in PFAS‐absorbing materials.

Funder

National Natural Science Foundation of China

Wageningen University and Research Centre

Publisher

Wiley

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