Abstract
Perfluorinated alkyl substances, such as perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA), are toxic materials that are known to globally contaminate water, air, and soil resources. Strategies for the simultaneous detection and removal of these compounds are desired to address this emerging health and environmental issue. Herein, we develop a type of guanidinocalix[5]arene that can selectively and strongly bind to PFOS and PFOA, which we use to demonstrate the sensitive and quantitative detection of these compounds in contaminated water through a fluorescent indicator displacement assay. Moreover, by co-assembling iron oxide nanoparticle with the amphiphilic guanidinocalix[5]arene, we are able to use simple magnetic absorption and filtration to efficiently remove PFOS and PFOA from contaminated water. This supramolecular approach that uses both molecular recognition and self-assembly of macrocyclic amphiphiles is promising for the detection and remediation of water pollution.
Highlights
Perfluorinated alkyl substances, such as perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA), are toxic materials that are known to globally contaminate water, air, and soil resources
We report the nanomolar binding of two different guanidinocalix[5]arenes (GC5A-6C and GC5A-12C, which feature 6 and 12 carbon atoms in each alkyl chains at the lower rim of the macrocycles, respectively) (Fig. 1) towards PFOS and PFOA
Based on these structural features, we explored GC5A-6C as a candidate receptor mainly due to its complementary size and shape compared to the chain structures of PFOS and PFOA, as well as its salt-bridge interactions
Summary
Perfluorinated alkyl substances, such as perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA), are toxic materials that are known to globally contaminate water, air, and soil resources. By co-assembling iron oxide nanoparticle with the amphiphilic guanidinocalix[5]arene, we are able to use simple magnetic absorption and filtration to efficiently remove PFOS and PFOA from contaminated water This supramolecular approach that uses both molecular recognition and self-assembly of macrocyclic amphiphiles is promising for the detection and remediation of water pollution. PFOS and PFOA can bind to proteins[9] and deposit within the body, resulting in undesirable effects[10], including kidney[11] and liver[12] damage, thyroid disease[13], immunotoxicity[14], reproductive toxicity[15], and cancer[16] These pollutants are highly stable as a result of the thermodynamic stability of the C–F bonds[17] and demonstrate significant bioaccumulation, making them a persistent chemical threat to the environment[18]. Typical absorbents are made of activated carbon[28], carbon nanotubes[29], resins[28], polymers[30], mineral
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