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Cationic water-soluble deep cavitands enable hierarchical assembly-based recognition, optical detection and extraction of perfluoroalkyl substances (PFAS) in aqueous solution. Recognition of the PFAS occurs at the lower rim crown of the cavitand, which triggers self-aggregation of a PFAS-cavitand complex, allowing extraction from water. In addition, when paired with an indicator dye that can be bound in the cavity of the host molecule, the PFAS-cavitand association causes a significant (>20-fold at micromolar [PFAS]) enhancement of dye fluorescence due to conformational rearrangement of the fluxional cavitand AMI, allowing optical sensing of PFAS. The cavitands are water-soluble, and the detection and recognition occur in purely aqueous solution. The association is most effective for long chain sulfonate PFAS, and as such, selective optical detection of perfluorooctanesulfonate is possible, with a LOD = 130 nM in buffered water, and 500 nM in real-world samples such as polluted canal water. By pairing the AMI host with multiple dyes in an array-based format, full discrimination of five other PFAS can be achieved at micromolar concentration via differential sensing. In addition, the aggregation process allows extraction of PFAS from solution, and a 99% reduction of PFOS concentration in water is possible with a single treatment of an equimolar concentration of AMI cavitand. The hierarchical nature of the cavitand recognition system allows both selective, sensitive optical detection and extraction of PFAS from water with a single scaffold.