Coupling of electron-deficient urea units with aliphatic chains gives rise to amphiphilic compounds that bind to phosphate and benzoate anions in the hydrogen bonding competitive solvent (DMSO) with KAss = 6 580 M-1 and KAss = 4 100 M-1, respectively. The anchoring of these receptor moieties to the dendritic support does not result in a loss of anion binding and enables new applications. Due to the formation of a microenvironment in the dendrimer, the high selectivity of the prepared compound toward benzoate is maintained even in the presence of aqueous media during extraction experiments. In the presence of binding sites at 5 mM concentration, the amount of benzoate corresponding to the full binding site occupancy is transferred into the chloroform phase from its 10 mM aqueous solution. A thorough investigation of the extraction behavior of the dendrimer reported here, supported by a series of molecular dynamics simulations, provides new insight into the fundamental principles of extraction of inorganic anions by amphiphiles.

Department of Bioorganic Chemistry and Biomaterials Institute of Chemical Process Fundamentals of the CAS v v i Rozvojová 135 Prague 6 16502 Czech Republic

Department of Organic Chemistry University of Chemistry and Technology Prague Technická 5 Prague 6 16628 Czech Republic

Department of Physical Chemistry University of Chemistry and Technology Prague Technická 5 Prague 6 16628 Czech Republic

Department of Solid State Chemistry University of Chemistry and Technology Prague Technická 5 Prague 6 16628 Czech Republic

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