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 K
Ass = 6 580 M–1 and K
Ass = 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.