Synthesis and application of an efficient calix[4]arene-based anion receptor bearing imidazole groups for Cr(VI) anionic species

We synthesized the new calix[4]arene amines bearing two and four imidazole or tert-butylamine moieties (9a,b/10a,b) by the reaction of di- or tetra-tosylated calix[4]arene derivatives (7 and 8, respectively) with 1-(3-aminopropyl)imidazole and/or tert-butylamine, respectively. After the characterization of 9a,b/10a,b their extraction abilities toward Cr(VI) anionic species (CAS) was evaluated and compared by the liquid-liquid extraction method. The extraction results revealed that calix[4]arene amine having four imidazole groups (10a) was an efficient anion receptor for CAS. Moreover, the extraction of CAS by 10a in the presence of other anions such as Cl−, NO3−, and PO43− showed that 10a could be a selective anion receptor for CAS in the presence of those anions.