Syntheses of two diamine substituted 1,3-distal calix[4]arene-based magnetite nanoparticles for extraction of dichromate, arsenate and uranyl ions

The synthesis of two new calixarene derivatives 4 and 5, functionalized at the lower rim with 4-amino-1-benzylpiperidine to give diamide and diamine derivatives of p-tert-butylcalix[4]arene, is described. They were obtained by the reaction of both the diester derivative of p-tert-butylcalix[4]arene (2) and the dialkyl bromide derivative of p-tert-butylcalix[4]arene (3) with 4-amino-1-benzylpiperidine. The 1H NMR spectra of calixarene derivatives show that 4 and 5 exist in the cone conformation. Moreover, these diamide and diamine derivatives of p-tert-butylcalix[4]arene (4 and 5) have been immobilized onto [3-(2,3-epoxypropoxy)-propyl]-trimethoxysilane-modified Fe3O4 magnetite nanoparticles to obtain calixarene-based magnetic nanoparticles M-DADBP-Calix (6) and M-DABP-Calix (7). The calix[4]arene immobilized materials were characterized by a combination of Fourier Transform Infrared Spectroscopy (FTIR), Transmission Electron Microscopy (TEM) and Thermogravimetric Analyses (TGA) and elemental analysis. Additionally, the studies regarding the removal of As(V)/Cr(VI) ions as well as U(VI) ion from aqueous solutions were also carried out by using these compounds in liquid–liquid/solid–liquid extraction experiments.