Synthesis of calix[4]aren compounds thioether derivatives and investigation of their ion transport properties

SYNTHESİS of CALİX[4]AREN COMPOUNDS THİOETHER DERİVATİVES and INVESTIGATİON of THEİR ION TRANSPORT PROPERTIES.Emel KARAOĞUL ÖZAfyonkarahisar Kocatepe UniversityFaculty of Science and ArtsDepartment of ChemistrySupervisor: Assist Prof. Dr. Gülderen Uysal AKKUŞThe project comprises synthesis of calix[4]arene thioether derivatives, their corresponding oligomers and copolymers that are selective extractants for toxic metal cations and anions and their liquid-liquid and solid-liquid extraction studies. Structures of these compounds were characterized by spectroscopic techniques (FTIR, 1H NMR), elemental analysis and CPC (gel permeability chromatography).Synthetic work was carried out according to the methods described in the literature Initially, 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetra-hydroxycalix[4]-arene (1) was synthesized followed by the synthesis of 5,11,17,23-tetra-tert-butyl-25-(4-nitrobenzyloxy)-26,27,28-trihidroxycalix[4]-arene (2) by treatment with p-nitrobenzylbromide in acetonitrile in the presence of K2CO3. Then compound 3 was obtained by means of treating compound 2 with 2-chloroethyl methyl sulfide in the presence of K2CO3 and NaI in dry acetone. Then nitro groups of this compound reduced to amino groups (4). The monomer 5 was obtained by treatment of compound 4 with acryloyl chloride in CHCl3 in the presence of pyridine. Finally the copolymer 6 was obtained by treatment of this monomer with styrene in toluene in the presence of radical initiator.Liquid-liquid extraction studies of these compounds were performed with transition metal (Cu2+, Co2+, Ni2+, Cd2+ and Hg2+) cations and Cr2O32- anion in order to observe their ion transport properties.2009, 81 pagesKeywords: calixarene, transition metal, copolymer, solvent extraction