Surface Modification of Aminopropylated Silica Gel with Tetraphosphorylated bis -Methoxycarbonylmethoxycalix[4]Arenes fo
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SURFACE MODIFICATION OF AMINOPROPYLATED SILICA GEL WITH TETRAPHOSPHORYLATED bis-METHOXYCARBONYLMETHOXYCALIX[4]ARENES FOR EFFECTIVE EUROPIUM(III) SORPTION O. A. Yesypenko,1 Yu. S. Boiko,1,3 K. N. Belikov,2,4 K. Yu. Bryleva,2 Z. Yu. Bunina,2 A. B. Rozhenko,1,5 S. V. Shishkina,2 A. B. Drapailo,1 R. V. Rodik,1 L. ². Atamas,1 A. A. Golub,3 and V. I. Kalchenko1
UDC 547.63+547.562+543.054
bis-Methoxycarbonylmethoxy derivatives capable of reacting with the surface of aminopropylated silica gel with the formation of chemically and thermally stable amide bonds were obtained by regioselective distal dialkylation of hydroxyl groups of phosphorylated tetrahydroxycalix[4]arenes in high yields. It was found that phosphine oxide and phosphonate P=O groups localized on the upper rim cooperatively bind Eu3+ cations and effectively sorb them from nitric acid solutions.
Keywords: calixarenes, complexing agents, sorbents, silica gel, europium, DFT, X-ray diffraction analysis.
Calixarenes are cup-shaped macrocyclic compounds that are easily obtained by precision cyclocondensation of para-substituted phenols with formaldehyde in the presence of catalytic amounts of alkali metal hydroxides [1]. Calixarenes have almost unlimited possibilities for chemical functionalization of the upper rim of the macrocycle (para-positions of phenolic rings) and the lower rim of the macrocycle (phenolic hydroxyl groups) by various groups [2]. Due to high selectivity, which is close to the selectivity of natural enzymes, functionalized calixarenes can recognize, bind into supramolecular complexes, and separate cations, anions, gases, organic molecules, and biomolecules [3-8]. Organophosphorus derivatives occupy an important place in the family of functionalized calixarenes [9]. They are used in the design of extractants and sorbents for analytical chemistry, radiochemistry, and extraction of actinide and lanthanide isotopes from spent nuclear fuel of nuclear power plants [10-14]. Phosphorylated calixarenes with reactive functional groups were used to modify the surface of porous matrices. For example, tetrahydroxythiacalixarene tetraphosphonate was chemically bound to the surface of the chloromethylated Merrifield resin, which showed efficient sorption of trivalent europium from nitric acid solution [15]. Tetrahydroxycalixarene with four carbamoyl phosphine oxide groups was bound to the silica surface by silicon tetrachloride [16]. The resulting sorbent effectively removes europium(III) from nitric acid solutions and separates americium and europium. In addition, the inherent ________ 1 Institute of Organic Chemistry, NAS of Ukraine, Kyiv, Ukraine. E-mail: [email protected]. 2 State Scientific Institution “Institute for Single Crystals,” NAS of Ukraine, Kharkiv, Ukraine. 3 National University of “Kyiv-Mohyla Academy,” Kyiv, Ukraine. 4 V. N. Karazin Kharkiv National University, Kharkiv, Ukraine. 5 National Technical University of Ukraine “Igor Sikorsky Kyiv Polytechnic Institute,” Kyiv, Ukraine. _______________________________________________________
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