Synthesis of water soluble molecular receptor from calix[4]arene-bis-crown-6

Nicod, Laurence; Pellet‐Rostaing, Stéphane; Chitry, Frédéric; Lemaire, Marc; Barnier, H.; Federici, V.

doi:10.1016/s0040-4039(98)02189-3

Cited by 32 publications

(6 citation statements)

References 15 publications

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“…This selectivity was mainly due to the excellent size match between the cation and the ether loop of the ligand, and to the impossibility for the crown part, attached to the calixarene, to wrap around the smaller Na + cation. However, they were lipophilic ligands, and the only way to use them in an aqueous medium for NF-complexation systems was to modify their structure by adding hydrophilic groups, 13,14 hopefully keeping them cesium selective. The resulting molecules had basic (6) or neutral (7), carboxylic (8 and 9), or phenolic (10 and 11) hydrophilic substituants.…”

Section: Determination Of Cs-ligand Complex Formation Constant By Nf-mentioning

confidence: 99%

New Cesium-Selective Hydrophilic Ligands: UV Measures of Their Interactions toward Cs and Cs/Na Separation by Nanofiltration Complexation

et al. 2000

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Separating traces of cesium from aqueous medium containing large sodium amounts is a difficult problem because cesium and sodium ions have a similar behavior in aqueous medium. We selected a highly cesiumselective ligand in aqueous medium, and we determined the best conditions for using this ligand in a nanofiltration-complexation process in order to achieve Cs + /Na + separation. We also tried to find a relation between the ligand structure and its activity toward cesium complexation. Tetrahydroxylated bis-crown-6 calix[4]arene was found to be very cesium selective (S ) (Cs + )/ (Na + ) ) 6600). Combined with a nanofiltration process, this ligand helped reaching 90% cesium retention in a highly concentrated aqueous medium ([NaNO 3 ] ) 3 mol/L). IntroductionAmong the different available separative methods (liquidliquid and solid-liquid extractions, ion-exchange resins), nanofiltration (NF) is a new pressure-driven membrane process which produces very few additional wastes. Located between ultrafiltration and reverse osmosis, nanofiltration membranes " cutoffs " are in the range of 300-1000 g/mol molecular weight. 1-3 Moreover, to increase ionic separation, nanofiltration can be combined with a selective complexation step: retention of the target element is improved because the complex with the ligand, of larger size and mass than the target ion, prevents this ion from passing through the membrane. 4 For such a purpose, water-soluble ligands with molecular weight of about 500 g/mol can be used in the case of the nanofiltrationcomplexation association, whereas micro-or ultrafiltrationcomplexation systems need larger ligands and induce some specific problems of increasing viscosity and precipitation. 5 Our laboratory has been developping the nanofiltrationcomplexation technique since 1993. [6][7][8][9] We showed that using EDTA with a Desal 5 DK or a Nanomax 50 membrane allowed a 100% retention (rejection) of Sr 2+ and other polyvalent ions, and only a 10% retention of Na + and Cs + ions. Then, with the use of a cesium-selective ligand such as resorcinarene, Cs + / Na + separation was also improved but not satisfactorily. In fact, to remove radioactive traces of cesium in highly salted aqueous medium, a minimum of 99% Cs + retention with a maximum of 10% Na + retention is required for industrial applications.So the aim of the present study was to select a highly cesiumselective ligand in aqueous medium, and then to determine the

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Section: Determination Of Cs-ligand Complex Formation Constant By Nf-mentioning

confidence: 99%

New Cesium-Selective Hydrophilic Ligands: UV Measures of Their Interactions toward Cs and Cs/Na Separation by Nanofiltration Complexation

et al. 2000

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“…With the aim of practical applications, we have prepared an analogue of 6 (Calix‐COU2) that is soluble in water. By using the method developed by Lemaire and co‐workers for introducing sulfonate groups onto calixarene,24 we synthesized compound 7 , which contains four sulfonyl groups 25. This compound is highly fluorescent ( Φ F = 0.4) and completely soluble in water.…”

Section: Caesium Sensingmentioning

confidence: 99%

Calixarene‐Based Fluorescent Molecular Sensors for Toxic Metals

2009

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There is an increasing interest in the early detection of toxic metals in the environment. In this context, fluorescence is a very attractive detection method because of its intrinsic sensitivity, its response time and the possibility of imaging via fluorescence microscopy. Of the various complexing units available for the detection of toxic metal ions (chelators, open‐chain structures, crown‐ethers, cryptands), calixarenes offer distinct advantages in term of selectivity and the easy incorporation of a fluorophore into the structure. In this microreview, after recalling the main classes offluorescent molecular sensors based on cation‐induced changes in excited‐state processes (photoinduced electron‐ or charge‐transfer, excimer formation, energy transfer), we present various calixarene‐based sensors designed for the detection of caesium, mercury, lead and cadmium.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…The preparation of water-soluble calix [4]arene-bis(crown ethers) 30a ± c has been described. These compounds were shown 91 to have high affinities for cesium ions. Calix [4]arene[-bis(tribenzo)-crown-6] (31) 90 and non-symmetrical calix [4]arene[bis-crown ethers] (32, 33) 96 were synthesised.…”

Section: Reprocessing Of Spent Nuclear Fuel and Extraction Of Fission...mentioning

confidence: 99%

Crown ethers in radiochemistry. Advances and prospects

Нестеров¹

2000

Russ. Chem. Rev.

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Methods for the immobilisation of dicyclohexano-and Methods for the immobilisation of dicyclohexano-and non-substituted crown ethers are reviewed. Data on the radiation non-substituted crown ethers are reviewed. Data on the radiation chemistry of these compounds and on the influence of irradiation chemistry of these compounds and on the influence of irradiation on the properties of crown-containing extraction systems pub-on the properties of crown-containing extraction systems published over the last decade are discussed systematically. Examples lished over the last decade are discussed systematically. Examples of the use of crown ethers in different fields of radiochemistry are of the use of crown ethers in different fields of radiochemistry are presented. The bibliography includes 199 references presented. The bibliography includes 199 references. .

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Synthesis of water soluble molecular receptor from calix[4]arene-bis-crown-6

Cited by 32 publications

References 15 publications

New Cesium-Selective Hydrophilic Ligands: UV Measures of Their Interactions toward Cs and Cs/Na Separation by Nanofiltration Complexation

New Cesium-Selective Hydrophilic Ligands: UV Measures of Their Interactions toward Cs and Cs/Na Separation by Nanofiltration Complexation

Calixarene‐Based Fluorescent Molecular Sensors for Toxic Metals

Crown ethers in radiochemistry. Advances and prospects

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