Synthesis and complexation properties of 1,3-alternate calix[4]arene-bis(crown-6) derivatives

Pellet‐Rostaing, Stéphane; Chitry, Frédéric; Nicod, Laurence; Lemaire, Marc

doi:10.1039/b009508g

Cited by 16 publications

(12 citation statements)

References 19 publications

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“…Many substituents, bromo [109,110], nitro [111], carboxylic [109,110], aldehyde [110] and hydroxy groups [111], can be selectively introduced at the para-positions of benzene rings of the 1,3-alternate calix [4]arene framework to provide desired properties. The bromo derivatives 41a and 41k are very useful for the introduction of other functional groups [109,110].…”

Section: Type (E) -Doubly-bridged 13-alternate Calix[4]arenes Rendermentioning

confidence: 99%

“…It was found that all 1,3-alternate calix [4]arene-crown-6 ligands containing ionizable groups at para-positions possessed higher Cs + extraction efficiencies than the conventional 1,3-alternate calix [4]arene-crown-6 [109,110]. The dihydroxycalix [4]arenebiscrown-6 41i exhibited a higher Cs + /Na + selectivity than the dicarboxylate 41h but lower than the tetrahydroxycalix [4]arene-biscrown-6 41l [110].…”

Section: Type (E) -Doubly-bridged 13-alternate Calix[4]arenes Rendermentioning

confidence: 99%

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1,3-Alternate, the Smart Conformation of Calix[4]arenes

Baklouti¹,

Harrowfield²,

Pulpoka³

et al. 2006

MROC

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Section: Type (E) -Doubly-bridged 13-alternate Calix[4]arenes Rendermentioning

confidence: 99%

Section: Type (E) -Doubly-bridged 13-alternate Calix[4]arenes Rendermentioning

confidence: 99%

1,3-Alternate, the Smart Conformation of Calix[4]arenes

Baklouti¹,

Harrowfield²,

Pulpoka³

et al. 2006

MROC

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“…Among them, NF is a pressure membrane process with molecular weight cutoff (MWCO) between reverse osmosis (RO) and ultrafiltration (UF). Among them, calixarenes such as tetrahydroxy-calix [4]arene-bis-crown [6] or 2,8,14,20-tetra(methyl) calix- [4]resorcinarene [7] (resorcinarene) are soluble in basic aqueous medium. [3] Because of these characteristics, the NF technique shows a great potential for the separation of ions in aqueous phase.…”

Section: Introductionmentioning

confidence: 99%

“…The NF-organic membranes are ideally suited for rejecting organics with molecular weights.200 Da and multivalent ions. [8,9] However multistep synthesis of calixarenes [6] and their solubility at pH .12 limit their used with NForganic membranes. These properties allow the separation of different ion valences, but this selectivity is not generally ensured for the separation of ions with the same valences.…”

Section: Introductionmentioning

confidence: 99%

Cs⁺/Na⁺ Separation by Nanofiltration-Complexation with Resorcinarene

Sorin

Pellet‐Rostaing

Favre‐Réguillon

et al. 2004

Separation Science and Technology

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Cesium-137 is considered as one of the most dangerous radioactive materials that can be very easy move into the environment and contaminate it. This study aims to determine the optimum conditions for cesium/ sodium separation by nanofiltration (NF)-complexation on Nanomax 50 membrane with resorcinarene as the complexing agent. Protonation constants of resorcinarene were determined by potentiometric titration in 0.1 mol/L NaNO 3 at 258C (log K H1 ¼ 9.24 + 0.06; log K H2 ¼ 10.21 + 0.03; log K H3 ¼ 8.59 + 0.07; log K H4 ¼ 7.85 + 0.08). The apparent formation constants of the Cs þ -resorcinarene (log K CsL ) were determined by UV spectrophotometry to evaluate the selectivity of resorcinarene toward cesium complex formation as a function of the pH.Parameters such as the pH, [resorcinarene]/[Cs þ ] ratio were studied to reach 80% of cesium rejection in 3 mol/L of NaNO 3 . The stability of resorcinarene was studied as a function of the pH and the concentration of NaNO 3 by 1 H and 13 C NMR studies in D 2 O. Resorcinarene stability up to 30 days in [NaNO 3 ] ¼ 2 mol/L at pH 9 was determined, although at pH 12 and with the same sodium concentration, resorcinarene stability was 5 days. Finally, the conditions to reach 80% of cesium rejection in the presence of 2 Â 10 4 fold of sodium were found at pH 10 with [resorcinarene]/[Cs þ ] ratio of 25 or at pH 11 with [resorcinarene]/[Cs þ ] ratio of 20.

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“…This could be improved by associating the nanofiltration step to a preliminary selective complexation step with water-soluble ligands of molecular weight higher than the 'cut off' of the membrane (300 -1000 g mol). In previous reports we described the synthesis and the evaluation of several water-soluble calix [4]arene-bis-(crown-6) 33,34 incorporating neutral or proton-ionizable substituents such as sulfonamide, sulfonate, carboxy and hydroxy groups at the para position of the aromatic ring. The selective complexation of caesium towards alkali ions (Na þ , K þ , Rb þ , Cs þ ) and with these ligands were studied in basic aqueous media by UV -Vis analysis, NMR spectroscopy and nanofiltration -complexation tests.…”

Section: Introductionmentioning

confidence: 99%

New water-soluble calix[4]arene-bis(benzocrown-6) for caesium–sodium separation by nanofiltration–complexation

Pellet‐Rostaing¹,

Chitry²,

Spitz³

et al. 2003

Tetrahedron

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Calix-bis(benzocrown-6) 6 and 7 were converted into the water-soluble receptors 9, 10, 12 and 15 by introducing hydroxy, carboxy, sulfato or diethanolamino groups at the para position of the phenolic ring and/or on the benzo-ether moieties. The complexation properties of these ionophores were studied for all alkali cations in methanolic and aqueous media. Stability constants were calculated by UV-Vis spectroscopy. All ligands showed a more or less affinity for the larger cations, depending on the nature and the position of the substituents grafted on the benzo-ether chain only or both on the calixarene ring and the benzo-ether loop. For selective Cs þ /Na þ separation, the efficiency of the ligands was evaluated by means of a nanofiltration system. In comparison with the known tetrahydroxylated bis-crown-6 calix[4]arene 1, compounds 9, 12 and 15 represent the most selective ligands for the Cs þ cation in a moderate salted medium ([NaNO 3 ]¼85 g/L).

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Synthesis and complexation properties of 1,3-alternate calix[4]arene-bis(crown-6) derivatives

Cited by 16 publications

References 19 publications

1,3-Alternate, the Smart Conformation of Calix[4]arenes

1,3-Alternate, the Smart Conformation of Calix[4]arenes

Cs⁺/Na⁺ Separation by Nanofiltration-Complexation with Resorcinarene

New water-soluble calix[4]arene-bis(benzocrown-6) for caesium–sodium separation by nanofiltration–complexation

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Synthesis and complexation properties of 1,3-alternate calix[4]arene-bis(crown-6) derivatives

Cited by 16 publications

References 19 publications

1,3-Alternate, the Smart Conformation of Calix[4]arenes

1,3-Alternate, the Smart Conformation of Calix[4]arenes

Cs+/Na+ Separation by Nanofiltration-Complexation with Resorcinarene

New water-soluble calix[4]arene-bis(benzocrown-6) for caesium–sodium separation by nanofiltration–complexation

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Product

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Cs⁺/Na⁺ Separation by Nanofiltration-Complexation with Resorcinarene