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Relevant academic research and scientific papers

Crown calix[4]arenes, method of preparation and use for selective extraction of caesium

PCT No. PCT/FR98/00401 Sec. 371 Date Jan. 27, 1999 Sec. 102(e) Date Jan. 27, 1999 PCT Filed Mar. 2, 1998 PCT Pub. No. WO98/39321 PCT Pub. Date Sep. 11, 1998The invention relates to new calixarenes of formula: in which R1 represents a crown ether chain that includes at least two aryl or cycloalkyl rings, R2 is a hydroxyl or alkoxy group, or the two R2 groups together form a crown ether chain such as R1, and R3 represents a hydrogen atom or an alkyl group. The calixarenes are used to selectively extract caesium from aqueous solutions that notably have high concentrations of sodium.

Calix[4]arene dibenzocrown ethers as caesium selective extractants

A series of 1,3-dialkyloxycalix[4]arene dibenzocrown ethers were synthesized in the fixed 1,3-alternate conformation with good yields by the reaction of 1,3-dialkyloxycalix[4]arenes with dibenzodimesylate in the presence of caesium carbonate. The three dimensional 1,3-alternate conformation was confirmed by X-ray crystal structure. Upon two phase extraction, NMR studies on the ligand-metal complex, single ion and competitive ion transport experiments through a bulk liquid membrane, 1,3-dipropyloxycalix[4]arene dibenzocrown-6, in which two benzo groups are symmetrically attached to the crown-6 linkage, gave one of the most efficient and selective extractabilities for caesium ion over other alkali metal ions. From supported liquid membrane experiments using 1 and 3 as organic carriers, permeation coefficients of the caesium ion were estimated to be 0.42 and 0.27 cm h-1, respectively. The selectivity of caesium over sodium ion was observed to increase with permeation time.

A new calix[4]arene-bis(crown ether) derivative displaying an improved caesium over sodium selectivity: Molecular dynamics and experimental investigation of alkali-metal ion complexation

In the light of computational studies suggesting enhanced cation-binding abilities for various benzo derivatives of calix[4]arene-bis-crown-6 macrocycles, the synthesis and properties of one of these ligands, BC6B2, have been investigated. In this compound, di(1,2-phenylene)-annelated glycolic chains link the 1,3- and 2,4-phenyl rings of the calixarene, thereby forcing it into the 1,3-alternate conformation. The detailed structures of BC6B2·CH3NO2 1 and Cs2(NO3)2BC6B2·CHCl 3·H2O 2 have been established by X-ray crystallography. Studies of coordination and solvent extraction of the alkali-metal ions have been used to compare this ligand with a number of related systems known previously.

Selective sensing of caesium ions by novel calix[4]arene bis(dibenzocrown) ethers in an aqueous environment

Calix[4]arene bis(dibenzocrown) ethers 3 and 4 were successfully synthesized in the fixed 1,3-alternate conformation in over 70% yield via the reaction of calix[4]arene with dibenzo dimesylates 6 and 7, respectively, in acetonitrile in the presence of caesium carbonate as base. Exhibiting typical 1H NMR spectrum patterns, 3 and 4 are in the 1,3-alternate conformation, which is confirmed by X-ray analysis. Among four synthetic compounds tested, 3 shows the best selectivity and efficiency for a caesium ion complexation over other alkali metal ions using the single flux method through a bulk liquid membrane system. Enhancement of the complexation ability is attributable to the flatness and lipophilicity of the ethereal linkages caused by introducing the dibenzo groups on the calix[4]arene moiety. Two phase extraction experiments using calix[4]arene bis(crown) ethers with caesium ions are found to give a 1:1 ligand-metal complexation ratio.

Macroring-Neutral Molecule Complexation. Synthesis of Biconcave Pyridino Hosts, Complex Formation, and X-ray Crystal Structures of Two Inclusion Compounds

A series of pyridino macrocycles 1-3(a-e) incorporating rigid bi- and triaryl ether segments in different ring positions have been synthesized.The effect of incorporation of these building blocks into a given macroring framework on the host properties for

Neutral Ligands with Surfactant-Type Structure - Synthesis, Complexation, and Ion Transfer

New lipophilic neutral ligands which combine crown ether and podand characteristics with structural features of surfactants (cf. formulas 1-12, 16-26) were synthesized.Their complexation behaviour was studied, their solid-to-liquid and liquid-to-liquid phase transfer properties as well as their efficiency in ion transport across a liquid model membrane.Crystalline stoichiometric complexes of the cycles 2a-4a and of 3e with NaSCN, Ba(SCN)2, and BaI2 can be isolated.Among the noncyclic representatives a crystalline complex is obtained only from 11 with BaI2.The ligand 8d behaves in aqueous solution as a typical surfactant showing micelle formation and cloud point.

Polytopic Cation Receptors. 2. Synthesis and Selective Complex Formation of Spiro-Linked "Multiloop Crown Compounds"

A new type of crown compound (1-10) featuring a spiro-linked assembly of two to four individual macrorings differing in ring size, rigidity, and donor characteristics is synthesized.Syntheses were achieved by means of high-dilution techniques and blocking/deblocking procedures beginning with pentaerythritol as the basic building block.The ability of the new ligands ("multiloop crown compounds") to selectively form crystalline polyhomonuclear/heteronuclear complexes is studied.It is found that the symmetrically looped molecules (1a-c, 4a, 6, 7d) can incorporate two orthree identical metal cations well matched in their diameter (Li+, Na+, K+, Ca2+, Ba2+).Cations which are too large to fit into the crown rings of 1a-c complex in a sandwich-like manner; those which are too small effect a high hydration in their complexes.Asymmetrical 1d and 9 allow the common uptake of different metal ions, e.g., a combination of Li+ and Ba2+ or of 2K+ and Co2+.The specific occupation of the different subrings is discussed.Ligand 1b is shown to discriminate Ca2+ from Na+; 1c and 6 preferentially complex Ba2+ from a Ba2+/K+ mixture.Thus, the new ligands act as manifold selective cation receptors, corresponding to the specification of their binding compartments.

ION TRANSPORT ABILITY AND SELECTIVITY RELATING TO THE STRUCTURE OF SYNTHETIC IONOPHORES

o-, m-, p-Substituted benzoic acids (1, 2, 3) with polyether chain bearing hydroxy group at the end and the methylether of 1 (4) were prepared.With active transport of Na+ and K+ by 1-4, 1 and 4 exhibited K+-selectivity ov