Synthesis, X-ray crystal structure and cation binding properties of a tetrahomodioxacalix[4]arene tetraester

Arnaud‐Neu, Françoise; Cremin, Suzanne; Cunningham, D.; Harris, Stephen J.; McArdle, Patrick; McKervey, M. Anthony; McManus, Maureen; Schwing‐Weill, Marie‐José; Ziat, Khadija

doi:10.1007/bf01133318

Cited by 31 publications

(8 citation statements)

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“…They are also readily functionalized, which allows their decoration with, e.g., the functionalized thiols 153, 154, and 155 containing a terminal trimethylalkyl ammonium group, an 18-crown-6 moiety, and a phenyl group, respectively. 1 H NMR spectroscopic binding studies and DOSY NMR analyses in D 2 O revealed that the novel AuNPs 157 were able to well bind Gly-Phe (157) and Gly-Gly (158). Presumably, this is the result of cooperative interactions involving the quaternary ammonium ions and the crown ether moieties, as well as electrostatic interactions between the ammonium groups on the AuNP surface and the peptide carboxylate groups in the guests.…”

Section: Chemical Reviewsmentioning

confidence: 97%

“…In an effort to enhance the affinity and selectivity of ion pair receptors, the Beer group prepared two heteroditopic calix[4]arene bisesters, compounds 95 and 96 (Figure ). In this case, a lower-rim ester-substituted calix[4]arene platform was employed mainly due to its unique selectivity toward Na + cations. , In fact, receptor 95 was found to bind the Na + cation more effectively than Li + (as their respective perchlorate salts) with association constants of 3500 and 470 M –1 being seen for these two cations, respectively, as determined by 1 H NMR spectroscopic methods in acetone- d 6 . Almost no interactions were observed in the case of K + and NH 4 + .…”

Section: Recognition With Macrocyclic Ion Pair Receptorsmentioning

confidence: 99%

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Macrocycles as Ion Pair Receptors

et al. 2019

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Cation and anion recognition have both played central roles in the development of supramolecular chemistry. Much of the associated research has focused on the development of receptors for individual cations or anions, as well as their applications in different areas. Rarely is complexation of the counterions considered. In contrast, ion pair recognition chemistry, emerging from cation and anion coordination chemistry, is a specific research field where co-complexation of both anions and cations, so-called ion pairs, is the center of focus. Systems used for the purpose, known as ion pair receptors, are typically di-or polytopic hosts that contain recognition sites for both cations and anions and which permit the concurrent binding of multiple ions. The field of ion pair recognition has blossomed during the past decades. Several smaller reviews on the topic were published roughly 5 years ago. They provided a summary of synthetic progress and detailed the various limiting ion recognition modes displayed by both acyclic and macrocyclic ion pair receptors known at the time. The present review is designed to provide a comprehensive and up-to-date overview of the chemistry of macrocycle-based ion pair receptors. We specifically focus on the relationship between structure and ion pair recognition, as well as applications of ion pair receptors in sensor development, cation and anion extraction, ion transport, and logic gate construction. CONTENTS 3.4.

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Section: Chemical Reviewsmentioning

confidence: 97%

Section: Recognition With Macrocyclic Ion Pair Receptorsmentioning

confidence: 99%

Macrocycles as Ion Pair Receptors

et al. 2019

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“…The ionophoric properties of the phosphonato cavitand 3 towards metal cations were first determined by using the picrate extraction method. [40,41] According to this procedure, the percentage of picrate extracted was estimated by measurement of the distribution of picrate salts between chloroform and aqueous phases in the presence of the host molecule. The results presented in Figure 2 clearly show that the phosphonato cavitand 3 efficiently extracts these various hard metal cations, with maxima in the alkali and alkaline earth metal series for Cs ϩ and Ba 2ϩ cations, respectively.…”

Section: Cation Extraction Experiments With Phosphonato Cavitandmentioning

confidence: 99%

Synthesis and Binding Properties of iiii (4i) Stereoisomers of Phosphonato Cavitands − Cooperative Effects in Cation Complexation in Organic Solvents

et al. 2001

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Syntheses and host-guest properties of tetrabridged phosphorylated cavitands in their iiii (4i) configurations are described. The tetraphosphonato cavitands 2 and 3, with the four P=O bonds oriented inwards (4i stereoisomer) were prepared in 25% and 53% yields respectively, from the corresponding resorc[4]arenes, dichloro(phenyl)phosphane oxide and base. The formation of the 4i stereoisomers is solventdependent and is attributable to the capability of an ammonium guest to form an inclusion complex. Only the iiio (3io) stereoisomer of 3 was isolated otherwise, in low yield. These phosphonato cavitands, in their 4i configurations, are particularly efficient extractants for metal ions. The free energies of complexation of 3 with alkali metal and ammonium cations

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“…These b values are even higher than those found for the alkali metal cations. In this respect, ketone 2 resembles tetrahomodioxacalix [4]arene tetraethyl ester, 27 which does not extract Ca 2 and Ba 2 ions (ca 1% E), but forms very strong complexes (log b b 6) with these cations. Towards Ba 2 , its log b (4.9) is the highest value determined in this work, and agrees with the preference shown by 2 in extraction.…”

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confidence: 98%

Alkali and alkaline-earth metal cation complexation and transport properties by tetraphenyl ketone ofp-tert-butyldihomooxacalix[4]arene

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et al. 1999

J. Phys. Org. Chem.

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The tetraphenyl ketone of p-tert-butyldihomooxacalix [4]arene (2) was synthesized for the first time. This derivative possesses the cone conformation in solution at room temperature, which was confirmed by NMR measurements ( 1 H, 13C and NOE 1D). Extraction studies with metal picrates from neutral aqueous solution into dichloromethane, transport experiments with metal picrates through a dichloromethane membrane and stability constant measurements by UV absorption spectroscopy in methanol and acetonitrile were performed to evaluate the binding ability of ketone 2 towards alkali and alkaline earth metal cations. The tetraphenylketone of p-tertbutylcalix[4]arene (3) was also studied, and the results for the two derivatives were compared. Compound 2 shows a preference for K and Ba 2 cations, being selective only in the alkaline earth metal cation series. Compound 3 is a stronger binder than 2, but is a weaker extractant. Both show transport rates that are not proportional to complex stability or to extraction efficiency. Ketone 2 can be characterized as a selective receptor.

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Synthesis, X-ray crystal structure and cation binding properties of a tetrahomodioxacalix[4]arene tetraester

Cited by 31 publications

References 4 publications

Macrocycles as Ion Pair Receptors

Macrocycles as Ion Pair Receptors

Synthesis and Binding Properties of iiii (4i) Stereoisomers of Phosphonato Cavitands − Cooperative Effects in Cation Complexation in Organic Solvents

Alkali and alkaline-earth metal cation complexation and transport properties by tetraphenyl ketone ofp-tert-butyldihomooxacalix[4]arene

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