Analytical Applications of Calixarenes

Agrawal, Utsav; Kunji, S.; Menon, Shobhana K.

doi:10.1515/revac.1998.17.2.69

Cited by 23 publications

(6 citation statements)

References 155 publications

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“…In 1982, Moshfegh and co-workers reported the first synthesis of a series of functionalized [1.1.1]MCPs, i.e., p-halocalix [3]-arenes 4a-c [23] (Figure 4). Many calixarene-based molecular receptors have been synthesized and studied, but calix [4]arenes and its derivatives with amide, ketone and ester functionalities at the lower rim, which have shown significant cation affinity [12,13], have received the most attention to date. In general, modifications of calixarenes have been via functionalization of their lower or upper rims.…”

Section: Calixarene-analogous Mcps Containing Three Aromatic Rings: Calix[3]arene Analoguesmentioning

confidence: 99%

“…Derivatives of 3a are well-known to be able to exist in four different major conformationally immobile conformers known as cone, partial-cone, 1,3-alternate, and 1,2-alternate conformers (Figure 3) and which can be selectively generated and isolated by introducing different functional groups onto the lower rim of 3a [11]. Many calixarene-based molecular receptors have been synthesized and studied, but calix [4]arenes and its derivatives with amide, ketone and ester functionalities at the lower rim, which have shown significant cation affinity [12,13], have received the most attention to date. In general, modifications of calixarenes have been via functionalization of their lower or upper rims.…”

Section: Introductionmentioning

confidence: 99%

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Calix[3]arene-Analogous Metacyclophanes: Synthesis, Structures and Properties with Infinite Potential

et al. 2020

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Calixarene-analogous metacyclophanes (CAMs) are a special class of cyclophanes that are cyclic polyaromatic hydrocarbons containing three or more aromatic rings linked by one or more methylene bridging groups. They can be considered to be analogues of calixarenes, since, in both types of molecules, the component aromatic rings are linked by methylene groups, which are meta to each other. Since the prototype or classical calix[4]arene consists of four benzene rings each linked by methylene bridges, which are also meta to each other, it can be considered to be an example of a functionalized [1.1.1.1]metacyclophane. A metacyclophane (MCP) that consists of three individual hydroxyl-group functionalized aromatic rings linked by methylene groups, e.g., a trihydroxy[1.1.1]MCP may therefore, by analogy, be termed in the broadest sense as a “calix[3]arene” or a “calix[3]arene-analogous metacyclophane”. Most of the CAMs reported have been synthesized by fragment coupling approaches. The design, synthesis and development of functionalized CAMs, MCPs, calixarenes and calixarene analogues has been an area of great activity in the past few decades, due their potential applications as molecular receptors, sensors and ligands for metal binding, and for theoretical studies, etc. In this review article, we focus mainly on the synthesis, structure and conformational properties of [1.1.1]CAMs, i.e., “calix[3]arenes” and their analogues, which contain three functionalized aromatic rings and which provide new scaffolds for further explorations in supramolecular and sensor chemistry.

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Section: Calixarene-analogous Mcps Containing Three Aromatic Rings: Calix[3]arene Analoguesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Calix[3]arene-Analogous Metacyclophanes: Synthesis, Structures and Properties with Infinite Potential

et al. 2020

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“…Their recognizing ability and discriminating functionality for metal ions are remarkable features as specific receptors due to (1)a rigid macrocyclic structure for selectivity; (2)having cyclic phenolic hydroxyl groups for chemical modification; (3)having multifunctionality for high extractability [6][7][8][9][10]. Specific properties have been also reported by our group [11][12][13][14] and in particular, such ion-discriminating compounds are effective for the mutual separation of cognatic atoms of different size.…”

Section: Introductionmentioning

confidence: 96%

Aluminum Group Extraction with Benzoic Acid – Acetic Acid Crossed Type Calix[4]arene Derivatives

Kawashima

Kawakita

Ohto

et al. 2012

SERDJ

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A calix [4]arene carboxylic acid derivative alternatively possessing benzoic acid and two acetic acid groups has been prepared to investigate the extraction behavior for the aluminum group of metals, such as aluminum, gallium, and indium from nitrate and chloride media and to compare with the tetraacetic acid derivative. The present extraction reagent exhibits a simple ion-exchange mechanism for all metals. Both extractants show that the selectivity series is In > Ga >> Al in nitrate media, while Ga > In >> Al is found for chloride media due to complexation of indium with chloride anions. The stoichiometry of the gallium complex with both extractants, determined by the continuous variation method, was determined to be 1 : 1. The complexation site of the present extractant for gallium was also determined using 1 H-NMR spectroscopy. The extraction ability and separation efficiency of both extractants for the three metal ions were estimated by using the half pH values. Stripping of the metal ions loaded on the present extractant with hydrochloric acid was also investigated.

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“…Calixarene derivatives, which are easily synthesized from p-substituted phenol and formaldehyde [17] and functionalized in various ways [18], have been noted as useful extractants for a variety of metal ions [17][18][19][20][21][22]. Suitably functionalized calixarenes can selectively host a target metal ion due to the effect of the cavity size of the cyclic molecule together with the chelating and cooperating effect of multifunctional groups [17][18][19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

“…Suitably functionalized calixarenes can selectively host a target metal ion due to the effect of the cavity size of the cyclic molecule together with the chelating and cooperating effect of multifunctional groups [17][18][19][20][21][22]. Therefore, functionalized calixarenes are most promising candidates as highly selective and efficient solvent extraction reagents towards the target species.…”

Section: Introductionmentioning

confidence: 99%

Selective Extraction of Ga(III) with <i>p-t</i>-Butylcalix[4]arene Tetrahydroxamic Acid

Chetry

Adhikari

Morisada

et al. 2015

SERDJ

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Solvent extraction behavior of p-tert-butylcalix [4]arene tetrahydroxamic acid towards some trivalent as well as divalent cations was studied. The extraction selectivity of some cations followed the order Ga(III) > In(III) > Fe(III) > Cu(II) >> Zn(II), Ni(II). Since the extraction reagent exhibited high selectivity for Ga (III) and In(III), the detailed extraction behavior for Ga(III) and In(III) was investigated by slope analysis, the continuous variation method, and by loading tests. It was confirmed that both metals formed 1:1 complexes with the extraction reagent. Since the pK a values for hydroxamic acids are 8-9, there was 6-7 units of pH shift in the metal extraction caused by the complexation of Ga(III) indicating that this ligand served as an excellent reagent for selective extraction of Ga(III). The coordination site of the ligand for both metals was qualitatively investigated by IR spectra before and after metal loading on the ligand. The loaded Ga(III) was quantitatively stripped by using dilute acidic solutions and the ligand was regenerated.

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Analytical Applications of Calixarenes

Cited by 23 publications

References 155 publications

Calix[3]arene-Analogous Metacyclophanes: Synthesis, Structures and Properties with Infinite Potential

Calix[3]arene-Analogous Metacyclophanes: Synthesis, Structures and Properties with Infinite Potential

Aluminum Group Extraction with Benzoic Acid – Acetic Acid Crossed Type Calix[4]arene Derivatives

Selective Extraction of Ga(III) with <i>p-t</i>-Butylcalix[4]arene Tetrahydroxamic Acid

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