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

Kim, Jong Seung; Suh, Il-Hwan; Kim, Jong Kuk; Cho, Moon Hwan

doi:10.1039/a803144d

Cited by 46 publications

(20 citation statements)

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“…19,20 Structural modifications of the calix and the binding sites and a variation in the cavity size have been mainly responsible for the use of calixarenes as selective sensing agents for ions other than sodium. [21][22][23][24][25][26][27] Calixarenes with soft donor atoms as binding sites have also been reported as ion-selective electrodes for heavymetal ions (silver, copper, lead). [28][29][30] Recently, silver and cesium ion-selective electrodes have been reported by our group.…”

Section: +mentioning

confidence: 99%

Mercury(II) Ion-Selective Electrodes Based on p-tert-Butyl Calix[4]crowns with Imine Units

Mahajan

Kaur

et al. 2004

ANAL. SCI.

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Due to the toxic nature of mercury, many methods have been developed for its detection and treatment in various chemical systems. Of these, potentiometric detection based on two types of ion-selective electrodes is described in the literature for the detection of mercury ions. 1,2 One is a solid-state mercury(II) sulfide electrode; 1 the other is a liquid-membrane electrode, 3 which is one of the most important types of chemical sensors. Liquid-membrane electrodes, prepared with a poly(vinyl chloride) immobilized carrier, are easy to implement, inexpensive and reliable. [4][5][6][7] These electrodes show good stability, a relatively fast response time and a wide dynamic range. Many organic and inorganic compounds have been investigated as sensing agents in producing ISEs. 8-11Dithiazone, 12 1,4-dithia-12-crown-4, 13 hexathia-18-crown-6-tetrone, 14 and 2-mercaptobenzimidazole 15 have been reported in the literature as Hg 2+-PVC-based membrane electrodes having a good Nernstian response and a high ion selectivity.Calixarenes, due to their suitable complexation characteristics with cations, have been used as neutral ionophores in ionselective electrodes. [16][17][18][19] Calixarene tetraesters and related derivatives have been used as sensing agents in sodium-sensors for the chemical analysis of sodium in body fluids. 19,20 Structural modifications of the calix and the binding sites and a variation in the cavity size have been mainly responsible for the use of calixarenes as selective sensing agents for ions other than sodium. [21][22][23][24][25][26][27] Calixarenes with soft donor atoms as binding sites have also been reported as ion-selective electrodes for heavymetal ions (silver, copper, lead). [28][29][30] Recently, silver and cesium ion-selective electrodes have been reported by our group. [24][25][26][27] Continuing efforts in the same direction, the present paper deals with a mercury(II) ion-selective electrode based on the p-tert-butyl calix[4]crown derivative with imine units as an ionophore (Scheme 1). The electrode exhibits a good response for mercury(II) ions over a concentration range of 5.0 × 10 -5 -1.0 × 10 -1 M with a near-Nernstian slope of 27.3 mV per decade. The electrode shows high selectivity for mercury(II) ions over most of the alkali, alkaline-earth and transition metal ions (Na + , ExperimentalIonophore p-tert-Butyl calix[4]crowns with imine units used as an ionophore in this work was synthesized in our laboratory. Synthesis of the ionophore involved the formation of an aldehyde by generating a phenoxide ion, followed by an attack on the bromides to give dialdehyde, which was then condensed with the calixamine to give a [1+1] Schiff base product (Scheme 1). Other reagentsAll of the reagents used were of analytical-reagent grade. High-molecular-weight poly(vinyl chloride) (PVC), bis(2-ethylhexyl)sebacate (DOS), bis(2-ethylhexyl)phthalate (DOP), bis(2-ethylhexyl)adipate (DOA), tri-n-butylphosphate (TBP), 1-decanol, and especially dried tetrahydrofuran were used as received from Fluka. Sodiu...

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Section: +mentioning

confidence: 99%

Mercury(II) Ion-Selective Electrodes Based on p-tert-Butyl Calix[4]crowns with Imine Units

Mahajan

Kaur

et al. 2004

ANAL. SCI.

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“…Starting materials 8-13 were prepared accord- ing to the literature. 16,17 Reaction of 8 with 2.1 equiv of 1-pyrenemethol and NaH as a base in dry THF afforded 1 in quantitative yield. Alkylation of 1-pyrenemethanol with 1-iodopropane and NaH in THF provided 7 in 74% yield.…”

Section: Resultsmentioning

confidence: 99%

Highly Selective Fluorescent Signaling for Al³⁺in Bispyrenyl Polyether

2007

Bulletin of the Korean Chemical Society

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A series of bispyrenyl-polyether have been synthesized and investigated as a fluorescent chemosensor for metal ions. The results showed that bispyrenyl-polyether system is selective towards Al 3+ ion over other ions tested. In free ligand, excited at 343 nm, it displays a strong excimer emission at around 475 nm with a weak monomer emission at 375 nm. A ratiometry of monomer (375 nm) increase and excimer (475 nm) quenching was shown only when Al 3+ ion is bound to ligand, because two facing pyrene groups form a less efficient overlap of π−π stacking compared with that of free ligand.

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“…Stoichiometry of the complex formed was determined by utilizing Eq. 6 which was derived as follows [56]:…”

Section: Stoichiometry Of P-imidazolylcalix[n]arene-silver Complexesmentioning

confidence: 99%

Evaluation of deep cavity imidazolylcalix[n]arenes for selective extraction of silver

Chawla

Santra

Pant

et al. 2011

J Incl Phenom Macrocycl Chem

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A series of diphenylimidazolyl calix[n]arenes (n = 4, 6, 8) obtained from readily available starting materials have been examined for selective extraction of monovalent (sodium, potassium, caesium and silver) and bivalent ions (barium and lead). It has been determined that the synthesized deep cavity imidazolyl calix[n]arenes can selectively recognize silver ions through interaction with the imidazolyl groups appended at their upper rim in contrast to their usually encountered complexation with the ester functionalities present at the lower rim. The silver extraction efficiency is limited in the absence of the calix[n]arene skeleton while it is radically influenced by the ring size of imidazolylcalix[n]arenes examined.

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

Cited by 46 publications

References 12 publications

Mercury(II) Ion-Selective Electrodes Based on p-tert-Butyl Calix[4]crowns with Imine Units

Mercury(II) Ion-Selective Electrodes Based on p-tert-Butyl Calix[4]crowns with Imine Units

Highly Selective Fluorescent Signaling for Al³⁺in Bispyrenyl Polyether

Evaluation of deep cavity imidazolylcalix[n]arenes for selective extraction of silver

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

Cited by 46 publications

References 12 publications

Mercury(II) Ion-Selective Electrodes Based on p-tert-Butyl Calix[4]crowns with Imine Units

Mercury(II) Ion-Selective Electrodes Based on p-tert-Butyl Calix[4]crowns with Imine Units

Highly Selective Fluorescent Signaling for Al3+in Bispyrenyl Polyether

Evaluation of deep cavity imidazolylcalix[n]arenes for selective extraction of silver

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Highly Selective Fluorescent Signaling for Al³⁺in Bispyrenyl Polyether