New Calix[4]arene Dibenzocrown Ethers for Selective Sensing of Cesium Ion in an Aqueous Environment

Jong Seung Kim, Ill Yong Yu, Jin Hyun Pang, Jong Kuk Kim, Yong I. Lee, Kune Woo Lee, Won Z. Oh

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

1,3-Dialkoxycalix[4]arene dibenzocrown ethers (6-9) were successfully synthesized in the fixed 1,3-alternate conformation, with greater than 90% yields by reaction of the corresponding 1,3-dialkoxycalix[4]arenes 2-5 with dibenzodimesylate 13 in acetonitrile as a solvent in the presence of cesium carbonate as a base. In view of the cyclization yield, dimesylate is better than dibenzoditosylate. Because of an unusual AB pattern in the 1H NMR spectrum for compound 9, it is suggested that the conformational structure of 1,3-diallyloxy calix[4]arene dibenzocrown ether is less flexible than that of usual 1,3-alternate calixcrown ether, probably due to steric effects of two allyl groups. Complexation of the corresponding calix[4]arene ethers 6-9 to alkali metal ions using the single-flux method through a bulk liquid membrane system was found to give high cesium selectivity.

Original languageEnglish
Pages (from-to)225-235
Number of pages11
JournalMicrochemical Journal
Volume58
Issue number2
Publication statusPublished - 1998 Feb 1
Externally publishedYes

Fingerprint

Cesium
Ethers
Ether
Ions
Alkali Metals
Liquid membranes
Cyclization
Complexation
Metal ions
Conformations
Nuclear magnetic resonance
Fluxes
calix(4)arene
cesium carbonate
acetonitrile

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy

Cite this

Kim, J. S., Yu, I. Y., Pang, J. H., Kim, J. K., Lee, Y. I., Lee, K. W., & Oh, W. Z. (1998). New Calix[4]arene Dibenzocrown Ethers for Selective Sensing of Cesium Ion in an Aqueous Environment. Microchemical Journal, 58(2), 225-235.

New Calix[4]arene Dibenzocrown Ethers for Selective Sensing of Cesium Ion in an Aqueous Environment. / Kim, Jong Seung; Yu, Ill Yong; Pang, Jin Hyun; Kim, Jong Kuk; Lee, Yong I.; Lee, Kune Woo; Oh, Won Z.

In: Microchemical Journal, Vol. 58, No. 2, 01.02.1998, p. 225-235.

Research output: Contribution to journalArticle

Kim, JS, Yu, IY, Pang, JH, Kim, JK, Lee, YI, Lee, KW & Oh, WZ 1998, 'New Calix[4]arene Dibenzocrown Ethers for Selective Sensing of Cesium Ion in an Aqueous Environment', Microchemical Journal, vol. 58, no. 2, pp. 225-235.
Kim, Jong Seung ; Yu, Ill Yong ; Pang, Jin Hyun ; Kim, Jong Kuk ; Lee, Yong I. ; Lee, Kune Woo ; Oh, Won Z. / New Calix[4]arene Dibenzocrown Ethers for Selective Sensing of Cesium Ion in an Aqueous Environment. In: Microchemical Journal. 1998 ; Vol. 58, No. 2. pp. 225-235.
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N2 - 1,3-Dialkoxycalix[4]arene dibenzocrown ethers (6-9) were successfully synthesized in the fixed 1,3-alternate conformation, with greater than 90% yields by reaction of the corresponding 1,3-dialkoxycalix[4]arenes 2-5 with dibenzodimesylate 13 in acetonitrile as a solvent in the presence of cesium carbonate as a base. In view of the cyclization yield, dimesylate is better than dibenzoditosylate. Because of an unusual AB pattern in the 1H NMR spectrum for compound 9, it is suggested that the conformational structure of 1,3-diallyloxy calix[4]arene dibenzocrown ether is less flexible than that of usual 1,3-alternate calixcrown ether, probably due to steric effects of two allyl groups. Complexation of the corresponding calix[4]arene ethers 6-9 to alkali metal ions using the single-flux method through a bulk liquid membrane system was found to give high cesium selectivity.

AB - 1,3-Dialkoxycalix[4]arene dibenzocrown ethers (6-9) were successfully synthesized in the fixed 1,3-alternate conformation, with greater than 90% yields by reaction of the corresponding 1,3-dialkoxycalix[4]arenes 2-5 with dibenzodimesylate 13 in acetonitrile as a solvent in the presence of cesium carbonate as a base. In view of the cyclization yield, dimesylate is better than dibenzoditosylate. Because of an unusual AB pattern in the 1H NMR spectrum for compound 9, it is suggested that the conformational structure of 1,3-diallyloxy calix[4]arene dibenzocrown ether is less flexible than that of usual 1,3-alternate calixcrown ether, probably due to steric effects of two allyl groups. Complexation of the corresponding calix[4]arene ethers 6-9 to alkali metal ions using the single-flux method through a bulk liquid membrane system was found to give high cesium selectivity.

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