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Calix[4]arenes Bridged with Two Different Crown Ether Loops: Influence of Crown Size on Metal Ion Recognition

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Abstract

A series of calix[4]arene-bis-crownethers were synthesized in a fixed 1,3-alternateconformation with good yields by the reaction of amonocyclic calixcrown ether with multi-ethyleneglycoldi-p-toluenesulfonate in the presence of cesiumcarbonate. In the preparation of the monocycliccalixcrown ethers (1 and 2), the use ofpotassium carbonate as a base provided the best yieldregardless of the template concept. In two phaseextraction and competitive transport experiments forligand-metal complexation, calix[4]arene biscrown(5) provided the best selectivity for potassiumion. When a calixbiscrown ether (4) bearingdifferent sized crown ether loops coordinates to K+and Cs+, respectively, the changes of peak splittingpatterns and chemical shift on 1H NMR spectra aredependent on the complexed metal ion species.

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Authors and Affiliations

  1. Department of Chemistry, Konyang University, Nonsan, 320-711, Korea

    Jong Seung Kim, Won Ku Lee & Wonbo Sim

  2. Department of Chemistry, Kangwon National University, Chuncheon, 200-701, Korea

    Jong Won Ko & Moon Hwan Cho

  3. Korea Ginseng & Tobacco Research Institute, Taejon, 305-345, Korea

    Do Young Ra

  4. Department of Clinical Pathology, College of Medicine, Dankook University, Cheonan, 330-714, Korea

    Jong Wan Kim

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  1. Jong Seung Kim
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  2. Won Ku Lee
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Kim, J.S., Lee, W.K., Sim, W. et al. Calix[4]arenes Bridged with Two Different Crown Ether Loops: Influence of Crown Size on Metal Ion Recognition. Journal of Inclusion Phenomena 37, 359–370 (2000). https://doi.org/10.1023/A:1008149218391

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