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Issue 5, 2000
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A dibenzo-16-crown-5 fluoroionophore for selective emission ratio sensing of Na+ in basic aqueous dioxane solution

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Abstract

For alkali metal cation sensing in aqueous dioxane solution, a novel dibenzo-16-crown-5 (DB16C5) fluoroionophore 1, N-(pyren-1-yl)-sym-(propyl)dibenzo-16-crown-5-oxyacetamide, has been synthesized. Examination of fluorescent behavior for 1 in 4∶1 1,4-dioxane–water (v/v) containing tetramethylammonium hydroxide (TMAOH) reveals that proton dissociation of the carboxamido moiety is promoted by Na+ binding, which results in an emission ratio response due to internal charge transfer (ICT) from the donor carboxamido anion to the pyrene acceptor. The emission intensity ratio (I459 /I387) increases with enhancement of the Na+ concentration. No fluorescent response is induced by the presence of Li+, K+, or Cs+. This high Na+ selectivity is attributed to a preorganized structure of DB16C5 lariat ether binding site in which Na+ binds tightly to the carbonyl oxygen of the side arm to induce selective proton dissociation. Thus a ratiometric emission response with high Na+ selectivity has been obtained for 1 in 4∶1 1,4-dioxane–water (v/v) containing TMAOH.

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Publication details

The article was received on 07 Dec 1999, accepted on 25 Feb 2000 and first published on 18 Apr 2000


Article type: Paper
DOI: 10.1039/A909638H
Citation: J. Chem. Soc., Perkin Trans. 2, 2000,0, 1003-1006
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    A dibenzo-16-crown-5 fluoroionophore for selective emission ratio sensing of Na+ in basic aqueous dioxane solution

    T. Hayashita, S. Taniguchi, Y. Tanamura, T. Uchida, S. Nishizawa, N. Teramae, Y. S. Jin, J. C. Lee and R. A. Bartsch, J. Chem. Soc., Perkin Trans. 2, 2000, 0, 1003
    DOI: 10.1039/A909638H

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