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

Takashi Hayashita, Shinichiro Taniguchi, Yoshihiko Tanamura, Tatsuya Uchida, Seiichi Nishizawa, Norio Teramae, Yong Suk Jin, Jong Chan Lee, Richard A. Bartsch

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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.

Original languageEnglish
Pages (from-to)1003-1006
Number of pages4
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number5
Publication statusPublished - 2000 May 1

ASJC Scopus subject areas

  • Chemistry(all)

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    Hayashita, T., Taniguchi, S., Tanamura, Y., Uchida, T., Nishizawa, S., Teramae, N., Jin, Y. S., Lee, J. C., & Bartsch, R. A. (2000). A dibenzo-16-crown-5 fluoroionophore for selective emission ratio sensing of Na+ in basic aqueous dioxane solution. Journal of the Chemical Society. Perkin Transactions 2, (5), 1003-1006.