Abstract
Two fluorescent ionophores of N-dansyl sym-(R)-dibenzo-16-crown-5-oxyacetamide HDAC (R=H) and PDAC (R=propyl) are developed for alkali metal cation sensing. Extraction of certain alkali metal cations into 1,2-dichloroethane by each ionophore result in a hypsochromic band shift and a fluorescence intensity increase in its emission spectrum. This fluorescent response is based upon the proton-ionizable function of the dansylamide fluorophore. Extraction constants ( K ex) and selectivity coefficients ( S) for Li +, Na +, and K + are obtained. HDAC exhibits strong binding ability for both Na + and K +, whereas PDAC shows a much stronger binding ability for Na + than K +. It is proposed that PDAC has a preorganized conformation in which the geminal propyl group orients the carboxyl group of the fluoroionophore-containing side arm over the crown ether cavity favoring Na + complexation.
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