The "Off-On" Fluorescence Detection of Alkaline Earth Metal Ions by Using 1-Naphthylacetanilide Derivatives: New Cation Sensors Based on Oligo-ethylene Oxides Connecting 1-Naphthylacetanilide at Its Terminals

MOROZUMI Tatsuya, HAMA Hiroya, NAKAMURA Hiroshi

doi:10.2116/analsci.22.659

The "Off-On" Fluorescence Detection of Alkaline Earth Metal Ions by Using 1-Naphthylacetanilide Derivatives: New Cation Sensors Based on Oligo-ethylene Oxides Connecting 1-Naphthylacetanilide at Its Terminals

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MOROZUMI Tatsuya

Section of Materials Science, Research Faculty of Environmental Earth Science, Hokkaido University
HAMA Hiroya

Division of Environmental Material Science, Graduate School of Environmental Science, Hokkaido University
NAKAMURA Hiroshi

Section of Materials Science, Research Faculty of Environmental Earth Science, Hokkaido University

書誌事項

タイトル別名

Off On Fluorescence Detection of Alkaline Earth Metal Ions by Using 1 Naphthylacetanilide Derivatives New Cation Sensors Based on Oligo ethylene Oxides Connecting 1 Naphthylacetanilide at Its Terminals

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抄録

New fluorescent ionophores containing the 1-naphthylacetanilide moiety based on oligo-ethylene oxide (1₄ and 1₅) have been synthesized, and their photochemical behaviors have been studied. In the absence of a metal ion, the 1-naphthylacetanilide moiety showed a weak fluorescence emission (fluorescence “off state”). However, complexation with Ca²⁺ induced a large enhancement effect on the fluorescence intensity of 1₄ and 1₅ from the naphthalene ring (fluorescence “on” state). This behavior can be explained in terms of a similar twisted intramolecular charge-transfer relaxation mechanism. Such “off-on” fluorescence responses of 1₄ and 1₅ provide the digital detection of alkaline earth metal ions.