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Issue 20, 2017
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A ratiometric fluorescent pH probe based on keto–enol tautomerization for imaging of living cells in extreme acidity

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Abstract

6-(Diethylamino)-2,3-dihydro-1H-xanthene-4-carbaldehyde (DDXC), a reported synthetic intermediate for near-infrared fluorescent dyes, was developed into a fluorescent pH probe for extreme acidity. The unique sensing mechanism of DDXC for pH is based on the reversible protonation of the carbonyl oxygen followed by keto–enol tautomerization. The probe displays a linear ratiometric fluorescence response (I512/I580) to H+ over the extremely acidic range of pH 2.0–4.0 with a pKa of 3.11, and features high fluorescence quantum yield (Φ = 0.60) and excellent selectivity. More importantly, the probe can be applied to ratiometric fluorescence imaging of pH changes in living cells, making it a potential molecular tool for pH-related cell biology study.

Graphical abstract: A ratiometric fluorescent pH probe based on keto–enol tautomerization for imaging of living cells in extreme acidity

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Publication details

The article was received on 02 Jul 2017, accepted on 26 Aug 2017 and first published on 30 Aug 2017


Article type: Paper
DOI: 10.1039/C7AN01103B
Citation: Analyst, 2017,142, 3906-3912
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    A ratiometric fluorescent pH probe based on keto–enol tautomerization for imaging of living cells in extreme acidity

    Z. Tong, W. Liu, H. Huang, H. Chen, X. Liu, Y. Kuang and J. Jiang, Analyst, 2017, 142, 3906
    DOI: 10.1039/C7AN01103B

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