Abstract
Hypochlorite anion (ClO−) is a widely-used disinfectant and a microbicidal agent in the immune system. Accurate detection of ClO− in environmental and biological samples by simply prepared chemosensors/chemodosimeters is important. Herein, we report that a naphthalimide–sulfonylhydrazine conjugate with an imine (C=N) linker, prepared via simple condensation, acts as an effective fluorescent chemodosimeter for ClO−. The molecule exhibits a weak emission, but ClO−-selective cleavage of its C=N bond creates a strong green emission. Ab initio calculation showed that the emission enhancement by ClO− originates from the suppression of intramolecular electron transfer from the photoexcited naphthalimide through the C=N linker. This response enables selective and sensitive detection of ClO− at physiological pH range (7–9) and allows fluorometric ClO− imaging in the presence of cells.
Highlights
Hypochlorous acid (HClO) is one important reactive oxygen species (ROS)
HClO is formed in vivo by the enzymatic reaction of hydrogen peroxide (H2 O2 ) with chloride anion (Cl– ) in some specialized cells such as neutrophils [1]
We demonstrated that a simple naphthalimide–sulfonylhydrazine dye (1) acts as a fluorescent chemodosimeter for ClO− . 1 shows almost no fluorescence, but ClO– -selective oxidative cleavage of its
Summary
Hypochlorous acid (HClO) is one important reactive oxygen species (ROS). HClO is formed in vivo by the enzymatic reaction of hydrogen peroxide (H2 O2 ) with chloride anion (Cl– ) in some specialized cells such as neutrophils [1]. Deprotonation of HClO at a physiological pH range produces hypochlorite anion (ClO− ) [2], which acts as an microbicidal agent in immune system [3]. Considerable amounts of HClO are used industrially or at home for sterilization, high residual amounts of ClO− is hazardous [9]. A simple but inexpensive method to quantitatively detect small amount of ClO− is necessary
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