Novel water soluble styrylquinolinium boronic acid as a ratiometric reagent for the rapid detection of hypochlorite ion

• A water soluble styrylquinolinium boronic acid has been synthesized.
• A selective oxidation of a C–B bond of the dye by hypochlorite was disclosed.
• Styrylquinolinium dye was selected as both colorimetric and fluorescent reporting group.
• The dye was shown to be an excellent ClO−-selective chemosensor based on the oxidation induced ICT mechanism.
• The selective reaction with ClO− leads to a visible change in color from light green to orange red.

A novel water soluble styrylquinolinium boronic acid has been synthesized in good yield. A selective oxidation of the C–B bond of the dye by hypochlorite was observed. During the oxidation of the dye, the replacement of the strong electron-withdrawing group (–BOH2) by the electron-donating group (–OH) on the fluorophore resulted in a large red shift of the absorption and emission spectra due to the intramolecular charge-transfer process. Based on the oxidation induced intramolecular charge-transfer mechanism, the application of the dye as a ratiometric optical chemosensor for ClO− has been investigated in detail. It exhibited high selectivity for ClO− anions over other relevant metal ions, anions and highly reactive oxygen species. Meanwhile, the fast oxidation event along with the characterized color changes allowed the dye to be developed as selective visual chemosensor for ClO−.

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