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Issue 49, 2019
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A coumarin–dihydroperimidine dye as a fluorescent chemosensor for hypochlorite in 99% water

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Abstract

The hypochlorite anion (OCl), a reactive oxygen species (ROS), is an important microbicidal agent in the immune system. Accurate and selective detection of OCl in environmental and biological samples by a fluorescent molecular sensor is an important subject. All previously reported sensors, however, have suffered from tedious multi-step synthesis for the sensors and the use of large amounts of organic solvents for the analysis. Herein, we report that a coumarin–dihydroperimidine dye prepared by facile condensation behaves as a fluorescent sensor for OCl in 99% water. The sensor exhibits weak fluorescence, but OCl-selective dehydrogenation of its dihydroperimidine unit creates a strong blue fluorescence. This turn-on fluorescence response facilitates selective and sensitive detection of OCl in the physiological pH range. Ab initio calculation revealed that the fluorescence enhancement by OCl is triggered by intramolecular proton transfer from the coumarin –OH to the imine nitrogen of the formed perimidine moiety.

Graphical abstract: A coumarin–dihydroperimidine dye as a fluorescent chemosensor for hypochlorite in 99% water

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Publication details

The article was received on 18 Jul 2019, accepted on 05 Sep 2019 and first published on 11 Sep 2019


Article type: Paper
DOI: 10.1039/C9RA05533A
RSC Adv., 2019,9, 28636-28641
  • Open access: Creative Commons BY license
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    A coumarin–dihydroperimidine dye as a fluorescent chemosensor for hypochlorite in 99% water

    Y. Shiraishi, C. Yamada and T. Hirai, RSC Adv., 2019, 9, 28636
    DOI: 10.1039/C9RA05533A

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