A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite
Hypochlorite anion (ClO<sup>−</sup>) is a widely-used disinfectant and a microbicidal agent in the immune system. Accurate detection of ClO<sup>−</sup> in environmental and biological samples by simply prepared chemosensors/chemodosimeters is important. Herein, we report that...
| الحاوية / القاعدة: | Chemosensors |
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| المؤلفون الرئيسيون: | , , , , |
| التنسيق: | مقال |
| اللغة: | الإنجليزية |
| منشور في: |
MDPI AG
2020-12-01
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| الموضوعات: | |
| الوصول للمادة أونلاين: | https://www.mdpi.com/2227-9040/8/4/123 |
| _version_ | 1850093190975062016 |
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| author | Yasuhiro Shiraishi Rikako Nakatani Shunsuke Takagi Chiharu Yamada Takayuki Hirai |
| author_facet | Yasuhiro Shiraishi Rikako Nakatani Shunsuke Takagi Chiharu Yamada Takayuki Hirai |
| author_sort | Yasuhiro Shiraishi |
| collection | DOAJ |
| container_title | Chemosensors |
| description | Hypochlorite anion (ClO<sup>−</sup>) is a widely-used disinfectant and a microbicidal agent in the immune system. Accurate detection of ClO<sup>−</sup> 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<sup>−</sup>. The molecule exhibits a weak emission, but ClO<sup>−</sup>-selective cleavage of its C=N bond creates a strong green emission. Ab initio calculation showed that the emission enhancement by ClO<sup>−</sup> 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<sup>−</sup> at physiological pH range (7–9) and allows fluorometric ClO<sup>−</sup> imaging in the presence of cells. |
| format | Article |
| id | doaj-art-b11d3374472e4dcfa9cca721befbd4bc |
| institution | Directory of Open Access Journals |
| issn | 2227-9040 |
| language | English |
| publishDate | 2020-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| spelling | doaj-art-b11d3374472e4dcfa9cca721befbd4bc2025-08-20T00:08:04ZengMDPI AGChemosensors2227-90402020-12-018412310.3390/chemosensors8040123A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for HypochloriteYasuhiro Shiraishi0Rikako Nakatani1Shunsuke Takagi2Chiharu Yamada3Takayuki Hirai4Research Center for Solar Energy Chemistry, and Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University, Toyonaka 560-8531, JapanResearch Center for Solar Energy Chemistry, and Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University, Toyonaka 560-8531, JapanResearch Center for Solar Energy Chemistry, and Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University, Toyonaka 560-8531, JapanResearch Center for Solar Energy Chemistry, and Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University, Toyonaka 560-8531, JapanResearch Center for Solar Energy Chemistry, and Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University, Toyonaka 560-8531, JapanHypochlorite anion (ClO<sup>−</sup>) is a widely-used disinfectant and a microbicidal agent in the immune system. Accurate detection of ClO<sup>−</sup> 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<sup>−</sup>. The molecule exhibits a weak emission, but ClO<sup>−</sup>-selective cleavage of its C=N bond creates a strong green emission. Ab initio calculation showed that the emission enhancement by ClO<sup>−</sup> 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<sup>−</sup> at physiological pH range (7–9) and allows fluorometric ClO<sup>−</sup> imaging in the presence of cells.https://www.mdpi.com/2227-9040/8/4/123chemodosimeterhypochloritefluorescencenaphthalimidesulfonylhydrazine |
| spellingShingle | Yasuhiro Shiraishi Rikako Nakatani Shunsuke Takagi Chiharu Yamada Takayuki Hirai A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite chemodosimeter hypochlorite fluorescence naphthalimide sulfonylhydrazine |
| title | A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite |
| title_full | A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite |
| title_fullStr | A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite |
| title_full_unstemmed | A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite |
| title_short | A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite |
| title_sort | naphthalimide sulfonylhydrazine conjugate as a fluorescent chemodosimeter for hypochlorite |
| topic | chemodosimeter hypochlorite fluorescence naphthalimide sulfonylhydrazine |
| url | https://www.mdpi.com/2227-9040/8/4/123 |
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