A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite

Chemosensors

Yasuhiro Shiraishi¹  Shunsuke Takagi¹  Rikako Nakatani¹  Takayuki Hirai¹  Chiharu Yamada¹ 

[1] Research Center for Solar Energy Chemistry, and Division of Chemical Engineering, Graduate School of Engineering Science, Osaka University, Toyonaka 560-8531, Japan;

关键词: chemodosimeter;    hypochlorite;    fluorescence;    naphthalimide;    sulfonylhydrazine;   

DOI  :  10.3390/chemosensors8040123

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown