Analytica chimica acta · 2025
A diarylethene-based colorimetric sensor for discriminative detection of H2S and CN- with fluorescent imaging in live cells.
СтатьяПоддержка исследования: вне правительства СШАНазвание и аннотация: Перевод в очереди
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Wang Nan, Wang Jiajia, Huang Shuqin, Zheng Chunhong, Cui Shiqiang, Pu Shouzhi
Аннотация
BACKGROUND: Hydrogen sulfide (H2S) and cyanide anions (CN-) are toxic, significantly affecting environmental and human health. Although numerous chemosensors for H2S or CN- detection have been reported, most enable only separate detection. Differentiating between H2S and CN- using a single sensor remains challenging owing to their comparable nucleophilicity. A few H2S sensors have been developed by utilizing the thiolysis reaction of DNPS ether combined with an aldehyde moiety; nonetheless, this strategy has not been employed to develop sensors for CN- detection.
RESULTS: Herein, a unique diarylethene derivative functionalized with a 2,4-dinitrobenzenesulfonyl salicylaldehyde moiety is designed and synthesized. In this system, DNPS cleavage and nucleophilic addition to the aldehyde (-CHO) group collectively enable discriminative sensing. Consequently, both open- and closed-ring isomers demonstrated highly selective, sensitive dual colorimetric detection of H2S and CN-. Notably, the closed-ring isomer exhibited simultaneous discriminative detection, yielding distinct colorimetric responses for H2S and CN-, rapid response (<1 min), and micromolar-level sensitivity. Mechanistic studies revealed that H2S detection proceeded via rapid nucleophilic addition to the ortho-aldehyde group, followed by spontaneous intramolecular thiolysis, while CN- detection proceeded via 2,4-dinitrobenzenesulfonyl ester cleavage, followed by nucleophilic addition. CN- also induced pronounced fluorescence enhancement, enabling successful bioimaging of CN- in HeLa cells with excellent biocompatibility and low phytotoxicity.
SIGNIFICANCE AND NOVELTY: A diarylethene-based dual-functional colorimetric sensor for discriminative detection of H2S and CN- was synthesized. Colorimetric discrimination of H2S and CN-, along with rapid, highly sensitive fluorometric detection of CN-, was achieved. Visual detection of H2S and CN- using sensor-coated paper strips, together with bioimaging of CN- in HeLa cells was successfully achieved. These findings offer insights into the design of novel diarylethene derivatives for a multi-ion-responsive unimolecular system.
RESULTS: Herein, a unique diarylethene derivative functionalized with a 2,4-dinitrobenzenesulfonyl salicylaldehyde moiety is designed and synthesized. In this system, DNPS cleavage and nucleophilic addition to the aldehyde (-CHO) group collectively enable discriminative sensing. Consequently, both open- and closed-ring isomers demonstrated highly selective, sensitive dual colorimetric detection of H2S and CN-. Notably, the closed-ring isomer exhibited simultaneous discriminative detection, yielding distinct colorimetric responses for H2S and CN-, rapid response (<1 min), and micromolar-level sensitivity. Mechanistic studies revealed that H2S detection proceeded via rapid nucleophilic addition to the ortho-aldehyde group, followed by spontaneous intramolecular thiolysis, while CN- detection proceeded via 2,4-dinitrobenzenesulfonyl ester cleavage, followed by nucleophilic addition. CN- also induced pronounced fluorescence enhancement, enabling successful bioimaging of CN- in HeLa cells with excellent biocompatibility and low phytotoxicity.
SIGNIFICANCE AND NOVELTY: A diarylethene-based dual-functional colorimetric sensor for discriminative detection of H2S and CN- was synthesized. Colorimetric discrimination of H2S and CN-, along with rapid, highly sensitive fluorometric detection of CN-, was achieved. Visual detection of H2S and CN- using sensor-coated paper strips, together with bioimaging of CN- in HeLa cells was successfully achieved. These findings offer insights into the design of novel diarylethene derivatives for a multi-ion-responsive unimolecular system.