A novel rhodol-based fluorescence turn-on probe for selective hydrogen sulfide detection in environment water and living cells

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Vol. 423; p. 113598
• Main Authors: Gao, Zhigang, Zhang, Ling, Liu, Haibo, Yan, Minchuan, Lu, Shaohui, Lian, Huihui, Zhang, Peng, Zhu, Jing, Jin, Mingjie
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.01.2022
• Subjects: Cell imaging; Fluorescence probe; Hydrogen sulfide; Rhodol; Hydrogen sulfide; Rhodol; Fluorescence probe; Cell imaging
• ISSN: 1010-6030; 1873-2666
• DOI: 10.1016/j.jphotochem.2021.113598

[Display omitted] •The probe was designed and synthesized based on a rhodol derivate anchored with the 2,4-dinitrophenyl group.•The fluorescent response was fast within 12 min and a dramatic color change (from colorless to pink) could be observed by naked eyes.•The detection limit of the probe was 0.097 μM.•The probe was successfully applied to detecting H2S in real water samples and HeLa cells. In this work, a reaction-based fluorescence turn-on probe RCHO, a rhodol derivate anchored with the 2,4-dinitrophenyl moiety, was designed and synthesized for H2S detection. The 2,4-dinitrophenyl moiety, as an electron-withdrawing group, was used for quenching the fluorescence of the fluorophore. The probe RCHO could quantitively detect H2S with high selectivity and fast response by introducing aldehyde groups in the ortho position of 2,4-dinitrobenzene. After addition of H2S, H2S was quickly added to the aldehyde group through a nucleophilic addition reaction, and then the dinitrophenyl ether underwent effective intramolecular thiolysis, which resulting in the release of the fluorophore and a rapid fluorescence turn-on response. The detect limit was calculated to be 0.097 μM. Furthermore, in the presence of H2S, a remarkable color change from colorless to pink was observed, indicating that the probe RCHO could monitor H2S by the naked eyes. More importantly, the probe could be used as a highly efficient tool for H2S detection in living cells and environmental water.