Citation: Jiakun BAI, Ting XU, Lu ZHANG, Jiang PENG, Yuqiang LI, Junhui JIA. A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid[J]. Chinese Journal of Inorganic Chemistry, ;2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002 shu

A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid

Jiakun BAI ^1,, ,
Ting XU ¹ ,
Lu ZHANG ¹ ,
Jiang PENG ¹ ,
Yuqiang LI ^2,, ,
Junhui JIA ^1,,

1.
Key Laboratory of Magnetic Molecules and Magnetic Information Material, Ministry of Education, College of Chemistry and Material Science, Shanxi Normal University, Taiyuan 030032, China
2.
School of Chemistry and Chemical Engineering, North University of China, Taiyuan 030051, China

Corresponding author: Jiakun BAI, jiakun_bai@163.com Yuqiang LI, yuqiangli@nuc.edu.cn Junhui JIA, jiajunhui@sxnu.edu.cn
Received Date: 1 January 2024
Revised Date: 5 April 2024

Figures(10)

An optical probe (3) with a donor-π-acceptor (D-π-A) structure for the detection of hypochlorous acid (HClO) was synthesized by a one-step reaction. It employed a barbituric acid derivative as the electron acceptor and 4-(dimethylamino)cinnamaldehyde as the electron donor. The probe exhibited high sensitivity and selectivity for the detection of HClO, rapidly responding with distinct colorimetric and fluorescent "on-off" signals (about 15 s). The probe displayed a linear relationship between fluorescence intensity and HClO concentration, with a low detection limit (LOD) of 14 nmol·L^-1, which made it suitable for quantitative HClO detection. Moreover, the probe exhibited red light emission (628 nm) with a significant Stokes shift (158 nm) and good photostability, which provided advantages for its application in cell imaging. The proposed reaction mechanism, which was deduced from high-resolution mass spectrometry data, involved electrophilic addition and oxidative cleavage of the C=C bond by ClO^-, which led to the disruption of the probe′s D-π-A structure. Consequently, this effectively halted the intramolecular charge transfer (ICT) process of the probe. MTT cytotoxicity assays demonstrated minimal toxicity of the probe following 12, 24, and 48 h of incubation with HepG2 cells. The probe was successfully applied to living cell imaging and enabled the detection of HClO via fluorescence quenching within the living cellular milieu.
- large Stokes shift,
- hypochlorite detection,
- colorimetric and fluorescent dual-response,
- red-emitting,
- cell imaging
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