Chlorination-induced pKa decrease: an improved strategy to design ratiometric hypochlorite fluorescent probes with ideally high selectivity

Based on the selective ClO−-triggered chlorination reaction and the subsequent pKa decrease of phenols, a new strategy was developed for rationally designing ratiometric ClO− fluorescent probes with high selectivity. By investigating the fluorescence responses of 6-cyano-2-naphthol toward ClO− and t...

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Bibliographic Details
Published in:Analyst (London) 2022-11, Vol.147 (23), p.5300-5305
Main Authors: Han, Shaohui, Ding, Binghui, Xiong, Haiqing, Zuo, Bojun, Ye, Yong, Li, Haipu, Song, Xiangzhi
Format: Article
Language:English
Subjects:
Chlorination
Fluorescent indicators
Phenols
Photons
Selectivity
Online Access:Get full text
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Summary:Based on the selective ClO−-triggered chlorination reaction and the subsequent pKa decrease of phenols, a new strategy was developed for rationally designing ratiometric ClO− fluorescent probes with high selectivity. By investigating the fluorescence responses of 6-cyano-2-naphthol toward ClO− and the pKa-dependent response mechanism, we developed a rapid, sensitive and selective two-photon ratiometric fluorescent probe, Naph-DFOB, to detect ClO−. This probe displayed a ratiometric fluorescence change (from 509 nm to 628 nm) toward ClO− and was successfully applied to image intracellular ClO− in living cells with two-photon excitation. Using Naph-DFOB as a useful tool, the investigation of lipopolysaccharide (LPS)-induced acute lung injury in a mouse model was effectively performed.
ISSN:0003-2654
1364-5528
DOI:10.1039/d2an01476a