Abstract

A highly sensitive “turn-on” fluorescent probe, methyl (6 R ,9a S )-2-(4′-(2,2-dicyanovinyl)-[1,1′-biphenyl]-4-yl)-11-(4-methoxyphenyl)-6,9a-dimethyl-4,5,5a,6,7,8,9,9a-octahydro-3H-phenanthro[1,2- d ]imidazole-6-carboxylate ( DBMB ), was synthesized from renewable natural product dehydroabietic acid for detecting HSO 3 − . Based on the nucleophilic addition reaction, DBMB can be utilized to detect HSO 3 − with a low detection limit (8.63 ± 0.17 nM), high selectivity, and rapid response time (80 s). The recognition mechanism was verified by 1 H nuclear magnetic resonance ( 1 H NMR) titration, high resolution mass spectrometry (HR-MS), and density functional theory (DFT) calculation. More importantly, the probe DBMB could determine HSO 3 − with good recoveries in common sugar samples. Furthermore, the confocal fluorescent assays of HSO 3 − in zebrafishes and living cells indicated that the probe DBMB has great potential for bioimaging in living systems.

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