Chinese Journal of Organic Chemistry >
A Near-Infrared Fluorescent Probe with 2-Hydroxy-N,N-dimethyl- benzylamine as a New Recognition Fragment for Pd2+ Detection and Bioimaging
Received date: 2021-12-02
Revised date: 2022-01-08
Online published: 2022-02-25
Supported by
Scientific Research Foundation of Hunan Provincial Education Department(19B390); Scientific Research Foundation of Hunan Provincial Education Department(19C1254); Hunan Provincial Natural Science Foundation of China(2020JJ4445); Hunan Provincial Natural Science Foundation of China(2020JJ5390)
A near-infrared fluorescent probe DHDM bearing isophorone skeleton and 2-hydroxy-N,N-dimethylbenzylamine has been rationally designed and synthesized. DHDM showed excellent Pd2+ specificity with a low detection limit of 53 nmol/L and a large Stokes shift (220 nm). The fluorescence intensity at 660 nm was linear to Pd2+ concentrations in a wide range (0~70 μmol/L). Additionally, a possible sensing mechanism was proposed based on the results of the mass spectroscopy, infrared spectrum, a comparative experiment and density functional theory (DFT) calculations. Finally, DHDM was further successfully used to image Pd2+ in live cells, suggesting its potential applications in biological systems. The design strategy based on 2-hydroxy-N,N-dimethylbenzylamine or one of its analogues as a new recognition fragment will inspire researchers to construct privileged fluorescence probes in the future.
Xiangyang Zhang , Qinglin Wu , Feifei Wang , Youming Shen , Yucai Tang . A Near-Infrared Fluorescent Probe with 2-Hydroxy-N,N-dimethyl- benzylamine as a New Recognition Fragment for Pd2+ Detection and Bioimaging[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1786 -1791 . DOI: 10.6023/cjoc202112004
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