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An Excited-State Intramolecular Proton Transfer (ESIPT) Plus Ag-gregation Induced Emission (AIE) Phenanthro[9, 10-d]imidazole-Based Fluorescence Probe for Detection of Fe3+ in Living Cells
Received date: 2019-04-30
Online published: 2019-06-19
Supported by
the National Natural Science Foundation of China(21506106);the Natural Science Foundation of Heilongjiang Province(LC2017004);the Fundamental Research Funds in Heilongjiang Provincial Universities(135209209);the Fundamental Research Funds in Heilongjiang Provincial Universities(YSTSXK201853);the Fundamental Research Funds in Heilongjiang Provincial Universities(YSTSXK201859);the Qiqihar University Graduate Innovation Fund Grants(YJSCX2018-ZD18)
Selective detection of Fe3+ has considerable importance due to its active involvement in various biological processes. Based on the mechanism of excited-state intramolecular proton transfer (ESIPT) plus aggregation induced emission (AIE), a fluorescence probe of phenanthro[9, 10-d]imidazole modified by the phenolic hydroxyl (PIP-o-OH) had been designed, synthesized and applied in the detection of Fe3+. The structure of PIP-o-OH was characterized by 1H NMR, 13C NMR, IR, HRMS and X-ray single diffraction. Furthermore, a clear intramolecular hydrogen bond was observed between hydroxyl O-H and imidazole N atom in X-ray single structure, which improved the impossibility of ESIPT activity. ESIPT and AIE activities of PIP-o-OH were adequately determined by absorption, emission spectra and scanning electron microscope (SEM). The aggregated PIP-o-OH in MeOH/H2O (V:V=1:9, Hepes 10 μmol/L, pH=7.4) exhibited a good sensitivity towards Fe3+ with "turn-off" fluorescence response just after 20 s. The limit of detection (LOD) was calculated as low as 0.49 μmol/L. So it could be utilized to detect Fe3+ in biology and environmental samples. In addition, the calculation of the density functional theory (DFT) confirmed the formation of PIP-o-OH-Fe3+ complex. Also, PIP-o-OH was successfully applied to monitor Fe3+ in HeLa cells by the fluorescence change and quantificationally detect Fe3+ in water samples.
Key words： phenanthro[9, 10-d]imidazole; Fe3+; fluorescence probe; cell imaging; water samples
Yuqian He , Bing Zhao , Wei Kan , Liyan Wang , Bo Song , Guangming Yin , Ye Bi , Shuwen Chen . An Excited-State Intramolecular Proton Transfer (ESIPT) Plus Ag-gregation Induced Emission (AIE) Phenanthro[9, 10-d]imidazole-Based Fluorescence Probe for Detection of Fe3+ in Living Cells[J]. Chinese Journal of Organic Chemistry, 2019 , 39(11) : 3250 -3257 . DOI: 10.6023/cjoc201904078
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