Citation: He Yuqian, Zhao Bing, Kan Wei, Wang Liyan, Song Bo, Yin Guangming, Bi Ye, Chen Shuwen. 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 shu

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

He Yuqian ^a ,
Zhao Bing ^a,, ,
Kan Wei ^a,, ,
Wang Liyan ^a ,
Song Bo ^a ,
Yin Guangming ^a ,
Bi Ye ^a ,
Chen Shuwen ^b,,

a.
Chemistry and Chemical Engineering Institute, Qiqihar University, Qiqihar, Heilongjiang 161006
b.
School of Materials and Metallurgy, University of Science and Technology Liaoning, Anshan, Liaoning 114051

Corresponding author: Zhao Bing, zhao_submit@aliyun.com Kan Wei, kan_submit@aliyun.com Chen Shuwen, anshancsw@126.com
Received Date: 30 April 2019
Revised Date: 30 May 2019
Available Online: 19 November 2019
Fund Project: the National Natural Science Foundation of China 21506106the Fundamental Research Funds in Heilongjiang Provincial Universities YSTSXK201859Project supported by the National Natural Science Foundation of China (No. 21506106), the Natural Science Foundation of Heilongjiang Province (No. LC2017004), the Fundamental Research Funds in Heilongjiang Provincial Universities (Nos. 135209209, YSTSXK201853, YSTSXK201859) and the Qiqihar University Graduate Innovation Fund Grants (No. YJSCX2018-ZD18)the Fundamental Research Funds in Heilongjiang Provincial Universities YSTSXK201853the Fundamental Research Funds in Heilongjiang Provincial Universities 135209209the Qiqihar University Graduate Innovation Fund Grants YJSCX2018-ZD18the Natural Science Foundation of Heilongjiang Province LC2017004

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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.
- phenanthro[9, 10-d]imidazole,
- Fe³⁺,
- fluorescence probe,
- cell imaging,
- water samples
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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

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通讯作者: 陈斌, bchen63@163.com

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