Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3250-3257.DOI: 10.6023/cjoc201904078 Previous Articles     Next Articles

Special Issue: 荧光探针-生物传感合辑 有机超分子化学合辑


何玉倩a, 赵冰a*(), 阚伟a*(), 王丽艳a, 宋波a, 殷广明a, 毕野a, 陈书文b*()   

  1. a齐齐哈尔大学化学与化学工程学院 黑龙江齐齐哈尔 161006
    b 辽宁科技大学材料与冶金学院 辽宁鞍山 114051
  • 收稿日期:2019-04-30 发布日期:2019-06-19
  • 通讯作者: 赵冰,阚伟,陈书文;;
  • 基金资助:

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 Yuqiana, Zhao Binga*(), Kan Weia*(), Wang Liyana, Song Boa, Yin Guangminga, Bi Yea, Chen Shuwenb*()   

  1. 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
  • Received:2019-04-30 Published:2019-06-19
  • Contact: Zhao Bing,Kan Wei,Chen Shuwen;;
  • 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