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Ratio-dependent florescent probe for identifying Zn<2+> and S<2-> in relayed manner as well as synthesis method and application of ratio-dependent florescent probe

A technology of fluorescent probes and synthesis methods, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of fluorescence enhancement, environmental hazards, quenching, etc., and achieve simple product separation and purification process and avoid external factors The effect of accurate detection

Active Publication Date: 2014-09-17
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In the design and synthesis of fluorescent probes that recognize negative divalent sulfide ions, the combination of fluorescent probes with metal ions (such as Cu 2+ or Hg 2+ ) formed a complex, based on the method of metal ion displacement to identify S 2- , but these methods show fluorescence enhancement or quenching at the original emission position, and use copper ions or mercury ions that are harmful to the environment

Method used

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  • Ratio-dependent florescent probe for identifying Zn&lt;2+&gt; and S&lt;2-&gt; in relayed manner as well as synthesis method and application of ratio-dependent florescent probe
  • Ratio-dependent florescent probe for identifying Zn&lt;2+&gt; and S&lt;2-&gt; in relayed manner as well as synthesis method and application of ratio-dependent florescent probe
  • Ratio-dependent florescent probe for identifying Zn&lt;2+&gt; and S&lt;2-&gt; in relayed manner as well as synthesis method and application of ratio-dependent florescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Synthetic relay recognition Zn 2+ and S 2- The reaction formula of the ratiometric fluorescent probe:

[0042]

[0043] (2) Synthetic relay recognition of Zn 2+ and S 2- The specific steps of the ratiometric fluorescent probe:

[0044] Weigh 300mg of the intermediate N -(2-(1H-Benzimidazolyl)phenyl)-2-chloroacetamide (compound 2) and 418mg of raw material bis-(pyridylmethylene)amine (compound 3), dissolved in 20ml of N,N - In dimethylformamide (DMF), stir the reaction for 7 hours at room temperature, add 100ml of distilled water, adjust the pH value to 6 with dilute hydrochloric acid, collect the resulting precipitate by filtration, and recrystallize with acetonitrile to obtain a fluorescent probe N -(2-(1H-Benzimidazolyl)phenyl)-2-bis(2-pyridinemethylamino)acetamide (Compound 1), the yield was 56%.

Embodiment 2

[0046] Weigh 300mg of the intermediate N -(2-(1H-Benzimidazolyl)phenyl)-2-chloroacetamide and 630mg of bis-(pyridylmethylene)amine were dissolved in 20ml of DMF, stirred and reacted for 9h at room temperature, Add 150ml of distilled water, adjust the pH to 7 with dilute hydrochloric acid, collect the resulting precipitate by filtration, and recrystallize with acetonitrile to obtain a fluorescent probe N -(2-(1H-Benzimidazolyl)phenyl)-2-bis(2-pyridinemethylamino)acetamide, the yield is 68%.

Embodiment 3

[0048] Weigh 300mg of the intermediate N -(2-(1H-Benzimidazolyl)phenyl)-2-chloroacetamide and 835mg of bis-(pyridylmethylene)amine were dissolved in 20ml of DMF, and stirred at room temperature for 10h, Add 150ml of distilled water, adjust the pH to 7 with dilute hydrochloric acid, collect the resulting precipitate by filtration, and recrystallize with acetonitrile to obtain a fluorescent probe N -(2-(1H-Benzimidazolyl)phenyl)-2-bis(2-pyridinemethylamino)acetamide, the yield was 72%.

[0049] The fluorescent probe of embodiment 1~embodiment 3 N Basic data for -(2-(1H-benzoimidazolyl)phenyl)-2-bis(2-pyridinemethylamino)acetamide:

[0050] Melting point: 177℃~179℃;

[0051] 1 H NMR (400 MHz, DMSO- d 6 ) δ 13.20 (s, 1H), 13.09 (s, 1H), 8.72 (d, J = 8.4 Hz, 1H), 8.41 (d, J = 4.3 Hz, 2H), 8.04 (d, J = 7.8 Hz, 1H), 7.75 (d, J = 7.8 Hz, 2H), 7.57 (s, 2H), 7.47-7.31 (m, 3H), 7.32-7.04 (m, 5H), 4.13-3.84 (m, 4H), 3.39 (S, 2H). (eg figure 1 ).

[0052] 13 C NMR (100 ...

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Abstract

A ratiometric fluorescent probe for relay recognition of Zn2+ and S2-. The molar ratio of chloroacetamide and bis-(pyridylmethylene)amine is 1:2~1:4, and the reaction is stirred at room temperature for 7h~10h; add distilled water, adjust the pH=6~7 with dilute hydrochloric acid, filter, and collect the resulting Precipitate and recrystallize with acetonitrile to obtain fluorescent probe N-(2-(1H-benzimidazolyl)phenyl)-2-bis(2-pyridineamino)acetamide. The advantages are: it has good sensitivity, strong anti-interference ability and is friendly to the environment in the monitoring analysis and tracing of Zn2+ and S2- in water environment system and biological cell system.

Description

technical field [0001] The invention relates to a relay identification Zn 2+ and S 2- The ratiometric fluorescent probe and its synthesis method and application. Background technique [0002] Zinc ions are the second most abundant transition metal ions in the human body after iron ions. Zinc plays a very important role in the growth and development of the human body. It is the main component of dozens of enzymes in the human body and an essential trace element for human brain development. At the same time, zinc can also promote the proliferation and activity of lymphocytes. It also plays a very important role in maintaining normal epithelial tissue and mucosal tissue and preventing bacterial and viral invasion. Therefore, the detection of zinc ions is of great significance to biological science and medicine. [0003] Negative divalent sulfide ions mainly exist in the form of inorganic sulfides. In the biological system environment, when the content of negative divalent s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C09K11/06G01N21/64
Inventor 汤立军蔡明君钟克利侯淑华边延江
Owner BOHAI UNIV
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