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A kind of pyridine-coumarin pH fluorescent probe and its application

A fluorescent probe, coumarin-based technology, applied in fluorescence/phosphorescence, luminescent materials, material analysis by optical means, etc., can solve the problems of strong acid/strong base unstable luminophore, non-linear relationship, poor selectivity, etc. , to achieve the effect of good reversible response, high sensitivity and stable probe

Active Publication Date: 2021-05-18
CHINA THREE GORGES UNIV
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  • Claims
  • Application Information

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Problems solved by technology

However, they have luminophores that are unstable to strong acids / bases, so there are few reports on fluorescent probes for extremely acidic (pH10), and a few have fluorescence at low pH Due to the addition of too many proton sensing groups in the responsive fluorescent probe, the fluorescence intensity is not linearly related to the pH value, so accurate pH measurement cannot be performed, and the selectivity is poor.

Method used

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  • A kind of pyridine-coumarin pH fluorescent probe and its application
  • A kind of pyridine-coumarin pH fluorescent probe and its application
  • A kind of pyridine-coumarin pH fluorescent probe and its application

Examples

Experimental program
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Embodiment 1

[0050] Synthesis of embodiment 1pH fluorescent probe 2-amino-4-phenyl-6-(7-diethylaminocoumarin-3-yl)pyridinecarbonitrile (I-1)

[0051] Add 1.00g (3.86mmol) of 7-diethylaminocoumarin-3-ethanone to a 50ml reaction flask, add 25mL of ethanol and stir to dissolve, then add 0.40g (3.86mmol) of benzaldehyde and 0.25g of malononitrile (3.86mmol), ammonium acetate 2.40g (30.80mmol), piperidine 0.1g, reflux at 80 ° C, TLC spot plate tracking until the reaction is complete, natural cooling, an orange solid precipitates, suction filtration, recrystallization with absolute ethanol, 1.18g of yellow solid was obtained, yield: 75.06%, m.p.: 224-226°C. 1 H NMR (400MHz, CDCl 3 )δ (ppm): 8.75 (s, 1H), 8.09 (s, 1H), 7.74–7.61 (m, 2H), 7.49 (m, J = 7.0Hz, 3H), 7.41 (d, J = 8.9Hz, 1H), 6.62(dd, J=8.9, 2.3Hz, 1H), 6.51(d, J=2.1Hz, 1H), 5.25(s, 2H), 3.44(dd, J=7.1Hz, 4H), 1.23( t,J=7.1Hz,6H). 13 C NMR (100MHz, CDCl 3 )δ(ppm):160.81,159.28,157.17,154.91,154.63,151.81,144.51,137.03,130.51,129.6...

Embodiment 2

[0054] Example 2 Synthesis of pH fluorescent probe 2-amino-4-(4-methoxy)phenyl-6-(7-diethylaminocoumarin-3-yl)pyridinecarbonitrile (I-2)

[0055] Add 1.00g (3.86mmol) 7-diethylaminocoumarin-3-ethanone to the 50ml reaction bottle, add 25mL ethanol and stir to dissolve, then add p-methoxybenzaldehyde 0.53g (3.86mmol), acetone 0.25g (3.86mmol) of dinitrile, 2.40g (30.80mmol) of ammonium acetate, reflux at 80°C, follow the TLC spot plate until the reaction is complete, cool naturally, precipitate an orange solid, filter with suction, wash with ethanol (95%), The solid was recrystallized from absolute ethanol to obtain 1.39g of a yellow solid, yield: 82.05%, m.p.: 235-237°C. 1H NMR (400MHz, CDCl 3 )δ (ppm): 8.75 (s, 1H), 8.07 (s, 1H), 7.65 (d, J = 8.8Hz, 2H), 7.44–7.42 (d, 1H), 7.02 (d, J = 8.8Hz, 2H), 6.64(d, J=2.4Hz, 1H), 6.62(d, J=2.4Hz, 1H), 6.52(d, J=2.3Hz, 1H), 5.24(s, 1H), 3.87(s, 3H), 3.46(dd, J=7.1Hz, 4H), 1.24(t, J=7.1Hz, 6H). 13 C NMR (100MHz, CDCl 3 )δ(ppm):160.95,1...

Embodiment 3

[0058] Example 3 Synthesis of pH fluorescent probe 2-amino-4-(4-fluoro)phenyl-6-(7-diethylaminocoumarin-3-yl)pyridinecarbonitrile (I-3)

[0059] Add 1.00g (3.86mmol) 7-diethylaminocoumarin-3-ethanone to a 50ml reaction flask, add 25mL ethanol and stir to dissolve, then add 0.48g (3.86mmol) p-fluorobenzaldehyde, malononitrile 0.25g (3.86mmol), 2.40g (30.80mmol) of ammonium acetate, reflux at 80 ° C, TLC spot plate tracking until the reaction is complete, naturally cool, precipitate orange solid, filter with suction, wash with ethanol (95%), ethanol weight Crystallization gave 1.41g of orange solid, yield: 85.24%, m.p.: 243-245°C. 1HNMR (400MHz, CDCl 3 )δ (ppm): 8.77 (s, 1H), 8.07 (s, 1H), 7.66 (dd, J = 8.5, 5.3Hz, 2H), 7.43 (d, J = 8.9Hz, 1H), 7.19 (t, J=8.5Hz, 2H), 6.64(dd, J=8.9, 2.2Hz, 1H), 6.52(d, J=2.1Hz, 1H), 5.25(s, 2H), 3.46(dd, J=7.1Hz, 4H), 1.25(t, J=7.1Hz, 6H). 13 C NMR (100MHz, CDCl 3 )δ(ppm):159.31,157.28,157.20,154.84,153.88,151.92,147.83,144.72,144.29,130.64,...

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Abstract

The pyridine-coumarin compound used as a pH fluorescent probe disclosed by the present invention has a structural formula such as (1), wherein R is a substituted or unsubstituted aromatic group. These compounds are prepared by a four-component one-pot method of coumarin ethyl ketone, aromatic aldehyde, malononitrile and ammonium acetate. H + Response sensitive, fast, reversible, good selectivity, strong anti-interference. Compared with the existing pH fluorescent probes, this type of probes has the advantages of low synthesis cost, easy operation and high yield, and can realize the detection of H in the pH range of 1.0-3.5. + Quantitative detection has broad application prospects in chemical reaction, microbial engineering, environmental monitoring, sewage detection, ecological protection, etc. to detect acidity.

Description

technical field [0001] The invention relates to the field of organic small molecule fluorescent probes, in particular to a pH fluorescent probe 3-multi-substituted pyridine-7-diethylaminocoumarin and its application. Background technique [0002] pH is a key parameter in a wide range of fields, and has applications in human health, microbial engineering, environmental protection, sewage detection, ecological protection, and chemical production. Especially in industrial production, a large amount of strongly acidic industrial wastewater is often produced, which has caused great pressure on the environment and ecological protection. Therefore, it is of great significance to accurately measure the pH value, especially the pH in a strongly acidic system. Compared with glass electrode method, nuclear magnetic resonance method, absorption spectroscopy method, indicator method and other methods for detecting pH value, fluorescence method has the advantages of good selectivity, high...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C09K11/06G01N21/64
CPCC07D405/04C09K11/06C09K2211/1029C09K2211/1088G01N21/643
Inventor 但飞君唐倩曾晓燕潘常乐
Owner CHINA THREE GORGES UNIV