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Benzopyran nitrile-based sulfite fluorescence probe and preparation method thereof

A technology of methylchromene malononitrile and benzopyranonitrile, which is applied in the field of anion detection, can solve the problem of fewer types, and achieve the effects of high selectivity, strong penetration, and strong anti-interference ability

Inactive Publication Date: 2017-12-01
HENAN AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are relatively few types of reactive fluorescent probes that can detect anions at present, and further development is needed.

Method used

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  • Benzopyran nitrile-based sulfite fluorescence probe and preparation method thereof
  • Benzopyran nitrile-based sulfite fluorescence probe and preparation method thereof
  • Benzopyran nitrile-based sulfite fluorescence probe and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 1. Experimental part

[0046] Reagents and materials: All reagents were from Shanghai Jingchun Reagent Co., Ltd.

[0047] 1. Preparation of Intermediate I

[0048] In a 100mL round bottom flask, add 208mg (1mmol) 2-methylchromene malononitrile, 144mg (1.2mmol) p-hydroxybenzaldehyde, 20mL acetonitrile, 0.8×10 -2 mmol piperidine, heated to reflux for 6 hours, cooled, and the solvent was removed with a rotary evaporator, the residue was extracted with dichloromethane and 2% sodium bicarbonate solution, and the organic layer was washed with anhydrous Na 2 SO 4 After drying, filtering, and concentration, the residue was passed through a silica gel column (PE:EtOAc=3:1) to obtain 166 mg of an orange-red solid with a yield of 53%.

[0049] 1 H-NMRδ (400MHz, DMSO, ppm): 10.15(s, 1H), 8.686-8.707(d, J=8.4Hz, 1H), 7.871-7.910(t, 1H), 7.742-7.763(d, J=8.4 Hz, 1H), 7.557-7.673 (m, 4H), 7.211-7.251 (t, J=16Hz, 1H), 6.835-6.908 (t, J=8.0Hz, 3H).

[0050] 2. Preparation of sulfi...

Embodiment 2

[0065] 1. Experimental part

[0066] Reagents and materials: All reagents were from Shanghai Jingchun Reagent Co., Ltd.

[0067] 1. Preparation of Intermediate I

[0068] In a 100mL round bottom flask, add 208mg (1mmol) 2-methylchromene malononitrile, 120mg (1mmol) p-hydroxybenzaldehyde, 20mL toluene, 1.0×10 -2 mmol piperidine, heated to reflux at 80°C for 24 hours, cooled, and removed the solvent with a rotary evaporator, the residue was extracted with dichloromethane and 2% sodium bicarbonate solution, and the organic layer was washed with anhydrous Na 2 SO 4 After drying, filtering, and concentration, the residue was passed through a silica gel column (PE:EtOAc=3:1) to obtain 128 mg of an orange-red solid with a yield of 41%.

[0069] 1 H-NMRδ (400MHz, DMSO-d 6 , ppm): 10.15 (s, 1H), 8.686-8.707 (d, J=8.4Hz, 1H), 7.871-7.910 (t, 1H), 7.742-7.763 (d, J=8.4Hz, 1H), 7.557- 7.673 (m, 4H), 7.211-7.251 (t, J=16Hz, 1H), 6.835-6.908 (t, J=8.0Hz, 3H).

[0070] 2. Preparation ...

Embodiment 3

[0085] 1. Experimental part

[0086] Reagents and materials: All reagents were from Shanghai Jingchun Reagent Co., Ltd.

[0087] 1. Preparation of Intermediate I

[0088] In a 100mL round bottom flask, add 208mg (1mmol) 2-methylchromene malononitrile, 180mg (1.5mmol) p-hydroxybenzaldehyde, 20mL n-propanol, 1.5×10 -2 mmol piperidine, heated to reflux at 100°C for 15 hours, cooled, removed the solvent with a rotary evaporator, extracted the residue with dichloromethane and 10% sodium bicarbonate solution, and washed the organic layer with anhydrous Na 2 SO 4 After drying, filtration and concentration, the residue was passed through a silica gel column (PE:EtOAc=3:1) to obtain 150 mg of an orange-red solid with a yield of 48%.

[0089] 1 H-NMRδ (400MHz, DMSO-d 6 , ppm): 10.15 (s, 1H), 8.686-8.707 (d, J=8.4Hz, 1H), 7.871-7.910 (t, 1H), 7.742-7.763 (d, J=8.4Hz, 1H), 7.557- 7.673 (m, 4H), 7.211-7.251 (t, J=16Hz, 1H), 6.835-6.908 (t, J=8.0Hz, 3H).

[0090] 2. Preparation of su...

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Abstract

The invention belongs to the technical field of anion detection and relates to a benzopyran nitrile-based sulfite fluorescence probe and a preparation method thereof. The preparation method comprises the following steps: reacting 2-methylbenzopyran malononitrile and p-hydroxy benzaldehyde to produce 2-(1-hydroxyvinyl phenyl) benzopyran malononitrile, and reacting with acetylpropionic acid to prepare the product. After sulfite ions are added, fluorescence appears at 710nm, the fluorescence peak is enhanced along with increase of the concentration of the sulfite ions, the fluorescence intensity presents a linear relation with the sulfite ion concentration in a range (0-8)*10<-6>M of the concentration of the sulfite ions. The solution color is changed from yellow to blue so as to achieve a colorimetric detection effect. The probe molecule has the characteristic of high interference resistance in a coexistence system of the sulfite ions and other multiple negative ions, and the fluorescence probe is high in selectivity, high in sensitivity and fast in response and can be well applied to sulfite detection in the environment.

Description

technical field [0001] The invention belongs to the technical field of anion detection, and relates to a benzopyranonitrile-based sulfite fluorescent probe and a preparation method thereof. Background technique [0002] Chemical probes play an important role in analytical chemistry, clinical medicine, life science, environmental science and other fields. Fluorescent probe technology has the advantages of high sensitivity, good selectivity, rapid detection, and real-time monitoring. Organic small molecule fluorescent probes have received special attention due to their ease of synthesis. [0003] Some anions play extremely important roles in many chemical and biological processes. Organic small molecule fluorescent probes for identifying anions are one of the important contents of current supramolecular chemistry research. Among them, the anionic fluorescent probes based on chemical reactions are reactive fluorescent probes, which are mainly aimed at anions that can undergo...

Claims

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Application Information

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IPC IPC(8): C07D311/58C09K11/06G01N21/64G01N21/78
CPCC07D311/58C09K11/06C09K2211/1088G01N21/6486G01N21/78
Inventor 谢普会郭丰启高光芹黄雪伟王志敏金秋涂鹏孟维雪
Owner HENAN AGRICULTURAL UNIVERSITY
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