Biphenyl nitrile derivative with AIE and ESIPT characteristics as well as synthesis method and application of biphenyl nitrile derivative

A synthesis method and technology of biphenylnitrile, applied in chemical instruments and methods, measurement of color/spectral characteristics, and analysis through chemical reaction of materials, etc., can solve problems such as unidentifiable with naked eyes, poor water solubility, and low sensitivity , to achieve clear results, low detection cost, and simple detection methods

Active Publication Date: 2021-09-17
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the sensing systems reported in some literatures still have problems such as poor water solubility, low sensitivity, poor specificity, and inability to be recognized by naked eyes.

Method used

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  • Biphenyl nitrile derivative with AIE and ESIPT characteristics as well as synthesis method and application of biphenyl nitrile derivative
  • Biphenyl nitrile derivative with AIE and ESIPT characteristics as well as synthesis method and application of biphenyl nitrile derivative
  • Biphenyl nitrile derivative with AIE and ESIPT characteristics as well as synthesis method and application of biphenyl nitrile derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis and characterization of embodiment 1 biphenyl nitrile derivative

[0036]Synthesis of 3'-formyl-4'-hydroxyl-4-cyanobiphenyl: According to the literature (A cyanobiphenylcontaining fluorescence "turn on" sensor for Al 3+ ion in CH 3 CN-water, Onder Alici, et al, "Sensors and Actuators B:Chemical", volume 208, pages 159-163) report method to synthesize: 4'-hydroxyl-4-biphenylcarbonitrile (0.5g , 2.56mmol) and hexamethylenetetramine (HMTA, 2.15g, 15.36mmol) in a solution of trifluoroacetic acid (40mL) was refluxed for 4h. After completion, the reaction mixture was cooled to room temperature and 1.0M HCl (100 mL) was added, the resulting mixture was extracted with dichloromethane (100 mL), the organic layer was washed 3 times with water and once with saturated brine, and dried over magnesium sulfate. After filtration, the solvent was removed to give 3'-formyl-4'-hydroxy-4-biphenylcarbonitrile (40.59 mg, 71%) as a yellow solid. 1 H NMR (DMSO-d 6 )δ (ppm): 11.07...

Embodiment 2

[0038] Embodiment 2 biphenyl nitrile derivatives are used for HSO 3 - UV selectivity determination of

[0039] 1mM NBD derivative stock solution in DMSO, 0.01M HSO in distilled water 3 - Solution, and configure HEPES buffer solution with pH=7.4 and concentration of 0.025M; take 100 μL of biphenyl nitrile derivative stock solution and add it to a clean colorimetric tube, add a certain amount of anion stock solution (F - , Cl - ,Br - ,I - ,AcO - ,CN - ,NO 3 - ,H 2 PO 4 - , HSO 4 - , SO 4 2- , SO 3 2- , HSO 3 - ,S 2- ,CO 3 2- , HCO 3 - ), add 0.5mL HEPES buffer, dilute to 5mL with secondary water, shake well, take 2.5mL into a clean cuvette, and detect it on a UV-Vis spectrophotometer. HIBC itself has two absorption peaks at 275nm and 395nm. After adding common anions, only HSO 3 - Reduce the absorption peak of HIBC at 395nm, and enhance the absorption peak at 275nm, indicating that HIBC has the effect on HSO 3 - There is good selectivity. UV select...

Embodiment 3

[0040] Embodiment 3 biphenyl nitrile derivatives are used for HSO 3 - UV absorbance determination

[0041] Take 100 μL of biphenyl nitrile derivative stock solution and add it to a clean colorimetric tube, add different volumes of HSO 3 - (2μL, 4μL, 6μL, 8μL, 10μL, 12μL, 14μL, 16μL), add 0.5mL HEPES buffer, dilute to 5mL with secondary water, shake well and add 2.5mL to a clean cuvette, visible in UV detected on a spectrophotometer, with HSO 3 - The addition of the solution gradually changed from yellow to colorless, the absorption peak at 395nm gradually decreased, the absorption peak at 275nm gradually increased, and the isosbestic point appeared at 318nm. The UV spectrum absorption diagram is shown in image 3 .

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Abstract

The invention provides a biphenyl nitrile derivative with AIE and ESIPT characteristics and a synthesis method and application thereof, and belongs to the field of biphenyl nitrile derivatives and the field of bisulfite detection. The synthetic method of the biphenyl nitrile derivative comprises the following steps: firstly, synthesizing 3 '-formyl-4'-hydroxy-4-cyanobiphenyl according to a method reported in literatures; and then, adding the 3 '-formyl-4'-hydroxy-4-cyanobiphenyl and 2-aminoimidazole into ethanol, heating and refluxing, and recrystallizing to obtain the product, namely the biphenyl nitrile derivative. The invention further provides a method for detecting the bisulfite. The biphenyl nitrile derivative is used as a probe, and the content of the bisulfite is quantitatively detected in a full-water (pH = 7.4) solution. The detection method can detect the bisulfite in the aqueous solution with high selectivity and high sensitivity, and is simple, convenient and fast to operate. Meanwhile, the test paper for detecting the bisulfite is provided, so that the bisulfite is more convenient to detect.

Description

technical field [0001] The invention relates to the field of bisulfite detection, in particular to a biphenylnitrile derivative with AIE and ESIPT characteristics, a synthesis method thereof and an application in detection of bisulfite. Background technique [0002] As we all know, NaHSO 3 a lot of uses. For example, it can be used as a bleaching agent and preservative for food-grade products, and can also be used as a reducing agent in the production of papermaking, chemical synthesis and other industries. But NaHSO 3 The harm should not be underestimated, exposure to excessive NaHSO 3 It will have an irritating effect on the skin, eyes, and respiratory tract, and can cause adverse reactions such as allergies, corneal damage, even blindness, and asthma. On the other hand, NaHSO 3 Exposure to air will decompose SO 2 , acidify rainwater and cause environmental pollution. Therefore, detection of HSO 3 - Content is an important task. [0003] At present, methods such ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/30C09K11/06G01N21/31G01N21/64G01N21/78
CPCC07D235/30C09K11/06G01N21/78G01N21/643G01N21/31C09K2211/1007C09K2211/1044G01N2021/7759G01N2021/775G01N2021/6417
Inventor 王建华韩佳红王煜双少敏
Owner SHANXI UNIV
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