CN107505296B - Application of the 3- bipyridine methyl benzene imidodicarbonic diamide in detection phenol - Google Patents
Application of the 3- bipyridine methyl benzene imidodicarbonic diamide in detection phenol Download PDFInfo
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- CN107505296B CN107505296B CN201710651785.2A CN201710651785A CN107505296B CN 107505296 B CN107505296 B CN 107505296B CN 201710651785 A CN201710651785 A CN 201710651785A CN 107505296 B CN107505296 B CN 107505296B
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- methyl benzene
- imidodicarbonic diamide
- bipyridine methyl
- phenol
- benzene imidodicarbonic
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N2021/6432—Quenching
Abstract
Application the present invention relates to 3- bipyridine methyl benzene imidodicarbonic diamide as fluorescent reagent in detection phenol, the 3- bipyridine methyl benzene imidodicarbonic diamide are protonation 3- bipyridine methyl benzene imidodicarbonic diamide.The 3- bipyridine methyl benzene imidodicarbonic diamide is placed in dimethylformamide the preparation method is as follows: 3- aminomethyl-pyridine and pyromellitic dianhydride are mixed, it is heated to reflux 10h under the conditions of 350 DEG C, reactant is cooled to room temperature, is filtered, washed and recrystallizes up to the 3- bipyridine methyl benzene imidodicarbonic diamide.3- bipyridine methyl benzene imidodicarbonic diamide encounters the characteristic that phenol has fluorescent quenching, easy to operate for making fluorescence detection phenol reagent, fluorescence detection phenol high sensitivity.Under conditions of pH value is 6, after 3- bipyridine methyl benzene imidodicarbonic diamide is dissolved in dimethylformamide, fluorescence is issued under 285nm exciting light, maximum emission wavelength is located at 345nm；There is fluorescent quenching property for phenol, the minimum concentration to fluorescence detection phenol is 10‑6 mol/L。
Description
Technical field
The invention belongs to environmental testings, and in particular, to 3- bipyridine methyl benzene imidodicarbonic diamide is in detection phenol
Application.
Background technique
Phenol is a kind of important Organic Chemicals, and the phenol in environment is mainly derived from coking oil refining petrochemical industry
The processes such as fertile pesticide plastics manufacture burning.Phenol category high poison substance, mainly enters human body by respiratory tract and skin and causes
Poison, low concentration can make protein denaturation, and high concentration can make protein precipitation, therefore have direct damage to cell, can make mucous membrane, painstaking effort
Pipe and central nervous system are damaged and are inhibited by burn into, big to the harm of organism, can cause seriously to pollute to environment.
Currently, the measuring method of phenol is constantly brought forth new ideas and improved in environment, traditional amino-antipyrine is divided light
The pre-treatment of degree method water sample is cumbersome, and complicated for operation and interference is more, and the result of measurement is easy to be affected by various factors, side
The reproducibility and poor sensitivity of method.Fluorimetry measure quick and precisely, high sensitivity and by pro-gaze.Chromatography operation side
Just, it is convenient for on-line analysis.Zhang Liping etc. has studied in phosphate buffer solution, phenol and amino-antipyrine and the potassium ferricyanide
Reaction generates weld, after chloroform extraction, is measured and is absorbed using spectrophotometry, the method is used for phenol in wastewater
Measurement when accurate stable, but this water sample pre-treatment is cumbersome, and complicated for operation and disturbing factor is more, and the result of measurement is easy
It is affected, reproducibility and poor sensitivity.Tang Qinghua etc. is based on Determination of Trace Phenol and is made to potassium metaperiodate oxidation isatin reaction by catalysis
With having studied using Determination of Trace Phenol in Waste Water by Spectrophotometric, work well.Money is beautiful etc. to be had studied in hydrochloric acid medium
Using starch as color developing agent, by content preservative phenol in ultraviolet-visible Rapid Photometric Determination cosmetics, phenol quality is dense
Spending is in good linear relationship within the scope of 0.05~2.5mg/L, Monitoring lower-cut 0.01mg/L, and this law is easy to operate, quick, clever
It is quick.Xu Gaoyang etc. proposes that dual-wavelength ultraviolet spectrophotometry measures the method containing phenol in 1,4-benzoquinone and phenol mixed liquor, solves
The problem of 1,4-benzoquinone disturbed specimen measurement, phenol detection limit 0.1mg/L, recovery of standard addition 99~105%, relative standard deviation
Less than 2.2%.There are the detection phenol processes such as spectrophotometry and chromatography traditional at present low, complex steps of sensitivity etc. to lack
Point.
Therefore, it is necessary to research and develop a kind of easy to operate, high sensitivity fluorescent reagent that can be used in detecting phenol.
Summary of the invention
It is an object of the invention to overcome the deficiencies of the prior art and provide 3- bipyridine methyl benzene imidodicarbonic diamide as fluorescence
Application of the reagent in detection phenol.3- bipyridine methyl benzene imidodicarbonic diamide encounters the characteristic that phenol has fluorescent quenching, is used for
Make fluorescence detection phenol reagent, easy to operate, fluorescence detection phenol high sensitivity.
To achieve the above object, the present invention adopts the following technical scheme:
Application of the 3- bipyridine methyl benzene imidodicarbonic diamide as fluorescent reagent in detection phenol.
In the present invention, the molecular formula of the 3- bipyridine methyl benzene imidodicarbonic diamide is C22H14N4O4, molecular weight is
398.4, structural formula is as follows:
Preferably, the 3- bipyridine methyl benzene imidodicarbonic diamide is protonation 3- bipyridine methyl benzene imidodicarbonic diamide.
In the present invention, the 3- bipyridine methyl benzene imidodicarbonic diamide the preparation method is as follows:
3- aminomethyl-pyridine and pyromellitic dianhydride are mixed and are placed in dimethylformamide, in 140~150 DEG C of conditions
Under be heated to reflux 9~11h, reactant is cooled to room temperature, is filtered, washed and recrystallizes up to two acyl of 3- bipyridine methyl benzene
Imines.Preferably, heating temperature is 150 DEG C, heating time 10h.
Specific synthesis step reaction equation is as follows:
Preferably, it is described protonation 3- bipyridine methyl benzene imidodicarbonic diamide the preparation method comprises the following steps: by 3- bipyridine methyl benzene
Imidodicarbonic diamide is dissolved in dimethylformamide, is stirred at room temperature, and then adjusting pH is 6 to get protonation two acyl of 3- bipyridine methyl benzene
Imines.
Preferably, the detectable concentration of the 3- bipyridine methyl benzene imidodicarbonic diamide Pyrogentisinic Acid is 10-6mol/L。
Compared with prior art, the invention has the following beneficial effects:
The present invention provides a kind of new fluorescence detection phenol reagents, under the conditions of pH value is 6,3- bipyridine methyl benzene two
Imido DMF solution has fluorescence emission peak at 345nm, with the addition of phenol, 3- bipyridine methyl benzene imidodicarbonic diamide with
Phenol forms hydrogen bond action, and the fluorescence emission spectrum of the compound has been quenched, and can be detected 10-6The phenol concentration of mol/L.3- bis-
The synthesis of picolyl benzene imidodicarbonic diamide simply, conveniently, has application prospect in terms of food, environment measuring phenol.
Specific embodiment
Present invention will be further explained below with reference to specific examples.These embodiments are merely to illustrate the present invention and do not have to
In limiting the scope of the invention.Test method without specific conditions in lower example embodiment, usually according to this field conventional strip
Part or the condition suggested according to manufacturer.Any unsubstantiality that those skilled in the art is done on the basis of the present invention
Variation and replacement belong to scope of the present invention.
The synthesis of 1 3- bipyridine methyl benzene imidodicarbonic diamide of preparation example
3- aminomethyl-pyridine (2.16g, 0.020mol) and pyromellitic dianhydride (2.18g, 0.010mmol) are mixed in
DMF solvent (20mL) is heated to reflux 10 hours reactants under the conditions of 150 DEG C and is cooled to room temperature, obtains the solid powder of white.
Then it filters, ethanol washing 3 times, recrystallizes, obtain clear crystal 3- bipyridine methyl benzene imidodicarbonic diamide, yield 2.16g is produced
Rate is 54.3%.
Elemental analysis: C22H14N4O4, calculated value C, 66.33%；H, 3.54%；N, 14.06%, experiment value C,
66.15%；H, 3.91%；N, 13.87%；Infrared spectroscopy: IR (KBr, cm-1):3431m,2959vs,1766w,1707vs,
1430m,1391s,1309w,1230w,1153m,1091m,1026w,929w,864w,774w,737m,713w,628w,558w；
Mono-crystalline structures are as follows.
The method of 1 3- bipyridine methyl benzene imidodicarbonic diamide fluorescence detection phenol of embodiment
3- bipyridine methyl benzene imidodicarbonic diamide (0.4mg, 1.0 μm of ol) is dissolved in 100ml DMF solvent.Solution room temperature
Stirring 20 minutes, it is 6 that perchloric acid, which is added, and adjusts pH value, obtains protonation 3- bipyridine methyl benzene imidodicarbonic diamide fluorescent reagent.
The reagent emits fluorescence under the excitation of 285nm wavelength light, maximum emission wavelength 345nm, as shown in Figure 1, 2.When adding
After the phenol for entering low concentration, solution has fluorescent quenching in 345nm transmitted wave strong point, but to benzene, toluene, ortho-xylene, diformazan
Benzene and paraxylene do not generate fluorescent quenching variation.It can detecte phenol based on this principle, it is easy to operate.
Claims (6)
- Application of the 1.3- bipyridine methyl benzene imidodicarbonic diamide as fluorescent reagent in detection phenol, the bis- pyridine first of 3- The molecular formula of base benzene imidodicarbonic diamide is C22H14N4O4, molecular weight 398.4, structural formula is as follows:
- 2. applying according to claim 1, which is characterized in that the 3- bipyridine methyl benzene imidodicarbonic diamide is protonation 3- bis- Picolyl benzene imidodicarbonic diamide.
- 3. applying according to claim 1, which is characterized in that the preparation method of the 3- bipyridine methyl benzene imidodicarbonic diamide is such as Under:3- aminomethyl-pyridine and pyromellitic dianhydride are mixed and are placed in dimethylformamide, is added under the conditions of 140~150 DEG C Heat 9~11h of reflux, reactant is cooled to room temperature, be filtered, washed recrystallize it is sub- up to two acyl of 3- bipyridine methyl benzene Amine.
- 4. applying according to claim 3, which is characterized in that heating temperature is 150 DEG C, heating time 10h.
- 5. applying according to claim 1, which is characterized in that the detection of the 3- bipyridine methyl benzene imidodicarbonic diamide Pyrogentisinic Acid It is limited to 10-6mol/L。
- 6. applying according to claim 2, which is characterized in that the preparation of the protonation 3- bipyridine methyl benzene imidodicarbonic diamide Method are as follows: 3- bipyridine methyl benzene imidodicarbonic diamide is dissolved in dimethylformamide, is stirred at room temperature, then adjusting pH is 6 to get matter Sonization 3- bipyridine methyl benzene imidodicarbonic diamide.
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| CN117110256B (en) * | 2023-05-29 | 2024-04-19 | 兰州大学第一医院 | Urine tyrosine detection reagent and detection method based on N-GQDs fluorescence quenching principle |
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| CN106543126A (en) * | 2016-10-25 | 2017-03-29 | 中国工程物理研究院化工材料研究所 | Based on coumarin to NO2The fluorescent probe of fluorescent quenching effect and its preparation method and application |
| CN106588968A (en) * | 2016-12-13 | 2017-04-26 | 济南大学 | Preparation and application of boron-dipyrromethene-based diethyl chlorophosphate fluorescent probe |
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2017
- 2017-08-02 CN CN201710651785.2A patent/CN107505296B/en active Active
Patent Citations (3)
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|---|---|---|---|---|
| US5445944A (en) * | 1992-07-31 | 1995-08-29 | Syntex (U.S.A.) Inc. | Methods for determining peroxidately active substances |
| CN106543126A (en) * | 2016-10-25 | 2017-03-29 | 中国工程物理研究院化工材料研究所 | Based on coumarin to NO2The fluorescent probe of fluorescent quenching effect and its preparation method and application |
| CN106588968A (en) * | 2016-12-13 | 2017-04-26 | 济南大学 | Preparation and application of boron-dipyrromethene-based diethyl chlorophosphate fluorescent probe |
Non-Patent Citations (3)
| Title |
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| 3(4)-二吡啶甲基端基萘(苯)二酰亚胺配体与过渡金属的自组装和配合物性能研究;李国璧;《中国博士学位论文全文数据库》;20110315;B014-10 * |
| A Noninterpenetrated 1D Molecular Ladder and 2D Butterfly Network:Effect of Positional Isomerism of Semirigid Bis(pyridylmethyl)pyromellitic Diimide Ligands on the Architecture ofTheir Metal(II) Complexes;Xing-Qiang Lu;《Inorganic Chemistry》;20051231;第44卷(第6期);第1810-1817页 * |
| Synthesis, crystal structure, fluorescence properties of 1D chain Manganese (II) and Cadmium (II) complexes;Guo-Bi Li;《Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy》;20170702;第187卷;第168-173页 * |
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