CN110361432A - A kind of preparation method and application of chiral helical polyaniline@MOF nanocomposite - Google Patents
A kind of preparation method and application of chiral helical polyaniline@MOF nanocomposite Download PDFInfo
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- CN110361432A CN110361432A CN201910813051.9A CN201910813051A CN110361432A CN 110361432 A CN110361432 A CN 110361432A CN 201910813051 A CN201910813051 A CN 201910813051A CN 110361432 A CN110361432 A CN 110361432A
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- polyaniline
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- tyrosine
- mof
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
- G01N27/308—Electrodes, e.g. test electrodes; Half-cells at least partially made of carbon
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
- G01N27/48—Systems using polarography, i.e. measuring changes in current under a slowly-varying voltage
Abstract
It is used to detect the application of enantiomers of chiral drugs the invention discloses a kind of chiral helical polyaniline@MOF nanocomposite preparation method and based on the composite material, belongs to nanocomposite, chiral electrochemical sensing detection technique field.It has main steps that cobalt nitrate is blended with the precursor solution of preparation spiral polyaniline after, overnight, 2-methylimidazole solution is added in products therefrom for 20 DEG C of constant temperature reactions, the obtained chiral helical polyaniline MOF nanocomposite of self-assembling reaction under normal temperature condition.Chiral sensor is constructed using the composite material, the Sensitive Detection for l-tyrosine and D-Tyrosine Enantiomeric excess.The chiral sensor, method is simple, easy to operate, and chiral detection effect is significant.
Description
Technical field
The present invention relates to a kind of chiral helical polyaniline@MOF nanocomposites and its preparation method and application, belong to and receive
Rice material, Metal-organic frame nano material and chiral electrochemical technology field.
Background technique
Chiral phenomenon is widely present in nature, such as people's vivo acid is L-configuration, Portugal in plant in nature
Grape sugar is with the presence of D configuration.Many drugs, nutrient and healthcare products and pesticide etc. are most of with one group of mapping in mirror symmetry
Body, however these enantiomers typically exhibit different bioactivity and pharmacological reaction.The group of drug, nutrient and healthcare products and pesticide
It is related to the wherein content of the amino acid of a certain configuration at, function and its safety.Therefore, chiral material how is identified always
It is one of the problem that numerous quiral products productions and exploitation must solve.
What chiral metal organic framework materials (MOFs) were usually grown by chiral ligand and metal ion or metal cluster
Periodically ordered porous crystalline material, chiral MOFs is in Heterogeneous asymmetric catalysis, the neck such as Selective recognition and chiral sensing
Domain is applied.However, chiral MOFs quantity is few compared with a large amount of reported achirality MOFs materials, progress is slow
Slowly.One major reason is that chiral ligand synthesis is complicated, at high cost, synthetic yield is low, for this purpose, by achirality MOFs Material synthesis
Chiral MOFs composite material is of great significance.
Spiral polyaniline is a kind of conductive organic polymer, it not only has the series of advantages of polyaniline, also as its
The helical structure of itself has chirality, has well in chiral resolution, chiral Recognition with electrochemical technology fields such as chiral catalysis
Prospect and application.
Summary of the invention
Technical assignment of the invention first is that in order to make up for the deficiencies of the prior art, providing a kind of chiral helical polyaniline
MOF nanocomposite and preparation method thereof, this method is raw materials used at low cost, and preparation process is simple, and energy consumption of reaction is low, has
Prospects for commercial application.
The two of technical assignment of the invention are to provide the purposes of the chiral helical polyaniline MOF nanocomposite, i.e.,
The chiral helical polyaniline@MOF nanocomposite is used for the content of efficient detection l-tyrosine and D-Tyrosine enantiomer,
The detection sensor is at low cost, analysis efficiency is high, easy to operate, and operating technology requires low.
To achieve the above object, technical scheme is as follows:
1. a kind of preparation method of chiral helical polyaniline@MOF nanocomposite
(1) spiral polyaniline load C o is prepared2+Intermediate
1-2 mmol cobalt nitrate, 40-60 μ L aniline and 6-8 mL isopropanol are dissolved in the acid solution of 8-12 mL, 5- is stirred
10 min obtain clear aniline-cobalt nitrate mixed solution；
0.8-1.0 mmol ammonium persulfate is dissolved in 2-3mL water, clear ammonium persulfate solution is obtained;
Ammonium persulfate solution is added in aniline-cobalt nitrate mixed solution, is uniformly mixed, the reaction solution is placed in 20 DEG C immediately
Under constant temperature, after reaction overnight, filters, drying at room temperature, spiral polyaniline load C o is made2+Intermediate；
(2) chiral helical polyaniline@MOF nanocomposite is prepared
By 0.5-0.8 g spiral polyaniline load C o2+Intermediate ultrasonic disperse in 3-5 mL water, obtain spiral polyaniline
Load C o2+Intermediate suspension；
The 2-methylimidazole of 1-2 mmol is dissolved in 4-7 mL water, clear 2-methylimidazole solution is obtained；
By 2-methylimidazole solution and spiral polyaniline load C o2+Intermediate suspension be uniformly mixed, 3-5 h is stirred at room temperature,
Centrifuge separation, is washed with water 3 times, and 85 DEG C drying to constant weight, and spiral Polyaniline-Supported ZIF-67 nanocrystal composite is made,
That is chiral helical polyaniline@MOF nanocomposite.
Acid solution as described above, selected from concentration be 0.01-1.0 mmol/L dilute sulfuric acid, 0.05-2mmol/L dilute hydrochloric acid or
0.05-1.5 mmol/L dilute nitric acid solution.
2. the chiral helical polyaniline@MOF nanocomposite of preparation method preparation as described above is passed for electrochemistry
The application of sense detection tyrosine enantiomer
(1) chiral sensor working electrode is prepared
After the glass-carbon electrode that diameter is 4 mm is polished with alumina powder, water and ethyl alcohol clean surface, pipette 10 μ L chirality spiral shells
Polyaniline@MOF Nanocomposite solution is revolved, room temperature dries, obtains chiral helical polyaniline@MOF nanocomposite and repair
The chiral sensor working electrode of decorations；
The chiral helical polyaniline@MOF Nanocomposite solution is that 6 mg chiral helical polyaniline@MOF are nano combined
Material is blended with 250 μ L ethyl alcohol, 720 μ L water and 30 μ L Nafion, and 180W ultrasound 10-15min is made；
(2) l-tyrosine and D-Tyrosine enantiomer are detected
Working electrode made from step (1), Ag/AgCl reference electrode and platinized platinum auxiliary electrode are connected to electrochemical workstation
On, chiral helical polyaniline@MOF electrochemistry chiral sensor is made；
With 0.1 mol L-1KOH be that electrolyte solution using differential pulse voltammetry utilizes chiral helical polyaniline@
MOF electrochemistry chiral sensor measures the l-tyrosine of various concentration and the current value of D-Tyrosine standard solution respectively, draws
L-tyrosine and D-Tyrosine enantiomer working curve based on chiral helical polyaniline@MOF electrochemistry chiral sensor；It will be to
The solution of sample replaces l-tyrosine and D-Tyrosine standard solution, carries out l-tyrosine and D-Tyrosine content in sample
Detection.
The chiral sensor is 1.0 × 10 to the detection range of l-tyrosine and D-Tyrosine mapping liquid solution-2-6.5×
10-9 mmol/mL。
The beneficial technical effect of the present invention is as follows:
(1) preparation of chiral helical polyaniline MOF nanocomposite of the present invention, since spiral polyaniline itself has chirality,
MOF is grown in spiral polyaniline surface self-organization, causes MOF spiral polyaniline nano-composite material to generate chiral.
(2) preparation process uses self-assembled growth method, and cost of material is low, and simple process is easily-controllable, before wide application
Scape.
(3) chiral helical polyaniline@MOF nanocomposite electrochemistry chiral sensor provided by the invention, is by hand
Property spiral polyaniline MOF nanocomposite is coated to glassy carbon electrode surface, and preparation method is simple, easy to operate.Spiral polyaniline
More and different active sites is exposed with MOF crystal, has played the synergistic effect of MOF and spiral polyaniline, so that base
In the chiral sensor of composite material preparation, the content of l-tyrosine and D-Tyrosine chiral enantiomer is detected, is had quick
Response, detection range is wide, high sensitivity, it is easy to operate, time saving the features such as.
Specific embodiment
The present invention will be further described below with reference to examples, but protection scope of the present invention is not only limited to implement
Example, professionals in the field change to made by technical solution of the present invention, are within the scope of protection of the invention interior.
A kind of preparation method of the chiral helical polyaniline@MOF nanocomposite of embodiment 1
(1) spiral polyaniline load C o is prepared2+Intermediate
1 mmol cobalt nitrate, 40 μ L aniline and 6 mL isopropanols are dissolved in 8 mL, concentration is 0.01-1.0 mmol/L dilute sulfuric acid
In solution, 5-10 min is stirred, clear aniline-cobalt nitrate mixed solution is obtained；
0.8 mmol ammonium persulfate is dissolved in 2 mL water, clear ammonium persulfate solution is obtained;
Ammonium persulfate solution is added in aniline-cobalt nitrate mixed solution, is uniformly mixed, the reaction solution is placed in 20 DEG C immediately
Under constant temperature, after reaction overnight, filters, drying at room temperature, spiral polyaniline load C o is made2+Intermediate；
(2) chiral helical polyaniline@MOF nanocomposite is prepared
By 0.5 g spiral polyaniline load C o2+Intermediate ultrasonic disperse in 3 mL water, obtain spiral polyaniline load C o2+
Intermediate suspension；
The 2-methylimidazole of 1 mmol is dissolved in 4 mL water, clear 2-methylimidazole solution is obtained；
By 2-methylimidazole solution and spiral polyaniline load C o2+Intermediate suspension be uniformly mixed, 3 h are stirred at room temperature, from
Heart separation, is washed with water 3 times, and 85 DEG C drying to constant weight, spiral Polyaniline-Supported ZIF-67 nanocrystal composite is made, i.e.,
Chiral helical polyaniline@MOF nanocomposite.
A kind of preparation method of the chiral helical polyaniline@MOF nanocomposite of embodiment 2
(1) spiral polyaniline load C o is prepared2+Intermediate
1.5 mmol cobalt nitrates, 50 μ L aniline and 7 mL isopropanols are dissolved in 10 mL, concentration is 0.05-2mmol/L dilute hydrochloric acid
In, 8 min are stirred, clear aniline-cobalt nitrate mixed solution is obtained；
0.9 mmol ammonium persulfate is dissolved in 2.5 mL water, clear ammonium persulfate solution is obtained;
Ammonium persulfate solution is added in aniline-cobalt nitrate mixed solution, is uniformly mixed, the reaction solution is placed in 20 DEG C immediately
Under constant temperature, after reaction overnight, filters, drying at room temperature, spiral polyaniline load C o is made2+Intermediate；
(2) chiral helical polyaniline@MOF nanocomposite is prepared
By 0.65 g spiral polyaniline load C o2+Intermediate ultrasonic disperse in 4 mL water, obtain spiral polyaniline load C o2 +Intermediate suspension；
The 2-methylimidazole of 1.5 mmol is dissolved in 5.5 mL water, clear 2-methylimidazole solution is obtained；
By 2-methylimidazole solution and spiral polyaniline load C o2+Intermediate suspension be uniformly mixed, 4 h are stirred at room temperature, from
Heart separation, is washed with water 3 times, and 85 DEG C drying to constant weight, spiral Polyaniline-Supported ZIF-67 nanocrystal composite is made, i.e.,
Chiral helical polyaniline@MOF nanocomposite.
A kind of preparation method of the chiral helical polyaniline@MOF nanocomposite of embodiment 3
(1) spiral polyaniline load C o is prepared2+Intermediate
By 2 mmol cobalt nitrates, 60 μ L aniline and 8 mL isopropanols be dissolved in 12 mL, concentration be 1.0 mmol/L dust technologies in,
10 min are stirred, clear aniline-cobalt nitrate mixed solution is obtained；
01.0 mmol ammonium persulfate is dissolved in 3mL water, clear ammonium persulfate solution is obtained;
Ammonium persulfate solution is added in aniline-cobalt nitrate mixed solution, is uniformly mixed, the reaction solution is placed in 20 DEG C immediately
Under constant temperature, after reaction overnight, filters, drying at room temperature, spiral polyaniline load C o is made2+Intermediate；
(2) chiral helical polyaniline@MOF nanocomposite is prepared
By 0.8 g spiral polyaniline load C o2+Intermediate ultrasonic disperse in 5 mL water, obtain spiral polyaniline load C o2+
Intermediate suspension；
The 2-methylimidazole of 2 mmol is dissolved in 7 mL water, clear 2-methylimidazole solution is obtained；
By 2-methylimidazole solution and spiral polyaniline load C o2+Intermediate suspension be uniformly mixed, 5 h are stirred at room temperature, from
Heart separation, is washed with water 3 times, and 85 DEG C drying to constant weight, spiral Polyaniline-Supported ZIF-67 nanocrystal composite is made, i.e.,
Chiral helical polyaniline@MOF nanocomposite.
4 chiral helical polyaniline@MOF nanocomposite of embodiment is for electrochemical sensing detection tyrosine enantiomer
Using
(1) chiral sensor working electrode is prepared
After the glass-carbon electrode that diameter is 4 mm is polished with alumina powder, water and ethyl alcohol clean surface, pipette 10 μ L chirality spiral shells
Polyaniline@MOF Nanocomposite solution is revolved, room temperature dries, obtains chiral helical polyaniline@MOF nanocomposite and repair
The chiral sensor working electrode of decorations；
The chiral helical polyaniline@MOF Nanocomposite solution is by 6 mg embodiments 1 or embodiment 2 or embodiment 3
The chiral helical polyaniline@MOF nanocomposite of preparation is blended with 250 μ L ethyl alcohol, 720 μ L water and 30 μ L Nafion,
180 W, 13 min of ultrasound are made；
(2) l-tyrosine and D-Tyrosine enantiomer are detected
Working electrode made from step (1), Ag/AgCl reference electrode and platinized platinum auxiliary electrode are connected to electrochemical workstation
On, chiral helical polyaniline@MOF electrochemistry chiral sensor is made；
With 0.1 mol L-1KOH be that electrolyte solution using differential pulse voltammetry utilizes chiral helical polyaniline@
MOF electrochemistry chiral sensor measures the l-tyrosine of various concentration and the current value of D-Tyrosine standard solution respectively, draws
L-tyrosine and D-Tyrosine enantiomer working curve based on chiral helical polyaniline@MOF electrochemistry chiral sensor；It will be to
The solution of sample replaces l-tyrosine and D-Tyrosine standard solution, carries out l-tyrosine and D-Tyrosine content in sample
Detection；
Embodiment 1 or the chiral sensor of embodiment 2 or embodiment 3 preparation are to l-tyrosine and D-Tyrosine mapping liquid solution
Detection range is 1.0 × 10-2-6.5×10-9 mmol/mL。
Claims (4)
1. a kind of preparation method of chiral helical polyaniline@MOF nanocomposite, which is characterized in that steps are as follows:
(1) spiral polyaniline load C o is prepared2+Intermediate
1-2 mmol cobalt nitrate, 40-60 μ L aniline and 6-8 mL isopropanol are dissolved in the acid solution of 8-12 mL, 5- is stirred
10 min obtain clear aniline-cobalt nitrate mixed solution；
0.8-1.0 mmol ammonium persulfate is dissolved in 2-3mL water, clear ammonium persulfate solution is obtained;
Ammonium persulfate solution is added in aniline-cobalt nitrate mixed solution, is uniformly mixed, the reaction solution is placed in 20 DEG C immediately
Under constant temperature, after reaction overnight, filters, drying at room temperature, spiral polyaniline load C o is made2+Intermediate；
Prepare chiral helical polyaniline@MOF nanocomposite
By 0.5-0.8 g spiral polyaniline load C o2+Intermediate ultrasonic disperse in 3-5 mL water, it is negative to obtain spiral polyaniline
Carry Co2+Intermediate suspension；
The 2-methylimidazole of 1-2 mmol is dissolved in 4-7 mL water, clear 2-methylimidazole solution is obtained；
By 2-methylimidazole solution and spiral polyaniline load C o2+Intermediate suspension be uniformly mixed, 3-5 h is stirred at room temperature,
Centrifuge separation, is washed with water 3 times, and 85 DEG C drying to constant weight, and spiral Polyaniline-Supported ZIF-67 nanocrystal composite is made,
That is chiral helical polyaniline@MOF nanocomposite.
2. a kind of preparation method of chiral helical polyaniline@MOF nanocomposite as described in claim 1, feature exist
In the acid solution is 0.01-1.0 mmol/L dilute sulfuric acid, 0.05-2mmol/L dilute hydrochloric acid or 0.05-1.5 selected from concentration
Mmol/L dilute nitric acid solution.
3. the chiral helical polyaniline@MOF nanocomposite of preparation method preparation as described in claim 1 is used for electrochemistry
The application of sensing detection tyrosine enantiomer.
4. the application of electrochemical sensing detection tyrosine enantiomer as claimed in claim 3, which is characterized in that steps are as follows:
(1) chiral sensor working electrode is prepared
After the glass-carbon electrode that diameter is 4 mm is polished with alumina powder, water and ethyl alcohol clean surface, pipette 10 μ L chirality spiral shells
Polyaniline@MOF Nanocomposite solution is revolved, room temperature dries, obtains chiral helical polyaniline@MOF nanocomposite and repair
The chiral sensor working electrode of decorations；
The chiral helical polyaniline@MOF Nanocomposite solution is that 6 mg chiral helical polyaniline@MOF are nano combined
Material is blended with 250 μ L ethyl alcohol, 720 μ L water and 30 μ L Nafion, and 180W ultrasound 10-15min is made；
(2) l-tyrosine and D-Tyrosine enantiomer are detected
Working electrode made from step (1), Ag/AgCl reference electrode and platinized platinum auxiliary electrode are connected to electrochemical workstation
On, chiral helical polyaniline@MOF electrochemistry chiral sensor is made；
With 0.1 mol L-1KOH be that electrolyte solution using differential pulse voltammetry utilizes chiral helical polyaniline@MOF
Electrochemistry chiral sensor measures the l-tyrosine of various concentration and the current value of D-Tyrosine standard solution respectively, draws base
In the l-tyrosine and D-Tyrosine enantiomer working curve of chiral helical polyaniline@MOF electrochemistry chiral sensor；It will be to be measured
The solution of sample replaces l-tyrosine and D-Tyrosine standard solution, carries out the inspection of l-tyrosine and D-Tyrosine content in sample
It surveys.
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| CN111398379A (en) * | 2020-03-12 | 2020-07-10 | 济南大学 | Method for detecting tyrosine enantiomer by electrochemical chiral sensing |
| CN111398381A (en) * | 2020-04-17 | 2020-07-10 | 济南大学 | Electrochemical identification method for identifying non-electroactive amino acid enantiomer |
| CN114577864A (en) * | 2022-05-09 | 2022-06-03 | 成都晟铎传感技术有限公司 | MEMS hydrogen sulfide sensor for improving metal salt poisoning effect and preparation method thereof |
| CN115248244A (en) * | 2021-12-30 | 2022-10-28 | 兰州理工大学 | Method for synthesizing chiral polymer by inducing chiral nanochannels based on MOF and application |
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| CN111398379A (en) * | 2020-03-12 | 2020-07-10 | 济南大学 | Method for detecting tyrosine enantiomer by electrochemical chiral sensing |
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| CN114577864A (en) * | 2022-05-09 | 2022-06-03 | 成都晟铎传感技术有限公司 | MEMS hydrogen sulfide sensor for improving metal salt poisoning effect and preparation method thereof |
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