CN111483988B - Preparation method of antioxidant black phosphorus nanosheet - Google Patents
Preparation method of antioxidant black phosphorus nanosheet Download PDFInfo
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- CN111483988B CN111483988B CN202010305400.9A CN202010305400A CN111483988B CN 111483988 B CN111483988 B CN 111483988B CN 202010305400 A CN202010305400 A CN 202010305400A CN 111483988 B CN111483988 B CN 111483988B
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Abstract
A preparation method of an antioxidant black phosphorus nanosheet belongs to the field of two-dimensional layered materials. The method comprises the following steps: adding the black phosphorus nanosheet into an organic solvent to prepare an organic solvent dispersion liquid of the black phosphorus nanosheet, and simultaneously preparing a halogenated alkane modification solution of alkylamine as a surface modifier; mixing the black phosphorus nanosheet dispersion liquid with a surface modifier to obtain a mixture; placing the mixture in a sealed system heated in inert atmosphere for reflux reaction; and cooling the mixed solution, and then carrying out liquid-solid separation, washing and drying to obtain the antioxidant black phosphorus nanosheet. Dialkyl alkyl methylamine is grafted on the surface of the black phosphorus nanosheet through a P-C-N bond, wherein P is directly connected with methylene, dialkyl amine is exposed outside, the oxidation kinetics of the alkyl amine is slow, and the oxidation of the black phosphorus nanosheet can be effectively prevented. Meanwhile, compared with the existing aromatic azide chemical, the dialkyl methylamine is low in price and environment-friendly. The method is suitable for the fields of field effect transistors, photoelectric detectors and the like.
Description
Technical Field
The invention belongs to the field of two-dimensional layered materials, relates to a black phosphorus material, and particularly relates to a preparation method of an antioxidant black phosphorus nanosheet.
Background
In recent years, two-dimensional BP, as a semiconductor having a layered structure, has attracted extensive research interest from a large number of researchers. Unlike graphene, black phosphorus is a thickness-dependent semiconductor with a direct band from the band value of 0.3eV for bulk materials to 1.5eV for single-layer black phosphorus. Compared with molybdenum disulfide, black phosphorus has higher carrier mobility (200) -1000cm 2V-1 s-1) and larger on-off ratio (>105) And anisotropic properties. The excellent performances enable the black phosphorus to have wide application prospects in the field of nano photoelectric devices, and also have good application prospects in the fields of catalysis, sensing and intelligent equipment, particularly field effect transistors, anisotropic photoelectric detectors and the like.
Although black phosphorus possesses these excellent properties, its instability in air and water limits its application. It is well documented that black phosphorus readily reacts with oxygen and water at room temperature, causing compositional changes that degrade and degrade its optoelectronic properties (angelw. chem. int. ed,2016,128,5087). That is, the lone pair of electrons in BP readily reacts with oxygen to form phosphate, phosphite and some other PxOyThe compound greatly destroys the intrinsic physical and chemical properties of black phosphorus, such as electric conduction, optics and the like. Thus, scientists aimed at the oxidation resistance of black phosphorus nanoplatesA series of strategies were adopted, which mainly included covalent functional modifications (such as P-C bonds), non-covalent coordination chemistry (TiL)4) Electrostatic adsorption (PEG-NH)2) Or physical coating (alumina, graphene, boron nitride), etc. The covalent modification method can realize effective oxidation resistance of the black phosphorus due to strong interaction of the covalent modification method on the black phosphorus. At present, the passivation of the black phosphorus surface can be better realized by forming a P-C bond or a P-O-C bond on the black phosphorus surface to passivate the black phosphorus surface (Angew. chem. int. Ed.2017,56,9891). But still limited by insufficient stability, complex operation process, higher cost and the like. Therefore, there is a need for an improved technique to address the above-mentioned deficiencies.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides the preparation method of the antioxidant black phosphorus nanosheet, which is simple in method and low in cost, can enhance the stability of the black phosphorus nanosheet by covalently grafting dialkyl methylamine onto the surface of the black phosphorus nanosheet, and does not influence the physicochemical property of the black phosphorus nanosheet.
The invention comprises the following steps:
1) adding the black phosphorus nanosheet into an organic solvent to prepare an organic solvent dispersion liquid of the black phosphorus nanosheet, and simultaneously preparing a halogenated alkane modification solution of alkylamine as a surface modifier;
2) mixing the black phosphorus nanosheet dispersion liquid with a surface modifier to obtain a mixture;
3) placing the mixture in a sealed system heated in inert atmosphere for reflux reaction;
4) and cooling the mixed solution, and then carrying out liquid-solid separation, washing and drying to obtain the antioxidant black phosphorus nanosheet.
In the step 1), the thickness of the black phosphorus nanosheet can be 1-100 nm; the mass ratio of the black phosphorus nanosheet to the organic solvent to the halogenated alkane can be (0.01-1): 20-1000); the organic solvent may be selected from at least one of amide-based solvents, alcohol-based solvents, and the like, and the amide-based solvents may be selected from at least one of formamide, dimethylformamide, diethylformamide, dimethylacetamide, diethylacetamide, and the like; the alcoholic solvent may be at least one selected from monohydric alcohol, dihydric alcohol, polyhydric alcohol, etc.; the halogenated alkane may be selected from at least one of methyl chloride, methylene chloride, chloroform, carbon tetrachloride, ethyl chloride, dichloroethane, trichloroethane, etc.
In the step 2), the mass ratio of the surface modifier to the black phosphorus nanosheet dispersion may be (5-100): 0.01-1), and the surface modifier may be at least one selected from trimethylamine, N-diethylmethylamine, N-dimethylethylamine, triethylamine, N-diethylpropylamine, N-dipropylethylamine, tripropylamine, N-dipropylbutylamine, N-dibutylpropylamine, tributylamine, and the like.
In the step 3), a high-temperature and high-pressure resistant reaction container can be adopted for the reaction, the reaction temperature can be 20-300 ℃, and the reaction time can be 0.01-60 h; the reaction temperature is preferably 80-140 ℃, and the reaction time is 0.01-50 h.
In the step 4), dialkyl methylamine is modified on the surface of the oxidation-resistant black phosphorus nanosheet, and the dialkyl methylamine can be at least one of trimethylamine, diethyl methylamine, dipropyl methylamine, N-ethyl propyl methylamine, dibutyl methylamine and the like; the covalently grafted dialkylalkylmethylamine may be by way of a P-C-N bond.
Compared with the prior art, the invention has the advantages that:
1. according to the invention, dialkyl alkyl methylamine is grafted on the surface of the black phosphorus nanosheet through a P-C-N bond, wherein P is directly connected with methylene, dialkyl amine is exposed outside, the alkylamine oxidation kinetics is slow, and the oxidation of the black phosphorus nanosheet can be effectively prevented. Meanwhile, compared with the aromatic azide chemical in the prior literature, the dialkyl methylamine is low in price and environment-friendly.
2. The method is suitable for the black phosphorus nanosheets prepared by various methods, can be used for the black phosphorus nanosheets with different thicknesses, sizes and stable dispersing agents, and the prepared black phosphorus can be applied to the antioxidant field effect transistor.
3. Compared with the antioxidant black phosphorus nanosheet before modification, the antioxidant black phosphorus nanosheet prepared by the method disclosed by the invention has better antioxidant capacity, has better dispersibility in polar solvents such as ethanol and the like, and can be used in the fields of electrode materials, catalytic assistants and the like.
4. The method is simple to operate and low in cost, and can realize effective antioxidant modification of the black phosphorus nanosheet.
5. Compared with the black phosphorus nanosheet which is not treated by dialkyl methylamine, the treated black phosphorus nanosheet has unchanged contact resistance, and is suitable for the fields of field effect transistors, photoelectric detectors and the like.
Drawings
FIG. 1 is a schematic flow chart according to an embodiment of the present invention.
Fig. 2 is a scanning electron microscope photograph of the oxidation-resistant black phosphorus nanosheets prepared in accordance with example 2 of the present invention.
Fig. 3 is a transmission electron microscope photograph of black phosphorus nanosheets prepared according to example 3 of the present invention, placed in air for 3 days.
Fig. 4 is a transmission electron microscope photograph of the antioxidant black phosphorus nanosheets prepared in accordance with example 3 of the present invention, placed in air for 200 days.
Fig. 5 is a graph of the uv-vis spectra of black phosphorus nanoplates and oxidation-resistant black phosphorus nanoplates prepared according to example 5 of the present invention over time.
Fig. 6 is a graph of the trend of the relative conductivity of the black phosphorus nanoplates and the oxidation-resistant black phosphorus nanoplates prepared according to example 5 of the present invention over time.
Detailed Description
The following examples will further illustrate the present invention with reference to the accompanying drawings.
As shown in fig. 1, an embodiment of the present invention includes the following steps:
1) preparing black phosphorus nanosheet dispersion liquid, and preparing alkylamine modification solution at the same time;
2) mixing the black phosphorus nanosheet dispersion liquid with an alkylamine modification solution to obtain a mixture;
3) the mixture is reacted under the condition of sealing and heating;
4) and (4) separating the brown solid after the reaction, washing and drying to obtain the antioxidant black phosphorus nanosheet.
Specific examples are given below.
Example 1:
step 1: preparing a black phosphorus nanosheet with the diameter of 1-100 nm: dispersing BP material in anhydrous nitrogen-nitrogen dimethyl formamide/ethanol solution with mass concentration of 0.5mg mL-1Argon is introduced for 0.5h to remove oxygen, and ultrasonic treatment is carried out for 30h (KD250, 250W) under the ice bath condition. Standing overnight to remove the un-stripped BP precipitate, centrifuging the supernatant at 12000rpm for 20min to remove nitrogen and nitrogen dimethyl formamide solvent molecules, washing the precipitate with ethanol, and vacuum drying. Meanwhile, 7.59g Triethylamine (TEA) was dissolved in 50mL CH2Cl2To prepare a solution of the alkylamine.
Step 2: 50mg of black phosphorus nanosheet was dispersed in 50mL of anhydrous DMF solution, and the solution of the above alkylamine was added and mixed well by stirring for 1 h.
And step 3: and sealing the mixed solution, heating to 100 ℃ under the protection of Ar, and refluxing for 12h to fully react.
And 4, step 4: and cooling the reaction system to room temperature, centrifuging at 12000rpm for 20min to remove the solvent, centrifuging and cleaning the reaction system for several times by using acetone and ethanol, and drying in vacuum to obtain the antioxidant black phosphorus nanosheet. The flow chart of the steps can also be seen in fig. 1.
Example 2:
step 1: preparing a black phosphorus nanosheet with the diameter of 1-100 nm: dispersing BP material in anhydrous formamide/ethanol solution with mass concentration of 0.5mg mL-1Argon is introduced for 0.5h to remove oxygen, and ultrasonic treatment is carried out for 30h (KD250, 250W) under the ice bath condition. Standing overnight to remove the un-stripped BP precipitate, centrifuging the supernatant at 12000rpm for 20min to remove nitrogen and nitrogen dimethyl formamide solvent molecules, washing the precipitate with ethanol, and vacuum drying. While 9.59g of Diethylmethylamine (DEMA) were dissolved in 50mL of CH2ClCH2A solution of the alkylamine was prepared in Cl.
Step 2: and (3) dispersing 50mg of black phosphorus nanosheets in 50mL of anhydrous benzyl alcohol solution, adding the solution for preparing the alkylamine, and performing ultrasonic treatment for 1 hour to uniformly mix the solution.
And step 3: the mixture was heated to 140 ℃ under nitrogen blanket and refluxed for 10 h.
And 4, step 4: and cooling the reaction system to room temperature, centrifuging the obtained dispersion liquid at 12000rpm for 20min to remove the solvent, centrifuging and cleaning the dispersion liquid for several times by using acetone and ethanol, and drying the dispersion liquid in vacuum to obtain the antioxidant black phosphorus nanosheet.
A scanning electron micrograph of the oxidation-resistant black phosphorus nanoplates prepared in example 2 is shown in fig. 2.
Example 3:
step 1: preparing a black phosphorus nanosheet with the diameter of 1-100 nm: dispersing BP material in anhydrous N-methyl pyrrolidone solution with mass concentration of 0.5mg mL-1Argon is introduced for 0.5h to remove oxygen, and ultrasonic treatment is carried out for 30h (KD250, 250W) under the ice bath condition. Standing overnight to remove the un-stripped BP precipitate, centrifuging the supernatant at 12000rpm for 20min to remove NMP solvent molecules, washing the precipitate with ethanol, and vacuum drying. Meanwhile, 7.59g Triethylamine (TEA) was dissolved in 50mL CH2Cl2To prepare a solution of the alkylamine.
Step 2: and (3) dispersing 50mg of black phosphorus nanosheets in 50mL of anhydrous DMF solution, adding the solution for preparing the alkylamine, and ultrasonically mixing uniformly for 1 h.
And step 3: the mixture was heated to 90 ℃ under nitrogen and refluxed for 12 h.
And 4, step 4: and cooling the reaction system to room temperature, centrifuging the obtained dispersion liquid at 12000rpm for 20min to remove the solvent, centrifuging and cleaning the dispersion liquid for several times by using acetone and ethanol, and drying the dispersion liquid in vacuum to obtain the antioxidant black phosphorus nanosheet.
A transmission electron micrograph of the black phosphorus nanoplates prepared in example 3, which were left in air for 3 days, is shown in fig. 3, and it can be seen from fig. 3 that the lamellar structure of the black phosphorus was apparently destroyed to form some of the bubble-forming oxides of phosphorus. A transmission electron micrograph of the antioxidant black phosphorus nanosheet prepared in example 3, which was left in air for 200 days, is shown in fig. 4, and it can be seen from fig. 4 that the lamellar structure of the black phosphorus still remained intact.
Example 4:
step 1: preparing a black phosphorus nanosheet with the diameter of 1-100 nm: dispersing BP material in anhydrous nitrogen cyclohexyl pyrrolidone solution with the mass concentration of 1mg mL-1Argon is introduced for 1h to remove oxygen, and ultrasonic treatment is carried out for 24h (KD250, 250W) under the ice bath condition.Standing overnight to remove the un-stripped BP precipitate, centrifuging the supernatant at 12000rpm for 30min to remove nitrogen-cyclohexyl pyrrolidone solvent molecules, washing the precipitate with ethanol, and vacuum drying. Simultaneously, 8.39g of diethylpropylamine were dissolved in 50mL of CH2Cl2To prepare a solution of the alkylamine.
Step 2: and (3) dispersing 50mg of black phosphorus nanosheets in 50mL of anhydrous DMF solution, adding the solution for preparing the alkylamine, and ultrasonically mixing uniformly for 1 h.
And step 3: the mixture is heated to 80 ℃ under the protection of Ar and refluxed for 12 h.
And 4, step 4: and cooling the reaction system to room temperature, centrifuging the obtained dispersion liquid at 12000rpm for 20min to remove the solvent, centrifuging and cleaning the dispersion liquid for several times by using acetone and ethanol, and drying the dispersion liquid in vacuum to obtain the antioxidant black phosphorus nanosheet.
Example 5:
step 1: preparing a black phosphorus nanosheet with the diameter of 1-100 nm: dispersing BP material in ether solution with mass concentration of 1mg mL-1Argon is introduced for 1h to remove oxygen, and ultrasonic treatment is carried out for 48h (KD250, 250W) under the ice bath condition. Standing overnight to remove the un-stripped BP precipitate, centrifuging the supernatant at 12000rpm for 30min to remove ether solvent molecules, washing the precipitate with ethanol, and vacuum drying. Meanwhile, 12.28g of tripropylamine is dissolved in 50mL of chloroform to prepare a solution of an alkylamine.
Step 2: and (3) dispersing 50mg of black phosphorus nanosheets in 50mL of anhydrous formamide solution, adding the solution for preparing the alkylamine, and ultrasonically mixing uniformly for 1 h.
And step 3: the mixture is heated to 130 ℃ under the protection of Ar and refluxed for 12 h.
And 4, step 4: and cooling the reaction system to room temperature, centrifuging the obtained dispersion liquid at 12000rpm for 20min to remove the solvent, centrifuging and cleaning the dispersion liquid for several times by using acetone and ethanol, and drying the dispersion liquid in vacuum to obtain the antioxidant black phosphorus nanosheet.
The ultraviolet-visible spectrum change curves of the black phosphorus nanosheet prepared in example 5 and the antioxidant black phosphorus nanosheet are shown in fig. 5, and it can be seen from fig. 5 that the relative intensity of the characteristic peak of the black phosphorus nanosheet at 465nm is obviously reduced with time, which indicates that the black phosphorus is obviously oxidized in the air; the relative intensity of the characteristic peak of the antioxidant black phosphorus nanosheet at 465nm basically maintains stable along with time, and can be maintained to 87% of the original intensity even after 200 days of air exposure, which shows that the modified black phosphorus nanosheet can effectively resist oxidation. The trend graph of the relative conductivity of the black phosphorus nanoplates prepared in example 5 and the antioxidant black phosphorus nanoplates as a function of time is shown in fig. 6. Similarly, the conductivity of the black phosphorus nanosheet without being subjected to the antioxidant treatment sharply decreases with time, indicating that the nanosheet has been significantly oxidized; and after the alkylamine anti-oxidation treatment, the conductivity is maintained stable, and the conductivity can be maintained to be more than 80% of the original conductivity even under the air exposure condition of 2 months, so that the modification treatment of the invention can really realize the effective anti-oxidation of the black phosphorus nanosheet.
Example 6:
step 1: preparing a black phosphorus nanosheet with the diameter of 1-100 nm: dispersing BP material in nitrogen-nitrogen dimethyl formamide solution with mass concentration of 1mg mL-1Argon is introduced for 1h to remove oxygen, and ultrasonic treatment is carried out for 24h (KD250, 250W) under the ice bath condition. Standing overnight to remove the un-stripped BP precipitate, centrifuging the supernatant at 12000rpm for 30min to remove nitrogen and nitrogen dimethyl formamide molecules, washing the precipitate with ethanol, and vacuum drying. Meanwhile, 8.39g of diethylpropylamine was dissolved in 50mL of chloroform to prepare a solution of an alkylamine.
Step 2: and (3) dispersing 50mg of black phosphorus nanosheets in 50mL of anhydrous nitrogen-nitrogen dimethylformamide solution, adding the solution for preparing the alkyl amine, and ultrasonically mixing uniformly for 1 h.
And step 3: the mixture is heated to 80 ℃ under the protection of Ar and refluxed for 12 h.
And 4, step 4: and cooling the reaction system to room temperature, centrifuging the obtained dispersion liquid at 12000rpm for 30min to remove the solvent, centrifuging and cleaning the dispersion liquid for several times by using acetone and ethanol, and drying the dispersion liquid in vacuum to obtain the antioxidant black phosphorus nanosheet.
Example 7:
step 1: preparing a black phosphorus nanosheet with the diameter of 1-100 nm: dispersing BP material in N-dimethylformamide solution with mass concentration of 0.5mg mL-1Introducing argon for 0.5h to remove oxygen, and performing ultrasonic treatment for 30h (KD) under ice bath condition250, 250W). Standing overnight to remove the un-stripped BP precipitate, centrifuging the supernatant at 12000rpm for 30min to remove nitrogen and nitrogen dimethyl formamide molecules, washing the precipitate with ethanol, and vacuum drying. Meanwhile, a solution of the alkylamine was prepared by dissolving 12.46g of dipropylbutylamine in 50mL of chloroform.
Step 2: and (3) dispersing 50mg of black phosphorus nanosheets in 50mL of anhydrous nitrogen-nitrogen dimethylformamide solution, adding the solution for preparing the alkyl amine, and ultrasonically mixing uniformly for 1 h.
And step 3: the mixture is heated to 80 ℃ under the protection of Ar and refluxed for 12 h.
And 4, step 4: and cooling the reaction system to room temperature, centrifuging the obtained dispersion liquid at 12000rpm for 30min to remove the solvent, centrifuging and cleaning the dispersion liquid for several times by using acetone and ethanol, and drying the dispersion liquid in vacuum to obtain the antioxidant black phosphorus nanosheet.
The above-described embodiments are merely preferred embodiments of the present invention, and should not be construed as limiting the scope of the invention. All equivalent changes and modifications made within the scope of the present invention shall fall within the scope of the present invention.
Claims (9)
1. A preparation method of an antioxidant black phosphorus nanosheet is characterized by comprising the following steps:
1) adding the black phosphorus nanosheet into an organic solvent, preparing an organic solvent dispersion liquid of the black phosphorus nanosheet, and preparing a halogenated alkane solution with alkyl tertiary amine as a surface modifier;
2) mixing the black phosphorus nanosheet dispersion liquid with a surface modifier to obtain a mixture;
3) placing the mixture in a sealed system heated in inert atmosphere for reflux reaction;
4) cooling the mixed solution, and then carrying out liquid-solid separation, washing and drying to obtain the antioxidant black phosphorus nanosheet, wherein the surface of the antioxidant black phosphorus nanosheet is modified with dialkyl alkyl methylamine; the dialkyl alkyl methylamine is covalently grafted on the surface of the black phosphorus nanosheet in a P-C-N bond mode.
2. The preparation method of the oxidation-resistant black phosphorus nanosheet, according to claim 1, wherein in step 1), the thickness of the black phosphorus nanosheet is 1-100 nm.
3. The method for preparing an antioxidant black phosphorus nanosheet of claim 1, wherein in step 1), the mass ratio of the black phosphorus nanosheet, the organic solvent and the haloalkane is (0.01-1): 20-1000).
4. The method for preparing oxidation-resistant black phosphorus nanosheets according to claim 1, wherein in step 1), the organic solvent is at least one selected from the group consisting of amide solvents and alcohol solvents, wherein the amide solvents are at least one selected from the group consisting of formamide, dimethylformamide, diethylformamide, dimethylacetamide and diethylacetamide; the alcohol solvent is at least one selected from monohydric alcohol, dihydric alcohol and polyhydric alcohol.
5. A method for preparing oxidation-resistant black phosphorus nanoplate as claimed in claim 1, wherein in step 1), the halogenated alkane is selected from at least one of methyl chloride, dichloromethane, chloroform, carbon tetrachloride, ethyl chloride, dichloroethane and trichloroethane.
6. A method for preparing oxidation-resistant black phosphorus nanosheets as recited in claim 1 in step 2), wherein the surface modifier is a tertiary alkyl amine selected from at least one of trimethylamine, N, -diethylmethylamine, N, -dimethylethylamine, triethylamine, N, -diethylpropylamine, N, -dipropylethylamine, tripropylamine, N, -dipropylbutylamine, N, -dibutylpropylamine, and tributylamine.
7. The preparation method of the antioxidant black phosphorus nanosheet, according to claim 1, characterized in that in step 3), the reaction is carried out in a high-temperature and high-pressure resistant reaction vessel at a temperature of 20-300 ℃ for 0.01-60 h.
8. The preparation method of the antioxidant black phosphorus nanosheet as claimed in claim 7, wherein the reaction temperature is 80-140 ℃ and the reaction time is 0.01-50 h.
9. A method for preparing oxidation-resistant black phosphorus nanosheet as recited in claim 1 in step 4), wherein the dialkylmethylamine is at least one of trimethylamine, diethylmethylamine, dipropylmethylamine, N-ethylpropylmethylamine, and dibutylmethylamine.
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Granted publication date: 20201215 |