CN114735680B - Graphene nanoribbon and preparation method thereof - Google Patents
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Abstract
The invention relates to the technical field of carbon materials, in particular to a graphene nanoribbon and a preparation method thereof, wherein micromolecular polycyclic aromatic hydrocarbon and molten salt are dissolved in a solvent and stirred under inert atmosphere; adding a catalyst to perform a constant temperature reaction, and taking out a product after the reaction is finished; carbonizing under inert atmosphere, washing carbonized products with water, and performing ultrasonic treatment to obtain the graphene nanoribbon. The graphene nanoribbon provided by the invention has a definite molecular structure, and can realize the regulation and control of molecular weight through the control of a synthesis process, so as to regulate and control a band gap value; the molten salt carbonization method adopted has the advantages of rich sources of raw materials, low production cost, simple and controllable synthesis process and easy realization of large-scale production.
Description
Technical Field
The invention relates to the technical field of carbon materials, in particular to a graphene nanoribbon and a preparation method thereof.
Background
The unique electronic band structure and outstanding mechanical properties of graphene make it extremely potential in the field of field effect transistor development, but since graphene itself is a half-metallic material, the energy bands overlap at dirac points, without a band gap, and its switching cannot be controlled by changing the voltage as in conventional transistors, it is necessary to introduce a band gap in graphene in order to make graphene useful for the preparation of field effect transistors. It has been found that a semiconductor material with a certain energy gap can be obtained if two-dimensional graphene is cut into one-dimensional graphene nanoribbons.
Graphene Nanoribbons (GNRs) refer to ribbon-shaped graphene having a width of less than 100nm and an aspect ratio. The material can have different band gaps due to the edge effect (such as edge configuration and edge disorder) caused by the special structure of the graphene nanoribbon, and the band gap of the material can be adjusted by controlling the structure. The bandgap performance of GNRs is directly dependent on its structure, and thus accurate synthesis of GNRs with specific width and edge structures is a major challenge for practical implementation. There are two distinct pathways for the preparation of GNRs: the top-down method and the bottom-up method are divided into two methods, namely, a graphene or a graphite precursor is cut or etched into a graphene nanoribbon, and a carbon nanotube is longitudinally cut to prepare a corresponding graphene nanoribbon; the bottom-up method is also divided into two methods, namely a chemical vapor deposition method and an organic synthesis method based on precursor molecules, the organic synthesis method based on the precursor molecules overcomes the defect that other methods cannot accurately control the width and edge configuration of the GNRs, and the accurate control of the GNRs structure can be realized through the selection of the precursor molecules and the control of the process, so that the method is a preferred method for preparing the functionalized graphene nanoribbons.
The organic synthesis method based on precursor molecules reported in the literature mainly takes polycyclic aromatic hydrocarbon as a precursor and synthesizes the polycyclic aromatic hydrocarbon on the metal surface in situ in a high vacuum environment, but the precursor molecules selected by the method are complex in synthesis, high in cost, and harsh in process for synthesizing GNRs, and are not beneficial to realizing industrialization.
Disclosure of Invention
The invention aims to provide a graphene nanoribbon and a preparation method thereof, and the method can realize large-scale production of the graphene nanoribbon with controllable band gap width.
In order to achieve the above object, the technical scheme of the present invention is as follows:
a preparation method of a graphene nanoribbon comprises the following steps:
s1: dissolving small-molecule polycyclic aromatic hydrocarbon and molten salt in a solvent, and stirring for 0.5-1 h under inert atmosphere;
the small-molecular polycyclic aromatic hydrocarbon comprises one or more of naphthalene, methylnaphthalene, anthracene, phenanthrene and pyrene polycyclic aromatic hydrocarbon, the small-molecular polycyclic aromatic hydrocarbon is a structural unit of a graphene nanobelt, and the small-molecular polycyclic aromatic hydrocarbon is subjected to polymerization reaction under the action of a catalyst to generate large-molecular-weight polycyclic aromatic hydrocarbon, so that all the small-molecular-weight polycyclic aromatic hydrocarbon and derivatives thereof can be used as raw materials, but have influence on the structure and performance of a product;
the molten salt comprises one or more of sodium chloride, ferric chloride, barium chloride, calcium chloride, copper chloride and potassium chloride, the effect of the molten salt enables the synthesis reaction to be carried out uniformly, agglomeration of products in the synthesis process and the carbonization process is prevented, the products are ensured to be graphene nanoribbons, and all inorganic salts which can exist stably in the synthesis and carbonization processes can be used as molten salt, but the structure and the performance of the products are influenced;
the mole ratio of the small molecular polycyclic aromatic hydrocarbon to the fused salt is 1 (0-3),
preferably, the mole ratio of the small molecular polycyclic aromatic hydrocarbon to the molten salt is 1 (1-2),
more preferably, the mole ratio of the small molecular polycyclic aromatic hydrocarbon to the molten salt is 1 (1.5-2).
The solvent comprises one or more of dichloromethane, trichloromethane, tetrachloromethane, dichloroethane and nitrotoluene, and the reaction raw materials are better and uniformly contacted with each other under the action of the solvent; on the other hand, the sublimation of the small-molecule polycyclic aromatic hydrocarbon at the reaction temperature is inhibited, so that the smooth progress of the synthesis reaction is ensured;
the amount of inert gas used in this step is not critical, but the minimum amount should be such that oxygen and water in the air do not enter the reaction system. Preferably, the inert atmosphere is nitrogen or argon, more preferably, the inert atmosphere is a mixture of nitrogen and argon.
S2: adding a catalyst, performing constant-temperature reaction for 1-10 hours at the temperature of 0-80 ℃, and taking out a product after the reaction is finished;
the catalyst comprises Lewis acid, wherein the Lewis acid can catalyze small-molecular polycyclic aromatic hydrocarbon to generate polymerization reaction, and can catalyze and synthesize a product to generate graphene nanoribbons through dehydrocyclization, and all compounds with catalysis effect on the polymerization reaction of the small-molecular polycyclic aromatic hydrocarbon and derivatives thereof can be used as catalysts, but have influence on the molecular weight and structure of the product;
preferably, the catalyst comprises one or more of aluminum chloride, ferric chloride, copper chloride, boron trifluoride and titanium tetrachloride;
the mole ratio of the micromolecular polycyclic aromatic hydrocarbon to the catalyst is 1 (0.5-4),
preferably, the mole ratio of the small molecular polycyclic aromatic hydrocarbon to the catalyst is 1 (0.5-3),
more preferably, the mole ratio of the small molecular polycyclic aromatic hydrocarbon to the catalyst is 1 (1-2);
preferably, the constant temperature reaction temperature is 10-60 ℃ and the time is 2-6 h,
more preferably, the constant temperature reaction temperature is 20-40 ℃ and the time is 3-5 h.
S3: carbonizing the product of the step S2 for 1-3 hours at 650-1000 ℃ in an inert atmosphere, washing the carbonized product with water, and performing ultrasonic treatment to obtain the graphene nanoribbon.
Preferably, the carbonization temperature is 650-800 ℃ and the time is 1-2h,
more preferably, the carbonization temperature is 650-750 ℃ and the time is 1-2h.
Another object of the present invention is to provide a graphene nanoribbon having a relative molecular mass of 500-2000, a width of 1-2 nm, a length of 3.0-15 nm, a band gap width of 2.3-6 eV, and a main molecular structure of
Compared with the prior art, the invention has the following advantages:
1) In the preparation method provided by the invention, the synthetic reaction mechanism is that the cation polymerization and the Friedel-crafts alkylation of the polycyclic aromatic hydrocarbon exist simultaneously, so that the problem that the polycyclic aromatic hydrocarbon is difficult to generate a polymer in the prior art by catalyzing the polymerization of the polycyclic aromatic hydrocarbon by Lewis acid is solved, and the full polycyclic aromatic hydrocarbon compounds with different expected molecular weights can be synthesized by optimizing and synergetically using a solvent and a catalyst;
2) In the preparation method provided by the invention, the synthesis reaction occurs in the molten salt medium, the raw material solution can be fully diffused in the system, and the generated solid or semi-solid high-molecular-weight polycyclic aromatic hydrocarbon is attached to the molten salt compound, so that the homogenization of the molecular weight of the product is facilitated; on the other hand, the agglomeration and bonding of the product due to the large pi bond can be avoided, and excessive liquid molten salt can promote the further dispersion of the graphene nanoribbon in the carbonization process, so that the stripping process after the graphene is synthesized in the prior art is saved;
3) The graphene nanoribbon provided by the invention has a definite molecular structure, and can realize the regulation and control of molecular weight through the control of a synthesis process, so as to regulate and control a band gap value; the molten salt carbonization method adopted has the advantages of rich sources of raw materials, low production cost, simple and controllable synthesis process and easy realization of large-scale production.
Drawings
FIG. 1 is a mass spectrum and a molecular structure of a graphene nanoribbon prepared in example 1;
FIG. 2 is a mass spectrum and a molecular structure of the graphene nanoribbons prepared in example 2;
FIG. 3 is a mass spectrum and a molecular structure of the graphene nanoribbons prepared in example 3;
FIG. 4 is an atomic force electron micrograph of graphene nanoribbons prepared in example 1;
fig. 5 is an atomic force electron micrograph of the graphene nanoribbons prepared in example 3.
Detailed Description
The term as used herein:
"prepared from … …" is synonymous with "comprising". The terms "comprising," "including," "having," "containing," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion. For example, a composition, step, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, step, method, article, or apparatus.
When an equivalent, concentration, or other value or parameter is expressed as a range, preferred range, or a range bounded by a list of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when ranges of "1 to 5" are disclosed, the described ranges should be construed to include ranges of "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a numerical range is described herein, unless otherwise indicated, the range is intended to include its endpoints and all integers and fractions within the range.
"and/or" is used to indicate that one or both of the illustrated cases may occur, e.g., a and/or B include (a and B) and (a or B).
The technical solution of the present invention will be described in detail with reference to specific examples, but it will be understood by those skilled in the art that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention.
Example 1
A preparation method of a graphene nanoribbon comprises the following steps:
s1: adding 6.4g of naphthalene and 5.8g of sodium chloride (molar ratio 1:2) into a 250mL three-neck flask by using a DF-101S type oil bath pot as a reaction device and methyl silicone oil as an oil bath medium, adding 100mL of dichloromethane, introducing nitrogen at room temperature of 25 ℃ for bubbling, connecting an air outlet pipe with a silicone oil liquid seal, and stirring for 0.5h;
s2: 13.3g of aluminum chloride (molar ratio of naphthalene to aluminum chloride is 1:2) is added, the reaction is carried out for 6 hours under the condition of nitrogen protection and stirring at constant temperature, and the product is taken out after the reaction is finished;
s3: and (3) placing the reaction product into a 100ml crucible, placing the crucible into a carbonization furnace, heating to 800 ℃ at a speed of 5 ℃/min under nitrogen atmosphere, keeping the temperature for 1.5 hours for carbonization, cooling to room temperature under nitrogen atmosphere, taking out the carbonized product, cleaning the carbonized product with deionized water for 5 times, carrying out ultrasonic treatment for 30 minutes by taking ethanol as a dispersion medium, and drying at 80 ℃ to obtain black solid powder, namely the graphene nanoribbon product, wherein a mass spectrum and a molecular structure are shown in figure 1, and an atomic force electron microscope photo is shown in figure 4.
Example 2
A preparation method of a graphene nanoribbon comprises the following steps:
s1: using DF-101S type oil bath pot as a reaction device, using methyl silicone oil as an oil bath medium, adding 10.1 g of pyrene and 8.1g of ferric chloride (molar ratio 1:1) into a 250mL three-neck flask, adding 100mL of dichloroethane, introducing argon at room temperature of 25 ℃ for bubbling, and connecting an air outlet pipe with the silicone oil liquid seal and stirring for 1h;
s2: 3.35g of boron trifluoride (molar ratio of pyrene to boron trifluoride is 1:1) is added, the temperature is raised to 60 ℃ under the protection of argon and stirring, the reaction is carried out for 3 hours at constant temperature, and the product is taken out after the reaction is finished;
s3: and (3) placing the reaction product into a 100ml crucible, placing the crucible into a carbonization furnace, heating to 1000 ℃ at a speed of 5 ℃/min under argon atmosphere, carbonizing, cooling to room temperature under argon atmosphere, taking out the carbonized product, cleaning for 5 times with deionized water, performing ultrasonic treatment for 30min by taking ethanol as a dispersion medium, and drying at 80 ℃ to obtain black solid powder, namely the graphene nanoribbon product, wherein the mass spectrum and the molecular structure are shown in figure 2.
Example 3
A preparation method of a graphene nanoribbon comprises the following steps:
s1: using DF-101S type oil bath pot as a reaction device, using methyl silicone oil as an oil bath medium, adding 8.9g of anthracene and 0.82g of a mixture of barium chloride and potassium chloride (molar ratio 1:0.1) into a 250mL three-neck flask, adding 100mL of nitrotoluene, introducing nitrogen and argon at room temperature of 25 ℃ for bubbling, connecting a gas outlet pipe with a silicone oil liquid seal, and stirring for 0.8h;
s2: adding 3.35g of copper chloride (the molar ratio of anthracene to copper chloride is 1:0.5), heating to 80 ℃ under the protection of nitrogen and argon and stirring, reacting for 1h at constant temperature, and taking out the product after the reaction is finished;
s3: and (3) placing the reaction product into a 100ml crucible, heating to 650 ℃ at a speed of 5 ℃/min under nitrogen and argon atmosphere, carbonizing, cooling to room temperature under nitrogen and argon atmosphere, taking out the carbonized product, cleaning for 5 times with deionized water, performing ultrasonic treatment for 30min by taking ethanol as a dispersion medium, and drying at 80 ℃ to obtain black solid powder, namely the graphene nanoribbon product, wherein a mass spectrum and a molecular structure are shown in figure 3, and an atomic force electron microscope photo is shown in figure 5.
Example 4
A preparation method of a graphene nanoribbon comprises the following steps:
s1: adding 7.1g of methylnaphthalene and 16.5g of calcium chloride (molar ratio 1:3) into a 250mL three-neck flask by using a DF-101S type oil bath pot as a reaction device and methyl silicone oil as an oil bath medium, adding 100mL of chloroform, introducing nitrogen at room temperature of 25 ℃ for bubbling, connecting an air outlet pipe with a silicone oil liquid seal, and stirring for 0.6h;
s2: adding 32.4g of ferric trichloride (the molar ratio of methylnaphthalene to ferric trichloride is 1:4), cooling to 0 ℃ under the condition of nitrogen protection and stirring, reacting for 10 hours at constant temperature, and taking out the product after the reaction is finished;
s3: and (3) placing the reaction product into a 100ml crucible, placing the crucible into a carbonization furnace, heating to 700 ℃ at a speed of 5 ℃/min under nitrogen atmosphere, carbonizing at a constant temperature of 2 hours, cooling to room temperature under nitrogen atmosphere, taking out the carbonized product, cleaning the carbonized product with deionized water for 5 times, performing ultrasonic treatment for 30 minutes by taking ethanol as a dispersion medium, and drying at 80 ℃ to obtain black solid powder, namely the graphene nanoribbon product.
Example 5
A preparation method of a graphene nanoribbon comprises the following steps:
s1: adding 8.9g of phenanthrene and 10g of copper chloride (molar ratio 1:1.5) into a 250mL three-neck flask by using a DF-101S type oil bath pot as a reaction device and methyl silicone oil as an oil bath medium, adding 100mL of tetrachloromethane, introducing nitrogen at room temperature of 25 ℃ for bubbling, connecting an air outlet pipe with a silicone oil liquid seal, and stirring for 0.7h;
s2: 28.5g of titanium tetrachloride (molar ratio of phenanthrene to titanium tetrachloride is 1:3) is added, the temperature is raised to 40 ℃ under the condition of nitrogen protection and stirring, the reaction is carried out for 5 hours at constant temperature, and the product is taken out after the reaction is finished;
s3: and (3) placing the reaction product into a 100ml crucible, placing the crucible into a carbonization furnace, heating to 900 ℃ at a speed of 5 ℃/min under nitrogen atmosphere, keeping the temperature for 2.5 hours for carbonization, cooling to room temperature under nitrogen atmosphere, taking out the carbonized product, cleaning the carbonized product with deionized water for 5 times, performing ultrasonic treatment for 30 minutes by taking ethanol as a dispersion medium, and drying at 80 ℃ to obtain black solid powder, namely the graphene nanoribbon product.
Test example 1
The ultraviolet light absorption spectra of the graphene nanoribbons prepared in examples 1-3 were tested using an Shanghai precision instrument electrical separation L5S ultraviolet visible light spectrum analyzer and band gap widths were calculated, and the results are shown in Table 1.
TABLE 1 band gap Width of graphene nanoribbons
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and not for limiting the same; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some or all of the technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the invention.
Furthermore, those skilled in the art will appreciate that while some embodiments herein include some features but not others included in other embodiments, combinations of features of different embodiments are meant to be within the scope of the invention and form different embodiments. For example, in the claims below, any of the claimed embodiments may be used in any combination. The information disclosed in this background section is only for enhancement of understanding of the general background of the invention and should not be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person skilled in the art.
Claims (13)
1. The preparation method of the graphene nanoribbon is characterized by comprising the following steps of:
s1: dissolving small-molecule polycyclic aromatic hydrocarbon and molten salt in a solvent, and stirring under inert atmosphere; the small-molecule polycyclic aromatic hydrocarbon comprises one or more of naphthalene, methylnaphthalene, anthracene, phenanthrene and pyrene; the molten salt comprises one or more of sodium chloride, ferric chloride, barium chloride, calcium chloride, copper chloride and potassium chloride; the molar ratio of the small-molecule polycyclic aromatic hydrocarbon to the molten salt is 1 (0-3), wherein the dosage of the molten salt is not 0;
s2: adding a catalyst to perform a constant temperature reaction, and taking out a product after the reaction is finished; the catalyst comprises one or more of aluminum chloride, ferric trichloride, copper chloride, boron trifluoride and titanium tetrachloride; the molar ratio of the small molecular polycyclic aromatic hydrocarbon to the catalyst is 1 (0.5-4);
s3: and (3) carbonizing the product of the step (S2) in an inert atmosphere, and washing and ultrasonically treating the carbonized product to obtain the graphene nanoribbon.
2. The method according to claim 1, wherein in step S1, the solvent comprises one or more of dichloromethane, chloroform, tetrachloromethane, dichloroethane, and nitrotoluene.
3. The method of claim 1, wherein step S1 further satisfies one or more of the following conditions:
a. the inert atmosphere comprises nitrogen and/or argon;
b. the stirring time is 0.5-1 h.
4. The preparation method of claim 1, wherein the molar ratio of the small-molecule polycyclic aromatic hydrocarbon to the molten salt is 1 (1-2).
5. The method according to claim 4, wherein the molar ratio of the small-molecule polycyclic aromatic hydrocarbon to the molten salt is 1 (1.5-2).
6. The preparation method of claim 1, wherein the molar ratio of the small-molecule polycyclic aromatic hydrocarbon to the catalyst is 1 (0.5-3).
7. The preparation method of claim 6, wherein the molar ratio of the small-molecule polycyclic aromatic hydrocarbon to the catalyst is 1 (1-2).
8. The preparation method according to claim 1, wherein the constant temperature reaction temperature in step S2 is 0-80 ℃ and the time is 1-10 h.
9. The preparation method according to claim 8, wherein the constant temperature reaction temperature in step S2 is 10-60 ℃ for 2-6 hours.
10. The preparation method according to claim 9, wherein the constant temperature reaction temperature in step S2 is 20-40 ℃ for 3-5 hours.
11. The method according to claim 1, wherein the carbonization temperature in step S3 is 650-1000 ℃ for 1-3 hours.
12. The method according to claim 11, wherein the carbonization temperature in step S3 is 650-800 ℃ for 1-2 hours.
13. The method according to claim 12, wherein the carbonization temperature in step S3 is 650-750 ℃ for 1-2 hours.
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