Novel graphene nanoribbons and methods of making the same

Abstract

The graphene nanoribbon represented by the general formula (1) is a novel GNR obtained by a more simple and industrially advantageous GNR production method. In the formula (1), R 1 represents a linear alkyl group having 1 to 12 carbon atoms; R 3 4 and R 3 4 together form a group represented by -SiR 2a R 2b ; wherein R 2a and R 2b are the same or different and represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms optionally having a branch, or a phenyl group; and n represents an integer of 1 or more.​​

Description

Technical Field

[0001] This invention relates to an improved method for preparing graphene nanoribbons and novel graphene nanoribbons obtained by this method. Background Technology

[0002] Graphene nanoribbons (hereinafter, sometimes referred to as "GNRs") are a promising material for applications in semiconductors, solar cells, transparent electrodes, high-speed transistors, organic EL devices, and the like. Methods for manufacturing GNRs are generally classified into two types: top-down and bottom-up methods. The latter, in particular, is attractive because it allows for precise control of edge structure and width, enabling the large-scale synthesis of GNRs.

[0003] The inventors of this invention focused on the latter bottom-up approach and conducted in-depth research on the manufacturing method, resulting in the discovery of a manufacturing method for GNR with fewer steps and suppression of side reactions. This method uses alkyne compounds with specific structures, such as those used as initiators, to polymerize thiophene compounds (see, for example, Patent Document 1).

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: International Publication No. 2020 / 184625 Summary of the Invention

[0007] The technical problem to be solved by the present invention

[0008] However, when the method described in Patent Document 1 is implemented industrially, further improvements are required, and a simpler method for manufacturing GNR is needed.

[0009] Therefore, the object of the present invention is to provide a simpler and industrially advantageous method for manufacturing GNR, and a novel GNR obtained by the manufacturing method.

[0010] Technical means to solve technical problems

[0011] To address the aforementioned technical problems, the inventors of this invention conducted in-depth research and discovered that the following method enables a simpler and more industrially advantageous manufacture of GNRs, and provides the novel GNRs described later. Specifically, this invention includes the following inventions.

[0012] (1) A graphene nanoribbon, represented by general formula (1).

[0013] [Chemical Formula 1]

[0014]

[0015] In equation (1), R 1 R represents a straight-chain alkyl group having 1 to 12 carbon atoms; 3 and R 4 All are hydrogen atoms, or R 3 and R 4 Co-formation -SiR 2a R 2b - represents the group; where R 2a and R 2b Same or different, representing hydrogen atoms, alkyl or phenyl groups with 1 to 4 branched carbon atoms; n represents an integer greater than 1.

[0016] (2) The graphene nanoribbons according to (1) are represented by general formula (1-1) and / or general formula (1-2).

[0017] [Chemical Formula 2]

[0018]

[0019] In equation (1-1), R 1 R 2a and R 2b With the R 1 R 2a and R 2b Same; n a Represents integers greater than or equal to 1.

[0020] [Chemical Formula 3]

[0021]

[0022] In equation (1-2), R 1 With the R 1 Same, n b Represents an integer greater than or equal to 1.

[0023] (3) A method for manufacturing a graphene nanoribbon as described in (1) or (2), wherein a thiophene compound represented by general formula (2) is polymerized in the presence of a palladium compound, o-tetrachlorobenzoquinone and a silver compound in the presence of 0.01 to 0.4 moles of the thiophene compound represented by general formula (2) relative to 1 mole.

[0024] [Chemical Formula 4]

[0025]

[0026] In equation (2), R 1 R 2a and R 2b With the R 1 R 2a and R2b same.

[0027] (4) A graphene nanoribbon obtained by polymerizing a thiophene compound represented by general formula (2) in the presence of a palladium compound, o-tetrachlorobenzoquinone and a silver compound in the presence of 0.01 to 0.4 moles of the thiophene compound represented by general formula (2) relative to 1 mole.

[0028] [Chemical Formula 5]

[0029]

[0030] In equation (2), R 1 R represents a straight-chain alkyl group having 1 to 12 carbon atoms; 2a and R 2b This indicates an alkyl or phenyl group with 1 to 4 branched carbon atoms.

[0031] (5) A thiophene compound represented by general formula (3),

[0032] [Chemical Formula 6]

[0033]

[0034] In equation (3), n-Bu represents n-butyl; R 2a and R 2b "Same" or "different" refers to alkyl or phenyl compounds with 1 to 4 branched carbon atoms.

[0035] Invention Effects

[0036] According to the present invention, under the specific conditions described above, GNRs can be manufactured without using alkyne compounds represented by the following general formula (4A), K-block aromatic compounds represented by the following general formula (4B), dibenzocyclooctadiyne, benzothiophene, or benzofuran (hereinafter sometimes referred to as "initiator compounds"), which must be considered in initiating polymerization reactions to date. Therefore, since no additional initiator compounds are required, GNRs can be manufactured more cheaply and easily, and novel GNRs without units derived from initiator compounds, i.e., GNRs represented by general formula (1), which cannot be manufactured by conventional known methods, can be produced.

[0037] [Chemical Formula 7]

[0038]

[0039] In equation (4A), R 5a and R 5b"Same or different" indicates hydrogen atom, halogen atom, alkyl group, cycloalkyl group, (poly)ether group, ester group, alkylboronic acid or its ester group, monovalent aromatic hydrocarbon group or monovalent heterocyclic group; "same or different" indicates integers from 1 to 3; when k1 and k2 are integers greater than 2, each R 5a and / or R 5b Choose either the same or different.

[0040] [Chemical Formula 8]

[0041]

[0042] In equation (4B), R 6a R 6b R 6c R 6d R 6e and R 6f The same or different indicates a hydrogen atom, halogen atom, alkyl, cycloalkyl, (poly)ether group, ester group, alkylboronic acid or its ester group, monovalent aromatic hydrocarbon group or monovalent heterocyclic group; the same or different of a1 and a2 indicates a carbon atom or a nitrogen atom.

[0043] Furthermore, conventional manufacturing methods require the use of palladium compounds in amounts equivalent to or greater than those of thiophene compounds. However, the GNR manufacturing method according to the present invention can manufacture GNR using a catalytic amount (i.e., less than an equivalent amount of palladium compound relative to thiophene compounds). Simultaneously, since the amount of silver compound used can be reduced, the GNR manufacturing method according to the present invention can manufacture GNR more cost-effectively. Attached Figure Description

[0044] Figure 1 The thiophene compound obtained in Example 1 1 H-NMR spectrum.

[0045] Figure 2 The thiophene compound obtained in Example 1 13 C-NMR spectrum. Detailed Implementation

[0046] In this specification, "comprise" means to include the concepts of "consistes essentially of" and "consist of".

[0047] In this invention, unless otherwise specified, the range “A~B” refers to above A and below B.

[0048] (1) The manufacturing method of the GNR of the present invention

[0049] The method for manufacturing GNR of the present invention is characterized in that a thiophene compound having a specific structure represented by general formula (2) is polymerized in the presence of a palladium compound, o-tetrachlorobenzoquinone and a silver compound in the presence of 0.01 to 0.4 moles of the thiophene compound relative to 1 mole of the thiophene compound.

[0050] [Chemical Formula 9]

[0051]

[0052] In equation (2), R 1 R represents a straight-chain alkyl group having 1 to 12 carbon atoms; 2a and R 2b "Same" or "different" refers to hydrogen atoms, or optionally alkyl or phenyl groups with 1 to 4 branched carbon atoms.

[0053] (1-1) Thiol compounds

[0054] The thiophene compound used in this invention has the structure represented by the above general formula (2). In the above general formula (2), the substituent R 1 It needs to be a straight-chain alkyl group with 1 to 12 carbon atoms. When the substituent R... 1 When the substituent is a hydrogen atom or a branched alkyl group, the polymerization reaction hardly proceeds, and it is impossible to obtain a high molecular weight (specifically, a weight-average molecular weight (Mw) of polystyrene equivalent determined by size exclusion chromatography (hereinafter sometimes referred to as "SEC") of 3000 or more under the conditions described in the Examples section below). Furthermore, among straight-chain alkyl groups with 1 to 12 carbon atoms, straight-chain alkyl groups with 2 to 8 carbon atoms are preferred, and straight-chain alkyl groups with 4 carbon atoms (n-butyl) are particularly preferred. Additionally, the substituent R... 2a and R 2b The alkyl or phenyl group, consisting of 1 to 4 branched carbon atoms, is a hydrogen atom. Examples of branched alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl. From the perspective of ease of preparing the thiophene compound represented by the above general formula (2), R... 2a and R 2b Preferably methyl, ethyl, or phenyl, and R 2a and R 2b Preferably, they contain the same substituents. These thiophene compounds can be used alone or in combination of two or more.

[0055] The thiophene compound represented by the above general formula (2) can be prepared according to a known method (e.g., the method described in Patent Document 1). Specifically, it can be prepared by using R in the manner described in the Examples section below. 1Compounds in which halogen atoms (chlorine, bromine, iodine, etc.) are replaced by compounds (e.g., compound S23 of Synthesis Example 5 in Patent Document 1, etc.) 1 The compound is prepared by reacting a straight-chain alkyl group having 1 to 12 carbon atoms with a Grignard reagent having 1 to 12 carbon atoms in the presence of an iron compound, according to the method of Synthesis Example 6 of Patent Document 1.

[0056] (1-2) Palladium compounds

[0057] In this invention, known palladium compounds can be used as catalysts for the synthesis of polymers, etc., with divalent palladium compounds being preferred. Examples of usable palladium compounds include Pd(OH)₂, Pd(OCOCH₃)₂, Pd₂(dba)₃, Pd(OCOCF₃)₂, Pd(acac)₂, PdCl₂, PdBr₂, PdI₂, Pd(NO₃)₂, and Pd(CH₃CN)₄SbF₆)₂. Note that acac refers to acetylacetone, and dba refers to dibenzylacetone. In this invention, from the perspective of easily obtaining GNRs with higher molecular weights by using weakly cationic palladium compounds that do not easily damage the thiophene skeleton of the matrix, Pd(OH)2, Pd(OCOCH3)2, Pd(OCOCF3)2, PdBr2, PdI2, and Pd(CH3CN)4(SbF6)2 are preferred, more preferably Pd(OCOCH3)2, Pd(OCOCF3)2, PdBr2, PdI2, and Pd(CH3CN)4(SbF6)2, and particularly preferably Pd(OCOCH3)2. These palladium compounds can be used alone or in combination of two or more.

[0058] The amount of palladium compound used relative to 1 mole of thiophene compound is 0.01 to 0.4 moles, preferably 0.05 to 0.3 moles. When the amount of palladium compound used is less than 0.01 moles or more than 0.4 moles, it is impossible to obtain GNR with a higher molecular weight.

[0059] (1-3) o-Tetrachlorobenzoquinone

[0060] In this invention, the amount of o-tetrachlorobenzoquinone is not particularly limited. From the perspective of easily obtaining a higher molecular weight GNR, for example, it is 0.5 to 5.0 moles relative to 1 mole of thiophene compound, preferably 1.0 to 3.0 moles, and more preferably 1.5 to 2.5 moles. Furthermore, without the use of o-tetrachlorobenzoquinone, the polymerization reaction hardly occurs, and the GNR of this invention cannot be obtained.

[0061] (1-4) Silver compounds

[0062] The silver compounds used in this invention are not particularly limited, and examples include organic silver compounds such as silver acetate, silver pivalate (AgOPiv), silver trifluoromethanesulfonate (AgOTf), and silver benzoate (AgOCOPh); and inorganic silver compounds such as silver nitrate, silver fluoride, silver chloride, silver bromide, silver iodide, silver sulfate, silver oxide, silver sulfide, silver tetrafluoroborate (AgBF4), silver hexafluorophosphate (AgPF6), and silver hexafluoroantimonate (AgSbF6). In this invention, from the perspective of easily obtaining higher molecular weight GNRs, inorganic silver compounds are preferred, silver tetrafluoroborate (AgBF4), silver hexafluorophosphate (AgPF6), and silver hexafluoroantimonate (AgSbF6) are more preferred, silver tetrafluoroborate (AgBF4) and silver hexafluoroantimonate (AgSbF6) are even more preferred, and silver hexafluoroantimonate (AgSbF6) is particularly preferred. These silver compounds can be used alone or in combination of two or more.

[0063] The amount of silver compound used relative to 1 mole of palladium compound is, for example, 0.1 to 3.0 moles. From the perspective of easily obtaining GNR with a higher molecular weight, it is preferably 0.2 to 1.5 moles relative to 1 mole of palladium compound, and more preferably 0.3 to 1.3 moles.

[0064] (1-5) Others

[0065] This invention is preferably carried out in a solvent. Examples of usable solvents include aliphatic hydrocarbons such as pentane, hexane, heptane, and cyclohexane; aliphatic halogenated hydrocarbons such as dichloromethane, dichloroethane (DCE), chloroform (CHCl3), carbon tetrachloride, and trichloroethylene (TCE); and aromatic halogenated hydrocarbons such as monochlorobenzene (PhCl), dichlorobenzene (PhCl2), bromobenzene (PhBr), and 1,3,5-tribromobenzene (PhBr3). These solvents can be used alone or in combination of two or more. Among these solvents, aliphatic halogenated hydrocarbons and aromatic halogenated hydrocarbons are preferred, and monochlorobenzene (PhCl) and dichlorobenzene (PhCl2) are more preferred. Furthermore, in addition to the above-mentioned components, additives may be used appropriately without impairing the effects of this invention.

[0066] When using a solvent, the amount used is, for example, 2 to 20 parts by mass relative to 1 part by mass of the thiophene compound, preferably 5 to 15 parts by mass.

[0067] In this invention, it is preferably carried out under anhydrous conditions and in an inactive gas atmosphere (nitrogen, argon, etc.), and the reaction temperature is, for example, 50 to 200°C, preferably 80 to 150°C, and more preferably 90 to 130°C.

[0068] After the reaction is complete, the GNR of the present invention can be extracted from the reaction solution by conventional methods such as concentration, crystallization, and filtration. Furthermore, purification can be performed as needed, such as by removing metal components using silica gel column chromatography, separating or purifying the polymer using gel permeation chromatography (GPC).

[0069] (2) The GNR of the present invention

[0070] The GNR of the present invention has the structure represented by the following general formula (1):

[0071] [Chemical Formula 10]

[0072]

[0073] In equation (1), R 1 R represents a straight-chain alkyl group having 1 to 12 carbon atoms; 3 and R 4 All are hydrogen atoms, or R 3 and R 4 Co-formation -SiR 2a R 2b - represents the group; where R 2a and R 2b "Same" or "different" refers to hydrogen atoms or, optionally, alkyl or phenyl groups with 1 to 4 branched carbon atoms; n represents an integer greater than 1.

[0074] The GNR of the present invention is manufactured by the aforementioned manufacturing method of the GNR of the present invention. By carrying out this manufacturing method, firstly, a GNR (polymer) having the structure represented by general formula (1-1) is generated, and then, part or all of the polymer is subjected to a desilylation reaction to form a GNR (polymer) having the structure represented by the following general formula (1-2). Therefore, the GNR of the present invention can also be referred to as a GNR (polymer) containing the above-mentioned general formula (1-1) and / or (1-2).

[0075] [Chemical Formula 11]

[0076]

[0077] In equation (1-1), R 1 R represents a straight-chain alkyl group having 1 to 12 carbon atoms; 2a and R 2b Same or different, representing a hydrogen atom or optionally an alkyl or phenyl group with 1 to 4 branched carbon atoms; n a Represents an integer greater than or equal to 1.

[0078] [Chemical Formula 12]

[0079]

[0080] In equation (1-2), R 1 Indicates a straight-chain alkyl group with 1 to 12 carbon atoms; n b Represents an integer greater than or equal to 1.

[0081] In addition, the substituent R in the above general formulas (1), (1-1) and (1-2) 1 R 2a and R 2b All correspond to the substituent R of the above-mentioned thiophene compounds. 1 R 2a and R 2b Therefore, the types of substituents and preferred specific examples are also the same. Furthermore, according to the manufacturing method of the present invention described above, when using multiple thiophene compounds simultaneously, it is also possible to manufacture substituent R. 1 Different GNRs. Furthermore, according to the manufacturing method of the present invention, the GNR of the present invention can also contain polymers other than those represented by the GNRs (polymers) of the above general formulas (1), (1-1) and (1-2).

[0082] According to the method for manufacturing GNR of the present invention, it is also possible to manufacture GNR with a higher molecular weight. The number of repeating units of the GNR of the present invention (i.e., the degree of polymerization n in general formula (1) and the degree of polymerization n in general formula (1-1) are also possible. a and the degree of polymerization n in general formula (1-2) b There are no particular restrictions, and the number can be appropriately selected according to the required characteristics. For example, it can be set to 1 to 1000, preferably 3 to 500, and more preferably 5 to 100. Furthermore, the number of repeating units n, n... a and n b It can be calculated based on the number-average molecular weight (Mn) of polystyrene converted from SEC under the conditions described in the Examples section below.

[0083] The weight-average molecular weight (Mw) of the GNR of the present invention, measured under the conditions described in the following examples section, based on SEC and converted from polystyrene, is, for example, 2000 or more, preferably 3000 to 50000, and more preferably 4000 to 20000.

[0084] The GNR of the present invention is a type of GNR that cannot be produced by conventional methods and does not contain units derived from the initiator compound. Therefore, the GNR of the present invention has a more singular structure, and thus, compared with conventional GNRs, improved properties and different characteristics can be expected.

[0085] The GNR of the present invention can also be cyclically condensed using conventionally known methods (e.g., oxidation reaction, Scholl reaction, etc.) to form a cyclically condensed GNR (the armchair-type GNR described in conventionally known documents). This method can be performed, for example, based on the method described in Patent Document 1.

[0086] Example

[0087] The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.

[0088] (1) NMR measurement

[0089] for 1 H-NMR and 13 C-NMR was performed using tetramethylsilane as an internal standard and deuterated chloroform (CDCl3) as a solvent, using a JEOL-ESC600 ( 1 H 600MHz, 13 C 150MHz) or JEOL-ESC400 ( 1 H 400MHz, 13 The data was recorded using a 100MHz spectrometer. The data are recorded below.

[0090] Chemical shift, multiplicity (s = singlet, d = doublet, dd = doublet of doublets, t = triplet, sext = sextet, m = multiplet), bonding constant (Hz), and integration.

[0091] (2) Determination of molecular weight (weight-average molecular weight (Mw), number-average molecular weight (Mn)) of GNR using size exclusion chromatography (SEC)

[0092] The following apparatus was used, and the analysis was performed under the following conditions.

[0093] Installation: Acquity (Advanced Polymer Chromatography)

[0094] Chromatographic columns: Waters Corporation's ACQUITY APC XT 125 2.5μm 4.6×150mm and ACQUITY APC XT 200 2.5μm 4.6×150mm

[0095] Measurement temperature: 40℃

[0096] Solvent: Tetrahydrofuran

[0097] Standard molecular weight: based on standard polystyrene.

[0098] <Example 1: Synthesis of the thiophene compound represented by formula (3-1)>

[0099] [Chemical Formula 13]

[0100]

[0101] In the formula, n-Bu represents n-butyl; acac represents acetylacetonate; and THF represents tetrahydrofuran.

[0102] Under a nitrogen atmosphere, in a 20 mL round-bottom flask equipped with a magnetic stir bar, the compound represented by formula (5) (1.475 g, 5.0 mmol), tri(acetylacetone)ferric(III) (Fe(acac)3; 44.5 mg, 0.25 mmol), tetrahydrofuran (THF; 5.5 mL), and N-methyl-2-pyrrolidone (NMP; 3.4 mL) were added. The reaction mixture was cooled to 0 °C, and n-butylmagnesium bromide (1.0 M in THF, 7.5 mL, 7.5 mmol) was added at 0 °C. The mixture was then heated to room temperature and stirred for 14 hours at room temperature.

[0103] Then, water was added to quench the reaction, followed by the addition of ethyl acetate (15 mL) to extract the organic matter. After repeating this extraction operation a total of 3 times, the organic layers were combined, washed with saturated brine, and then Na2SO4 was added. The mixture was allowed to stand overnight to dry the organic layers. After drying, Na2SO4 was removed by filtration, and the solvent was removed under reduced pressure to obtain the crude product. The crude product was purified by silica gel chromatography (eluent: hexane) to obtain colorless crystals of (11,11-dimethyl-9-butyl-11H-benzo[b]naphtho[2,1-d]thiophene (the compound represented by formula (3-1)) (535 mg, 34%). The obtained compound represented by formula (3-1) 1 H-NMR and 13 The results of the C-NMR analysis are shown below. Furthermore, the following will be... 1 H-NMR and 13 The C-NMR spectrum is shown in Figures 1-2 .

[0104] 1H-NMR (400MHz, CDCl3) δ7.95(d,J=8.7Hz,1H),7.91(d,J=8.7Hz,1H),7.87-7.82(m,2H),7.80(d,J=7.8Hz,1H),7.53-7.47(m,2H),7.46-7.4 0m,1H),7.28(dd,J=1.8,7.8Hz,1H),2.68(t,J=7.3Hz,2H),1.71-1.62(m,2H),1.42(sext,J=7.3Hz,2H),0.97(t,J=7.3Hz,3H),0.58(s,6H).

[0105] 13 C-NMR (100MHz, CDCl3) δ146.9,145.7,142.1,139.2,136.8,136.5,132.84,132.81,130 .8,130.3,128.9,128.3,126.5,125.2,120.8,119.7,35.6,33.8,22.5,14.0,-2.7(2C).

[0106] <Manufacturing Examples of Examples 2-6 and Comparative Examples 1-5 GNR>

[0107] [Chemical Formula 14]

[0108]

[0109] <R in GNR represented by general formula (1) in Example 2> 1 =Example of manufacturing n-butyl GNR>

[0110] Under a nitrogen atmosphere, in a 20 mL Schlenk tube with a magnetic stir bar, a monomer (the compound represented by formula (3-1), i.e., in the above general formula (2), R) was added. 1 = n-Butyl, R 2a =R 2b =Methyl compounds (500 mg, 1.58 mmol), AgSbF6 (108.6 mg, 0.316 mmol), Pd(OCOCH3)2 (70.9 mg, 0.316 mmol), o-tetrachlorobenzoquinone (777 mg, 3.159 mmol), and 1,2-dichlorobenzene (3.5 mL). Then, the mixture was heated to 120 °C and stirred at 120 °C for 40 hours to obtain the reaction mixture.

[0111] After cooling the resulting reaction mixture to room temperature, it was washed with CH2Cl2 and passed through a shortpad column and a metal scavenger. Then, the solvent was removed under reduced pressure, methanol was added to suspend the mixture, and the mixture was filtered and dried to obtain GNR.

[0112] After analysis of the obtained GNR by size exclusion chromatography (SEC), Mn = 4,118, Mw = 7,385, and Mw / Mn(PDI) = 1.79.

[0113] <Examples 3-5, Comparative Examples 1-4>

[0114] In addition to changing the monomer to R in the above general formula (2), 1 =The substituents and R listed in Table 1 below 2a =R 2b Except for compounds containing methyl groups, the procedure was carried out in the same manner as in Example 2 to obtain GNRs. The analytical results of the obtained GNRs obtained by SEC are shown in Table 1 below.

[0115] [Table 1]

[0116]

[0117] In Table 1, n-Bu represents n-butyl, Me represents methyl, Et represents ethyl, n-octyl represents n-octyl, and tert-Bu represents tert-butyl. Furthermore, C13* represents substituents with the following structures:

[0118]

[0119] In the formula, n-octyl represents n-octyl, and the curved part represents the bonding point.

[0120] <Example 6>

[0121] Except for changing the amount of Pd(OCOCH3)2 to 0.158 mmol (0.1 equivalent relative to the monomer (the compound represented by formula (3-1)) and the amount of AgSbF6 to 0.158 mmol (0.1 equivalent relative to the monomer (the compound represented by formula (3-1))), the procedure was carried out in the same manner as in Example 2, and GNR was obtained. The analytical results of the obtained GNR obtained by SEC are shown in Table 2 below.

[0122] <Comparative Example 5>

[0123] Except for changing the amount of Pd(OCOCH3)2 to 0.79 mmol (0.5 equivalents relative to the monomer (the compound represented by formula (3-1)) and the amount of AgSbF6 to 0.79 mmol (0.5 equivalents relative to the monomer (the compound represented by formula (3-1))), the procedure was carried out in the same manner as in Example 2, and GNR was obtained. The analytical results of the obtained GNR obtained by SEC are shown in Table 2 below.

[0124] [Table 2]

[0125]

Claims

1. A graphene nanoribbon, represented by general formula (1), In equation (1), R 1 R represents a straight-chain alkyl group with 1 to 12 carbon atoms; 3 and R 4 All are hydrogen atoms, or R 3 and R 4 Co-formation -SiR 2a R 2b - represents the group; where, R 2a and R 2b Same or different, representing hydrogen atoms, alkyl or phenyl groups with 1 to 4 branched carbon atoms; n represents an integer greater than 1.

2. The graphene nanoribbons according to claim 1, wherein the graphene nanoribbons are represented by general formula (1-1) and / or general formula (1-2), In equation (1-1), R 1 R represents a straight-chain alkyl group with 1 to 12 carbon atoms; 2a and R 2b Same or different, representing hydrogen atoms, optionally alkyl or phenyl groups with 1 to 4 branched carbon atoms; n a Represents integers greater than or equal to 1. In equation (1-2), R 1 Indicates a straight-chain alkyl group with 1 to 12 carbon atoms; n b Represents an integer greater than or equal to 1.

3. A method for manufacturing graphene nanoribbons according to claim 1 or 2, wherein, The thiophene compound represented by general formula (2) was polymerized in the presence of 0.01 to 0.4 moles of palladium compound, o-tetrachlorobenzoquinone, and silver compound relative to 1 mole of the thiophene compound represented by general formula (2). In equation (2), R 1 R 2a and R 2b With the R 1 R 2a and R 2b same.

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