Aza non-alternating nanobelt material as well as preparation method and application thereof

Abstract

The invention discloses an aza non-alternating nanobelt material as well as a preparation method and application thereof. The nanobelt material has a structural formula as shown in a formula (I). 4, 7-dibromo-5, 6-dinitrobenzo [c] [1, 2, 5] thiadiazole is used as a raw material, and the triptycene-terminated aza non-alternating nanobelt material with accurate structure and different lengths is prepared mainly through Suzuki coupling reaction, Fe powder or lithium aluminum hydride reduction reaction and ketoamine condensation reaction. The synthetic route is efficient, raw materials are easy to obtain, and the material structure and property are easy to adjust. The nanobelt material disclosed by the invention shows good solubility, high nitrogen impurity content, good thermal stability and strong electron affinity, and has potential application prospects in the fields of organic field effect transistors, organic nonlinear optical limiting, organic lithium ion batteries, electrocatalysis and the like.

Description

Technical Field

[0001] The present invention belongs to the field of graphene nanoribbon functional materials, and in particular relates to an nitrogen-doped non-alternating nanoribbon material and a preparation method and application thereof. Background Art

[0002] Graphene nanoribbons, with their unique optoelectronic and electromagnetic properties, hold broad application prospects in high-spin materials, conductive nanowires, and semiconductor devices. Studies have found that their optoelectronic and electromagnetic properties are influenced by variables such as edge structure, length, width, heteroatom doping, and defect structure (e.g., four-membered rings, five-membered rings, seven-membered rings, and eight-membered rings). Therefore, synthesizing graphene nanoribbons with precise structure and studying the relationship between structure and properties are of great importance. Among the reported synthetic methods, organic solution synthesis enables the controllable synthesis of graphene nanoribbons with atomically precise precision, allowing precise tailoring of their molecular and electronic structures and the examination of optoelectronic properties such as solution processing performance, energy levels, absorption, and semiconductor properties. Graphene nanoribbons of various lengths, dimensions, functionalities, and heteroatom doping have been reported using this method. The synthesis and properties of soluble ultralong nitrogen-doped graphene nanoribbons have been the most extensively studied.

[0003] Despite the rapid development of soluble ultralong nitrogen-doped graphene nanoribbons, their synthesis still faces several challenges: as length increases, intermolecular aggregation between the large conjugated intermediates and their target nanoribbons increases, leading to poor solubility, extremely low yields, difficulties in separation and purification, and even hindering their structural and property characterization. Furthermore, the current focus is on developing alternating conjugated nitrogen-doped graphene nanoribbons with all six-membered rings, while reports on soluble non-alternating conjugated nitrogen-doped graphene nanoribbons containing five-membered rings are rare. Summary of the Invention

[0004] The purpose of the present invention is to provide an nitrogen-doped non-alternating nanoribbon material and its preparation method and application. The technical problem to be solved by the present invention is that ultra-long nitrogen-doped graphene nanoribbons have poor solubility, extremely low yield, and difficulty in separation and purification.

[0005] To achieve the above object, the technical solution provided by the present invention is as follows:

[0006] The present invention provides an aza-doped non-alternating nanoribbon material, wherein the aza-doped non-alternating nanoribbon material has the structural formula shown in the following formula (I):

[0007]

[0008] In formula (I), X is an oxygen atom or a sulfur atom; R is selected from one or more of a straight-chain alkyl group having 4 to 16 carbon atoms and a branched-chain alkyl group having 8 to 30 carbon atoms; and n is selected from an integer of 1 to 4.

[0009] Furthermore, the straight-chain alkyl group having a total carbon atom count of 4 to 16 is selected from one or more of n-butane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-undecane, n-dodecane, n-tridecane, n-tetradecane, n-pentadecyl, and n-hexadecane.

[0010] Further, the branched alkyl group having a total carbon atom count of 8 to 30 is selected from one or more of 2-ethylhexyl, 2-butylhexyl, 2-hexyloctyl, 4-hexyldecyl, 3-hexylundecyl, 2-octyldecyl, 2-octyldodecyl, 3-octyltridecyl, 2-decyldodecyl, 2-decyltetradecyl, 3-decylpentadecyl, 2-dodecylhexadecyl, 4-octyltetradecyl, 4-decylhexadecyl, 4-hexyldecyl, 4-octyldodecyl, 4-decyltetradecyl, and 4-dodecylhexadecyl.

[0011] Furthermore, the structural formula of the aza non-alternating nanobelt material is selected from one or more of the following formula (II), wherein R is isooctyl.

[0012]

[0013] As a general inventive concept, the present invention also provides a method for preparing the above-mentioned nitrogen-doped non-alternating nanoribbon material, comprising the following steps:

[0014] (1) Under nitrogen environment, 5-bromoresorcinol (Compound 1) reacts with bromoalkane to undergo nucleophilic substitution reaction to obtain Compound 2, the structural formula of which is:

[0015]

[0016] (2) Under nitrogen environment, compound 2 undergoes Miyaura boronation reaction with biboronic acid pinacol ester to obtain compound 3, the structural formula of compound 3 is:

[0017]

[0018] (3) Under nitrogen environment, 4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole (Compound 4) undergoes Suzuki coupling reaction with the Compound 3 to obtain Compound 5, the structural formula of the Compound 5 is:

[0019]

[0020] (4) Under a nitrogen environment, the compound 5 is first subjected to a reduction reaction with iron powder to obtain a first diamine functional intermediate; the first diamine functional intermediate directly undergoes a ketoamine condensation reaction with the vicinal diketone functional compound 6 to obtain compound 7. The structural formulas of the compounds 6 and 7 are:

[0021]

[0022] (5) Under nitrogen atmosphere, the compound 7 is first subjected to a reduction reaction with lithium aluminum tetrahydride to obtain a second diamine functional intermediate; the second diamine functional intermediate directly reacts with the tetraketone functional compound 8 to undergo a ketoamine condensation reaction to obtain compound 9. The structural formulas of the compounds 8 and 9 are:

[0023]

[0024] (6) Under nitrogen atmosphere, the first diamine functional intermediate prepared in step (4) is directly condensed with the tetraketone functional compound 8 to obtain compound 10 and compound 11. The structural formula of compound 10 is:

[0025]

[0026] The structural formula of the compound 11 is:

[0027]

[0028] (7) Under nitrogen environment, the second diamine functional intermediate prepared in step (5) directly undergoes ketoamine condensation reaction with compound 10 to obtain compound 12, the structural formula of which is:

[0029]

[0030] (8) Under a nitrogen environment, the second diamine functional intermediate prepared in step (5) directly undergoes a ketoamine condensation reaction with the compound 6 to obtain compound NR-11;

[0031]

[0032] (9) Under a nitrogen environment, the second diamine functional intermediate prepared in step (5) directly undergoes a ketoamine condensation reaction with the compound 8 to obtain compound NR-17;

[0033]

[0034] (10) Under nitrogen atmosphere, the compound 12 is first subjected to a reduction reaction with lithium aluminum tetrahydride to obtain a third diamine functional intermediate; the third diamine functional intermediate is directly subjected to a ketoamine condensation reaction with the compound 9 to obtain compound NR-23;

[0035]

[0036] (11) Under a nitrogen environment, the compound 11 first undergoes a reduction reaction with lithium aluminum tetrahydride to obtain a fourth diamine functional intermediate; the fourth diamine functional intermediate directly undergoes a ketoamine condensation reaction with the compound 9 to obtain compound NR-29.

[0037]

[0038] The preparation method of the above-mentioned aza-non-alternating nanobelt material, preferably, step (1) is specifically as follows: under a nitrogen environment, compound 1, K2CO3 and 18-crown-6 are added to a three-necked flask containing DMF solvent and placed at 60°C for reaction for 2 hours. Then, bromoisooctane is added, the temperature is raised to 60-120°C, and the reaction is carried out for 6-12 hours. After cooling to room temperature, the pH is adjusted to neutral, extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. Purification using a silica gel column chromatography obtains a colorless liquid compound 2. The molar ratio of the compound 1, K2CO3, 18-crown-6 and bromoisooctane is 1.0:2.0-4.0:0.01-0.05:2.0-4.0; more preferably, the ratio is 1.0:3.0:0.02:2.5; more preferably, the reaction temperature is 80°C; and more preferably, the reaction time is 9 hours.

[0039] In the preparation method of the above-mentioned aza-non-alternating nanobelt material, preferably, step (2) is specifically as follows: under a nitrogen environment, compound 2, bipyraclostrobin, potassium acetate, and palladium catalyst are added to a three-necked flask containing 1,4-dioxane solvent, and the mixture is placed at 80-120°C for reaction for 8-12 hours. After cooling to room temperature, the mixture is extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried by rotary evaporation to obtain a crude product. Purification using a silica gel column chromatography yields a colorless liquid compound 3. The molar ratio of compound 2, bipyraclostrobin, potassium acetate, and palladium catalyst is 1.0:1.0-3.0:1.0-3.0:0.01-0.03; more preferably, the ratio is 1.0:1.5:1.5:0.02; more preferably, the reaction temperature is 100°C; and more preferably, the reaction time is 10 hours.

[0040] In the preparation method of the above-mentioned aza-non-alternating nanobelt material, preferably, step (3) is specifically as follows: under a nitrogen environment, compound 4, compound 3, and a palladium catalyst are added to a three-necked flask containing toluene and K2CO3 (2M aqueous solution), and the mixture is placed at 80-100°C for reaction for 5-8 hours. After cooling to room temperature, the mixture is extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. Purification by silica gel chromatography obtains yellow solid compound 5. The molar ratio of compound 4, compound 3, and palladium catalyst is 1.0:2.0-4.0:0.05-0.5; more preferably, the ratio is 1.0:2.5:0.13; more preferably, the reaction temperature is 90°C; and more preferably, the reaction time is 7 hours.

[0041] The preparation method of the above-mentioned nitrogen-doped non-alternating nanobelt material, preferably, step (4) is specifically as follows: under a nitrogen environment, compound 5 and iron powder are added to an acetic acid solvent, placed at 75°C for reaction for 7 hours, and cooled to room temperature after the reaction is completed. The reaction solution is extracted with ethyl acetate and saturated brine, the organic phase is dried with anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. The obtained crude product and compound 6 are added to a mixed solution of chloroform and acetic acid, placed at 60-90°C for reaction for 6-12 hours. After cooling to room temperature, pour into a sodium bicarbonate solution and stir for 10 minutes, then extract with dichloromethane and saturated brine, dry with anhydrous magnesium sulfate, filter, and dry the solvent to obtain a crude product, which is purified by silica gel chromatography to obtain a red solid compound 7. Wherein, the molar ratio of the compound 5, iron powder and compound 6 is 1.0:10.0-20.0:0.5-1.0; more preferably, the ratio is 1.0:11.9:0.74; more preferably, the reaction temperature is 80°C; more preferably, the reaction time is 9 hours;

[0042] The preparation method of the above-mentioned nitrogen-doped non-alternating nanobelt material, preferably, step (5) is specifically as follows: under a nitrogen environment, compound 7 is added to THF solvent, placed in an ice bath and stirred for 10 minutes, and LiAlH4 is added in batches. The temperature is naturally raised to room temperature and the reaction is carried out for 6 hours. The reaction solution is extracted with ethyl acetate and saturated brine, the organic phase is dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. The obtained crude product and compound 8 are added to a mixed solution of chloroform and acetic acid, placed at 40-80°C and reacted for 3-7 hours. After cooling to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10 minutes, then extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product, which is purified by silica gel chromatography to obtain a red solid compound 9. The molar ratio of compound 7, LiAlH4 and compound 8 is 1.0:20.0-80.0:2.0-3.0; the more preferred ratio is 1.0:40.0:2.5; the more preferred reaction temperature is 65°C; the more preferred reaction time is 4 hours;

[0043] The preparation method of the above-mentioned nitrogen-doped non-alternating nanobelt material, preferably, step (6) is specifically as follows: under a nitrogen environment, compound 5 and iron powder are added to an acetic acid solvent and placed at 75°C for 7 hours. Cool to room temperature, extract the reaction solution with ethyl acetate and saturated brine, dry the organic phase with anhydrous magnesium sulfate, filter, and spin-dry the solvent to obtain a crude product. The obtained crude product and compound 8 are added to a mixed solution of chloroform and acetic acid, placed at 50-80°C for 2-7 hours. After cooling to room temperature, pour into a sodium bicarbonate solution and stir for 10 minutes, then extract with dichloromethane and saturated brine, dry with anhydrous magnesium sulfate, filter, and spin-dry the solvent to obtain a crude product. Purification by silica gel chromatography gives brown solid compound 10 and red solid compound 11. The molar ratio of compound 4, iron powder and compound 8 is 1.0:10.0-20.0:2.0-3.0; more preferably, the ratio is 1.0:11.9:2.5; more preferably, the reaction temperature is 65°C; and more preferably, the reaction time is 4 hours.

[0044] The preparation method of the above-mentioned nitrogen-doped non-alternating nanobelt material, preferably, step (7) is specifically as follows: under a nitrogen environment, compound 7 is added to THF solvent, placed in an ice bath and stirred for 10 minutes, and LiAlH4 is added in batches. The temperature is naturally raised to room temperature and the reaction is carried out for 6 hours. The reaction solution is extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. The obtained crude product and compound 10 are added to a mixed solution of chloroform and acetic acid, placed at 60-90°C and reacted for 6-12 hours. After cooling to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10 minutes, then extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. Purification by silica gel chromatography gives red solid compound 12. The molar ratio of compound 7, LiAlH4 and compound 10 is 1.0:20.0-80.0:1.0-3.0; the more preferred ratio is 1.0:40.0:1.3; the more preferred reaction temperature is 80°C; and the more preferred reaction time is 7 hours.

[0045] The preparation method of the above-mentioned nitrogen-doped non-alternating nanobelt material, preferably, step (8) is specifically as follows: under a nitrogen environment, compound 7 is added to THF solvent, placed in an ice bath and stirred for 10 minutes, and LiAlH4 is added in batches. The temperature is naturally raised to room temperature and the reaction is carried out for 6 hours. The reaction solution is extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. The obtained crude product and compound 6 are added to a mixed solution of chloroform and acetic acid, placed at 70-90°C and reacted for 6-12 hours. After cooling to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10 minutes, then extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. Purification by silica gel chromatography obtains an orange solid compound NR-11. The molar ratio of compound 7, LiAlH4 and compound 6 is 1.0:20.0-80.0:1.0-3.0; the more preferred ratio is 1.0:40.0:1.3; the more preferred reaction temperature is 80°C; and the more preferred reaction time is 8 hours.

[0046] The preparation method of the above-mentioned nitrogen-doped non-alternating nanobelt material, preferably, step (9) is specifically as follows: under a nitrogen environment, compound 7 is added to THF solvent, placed in an ice bath and stirred for 10 minutes, and LiAlH4 is added in batches. The temperature is naturally raised to room temperature and the reaction is carried out for 6 hours. The reaction solution is extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. The obtained crude product and compound 8 are added to a mixed solution of chloroform and acetic acid, placed at 60-90°C and reacted for 6-12 hours. After cooling to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10 minutes, then extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. Purification by silica gel chromatography obtains a red solid compound NR-17. The molar ratio of compound 7, LiAlH4 and compound 8 is 1.0:20.0-80.0:0.2-0.6; the more preferred ratio is 1.0:40.0:0.4; the more preferred reaction temperature is 80°C; and the more preferred reaction time is 7 hours.

[0047] The preparation method of the above-mentioned nitrogen-doped non-alternating nanobelt material, preferably, step (10) is specifically as follows: under a nitrogen environment, compound 12 is added to a THF solvent, placed in an ice bath and stirred for 10 minutes, and LiAlH4 is added in batches. The temperature is naturally raised to room temperature and the reaction is carried out for 6 hours. The reaction solution is extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. The above-mentioned crude product and compound 9 are added to a mixed solution of toluene and acetic acid, placed at 90-110°C and reacted for 24-48 hours. After cooling to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10 minutes, then extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. Purification by silica gel chromatography obtains a red solid compound NR-23. The molar ratio of compound 12, LiAlH4 and compound 9 is 1.0:20.0-80.0:1.0-3.0; the more preferred ratio is 1.0:40.0:1.3; the more preferred reaction temperature is 100°C; and the more preferred reaction time is 36 hours.

[0048] The preparation method of the above-mentioned nitrogen-doped non-alternating nanobelt material, preferably, step (11) is specifically as follows: under a nitrogen environment, compound 11 is added to a THF solvent, placed in an ice bath and stirred for 10 minutes, and LiAlH4 is added in batches. The temperature is naturally raised to room temperature and the reaction is carried out for 6 hours. The reaction solution is extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. The obtained crude product and compound 9 are added to a mixed solution of xylene and acetic acid, placed at 110-130°C and reacted for 24-72 hours. After cooling to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10 minutes, then extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent is dried to obtain a crude product. The red solid compound NR-29 is purified by silica gel chromatography. The molar ratio of compound 11, LiAlH4 and compound 9 is 1.0:20.0-80.0:2.0-4.0; the more preferred ratio is 1.0:40.0:2.5; the more preferred reaction temperature is 120°C; and the more preferred reaction time is 48 hours.

[0049] In the above-mentioned method for preparing the aza-non-alternating nanobelt material, preferably, in step (2) and step (3), the palladium catalyst is selected from at least one of tetrakis(triphenylphosphine)palladium, palladium acetate, bis(triphenylphosphine)palladium dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, and tris(dibenzylideneacetone)dipalladium. Step (2) is preferably [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride; step (3) is preferably bis(triphenylphosphine)palladium dichloride.

[0050] The preparation method of the nitrogen-doped non-alternating conjugated nanoribbon material provided by the present invention aims to develop a novel nitrogen-doped non-alternating conjugated nanoribbon material terminated with triptycene. The main molecular design ideas are as follows: 1) introducing two triptycene end groups and multiple alkoxyphenyl substitutions to construct a nanoribbon material with a three-dimensional backbone structure, weakening the aggregation between nanoribbon molecules and improving its solubility; 2) introducing multiple pyrazine rings into the nanoribbon conjugated skeleton to reduce the HOMO and LUMO energy levels of the nanoribbon material and improve its chemical stability; 3) introducing multiple five-membered rings into the nanoribbon conjugated skeleton to construct a unique non-alternating conjugated skeleton structure, further improving the chemical stability of the nanoribbon material; 4) constructing a rigid fused ring conjugated skeleton to enhance the thermal stability of the nanoribbon material; 5) adopting an iterative ketoamine condensation strategy to construct non-alternating conjugated nanoribbon materials with accurate structures and different lengths, enriching the variety of graphene nanoribbons and providing a new material research platform for clarifying the structure-activity relationship between graphene nanoribbon structure and photoelectric properties.

[0051] This invention uses 4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole as the raw material and synthesizes this type of nanoribbon material primarily through a Suzuki coupling reaction, Fe powder reduction reaction, lithium aluminum tetrahydride reduction reaction, and ketoamine condensation reaction. Using an iterative ketoamine condensation strategy, conjugated segments containing five-membered rings and pyrazine rings are condensed to construct a series of soluble ultra-long non-alternating conjugated nitrogen-doped graphene nanoribbons. This extends the conjugated length of the nanoribbons and provides synthesis and property characterization techniques and experience for the future development of soluble ultra-long graphene nanoribbons. By introducing 3D bulky triptycene end groups and alkoxyphenyl groups with multiple solubility-enhancing properties into the nanoribbon backbone, a 3D nanoribbon structure is constructed, thereby suppressing excessive aggregation between nanoribbon molecules and improving their solubility and processability.

[0052] Thanks to these unique advantages, the nanobelt materials shown in the present invention exhibit good solubility, high nitrogen impurity content, good chemical stability, high thermal stability and strong electron affinity, and have potential application prospects in the fields of organic field-effect transistors, organic nonlinear optical limiting, organic lithium-ion batteries and electrocatalysis.

[0053] Compared with the prior art, the advantages of the present invention are:

[0054] 1. The iterative ketoamine condensation strategy of the present invention has advantages such as good universality, high reproducibility of the synthetic route, and easy adjustment of the material structure and properties. It can be promoted to develop more nanoribbon materials with good solubility and accurate structure;

[0055] 2. The nanobelt NR-29 described in the present invention is the longest conjugated, soluble non-alternating conjugated nanobelt material reported so far;

[0056] 3. The conjugated skeleton of the nanobelt material of the present invention contains multiple pyrazine rings, which effectively reduces the HOMO and LUMO energy levels of the nanobelt material and improves its chemical stability and electrochemical activity;

[0057] 4. The conjugated skeleton of the nanobelt material of the present invention contains multiple five-membered rings, which constructs a unique non-alternating conjugated skeleton structure and further improves the chemical stability of the nanobelt material;

[0058] 5. The nanobelt materials shown in the present invention exhibit good solubility, high nitrogen impurity content, good thermal stability and strong electron affinity, fully demonstrating that this type of material has potential application prospects in the fields of organic field-effect transistors, organic nonlinear optical limiting, organic lithium-ion batteries and electrocatalysis. BRIEF DESCRIPTION OF THE DRAWINGS

[0059] Figure 1 1 is the absorption spectrum of NR-11 in chloroform solution and thin film state shown in Example 1 of the present invention;

[0060] Figure 2 This is the absorption spectrum of NR-17 in chloroform solution and thin film state shown in Example 2 of the present invention;

[0061] Figure 3 The absorption spectra of NR-23 in chloroform solution and thin film state shown in Example 3 of the present invention are shown;

[0062] Figure 4 This is the absorption spectrum of NR-29 in chloroform solution and thin film state shown in Example 4 of the present invention;

[0063] Figure 5 The fluorescence spectra of NRs in chloroform solution shown in Examples 1 to 4 of the present invention are shown;

[0064] Figure 6 The cyclic voltammetry curves of NRs shown in Examples 1 to 4 of the present invention in chloroform solution are shown;

[0065] Figure 7 1 is a thermogravimetric analysis curve of NRs shown in Examples 1 to 4 of the present invention. DETAILED DESCRIPTION

[0066] The present invention will be further described below in conjunction with the accompanying drawings and specific preferred embodiments of the specification, but the present invention is not limited to the following embodiments. The methods described are conventional methods unless otherwise specified. The raw materials described can be obtained from public commercial channels unless otherwise specified. The reaction substrates used in the following examples can all be obtained from commercial channels, and the remaining reaction solvents and catalysts can all be obtained from commercial channels. Among them, 5-bromoresorcinol (compound 1) and 4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole (compound 4) can be obtained from commercial channels; the diketone-functional compound 6 can be synthesized according to the literature Angew.Chem.Int.Ed., 2023, 62, e202306418; the tetraketone-functional compound 8 can be synthesized according to the literature J.Org.Chem., 1996, 61, 6052-6054.

[0067] Example 1:

[0068] A nitrogen-doped non-alternating conjugated nanobelt material, specifically a nitrogen-doped non-alternating conjugated nanobelt material with a chemical structure of NR-11, the synthesis route of which is as follows:

[0069]

[0070] (1) Synthesis of the compound of formula 2: Under nitrogen, compound 1 (3.5 g, 18.52 mmol), K2CO3 (7.7 g, 55.71 mmol), and 18-crown ether-6 (100 mg, 0.38 mmol) were added to a three-necked flask containing 25 mL of DMF solvent and placed in a 60°C oil pan. After reacting for 2 hours, bromoisoctane (8.94 g, 46.29 mmol) was added, and the temperature was raised to 80°C and reacted for 9 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude product. Purification by silica gel column chromatography gave a colorless liquid compound 2 with a yield of 87.6%.

[0071] The structural characterization is as follows:

[0072] 1 H NMR (400MHz, CDCl3) δ (ppm): 6.64 (d, J = 4.0Hz, 2H), 6.37 (t, J = 4.0Hz, 1H), 3. 83–3.75(m,4H),1.73–1.65(m,2H),1.48–1.23(m,16H),0.94–0.87(m,12H).

[0073] 13C NMR (100MHz, CDCl3) δ (ppm): 161.11, 122.91, 110.23, 100.63, 70.75, 39.43, 30.60, 29.18, 23.95, 23.18, 14.23, 11.23.

[0074] From the above, it can be seen that the structure of the compound is correct, that is, compound 2 shown.

[0075] (2) Synthesis of the compound of the chemical formula 3: Under nitrogen, compound 2 (3.40 g, 8.22 mmol), pinacol diboron (3.13 g, 12.33 mmol), potassium acetate (1.21 g, 12.33 mmol), and [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (120 mg, 0.16 mmol) were added to a three-necked flask containing 20 mL of 1,4-dioxane and reacted at 100°C for 10 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude product. Purification by silica gel column chromatography gave compound 3 as a colorless liquid with a yield of 71%.

[0076] The structural characterization is as follows:

[0077] 1 H NMR (400MHz, CDCl3) δ (ppm): 6.92 (d, J = 4.0 Hz, 2H), 6.56 (t, J = 4.0 Hz, 1H), 3. 88–3.80(m,4H),1.73–1.64(m,2H),1.49–1.26(m,28H),0.94–0.87(m,12H).

[0078] 13 C NMR (100MHz, CDCl3) δ (ppm): 160.33, 112.26, 105.02, 83.94, 70.36, 39.63, 30.70, 29.25, 24.97, 24.03, 23.20, 14.26, 11.29.

[0079] From the above, it can be seen that the structure of the compound is correct, that is, compound 3 shown.

[0080] (3) Synthesis of the compound of formula 5: Under nitrogen, compound 4 (300 mg, 0.78 mmol), compound 3 (900 mg, 1.95 mmol), and bis(triphenylphosphine)palladium dichloride (70 mg, 0.10 mmol) were added to a three-necked flask containing 15 mL of toluene and 5 mL of K2CO3 (2M), and the mixture was allowed to react at 90°C for 7 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude product. Purification by silica gel column chromatography gave compound 5 as a yellow solid with a yield of 50%.

[0081] The structural characterization is as follows:

[0082] 1 H NMR (400MHz, CDCl3) δ (ppm): 6.63 (s, 6H), 3.84 (d, J = 4.0Hz, 8H), 1.77–1.69 (m, 4H), 1.47–1.27 (m, 32H), 0.95–0.88 (m, 24H).

[0083] 13 C NMR (100MHz, CDCl3) δ (ppm): 160.86, 152.91, 142.44, 131.76, 129.23, 107.71, 103.32, 70.86, 39.41, 30.58, 29.16, 23.92, 23.17, 14.21, 11.23.

[0084] HRMS:m / z[M] + calcd for(C 50 H 74 N4O8S)890.5221; found 890.5221 (error=–0.1ppm).

[0085] From the above, it can be seen that the structure of the compound is correct, that is, compound 5 shown.

[0086] (4) Synthesis of the compound of formula 7: Under nitrogen, compound 5 (300 mg, 0.34 mmol) and iron powder (227 mg, 4.05 mmol) were added to a three-necked flask containing 15 mL of glacial acetic acid and allowed to react at 75°C for 7 hours. After cooling to room temperature, the mixture was slowly poured into a sodium bicarbonate solution and stirred for 20 minutes. The mixture was then extracted with ethyl acetate and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain the crude product compound.

[0087] The crude product and compound 6 (109 mg, 0.25 mmol) were mixed with 5 mL of chloroform and 2 mL of acetic acid. The reaction mixture was stirred at 80°C for 9 hours. After cooling to room temperature, the organic phase was extracted with CH2Cl2 and dried over magnesium sulfate. After removal of the solvent, the mixture was purified by silica gel column chromatography to yield compound 7 as a red solid in 80% yield.

[0088] The structural characterization is as follows:

[0089] 1 H NMR (400MHz, CDCl3) δ (ppm): 8.07 (d, J = 8.0Hz, 2H), 7.87 (s, 2H), 7.84 (d, J = 8.0Hz, 2H), 7.44 (dd, J = 8.0, 4.0Hz, 4H), 7.04 (q, J = 4.0Hz, 8H), 6.6 8(t,J=4.0Hz,2H),5.53(s,2H),3.94(d,J=4.0Hz,8H),1.82–1.75(m,4H),1.48–1.26(m,32H),0.94(t,J=8.0Hz,12H),0.88(t,J=8.0Hz,12H).

[0090] 13 C NMR (100MHz, CDCl3) δ (ppm): 159.95, 157.02, 153.48, 146.87, 144.70, 139.46, 138.83, 137.07, 136.91, 136.52, 131.13, 131. 07,125.55,124.02,123.82,122.40,119.11,111.22,101.79,70.61,54.55,39.51,30.66,29.19,24.03,23.20,14.25,11.28.

[0091] HRMS:m / z[M] + calcd for(C 82 H 90 N4O4S)1226.6677; found 1226.6670 (error=–0.6ppm).

[0092] From the above, it can be seen that the structure of the compound is correct, that is, compound 7 shown.

[0093] (5) Synthesis of the compound with the chemical formula NR-11: Under nitrogen, compound 7 (200 mg, 0.16 mmol) was added to 8 mL of THF solvent, stirred in an ice bath for 10 minutes, and LiAlH4 (247 mg, 6.51 mmol) was added. The temperature was naturally raised to room temperature and the reaction was allowed to proceed for 6 hours. After the reaction was completed, the mixture was cooled to room temperature and quenched with water. The reaction solution was extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain a crude product.

[0094] The above crude product and compound 6 (90 mg, 0.21 mmol) were added to a mixed solution of 5 mL of chloroform and 2 mL of acetic acid, and the mixture was reacted at 80°C for 8 hours. After the reaction solution was cooled to room temperature, it was poured into a sodium bicarbonate solution and stirred for 10 to 30 minutes. The mixture was then extracted with dichloromethane and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product. The product was purified by silica gel chromatography to obtain an orange solid compound NR-11 with a yield of 77%.

[0095] The structural characterization is as follows:

[0096] 1 H NMR (400MHz, CDCl3) δ (ppm): 8.01 (d, J = 8.0Hz, 4H), 7.81 (s, 4H), 7.76 (d, J = 4.0Hz, 4H), 7.43 (dd, J = 4.0, 4.0Hz, 8H), 7.03 (dd, J = 4.0, 4.0Hz, 8H), 6.96 (d ,J=4.0Hz,4H),6.71(s,2H),5.50(s,4H),3.96(d,J=4.0Hz,8H),1.84–1.77 (m,4H),1.48–1.23(m,32H),0.94(t,J=8.0Hz,12H),0.86(t,J=8.0Hz,12H).

[0097] 13 C NMR (100MHz, CDCl3) δ (ppm): 159.41, 156.70, 146.91, 144.80, 139.73, 139.59, 139.20, 138.26, 136.78, 136.47, 131.89, 131.66, 125.57,124.29,123.81,122.34,119.25,112.37,101.58,70.54,54.60,39.53,30.74,29.85,29.23,24.12,23.25,14.28,11.31.

[0098] HRMS:m / z[M] +calcd for(C 114 H 106 N4O4)1594.8208; found 1594.8205 (error=–0.2ppm).

[0099] From the above, it can be seen that the structure of the compound is correct, that is, the compound NR-11 shown.

[0100] Example 2

[0101] A nitrogen-doped non-alternating conjugated nanobelt material, specifically a nitrogen-doped non-alternating conjugated nanobelt material with a chemical structure of NR-17, the synthesis route of which is as follows:

[0102]

[0103] (1) Synthesis of the compound of chemical formula 2: Synthesize with reference to the synthesis method of Example 1 above.

[0104] (2) Synthesis of the compound of chemical formula 3: Synthesize by referring to the synthesis method of Example 1 above.

[0105] (3) Synthesis of the compound of chemical formula 5: Synthesize by referring to the synthesis method of Example 1 above.

[0106] (4) Synthesis of the compound of chemical formula 7: Synthesize with reference to the synthesis method of Example 1 above.

[0107] (5) Synthesis of the compound with the chemical formula NR-17: Under nitrogen atmosphere, compound 7 (200 mg, 0.16 mmol) was added to 8 mL of THF solvent, placed in an ice bath and stirred for 10 minutes, LiAlH4 (247 mg, 6.51 mmol) was added, and the temperature was naturally raised to room temperature and reacted for 6 hours; the reaction solution was extracted with ethyl acetate and saturated brine, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product.

[0108] The above crude product and compound 8 (15 mg, 0.064 mmol) were added to a mixed solution of 5 mL of chloroform and 2 mL of acetic acid, and the mixture was reacted at 80°C for 7 hours. After the reaction solution was cooled to room temperature, it was poured into a sodium bicarbonate solution and stirred for 10 to 30 minutes. The mixture was then extracted with dichloromethane and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product. The product was purified by silica gel chromatography to obtain a red solid compound NR-17 with a yield of 68%.

[0109] The structural characterization is as follows:

[0110] 1H NMR (400MHz, CDCl3) δ (ppm): 8.32 (s, 4H), 8.04 (d, J = 8.0Hz, 4H), 7.83 (s, 4H), 7 .78(d,J=8.0Hz,4H),7.44(dd,J=8.0,4.0Hz,8H),7.04(dd,J=8.0,4.0Hz,8H),7 .00(d,J=4.0Hz,8H),6.74(s,4H),5.51(s,4H),3.99(d,J=4.0Hz,16H),1.86–1 .79(m,8H),1.47–1.25(m,64H),0.95(t,J=8.0Hz,24H),0.86(t,J=8.0Hz,24H).

[0111] 13 C NMR(100MHz,CDCl3)δ(ppm):159.51,157.02,155.64,147.00,144.77,140 .09,139.86,139.15,138.50,138.23,136.68,136.60,135.96,134.33,131 .63,125.58,124.71,124.48,123.82,122.38,119.26,112.41,101.60,70. 62,54.59,39.52,30.76,29.84,29.24,24.12,23.24,22.83,14.28,11.31.

[0112] HRMS:m / z[M+H] + calcd for(C 178 H 185 N8O8)2562.4309; found 2562.4299 (error=0.4ppm).

[0113] From the above, it can be seen that the structure of the compound is correct, that is, the compound NR-17 shown.

[0114] Example 3:

[0115] A nitrogen-doped non-alternating conjugated nanobelt material, specifically a nitrogen-doped non-alternating conjugated nanobelt material with a chemical structure of NR-23, the synthesis route of which is as follows:

[0116]

[0117] (1) Synthesis of the compound of chemical formula 2: Synthesize with reference to the synthesis method of Example 1 above.

[0118] (2) Synthesis of the compound of chemical formula 3: Synthesize by referring to the synthesis method of Example 1 above.

[0119] (3) Synthesis of the compound of chemical formula 5: Synthesize by referring to the synthesis method of Example 1 above.

[0120] (4) Synthesis of the compound of chemical formula 7: Synthesize with reference to the synthesis method of Example 1 above.

[0121] (5) Synthesis of the compound of chemical formula 9: Under nitrogen atmosphere, compound 7 (200 mg, 0.16 mmol) was added to 8 mL of THF solvent, stirred in an ice bath for 10 minutes, and LiAlH4 (247 mg, 6.51 mmol) was added. The temperature was naturally raised to room temperature and the reaction was carried out for 6 hours. The reaction solution was extracted with ethyl acetate and saturated brine, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product.

[0122] The above crude product and compound 8 (96 mg, 0.41 mmol) were added to a mixed solution of 24 mL of chloroform and 5 mL of acetic acid, and the mixture was reacted at 65°C for 4 hours. After the reaction solution was cooled to room temperature, it was poured into a sodium bicarbonate solution and stirred for 10 to 30 minutes. The mixture was then extracted with dichloromethane and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product. The product was purified by silica gel chromatography to obtain a red solid compound 9 with a yield of 50%.

[0123] The structural characterization is as follows:

[0124] 1 H NMR (400MHz, CDCl3) δ (ppm): 8.44 (br, 2H), 8.27 (d, J = 8.0Hz, 2H), 7.99 (d, J = 8 .0Hz,2H),7.77(s,2H),7.70(br,2H),7.45(t,J=4.0Hz,4H),7.05(t,J=4.0Hz ,4H),6.98(s,4H),6.75(s,2H),5.49(s,2H),3.99(d,J=4.0Hz,8H),1.87–1.7 9(m,4H),1.53–1.23(m,32H),0.98(t,J=8.0Hz,12H),0.90(t,J=8.0Hz,12H).

[0125] 13C NMR (100MHz, CDCl3) δ (ppm): 185.88, 159.19, 156.51, 153.76, 147.50, 144.67, 141.53, 140.47, 139.52, 138.66, 138.28, 137.71, 136.05, 134. 88,131.34,131.16,129.22,125.59,123.94,122.27,119.31,112.64,1 01.86,70.62,54.64,39.72,30.73,29.30,24.10,23.30,14.33,11.43.

[0126] HRMS:m / z[M+H] + calcd for(C 96 H 95 N4O6)1399.7246; found 1399.7240 (error=-0.4ppm).

[0127] From the above, it can be seen that the structure of the compound is correct, that is, compound 9 shown.

[0128] (6) Synthesis of compounds with chemical formulas 10 and 11: Under nitrogen, compound 5 (300 mg, 0.34 mmol) and iron powder (224 mg, 4.01 mmol) were added to 15 mL of acetic acid and reacted at 75°C for 7 hours. After cooling to room temperature, the mixture was slowly poured into a sodium bicarbonate solution and stirred for 20 minutes. The mixture was then extracted with ethyl acetate and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain the crude product compound.

[0129] The above crude product and compound 8 (199 mg, 0.84 mmol) were added to a mixed solution of 24 mL of chloroform and 5 mL of acetic acid, and the mixture was reacted at 65°C for 4 hours. After the reaction solution was cooled to room temperature, it was poured into a sodium bicarbonate solution and stirred for 10 minutes. The mixture was then extracted with dichloromethane and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product. The product was purified by silica gel chromatography to obtain a brown solid (compound 10, yield 39%) and a red solid (compound 11, yield 20%).

[0130] The structural characterization is as follows:

[0131] Compound 10: 11H NMR (400 MHz, CDCl3) δ (ppm): 8.57 (d, J = 8.0 Hz, 2H), 8.38 (d, J = 8.0 Hz, 2H), 7.09 (d, J = 4.0 Hz, 4H), 6.74 (s, 2H), 3.96 (d, J = 8.0 Hz, 8H), 1.85–1.76 (m, 4H), 1.55–1.30 (m, 32H), 0.95 (t, J = 8.0 Hz, 12H), 0.90 (t, J = 8.0 Hz, 12H).

[0132] 13 13C NMR (100 MHz, CDCl3) δ (ppm): 186.40, 160.10, 154.62, 153.61, 142.60, 136.82, 136.52, 136.45, 135.97, 132.61, 129.43, 124.73, 124.15, 111.36, 101.95, 70.70, 39.50, 30.64, 29.18, 24.00, 23.20, 14.26, 11.28.

[0133] HRMS: m / z [M] + calcd for (C 64 H 78 N4O6S) 1030.5636; found 1030.5637 (error = –0.1 ppm).

[0134] Compound 11: 1 1H NMR (400 MHz, CDCl3) δ (ppm): 8.40 (s, 4H), 7.08 (d, J = 4.0 Hz, 8H), 6.72 (t, J = 4.0 Hz, 4H), 4.00–3.93 (m, 16H), 1.85–1.77 (m, 8H), 1.51–1.28 (m, 64H), 0.95 (t, J = 8.0 Hz, 24H), 0.88 (t, J = 8.0 Hz, 24H).

[0135] 13 13C NMR (100 MHz, CDCl3) δ (ppm): 160.10, 155.87, 153.63, 137.14, 136.76, 136.26, 133.91, 132.06, 124.61, 111.36, 102.03, 70.78, 39.57, 30.73, 29.25, 24.08, 23.22, 14.25, 11.31.

[0136] HRMS: m / z [M + H] +calcd for(C 114 H 153 N8O8S2)1826.1247; found 1826.1239 (error=0.4

[0137] ppm).

[0138] From the above, it can be seen that the structure of the compound is correct, namely compounds 10 and 11 shown.

[0139] (7) Synthesis of the compound of chemical formula 12: Compound 7 (200 mg, 0.16 mmol) was added to 8 mL of THF solvent, stirred in an ice bath for 5 to 20 minutes, and LiAlH4 (247 mg, 6.51 mmol) was added. The temperature was naturally raised to room temperature and the reaction was carried out for 6 hours. The reaction solution was extracted with ethyl acetate and saturated brine, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product.

[0140] The above crude product and compound 10 (218 mg, 0.21 mol) were added to a mixed solution of 5 mL of chloroform and 2 mL of acetic acid, and the mixture was reacted at 80°C for 7 hours. After the reaction solution was cooled to room temperature, it was poured into a sodium bicarbonate solution and stirred for 10 minutes. The mixture was then extracted with dichloromethane and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain a crude product. The product was purified by silica gel chromatography to obtain a red solid compound 12 with a yield of 60%.

[0141] The structural characterization is as follows:

[0142] 1 H NMR (400MHz, CDCl3) δ (ppm): 8.38 (dd, J = 12Hz, 8Hz, 4H), 8.05 (d, J = 8.0Hz, 2H), 7.83 ( s,2H),7.79(d,J=4.0Hz,2H),7.44(t,J=4.0Hz,4H),7.08(s,4H),7.04(t,J=4.0Hz,4H ),6.99(s,4H),6.75(s,2H),6.73(s,2H),5.52(s,2H),3.97(t,J=8.0Hz,16H),1.86– 1.77(m,8H),1.52–1.26(m,64H),0.95(t,J=8.0Hz,24H),0.88(dd,J=12Hz,8Hz,24H).

[0143] 13C NMR (100MHz, CDCl3) δ (ppm): 160.06, 159.81, 159.52, 157.07, 156.13, 155.31, 154.47, 153.64, 15 2.42,147.54,144.76,140.79,139.98,139.21,138.52,138.22,137.14,136.80,136.67,136.30, 135.38,134.50,133.74,132.31,131.94,131.68,125.58,124.78,124.48,123.80,122.43,119.31,112.44,111.35,70.80,70.67,54.62,39.56,30.77,29.84,29.27,24.14,23.25,14.27,11.31.

[0144] HRMS:m / z[M+H] + calcd for(C 146 H 169 N8O8S)2194.2778; found 2194.2754(error=1.1

[0145] ppm).

[0146] From the above, it can be seen that the structure of the compound is correct, that is, compound 12 shown.

[0147] (8) Synthesis of the compound with the chemical formula NR-23: Compound 12 (110 mg, 0.05 mmol) was added to 8 mL of THF solvent, stirred under an ice bath for 5 to 20 minutes, and LiAlH4 (76 mg, 2.00 mmol) was added. The temperature was naturally raised to room temperature and the reaction was carried out for 6 hours. The reaction solution was extracted with ethyl acetate and saturated brine, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product.

[0148] The above crude product and compound 9 (91 mg, 0.065 mmol) were added to a mixed solution of 5 mL of toluene and 2 mL of acetic acid, and the reaction was carried out at 100°C for 36 hours. After the reaction solution was cooled to room temperature, it was poured into a sodium bicarbonate solution and stirred for 10 to 30 minutes. The mixture was then extracted with dichloromethane and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product. The product was purified by silica gel chromatography to obtain a red solid compound NR-23 with a yield of 50%.

[0149] The structural characterization is as follows:

[0150] 1H NMR (400MHz, CDCl3) δ (ppm): 8.35 (s, 8H), 8.04 (d, J = 8.0Hz, 4H), 7.83 (s, 4H), 7.79 (d, J = 4.0Hz, 4H), 7.44 (dd, J = 4.0Hz, 4.0Hz, 8H), 7.06–6.99 (m, 20H) ),6.78(s,2H),6.75(s,4H),5.52(s,4H),4.00(d,J=4.0Hz,24H),1.86–1.8 0(m,12H),1.52–1.29(m,96H),0.99–0.94(m,36H),0.87(t,J=8.0Hz,36H).

[0151] 13 C NMR[100MHz, CDCl3 / TFA-d1(V∶V=3∶1)]δ(ppm):160.90,160.61,156.92,155.94,155.25,150.83,146.41,1 44.28,139.96,139.75,138.33,137.61,137.13,136.95,136.77,133.62,133.20,132.76,132.44,132.15,1 31.75,128.93,128.26,126.31,124.32,124.04,121.29,116.58,115.55,113.76,112.73,112.65,112.38,103.87,72.67,72.59,55.05,39.59,30.66,30.07,29.29,23.96,23.30,23.27,14.03,13.92,10.91,10.82.

[0152] HRMS:m / z[M+H] + calcd for(C 242 H 263 N 12 O 12 )3529.0332; found 3529.0357(error=0.7

[0153] ppm).

[0154] From the above, it can be seen that the structure of the compound is correct, that is, the compound NR-23 shown.

[0155] Example 4:

[0156] A nitrogen-doped non-alternating conjugated nanobelt material, specifically a nitrogen-doped non-alternating conjugated nanobelt material with a chemical structure of NR-29, the synthesis route of which is as follows:

[0157]

[0158] (1) Synthesis of the compound of chemical formula 2: Synthesize with reference to the synthesis method of Example 1 above.

[0159] (2) Synthesis of the compound of chemical formula 3: Synthesize by referring to the synthesis method of Example 1 above.

[0160] (3) Synthesis of the compound of chemical formula 5: Synthesize by referring to the synthesis method of Example 1 above.

[0161] (4) Synthesis of the compound of chemical formula 7: Synthesize with reference to the synthesis method of Example 1 above.

[0162] (5) Synthesis of the compound of chemical formula 9: Synthesize by referring to the synthesis method of Example 3 above.

[0163] (6) Synthesis of compounds with chemical structural formulas 10 and 11: Synthesize by referring to the synthesis method of Example 3 above.

[0164] (7) Synthesis of the compound with the chemical formula NR-29: Under nitrogen atmosphere, compound 11 (110 mg, 0.06 mmol) was added to 8 mL of THF solvent, stirred in an ice bath for 10 minutes, and LiAlH4 (91 mg, 2.40 mmol) was added. The temperature was naturally raised to room temperature and the reaction was carried out for 6 hours. The reaction solution was extracted with ethyl acetate and saturated brine, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product.

[0165] The above crude product and compound 9 (210 mg, 0.15 mmol) were added to a mixed solution of 5 mL of xylene and 2 mL of acetic acid, and the mixture was reacted at 120° C. for 48 hours. After the reaction solution was cooled to room temperature, it was poured into a sodium bicarbonate solution and stirred for 10 to 30 minutes. The mixture was then extracted with dichloromethane and saturated brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was dried to obtain a crude product. The product was purified by silica gel chromatography to obtain a red solid compound NR-29 with a yield of 51%.

[0166] The structural characterization is as follows:

[0167] 1H NMR[400MHz,CDCl3(0.3mL)+CS2(0.3mL)+5drops of TFA-d1]δ(ppm):8.49–8.41(m,12H),8.24(d,J=8.0Hz,4H),7.90(d,J=8.0Hz,4H),7.83(s,4H),7.42(dd,J=8.0,4.0Hz,8H),7.03(dd,J=4.0,4. 0Hz,8H),6.87–6.71(m,17H),5.48(s,4H),3.94(s,32H),1.84–1.76(m, 16H),1.48–1.25(m,128H),0.98–0.93(m,48H),0.89(t,J=8.0Hz,48H).

[0168] 13 C NMR[100MHz, CDCl3 / TFA-d1(V∶V=3∶1)]δ(ppm):160.73,160.45,156.70,155.90,155.74,155.18,150.40, 145.92,144.22,139.81,138.19,137.63,137.11,136.97,136.89,136.78,136.61,133.51,133.25,132.8 1,132.29,132.12,131.59,131.46,128.70,128.57,128.06,126.16,124.18,121.11,112.75,112.58,112.37,112.09,103.62,72.31,54.90,39.46,30.57,30.54,29.99,29.19,23.88,23.85,23.19,13.94,10.82.

[0169] HRMS:m / z[M+H] + calcd for(C 306 H 341 N 16 O 16 )4495.6356; found 4495.6358(error=0.1

[0170] ppm).

[0171] From the above, it can be seen that the structure of the product is correct, which is the compound NR-29 shown.

[0172] Test 1:

[0173] Determination of UV-visible absorption spectroscopy properties of nanobelt NR-11: Figure 1 The absorption spectra of nanobelt NR-11 in chloroform solution and thin film state. Figure 1 It can be seen that the absorption range of nanoribbon NR-11 in solution and film state is 300~560nm, the maximum absorption sideband value of its solution is about 523nm, and the corresponding optical band gap is 2.37eV (the optical band gap is calculated according to the formula E g =1240 / λ, where E g is the optical band gap, and λ is the maximum absorption sideband value of the solution).

[0174] Test 2:

[0175] Determination of UV-visible absorption spectroscopy properties of nanobelt NR-17: Figure 2 The absorption spectra of nanobelt NR-17 in chloroform solution and in thin film state are shown in Figure 2. Figure 2 It can be seen that the absorption range of nanoribbon NR-17 in solution and film state is 300~590nm, the maximum absorption sideband value of its solution is about 556nm, and the corresponding optical band gap is 2.23eV (the optical band gap is calculated according to the formula E g =1240 / λ, where E g is the optical band gap, and λ is the maximum absorption sideband value of the solution).

[0176] Test 3:

[0177] Determination of UV-visible absorption spectroscopy properties of nanobelt NR-23: Figure 3 The absorption spectra of nanobelt NR-23 in chloroform solution and in thin film state are shown in Figure 2. Figure 3 It can be seen that the absorption range of nanoribbon NR-23 in solution and film state is 300~610nm, the maximum absorption sideband value of its solution is about 564nm, and the corresponding optical band gap is 2.20eV (the optical band gap is calculated according to the formula E g =1240 / λ, where E g is the optical band gap, and λ is the maximum absorption sideband value of the solution).

[0178] Test 4:

[0179] Determination of UV-visible absorption spectroscopy properties of nanobelt NR-29: Figure 4 The absorption spectra of nanobelt NR-29 in chloroform solution and in thin film state are shown in Figure 2. Figure 4 It can be seen that the absorption range of nanoribbon NR-29 in solution and film state is 300~625nm, the maximum absorption sideband value of its solution is about 574nm, and the corresponding optical band gap is 2.16eV (the optical band gap is calculated according to the formula Eg =1240 / λ, where E g is the optical band gap, and λ is the maximum absorption sideband value of the solution).

[0180] Test 5:

[0181] Fluorescence spectroscopic properties of nanoribbons NR-11, NR-17, NR-23 and NR-29 were measured: Figure 5 The fluorescence spectra of nanobelts NR-11, NR-17, NR-23 and NR-29 in chloroform solution are shown in Figure 2. Figure 5 It can be seen that the maximum emission peak wavelengths of nanobelts NR-11, NR-17, NR-23 and NR-29 are 606, 617, 620 and 640 nm, respectively.

[0182] Test 6:

[0183] Electrochemical properties of nanobelts NR-11, NR-17, NR-23 and NR-29 were measured: Figure 6 The cyclic voltammograms of nanobelts NR-11, NR-17, NR-23 and NR-29 are shown in Figure 2. Figure 6 The first onset reduction potentials of the NR-11, NR-17, NR-23, and NR-29 nanoribbons are -0.98, -0.82, -0.74, and -0.67 V, respectively, and their corresponding LUMO values are calculated to be -3.44, -3.60, -3.68, and -3.75 eV. Combining the LUMO energy levels and optical band gap values determined by cyclic voltammetry, the HOMO values of NR-11, NR-17, NR-23, and NR-29 are calculated to be -5.81, -5.83, -5.88, and -5.91 eV, respectively. Analysis of the resulting HOMO / LUMO energy ratios indicates that the NR-11, NR-17, NR-23, and NR-29 nanoribbons have high electron affinities and extremely low HOMO values, indicating that these nanoribbons are n-type semiconductor materials with excellent chemical stability.

[0184] Test 7:

[0185] Thermal stability tests were performed on nanoribbons NR-11, NR-17, NR-23, and NR-29: Figure 7 The thermogravimetric curves of nanobelts NR-11, NR-17, NR-23 and NR-29 are shown in Figure 2. Figure 7The temperatures corresponding to 5% thermal weight loss for nanoribbons NR-11, NR-17, NR-23, and NR-29 were 515°C, 524°C, 509°C, and 518°C, respectively. The thermal decomposition temperatures of the resulting nanoribbons were all above 500°C, indicating that these trapezoidally fused nanoribbons possess extremely high thermal stability. Therefore, we predict that organic electronic devices constructed based on these nanoribbons will exhibit excellent thermal stability.

[0186] Furthermore, the triptycene-terminated aza-non-alternating nanoribbon material of formula (I) provided by the present invention has a three-dimensional molecular configuration, a rigid conjugated backbone, a high aza content, strong electron-deficient properties, excellent chemical stability, and high thermal stability, and has potential applications in fields such as organic field-effect transistors, organic nonlinear optical limiting, organic lithium-ion batteries, and electrocatalysis. The core synthesis method of the nanoribbon material of formula (I) provided by the present invention is the iterative ketoamine condensation method. This synthetic reaction method is simple and efficient, and does not require the use of precious metal catalysis. By rationally tailoring the molecular length, substituent groups, and end groups of the vicinal diketone and vicinal diamine functional conjugated segments, a series of aza-non-alternating nanoribbon materials with excellent comprehensive properties can be prepared. Therefore, the present invention enriches the variety of graphene nanoribbons, further expands the synthesis methods of non-alternating nanoribbons, provides a new material research platform for clarifying the structure-activity relationship between graphene nanoribbon structure and optoelectronic properties, and has guiding significance for the future development of ultra-long, soluble non-alternating nanoribbon materials.

[0187] The above description is only a preferred embodiment of the present invention and does not constitute any formal limitation to the present invention. Although the present invention has been disclosed as above in terms of a preferred embodiment, it is not intended to limit the present invention. Any person skilled in the art can, without departing from the spirit and technical solution of the present invention, use the methods and technical contents disclosed above to make many possible changes and modifications to the technical solution of the present invention, or modify it into an equivalent embodiment of equivalent changes. Therefore, any simple modification, equivalent replacement, equivalent change and modification made to the above embodiments based on the technical essence of the present invention without departing from the content of the technical solution of the present invention, still fall within the scope of protection of the technical solution of the present invention.

Claims

1. A nitrogen-doped non-alternating nanoribbon material, characterized in that: The nitrogen-doped non-alternating nanoribbon material has a structural formula shown in the following formula (I): In formula (I), X is an oxygen atom or a sulfur atom; R is selected from one or more of a straight-chain alkyl group having 4 to 16 carbon atoms and a branched-chain alkyl group having 8 to 30 carbon atoms; and n is selected from an integer of 1 to 4.

2. The nitrogen-doped non-alternating nanoribbon material according to claim 1, characterized in that: The straight-chain alkyl group having a total of 4 to 16 carbon atoms is selected from one or more of n-butane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-undecane, n-dodecane, n-tridecane, n-tetradecane, n-pentadecyl, and n-hexadecyl; The branched alkyl group having a total carbon atom count of 8 to 30 is selected from one or more of 2-ethylhexyl, 2-butylhexyl, 2-hexyloctyl, 4-hexyldecyl, 3-hexylundecyl, 2-octyldecyl, 2-octyldodecyl, 3-octyltridecyl, 2-decyldodecyl, 2-decyltetradecyl, 3-decylpentadecyl, 2-dodecylhexadecyl, 4-octyltetradecyl, 4-decylhexadecyl, 4-hexyldecyl, 4-octyldodecyl, 4-decyltetradecyl, and 4-dodecylhexadecyl.

3. The nitrogen-doped non-alternating nanoribbon material according to claim 1 or 2, characterized in that: The structural formula of the nitrogen-doped non-alternating nanoribbon material is selected from one or more of the following formula (II).

4. The method for preparing the nitrogen-doped non-alternating nanoribbon material according to any one of claims 1 to 3, characterized in that: The steps include: (1) Under nitrogen environment, 5-bromoresorcinol (Compound 1) reacts with bromoalkane to undergo nucleophilic substitution reaction to obtain Compound 2, the structural formula of which is: (2) Under nitrogen environment, compound 2 undergoes Miyaura boronation reaction with biboronic acid pinacol ester to obtain compound 3, the structural formula of compound 3 is: (3) Under nitrogen environment, 4,7-dibromo-5,6-dinitrobenzo[c][1,2,5]thiadiazole (Compound 4) and Compound 3 undergo Suzuki coupling reaction to obtain Compound 5, the structural formula of which is: (4) Under a nitrogen environment, the compound 5 is first subjected to a reduction reaction with iron powder to obtain a first diamine functional intermediate; the first diamine functional intermediate directly undergoes a ketoamine condensation reaction with the vicinal diketone functional compound 6 to obtain compound 7. The structural formulas of the compounds 6 and 7 are: (5) Under nitrogen atmosphere, the compound 7 is first subjected to a reduction reaction with lithium aluminum tetrahydride to obtain a second diamine functional intermediate; the second diamine functional intermediate directly reacts with the tetraketone functional compound 8 to undergo a ketoamine condensation reaction to obtain compound 9. The structural formulas of the compounds 8 and 9 are: (6) Under nitrogen atmosphere, the first diamine functional intermediate prepared in step (4) is directly condensed with the tetraketone functional compound 8 to obtain compound 10 and compound 11. The structural formula of compound 10 is: The structural formula of the compound 11 is: (7) Under nitrogen environment, the second diamine functional intermediate prepared in step (5) directly undergoes ketoamine condensation reaction with compound 10 to obtain compound 12, the structural formula of which is: (8) Under a nitrogen environment, the second diamine functional intermediate prepared in step (5) directly undergoes a ketoamine condensation reaction with the compound 6 to obtain compound NR-11; (9) Under a nitrogen environment, the second diamine functional intermediate prepared in step (5) directly undergoes a ketoamine condensation reaction with the compound 8 to obtain compound NR-17; (10) Under nitrogen atmosphere, the compound 12 is first subjected to a reduction reaction with lithium aluminum tetrahydride to obtain a third diamine functional intermediate; the third diamine functional intermediate is directly subjected to a ketoamine condensation reaction with the compound 9 to obtain compound NR-23; (11) Under a nitrogen environment, the compound 11 first undergoes a reduction reaction with lithium aluminum tetrahydride to obtain a fourth diamine functional intermediate; the fourth diamine functional intermediate directly undergoes a ketoamine condensation reaction with the compound 9 to obtain compound NR-29.

5. The method for preparing the nitrogen-doped non-alternating nanoribbon material according to claim 4, wherein: The step (1) specifically comprises: under a nitrogen environment, adding the compound 1, K2CO3 and 18-crown-6 into a three-necked flask filled with DMF, placing the mixture at 40-80°C for reaction for 1-3 hours; then adding bromoalkane, heating the mixture to 60-120°C, and reacting the mixture for 6-12 hours; cooling the mixture to room temperature, adjusting the pH to neutral, extracting the mixture with ethyl acetate and saturated saline, drying the mixture with anhydrous magnesium sulfate, filtering and collecting the organic phase, and drying the solvent to obtain a crude product; purifying the mixture with a silica gel column to obtain the compound 2 as a colorless liquid; wherein the molar ratio of the compound 1, K2CO3, 18-crown-6 and bromoalkane is 1.0:2.0-4.0:0.01-0.05:2.0-4.0; and / or, The step (2) specifically comprises: under a nitrogen environment, adding the compound 2, bipyraclostrobin, potassium acetate, and palladium catalyst into a three-necked flask containing 1,4-dioxane, placing the mixture at 80-120° C. for reaction for 8-12 hours; after cooling to room temperature, extracting with ethyl acetate and saturated brine, drying over anhydrous magnesium sulfate, filtering and collecting the organic phase, and drying the solvent to obtain a crude product; purifying with a silica gel column to obtain the colorless liquid compound 3; wherein the molar ratio of the compound 2, bipyraclostrobin, potassium acetate, and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride is 1.0:1.0-3.0:1.0-3.0:0.01-0.

03.

6. The method for preparing the nitrogen-doped non-alternating nanoribbon material according to claim 4, wherein: The step (3) is specifically as follows: under a nitrogen environment, the compound 4, the compound 3, and a palladium catalyst are added to a three-necked flask containing toluene and K2CO3 (2M aqueous solution), and the mixture is placed at 80-100°C for reaction for 5-8 hours; after cooling to room temperature, the mixture is extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is collected by filtration, and the solvent is dried to obtain a crude product; the compound 5 is purified by a silica gel column chromatography to obtain a yellow solid; wherein the molar ratio of the compound 4, the compound 3, and bis(triphenylphosphine)palladium dichloride is 1.0:2.0-4.0:0.05-0.5; and / or, The step (4) is specifically as follows: under a nitrogen environment, the compound 5 and iron powder are added to an acetic acid solvent, and the mixture is reacted at 70-80° C. for 5-9 hours; cooled to room temperature, the reaction solution is extracted with ethyl acetate and saturated brine, the organic phase is dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; the obtained crude product and the compound 6 are added to a mixed solution of chloroform and acetic acid, and the mixture is reacted at 60-90° C. for 6-12 hours. After the reaction solution is cooled to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10-30 minutes, and then extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product, which is purified by silica gel chromatography to obtain the red solid compound 7; wherein the molar ratio of the compound 5, the iron powder and the compound 6 is 1.0:10.0-20.0:0.5-1.

0.

7. The method for preparing the nitrogen-doped non-alternating nanoribbon material according to claim 4, wherein: The step (5) is specifically as follows: under a nitrogen environment, the compound 7 is added to a THF solvent, and the mixture is stirred at 0-10° C. for 5-20 minutes; then, LiAlH4 is added in batches, the temperature is naturally raised to room temperature, and the reaction is carried out for 6-9 hours; the reaction mixture is poured into ice water, and then extracted with ethyl acetate and saturated brine, the organic phase is dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; the obtained crude product and the compound 8 are added to a mixed solution of chloroform and acetic acid, and the mixture is stirred at 40-80° C. for 3-7 hours; after the reaction solution is cooled to room temperature, the mixture is poured into a sodium bicarbonate solution and stirred for 10-30 minutes, and then extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product, which is purified by silica gel chromatography to obtain the red solid compound 9; wherein the molar ratio of the compound 7, LiAlH4 and the compound 8 is 1.0:20.0-80.0:2.0-3.0; and / or, The step (6) is specifically as follows: under a nitrogen environment, the compound 5 and iron powder are added to an acetic acid solvent, and the mixture is reacted at 70-80°C for 5-9 hours; cooled to room temperature, the reaction solution is extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; the obtained crude product and the compound 8 are added to a mixed solution of chloroform and acetic acid, and the mixture is reacted at 50-80°C for 2-7 hours; after the reaction solution is cooled to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10-30 minutes, then extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; and purified by silica gel chromatography to obtain the brown solid compound 10 and the red solid compound 11. Wherein, the molar ratio of the compound 5, iron powder and compound 8 is 1.0:10.0-20.0:2.0-3.

0.

8. The method for preparing the nitrogen-doped non-alternating nanoribbon material according to claim 4, wherein: The step (7) is specifically as follows: under a nitrogen environment, the compound 7 is added to a THF solvent, and the mixture is stirred at 0-10°C for 5-20 minutes. Then, LiAlH4 is added in batches, the temperature is naturally raised to room temperature, and the reaction is carried out for 6-9 hours; the reaction mixture is poured into ice water, extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; the obtained crude product and the compound 10 are added to a mixed solution of chloroform and acetic acid, and the mixture is stirred at 60-90°C for 6-12 hours; after the reaction solution is cooled to room temperature, the mixture is poured into a sodium bicarbonate solution and stirred for 10-30 minutes, extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; the red solid compound 12 is purified by silica gel chromatography; wherein the molar ratio of the compound 7, LiAlH4 and the compound 10 is 1.0:20.0-80.0:1.0-3.0; and / or, The step (8) is specifically as follows: under a nitrogen environment, the compound 7 is added to a THF solvent, and the mixture is stirred at 0-10° C. for 5-20 minutes; then, LiAlH4 is added in batches, the temperature is naturally raised to room temperature, and the reaction is carried out for 6-9 hours; the reaction mixture is poured into ice water, extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; the obtained crude product and the compound 6 are added to a mixed solution of chloroform and acetic acid, and the mixture is stirred at 70-90° C. for 6-12 hours; after the reaction solution is cooled to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10-30 minutes, extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; and the compound NR-11 is purified by silica gel chromatography to obtain an orange solid; wherein the molar ratio of the compound 7, LiAlH4 and the compound 6 is 1.0:20.0-80.0:1.0-3.

0.

9. The method for preparing the nitrogen-doped non-alternating nanoribbon material according to claim 4, wherein: The step (9) is specifically as follows: under a nitrogen environment, the compound 7 is added to a THF solvent, placed at 0-10°C and stirred for 5-20 minutes; then, LiAlH4 is added in batches, the temperature is naturally raised to room temperature, and the reaction is carried out for 6-9 hours; the reaction mixture is poured into ice water, extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, filtered and collected, and the solvent is dried to obtain a crude product; the obtained crude product and the compound 8 are added to a mixed solution of chloroform and acetic acid, placed at 60-90°C and reacted for 6-12 hours; after the reaction solution is cooled to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10-30 minutes, then extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, filtered and collected, and the solvent is dried to obtain a crude product; the red solid compound NR-17 is purified by silica gel chromatography. Wherein, the molar ratio of the compound 7, LiAlH4 and the compound 8 is 1.0:20.0-80.0:0.2-0.6; and / or, The step (10) is specifically as follows: under a nitrogen environment, the compound 12 is added to a THF solvent, and the mixture is stirred at 0-10°C for 5-20 minutes; then, LiAlH4 is added in batches, the temperature is naturally raised to room temperature, and the reaction is carried out for 6-9 hours; the reaction mixture is poured into ice water, extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; the obtained crude product and the compound 9 are added to a mixed solution of toluene and acetic acid, and the mixture is stirred at 90-110°C for 24-48 hours; after the reaction solution is cooled to room temperature, the mixture is poured into a sodium bicarbonate solution and stirred for 10-30 minutes, extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; and the red solid compound NR-23 is purified by silica gel chromatography; wherein the molar ratio of the compound 12, LiAlH4 and the compound 9 is 1.0:20.0-80.0:1.0-3.0; and / or, The step (11) is specifically as follows: under a nitrogen environment, the compound 11 is added to a THF solvent, and the mixture is stirred at 0-10°C for 5-20 minutes; then, LiAlH4 is added in batches, the temperature is naturally raised to room temperature, and the reaction is carried out for 6-9 hours; the reaction mixture is poured into ice water, extracted with ethyl acetate and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; the obtained crude product and the compound 9 are added to a mixed solution of xylene and acetic acid, and the mixture is reacted at 110-130°C for 24-72 hours; after the reaction solution is cooled to room temperature, it is poured into a sodium bicarbonate solution and stirred for 10-30 minutes, extracted with dichloromethane and saturated brine, dried over anhydrous magnesium sulfate, the organic phase is filtered and collected, and the solvent is dried to obtain a crude product; and the red solid compound NR-29 is purified by silica gel chromatography; wherein the molar ratio of the compound 11, LiAlH4 and the compound 9 is 1.0:20.0-80.0:2.0-4.

0.

10. The method for preparing the nitrogen-doped non-alternating nanoribbon material according to claim 5 or 6, characterized in that: In steps (2) and (3), the palladium catalyst is selected from at least one of tetrakis(triphenylphosphine)palladium, palladium acetate, bis(triphenylphosphine)palladium dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, and tris(dibenzylideneacetone)dipalladium.

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