Triplet-state shell-opening double-free-radical shell-opening polycyclic aromatic hydrocarbon as well as preparation and application thereof

Abstract

The invention relates to the field of organic photoelectric carbon-based molecular materials, and particularly provides triplet-state shell-opening double-free-radical shell-opening polycyclic aromatic hydrocarbon as well as preparation and application thereof, and the triplet-state shell-opening double-free-radical shell-opening polycyclic aromatic hydrocarbon is a compound with a structure as shown in a formula 1 # imgabs0 #; in the formula 1, R1 is H, a C1-C6 alkyl group, a C1-C6 alkoxy group, a nitro group, a trifluoromethyl group or X; and X is halogen. The organic semiconductor material disclosed by the invention is high in glass transition temperature, has good photoelectromagnetic properties and global aromaticity, and can be applied to the field of photoelectricity.

Description

Technical Field

[0001] The present invention relates to the field of organic compounds, and particularly to a novel photo-electromagnetic material field. Background Art

[0002] As a novel carbon-based functional material, polycyclic aromatic hydrocarbons have attracted extensive attention due to their excellent physical properties. And novel magnetic carbon materials have excellent application prospects in room-temperature magnets, spintronics, and quantum devices due to their unique magnetic properties. It is intended to carry out application research on such materials in the field of spintronics.

[0003] For the characterization technology of polycyclic aromatic hydrocarbons, nuclear magnetic resonance technology is an efficient and simple method, which can be used to determine the structure and basic state of molecules. Compared with nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrometry, the X-ray single crystal diffraction technology can more intuitively confirm the structure of molecules. By testing the ultraviolet absorption spectrum of a substance, we can calculate the photochemical energy level of the substance and analyze the optical properties of the molecule. In polycyclic aromatic hydrocarbons, the electron spin resonance technology (ESR) can be used to observe the electron pairing situation within the molecule. The superconducting quantum interference device can be used to confirm with ESR.

[0004] Through traditional surface chemical synthesis technology, the geometric structure of graphene nanoribbons can be controlled by catalytic reactions on the surface of gold or copper. However, in the surface synthesis in an ultra-high vacuum system, the quality control of products is hindered, and the feasibility of product extraction and separation is very low; on the other hand, the interaction between molecules and the metal surface affects the test of the intrinsic properties of graphene nanoribbons.

[0005] The methods for preparing polycyclic aromatic hydrocarbon compounds by wet chemical synthesis mainly include catalytic synthesis, cyclization reaction, and photochemical synthesis, etc. The advantages of these synthesis methods are mild reaction conditions and high product selectivity. The catalytic synthesis method can achieve precise control of the structure and properties of open-shell polycyclic aromatic hydrocarbons, the photochemical synthesis method can achieve efficient synthesis of open-shell polycyclic aromatic hydrocarbons, the number of fused-ring aromatic hydrocarbons can be rapidly and accurately increased through the Suzuki reaction, and the Sonogashira coupling reaction can increase the diversity of compounds. In 1999, Kubo, Nakasuj et al. reported the first successful preparation of nonacene molecules with single radicals by wet chemical synthesis.

[0006] In the preparation of novel photo-electromagnetic materials, wet chemical synthesis technology is still the most effective technology. How to prepare open-shell graphene molecules with controllable edge structures through precise molecular design, theoretical calculation, and top-down wet chemical synthesis is a very challenging topic in the current graphene research field. Summary of the Invention

[0007] The first object of the present invention is to provide a triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon, aiming to provide a new compound that takes into account excellent stability, photo-electromagnetic properties, and is conducive to liquid-phase synthesis.

[0008] The second object of the present invention is to provide a preparation method of the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon.

[0009] The third object of the present invention is to provide the application of the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon in photo-electromagnetic materials.

[0010] The fourth object of the present invention is to provide a photo-electromagnetic material containing the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon.

[0011] A triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon is a compound having the structure of Formula 1;

[0012]

[0013] In Formula 1, R1 is H, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a trifluoromethyl group, or X; X is a halogen.

[0014] The present invention provides a compound with a new structure, which has excellent solubility, stability, and photo-electromagnetic properties. In addition, it also has good liquid-phase synthesizability. Research shows that the material of the present invention has unique magnetic properties and has good application prospects in room-temperature magnets, spin quantum science, and quantum devices.

[0015] In Formula 1 of the present invention, R1 is X; X is Cl, Br, or I.

[0016] In the present invention, the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon is a compound having the structure of Formula 1A;

[0017]

[0018] The present invention also provides a preparation method of the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon. The compound of Formula 2 and a dehydrogenating agent are subjected to a dehydrogenation reaction to obtain the compound of Formula 1;

[0019]

[0020] X and R1 in Formula 2 are the same as those in Formula 1.

[0021] The dehydrogenating agent can be, for example, tetrachlorobenzoquinone.

[0022] The molar amounts of Formula 2 and the dehydrogenating agent are 1:0.95 to 1.2.

[0023] The solvent for the dehydrogenation reaction is an organic solvent such as toluene or acetonitrile.

[0024] The temperature of the dehydrogenation reaction is 100 - 150 °C.

[0025] The time of the dehydrogenation reaction can be controlled according to existing in - process control means, for example, it can be 5 - 15 h.

[0026] In the present invention, the compound of formula 2 is obtained by the condensation reaction of formula 3 and formula 4;

[0027]

[0028]

[0029] X and R1 in the said formula 3 and formula 4 are the same as those in formula 1.

[0030] In the present invention, the said condensation reaction can be realized based on conventional format reaction means.

[0031] For example, the molar amounts of the said formula 3 and formula 4 are 1:2 - 15, and further can be 1:8 - 12.

[0032] The solvent for the condensation reaction is at least one of THF, boron trifluoride diethyl ether, and dichloromethane.

[0033] The temperature of the condensation reaction is below 35 °C, and further can be 5 - 25 °C.

[0034] Preferably, the time of the condensation reaction can be determined according to existing in - process control means, for example, it can be 0.5 - 5 h.

[0035] In the present invention, the said formula 3 is obtained by the oxidation reaction of formula 5;

[0036]

[0037] X and R1 in the said formula 5 are the same as those in formula 1.

[0038] In the present invention, the two methyl groups in formula 5 of the present invention can be oxidized to aldehyde groups based on known means.

[0039] For example, N - bromosuccinimide and benzoyl peroxide are added during the oxidation reaction; among them, N - bromosuccinimide is 5 - 15 times the molar amount of formula 5; benzoyl peroxide is 0.1 - 0.3 times the molar amount of formula 5. The oxidant during the oxidation reaction is silver nitrate, and its dosage is 5 - 15 times the molar amount of formula 5.

[0040] In the present invention, the said formula 5 is obtained by the Suzuki coupling reaction of formula 6 and formula 7;

[0041]

[0042]

[0043] In the present invention, the coupling of Formula 6 and Formula 7 can be achieved based on conventional Suzuki reaction means. For example, the Suzuki reaction process is carried out under the catalysis of a Pd catalyst. The Pd catalyst can be, for example, tris(dibenzylideneacetone)dipalladium, and its dosage can be 0.1 to 1 times the molar amount of Formula 6. During the Suzuki reaction process, a base scavenger is also added. The base scavenger includes, for example, at least one of sodium carbonate and potassium carbonate. The base scavenger is 1.5 to 4 times the molar amount of Formula 6.

[0044] In the present invention, Formula 6 is obtained by reacting with a borate ester of Formula 8;

[0045]

[0046] In the present invention, the borate ester can be triisopropyl borate.

[0047] The molar ratio of Formula 8 to the borate ester can be 1:2 to 4.

[0048] In the present invention, the reaction process of Formula 8 and the borate ester is carried out with the assistance of alkyllithium.

[0049] The present invention also provides an application of the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon, which is used to prepare photo-electromagnetic materials.

[0050] The present invention also provides a photo-electromagnetic material, which contains the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon, or is prepared from the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon.

[0051] Beneficial Effects

[0052] The present invention provides a compound with a novel structure, which has excellent solubility, stability and photo-electromagnetic properties. In addition, it also has good liquid-phase synthesizability.

[0053] The present invention also provides a method for synthesizing the compound with the novel structure based on a liquid-phase synthesis method. Brief Description of the Drawings

[0054] Figure 1 It is a structural diagram of Formula 1A;

[0055] Figure 2 It is a synthetic route diagram of Formula 1A;

[0056] Figure 3Absorption spectrum and electronic transition diagram of Formula 1A. Among them, (a) is the absorption spectrum of Formula 1A in DCM and the assignment of the lowest absorption band; (b) is the electronic transition of Formula 1A calculated by TD-DFT (UB3LYP / 6-31G(d,p)).

[0057] Figure 4 ACID calculation diagram of Formula 1A (only π electrons);

[0058] Figure 5 VT-ESR spectrum and two-dimensional ICSS diagram of Formula 1A. Among them, the upper figure is the VT-ESR spectrum of Formula 1A; the lower figure is the two-dimensional ICSS diagram of triplet Formula 1A;

[0059] Figure 6 (a) Measured EPR spectrum (black line) and simulated EPR spectrum (red line) of Formula 1A in a frozen toluene glass dish (1.1 mM) at 133 K; The ΔMs = 2 conversion is shown as an insert; (b) χM.T-T curve in the SQUID measurement of microcrystalline Formula 1A, and the measurement data are represented by circles;

[0060] Figure 7 X-ray crystal diagram of Formula 1A. Among them, a and d are top views of the structure; b and e are side views of the structure; c and f are top views of the skeleton with selected atom / ring labels;

[0061] Figure 8 Absorption spectrum diagram and intensity fitting diagram of Formula 1A. Among them, (a) is the absorption spectrum of Formula 1A in dichloromethane as a solvent under different exposure times to ambient air and light conditions; (b) is the fitting change diagram of absorbance at 405 nm over time. Detailed implementation mode

[0062] In order to make the objectives, technical solutions and advantages of the present invention clearer, the present invention will be further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.

[0063] Example 1

[0064] Step 1: Synthesis of target intermediate compound 2:

[0065]

[0066] Under a nitrogen atmosphere and with bubbling, 9-bromo-10-(2,6-dimethylphenyl)anthracene (2.00 g, 5.56 mmol) was dissolved in tetrahydrofuran (50 mL). After cooling at -78 °C for 20 minutes, n-BuLi (7 mL, 2 mol / L, 2.5 equivalents) was added dropwise, and the mixture was stirred at -78 °C for 2 hours. Finally, triisopropyl borate (3.84 mL, 3 eq) was added, and the stirring was continued at low temperature for 1 hour. Then the cooling bath was removed, and the reaction mixture was heated to room temperature overnight. After the reaction was completed, the reaction was quenched with an aqueous ammonium chloride solution. The solvent was removed under reduced pressure, and the residue was extracted with ethyl acetate and saturated brine and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the crude product was distilled under vacuum, and the residue was washed with hexane to obtain Compound 2 with a yield of about 88% (1.59 g).

[0067] The obtained target compound 2 was characterized by nuclear magnetic resonance, mass spectrometry and elemental analysis methods.

[0068] The nuclear magnetic resonance characterization data are as follows:

[0069] 1 HNMR(CDCl3, 500 MHz): δ ppm 8.90 (s, 2H), 8.11 (d, J = 8.45 Hz, 2H), 7.53 (t, J = 8.45 Hz, 2H), 7.42 - 7.38 (m, 3H), 7.33 - 7.31 (m, 4H), 1.66 (s, 6H).

[0070] 13 CNMR(CDCl3, 125 MHz): δ ppm 137.74, 137.25, 134.78, 133.18, 130.36, 128.79, 128.28, 128.08, 126.25, 125.68, 125.35, 67.49, 25.60, 20.20.

[0071] The high-resolution APCI mass spectrometry characterization data are as follows:

[0072] HR-MS(APCI): m / z = 326.1479, calcd, for C 22 H 19 BO2(M): m / z = 326.1477,

[0073] error = -0.7 ppm.

[0074] Step 2: Synthesis of the target intermediate compound 3:

[0075]

[0076] (10-(2,6-dimethylphenyl)anthracen-9-yl)boronic acid (1.5 g, 4.6 mmol), 2-bromo-1,3-dichlorobenzene (2.05 g, 9.2 mmol, 2 eq), tris(dibenzylideneacetone)dipalladium (411 mg, 0.5 eq), 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl (780 mg, 0.2 eq), and potassium phosphate (2.44 g, 2.5 eq) were added to a two-necked round-bottom flask. Then, toluene (100 mL) was added under a nitrogen atmosphere. After purging with nitrogen for half an hour, the mixture was heated under reflux at 110 °C for 24 h and then cooled to room temperature. The organic layer was dried over anhydrous sodium sulfate and then evaporated to dryness. The crude mixture was subjected to silica gel column chromatography (hexane / dichloromethane = 5 / 1) to obtain the target product 3 in a yield of 48% (0.94 g).

[0077] The obtained target compound 3 was characterized by nuclear magnetic resonance, mass spectrometry, and elemental analysis methods.

[0078] The nuclear magnetic resonance characterization data are as follows:

[0079] 1 HNMR(CDCl3, 500 MHz): δ ppm 8.90 (s, 2H), 8.11 (d, J = 8.45 Hz, 2H), 7.53 (t, J = 8.45 Hz, 2H), 7.42 - 7.38 (m, 3H), 7.33 - 7.31 (m, 4H), 1.66 (s, 6H).

[0080] 13 CNMR(CDCl3, 125 MHz): δ ppm 137.74, 137.25, 134.78, 133.18, 130.36, 128.79, 128.28, 128.08, 126.25, 125.68, 125.35, 67.49, 25.60, 20.20.

[0081] The high-resolution APCI mass spectrometry characterization data are as follows:

[0082] HR-MS(APCI): m / z = 326.1479, calcd, for C 22 H 19 BO2(M): m / z = 326.1477,

[0083] error = -0.7 ppm.

[0084] Step 3: Synthesis of the target intermediate compound 4:

[0085]

[0086] Take a 100 mL two-necked flask, and add compound 3 (0.85 g, 2.0 mmol), N-bromosuccinimide (3.92 g, 22 mmol, 11 eq), and benzoyl peroxide (96.70 mg, 0.4 mmol, 0.2 eq) into the dried two-necked flask. Add anhydrous carbon tetrachloride (30 mL) to the mixture under a nitrogen atmosphere and reflux for 36 hours. After removing the solvent, filter the residue, wash it with methanol and water, and use the crude product directly for the next step without purification. Dissolve the crude product in ethanol (100 mL), and add an aqueous silver nitrate solution (7 mL, 1.7 g, 10 mmol). Heat the resulting solution under reflux for 4 hours. After cooling to room temperature, add water, and extract the reaction mixture with chloroform. Dry the organic layer over sodium sulfate for 30 minutes, and then evaporate to dryness. Use a mixed solvent of hexane and DCM with a volume ratio of 1:1 as the eluent for column chromatography to obtain the target compound 4, with an overall yield of about 50% (0.45 g) for the two steps.

[0087] The structure of the obtained target compound 4 was characterized by nuclear magnetic resonance, mass spectrometry, and elemental analysis.

[0088] The nuclear magnetic resonance characterization data are as follows:

[0089] 1 HNMR(CDCl3, 500 MHz): δ ppm 9.32 (s, 2H), 8.51 (d, J = 8.00 Hz, 2H), 7.92 (d, J = 8.00 Hz, 1H), 7.64 (d, J = 8.30 Hz, 2H), 7.56 - 7.50 (m, 3H), 7.47 - 7.38 (m, 6H).

[0090] 13 CNMR(CDCl3, 125 MHz): δ ppm 190.58, 145.62, 136.60, 136.22, 135.90, 133.89, 132.92, 131.68, 130.31, 129.36, 128.82, 128.43, 127.30, 127.02, 126.60, 126.11, 125.93.

[0091] The high-resolution APCI mass spectrometry characterization data are as follows: HR-MS(APCI): m / z = 455.0588, calcd. for C 28 H 17 C l6 O2(M + 1): m / z = 455.0600, error = 2.6 ppm.

[0092] Step 4: Synthesis of intermediate compound 5:

[0093]

[0094] Compound 4 (227.0 mg, 0.5 mmol) was dissolved in tetrahydrofuran (10 mL) under nitrogen, and then (2,6-dichlorophenyl)magnesium bromide (10 mL, 5 mmol, 0.5 M in tetrahydrofuran solution) was added. After the solution was stirred at room temperature for 2 hours, the mixture was extracted with dichloromethane (50 mL). The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude product was washed with a 1:100 (v / v) dichloromethane / ethanol solution to obtain the diol intermediate as a pale yellow solid (370.0 mg, nearly quantitative yield), which was directly used in the next step. Boron trifluoride diethyl etherate (excess, 2.5 mL) was added to a solution of the diol intermediate (370.0 mg) in dichloromethane (20 mL), and the yellow solution immediately turned green. After 20 minutes, water (20 mL) was added to quench the reaction. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and then the residue was purified by silica gel column chromatography using a solution of n-hexane / dichloromethane (5:1, v / v) as the eluent to obtain Product 5 with a two-step yield of approximately 95% (0.34 g).

[0095] The obtained target compound 5 was characterized by nuclear magnetic resonance, mass spectrometry and elemental analysis.

[0096] The nuclear magnetic resonance characterization data are as follows:

[0097] 1 HNMR (CD2Cl2, 500 MHz): δ ppm 7.64 (m, 1H), 7.63 (m, 1H), 7.60 (m, 1H), 7.58 (m, 1H), 7.50 (t, J = 7.95 Hz, 2H), 7.31 - 7.23 (m, 8H), 7.09 (t, J = 7.65 Hz, 1H), 7.01 - 6.98 (m, 4H), 6.85 (d, J = 7.65 Hz, 1H).

[0098] The high-resolution APCI mass spectrometry characterization data are as follows:

[0099] HR-MS (APCI): m / z = 710.9752, calcd. for C40H21Cl6 (M + 1): m / z = 710.9769, error = 2.4 ppm.

[0100] Step 5: Synthesis of the target molecular formula 1A:

[0101]

[0102] In a glove box filled with argon, compound 5 (50 mg, 0.070 mmol), tetrachlorobenzoquinone (17.3 mg, 0.70 mmol, 10 eq), and anhydrous toluene (5 mL) were added to a 20 mL sealed tube equipped with a magnetic stir bar. The reaction mixture was heated to reflux for 8 h. After the reaction was completed, it was cooled to room temperature, and the excess tetrachlorobenzoquinone was discarded. The residue was recrystallized with acetonitrile to obtain the desired product of formula 1A in quantitative yield (49 mg).

[0103] The high-resolution APCI mass spectrometry characterization data of formula 1A are as follows:

[0104] HR-MS(APCI): m / z = 708.9611, calcd.forC 40 H 19 C l6 (M + 1): m / z = 708.9612,

[0105] error = 0.2 ppm.

[0106] The change value of the molar magnetic susceptibility measured by a superconducting quantum interference device was 0.9, close to the theoretical calculation of 1.0. The electron spin resonance signal increased with the decrease in temperature, determining that the ground state of the molecule of formula 1A was a triplet state.

[0107] Its maximum bandwidth was detected by ultraviolet absorption spectroscopy to be 472 nm, and its half-life exposed to air and light was measured to be 2.4 hours.

[0108] Through ACID and NICS theoretical calculations, it was proved that the TA-Cl core was globally aromatic and the π electrons were mainly delocalized along the periphery.

[0109] The three side chain groups of compound of formula 1A were approximately perpendicular to the main carbon skeleton, and the triplet diradical ground state brought good photo-electromagnetic properties to formula 1A.

[0110] Table 1 Main electronic transition calculation data of TA-Cl

[0111]

[0112]

[0113] By Figure 3It can be seen that TA-Cl has three main absorption bands, with the maximum absorption wavelengths at 333 nm, 405 nm, and 505 nm. The calculation results show that the minimum energy absorption band at 505 nm is related to the electron transitions of HOMO(α)→LUMO(α) (27%) and HOMO(β)→LUMO(β) (48%) (wavelength λ = 499 nm, oscillator strength f = 0.0016). Its maximum bandwidth is 472 nm, which is respectively related to the electron transitions of HOMO-1(α)→LUMO(α) (26%), HOMO-1(α)→LUMO(α) (12%), and HOMO(β)→LUMO+1(β) (43%) (wavelength λ = 491 nm, oscillator strength f = 0.001). At the maximum bandwidth of 405 nm, it is formed by multiple electron transitions of HOMO-n(α)→LUMO+m(α) and HOMO-n(β)→LUMO+m(β) (n, m = 0, 1, 2). The measured absorption spectrum is basically consistent with the TD-DFT calculation results. It should be noted that the frontier 2 π electrons on the HOMO(α) and HOMO-1(α) orbits are almost degenerate in energy, and their spectral lines show non-crossing characteristics.

[0114] It is consistent with the triplet ground state.

[0115] From Figure 4 It can be seen that the induced current density map shows a clockwise loop current flowing along the periphery of the triangulene core, indicating global aromatic characteristics. In addition, the nucleus-independent chemical shifts of all aromatic rings are negative values (-7.2 to -11 ppm), indicating again that the TA-Cl molecule has aromatic properties. At the same time, we can also see that the three six-membered rings at the three heads of the triangle have more nucleus-independent chemical shifts than other rings, indicating that they have stronger aromaticity than other rings.

[0116] From Figure 5 the above figure, it can be clearly seen that the intensity of electron spin increases with the decrease of temperature, indicating that its ground state is a triplet state. From Figure 5 the two-dimensional isochemical shielding surface map of the following figure, it can be seen that the inside of the compound TA-Cl has magnetic shielding and the outside has deshielding.

[0117] As mentioned above, the above are only the preferred specific embodiments of the present invention, but the protection scope of the present invention is not limited thereto. Any person skilled in the art within the technical scope disclosed by the present invention, according to the technical solution and inventive concept of the present invention, makes equivalent substitutions or changes, and should be covered by the protection scope of the present invention.

Claims

1. A triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon, characterized in that, It is a compound with the structure of Formula 1; In Formula 1, the said R1 is H, an alkyl group with 1 to 6 carbon atoms, an alkoxy group with 1 to 6 carbon atoms, nitro, trifluoromethyl or X; the said X is a halogen.

2. The triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon according to claim 1, characterized in that, In Formula 1, the said R1 is X; the said X is Cl, Br or I.

3. The triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon according to claim 1 or 2, characterized in that, The said triplet open-shell biradical open-shell polycyclic aromatic hydrocarbon is a compound with the structure of Formula 1A; 4. A method for preparing a triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon according to any one of claims 1 to 3, characterized in that, The said compound of Formula 1 is prepared by dehydrogenation reaction of a compound of Formula 2 and a dehydrogenating agent; X and R1 in the said Formula 2 are the same as those in Formula 1.

5. The preparation method of the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon according to claim 4, wherein The compound of Formula 2 is obtained by condensation reaction of Formula 3 and Formula 4; X and R1 in the said Formula 3 and Formula 4 are the same as those in Formula 1; Preferably, the molar amounts of the said Formula 3 and Formula 4 are 1:2 to 15.

6. The preparation method of the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon according to claim 5, characterized in that, The said Formula 3 is obtained by oxidation reaction of Formula 5; X and R1 in the said Formula 5 are the same as those in Formula 1.

7. The preparation method of the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon according to claim 6, characterized in that, The said Formula 5 is obtained by Suzuki coupling reaction of Formula 6 and Formula 7; 8. The preparation method of the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon according to claim 7, characterized in that, The said Formula 6 is obtained by reaction of Formula 8 and a borate ester; 9. Use of the triplet open-shell diradical open-shell polycyclic aromatic hydrocarbon according to any one of claims 1 to 3, characterized in that, It is used for preparing optoelectromagnetic materials.

10. A photo-electromagnetic material, characterized in that, It contains the triplet open-shell biradical open-shell polycyclic aromatic hydrocarbon described in any one of claims 1 to 3, or is prepared by the said triplet open-shell biradical open-shell polycyclic aromatic hydrocarbon.

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