A kind of triquetrum-like platinum complex

Abstract

The application discloses a kind of triquetrum-like platinum complexes, belong to electroluminescence technical field, the structure general formula of the triquetrum-like platinum complex is as shown in the following formula (I) and (II) described in formula:Wherein, Ar1 It is independently selected from the substituted or unsubstituted arylene of carbon atom number 6~12, the substituted or unsubstituted heteroarylene of carbon atom number 6~12 one kind;R1, R2 Each is independently selected from H, the alkyl of carbon atom number 1~5 and the aryl of carbon atom number 6~12 one kind;L1 It is bidentate chelate anion ligand.The triquetrum-like skeleton of the application is compared with the chiral structure that has been applied in photoelectric field, it is not easy to twist and bend, has good rigidity, can inhibit the non-radiative transition of molecule;Stereoconfiguration is stable and not easy to racemize, under the condition of separation and device preparation etc. high optical activity is maintained under illumination or heating, so it has circularly polarized luminescence property (CPL), high fluorescence quantum yield.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of electroluminescence, in particular to a kind of triptycene-like platinum complex. BACKGROUND

[0002] The non-racemic light-emitting system such as organic small molecules, polymers, metal complexes or supramolecular assemblies is called circularly polarized luminescence (CPL) when emitting left-handed and right-handed circularly polarized light with difference. As a special fluorescence phenomenon, circularly polarized luminescence materials have potential application value in display, information encryption, storage, optoelectronic devices and asymmetric photocatalysis. The principle of circularly polarized light is that two plane polarized lights with same frequency, perpendicular vibration direction and (2n+1 / 2)π phase correlation are superimposed to obtain circularly polarized light, but this process is difficult to achieve. Therefore, the more easily achieved method to obtain circularly polarized light (CPL) is that the linearly polarized light perpendicular incident to quarter-wave plate through polarizer, when the angle between the vibration direction of linearly polarized light and the optical axis of quarter-wave plate is plus or minus 45°, the light emitted from quarter-wave plate is circularly polarized light. However, in this process, there is a large light loss. Through literature research, we know that the synthesis of new chiral molecules to obtain high-performance circularly polarized luminescence (CPL) materials with high luminescence asymmetry factor (glum) can greatly reduce this loss.

[0003] The traditional fluorescent material has a fluorescence quantum yield of at most 25%. To solve the problem of low yield, the prior art uses noble metal phosphorescent materials, but the cost is too high. SUMMARY

[0004] In order to solve the problems of the prior art, the present application provides a triptycene-like platinum complex and a preparation method thereof. The technical solution is as follows:

[0005] On one hand, a triptycene-like platinum complex is provided, and the structure general formula of the triptycene-like platinum complex is shown in the following formula (I):

[0006] ;

[0007] (I) (II)

[0008] Wherein, Ar1 is independently selected from one of substituted or unsubstituted arylene with carbon atom number of 6-12, substituted or unsubstituted heteroarylene with carbon atom number of 6-12;

[0009] R1, R2 are each independently selected from one of H, alkyl with carbon atom number of 1-5 and aryl with carbon atom number of 6-12;

[0010] L1 is a bidentate chelating anionic ligand.

[0011] Further, the Ar1 is independently selected from one of phenylene, biphenylene, dibenzothiophene;

[0012] The R1, R2 are each independently selected from one of H, methyl, ethyl, n-propyl, i-propyl, t-butyl, phenyl, naphthyl, biphenyl;

[0013] The substituent in the Ar1 is independently selected from one of cyano, methoxy, halogen group, alkyl group with carbon atom number of 1-4.

[0014] In another aspect, a preparation method of a chiral triptycene platinum complex is provided, the method comprising:

[0015] S1: R2-anthracene and cyclopentenone construct a chiral triptycene structure through Lewis acid promoted Diels-Alder reaction to obtain an enantiomer;

[0016] S2: the enantiomer is reacted with a chiral resolution reagent to obtain a pair of diastereoisomers in the presence of tetraethyl titanate;

[0017] S3: the pair of diastereoisomers is separated to obtain a resolved enantiomer;

[0018] S4: the resolved enantiomer is reacted with hydroxylamine to obtain a chiral oxime intermediate;

[0019] S5: the chiral oxime intermediate is subjected to reductive acylation to obtain a chiral acetamide;

[0020] S6: the chiral acetamide is subjected to Vilsmeier-Haack reaction to obtain a chiral chloropyridine;

[0021] S7: the chiral chloropyridine is reacted with R1-B(OH)2 to obtain a chiral chloropyridine with R1,

[0022] S8: the chiral chloropyridine with R1 is subjected to C-C coupling reaction with Ar1-B(OH)2 to obtain a chiral triptycene substituted arylpyridine;

[0023] S9: the chiral triptycene substituted arylpyridine is reacted with potassium chloroplatinate to obtain a chiral dimer platinum;

[0024] S10: the chiral dimer platinum is reacted with acetylacetone in the presence of a base as an additive to obtain the chiral triptycene platinum complex.

[0025] Further, the S1 comprises:

[0026] Aluminum trichloride is cooled and dissolved in the first solvent under the protection of an inert gas to obtain the first solution;

[0027] R2-anthracene and cyclopentenone were added to the first solution and reacted to obtain a first mixture;

[0028] The first mixture was cooled, quenched with water, extracted with an extraction solvent, washed with water and brine, dried with a desiccant, and concentrated and distilled under reduced pressure to obtain a crude residue. The crude residue was recrystallized to obtain the enantiomer.

[0029] In S1, the cooling temperature of aluminum trichloride is 0°C, and the cooling temperature of the first mixture is 0°C.

[0030] The molar ratio of aluminum trichloride, R2-anthracene, and cyclopentenone is 0.7~0.9:1:1~2, and the mass-volume ratio of aluminum trichloride to the first solvent is 0.1~0.15 g / ml;

[0031] The first solvent is selected from at least one of 1,2-dichloroethane and dichloromethane;

[0032] The reaction conditions are: reaction time of 2-4 days and reaction temperature of 35-45℃;

[0033] The extractant is selected from at least one of ethyl acetate and dichloromethane; the drying agent is selected from at least one of anhydrous sodium sulfate and anhydrous magnesium sulfate.

[0034] Further, S2 includes:

[0035] The enantiomers were dissolved in a second solvent under nitrogen atmosphere to obtain a second solution.

[0036] R / S-tert-butylsulfinamide and tetraethyl titanate were added to the second solution and reacted to obtain a second mixture;

[0037] The second mixture was cooled, treated with saturated ammonium chloride, extracted with an extraction solvent, washed with water and brine, dried with a desiccant, and concentrated by vacuum distillation to obtain a first crude residue. The first crude residue was then subjected to chromatography on a silica column to obtain the pair of diastereomers.

[0038] In S2, the second solvent is selected from at least one of tetrahydrofuran and 1,2-dichloroethane;

[0039] The reaction conditions are: reaction time 12~16h, reaction temperature 55~65℃;

[0040] The cooling temperature of the second mixture is 20~35℃;

[0041] The molar ratio of the enantiomer, the R / S-tert-butylsulfinamide, and the tetraethyl titanate is 1:1.0~2.0:1.5~2.5;

[0042] The silica column chromatography ratio is petroleum ether: ethyl acetate = 15:1~3:1;

[0043] The enantiomer to the second solvent has a mass-to-volume ratio of 0.05~0.06 g / ml;

[0044] The extractant is selected from at least one of ethyl acetate and dichloromethane; the drying agent is selected from at least one of anhydrous sodium sulfate and anhydrous magnesium sulfate.

[0045] Further, S3 includes:

[0046] The pair of diastereomers were hydrolyzed with hydrochloric acid, the pH was neutralized to neutral by neutralizing alkali, then extracted with an extractant and dried with a drying agent to obtain a third mixture;

[0047] The third mixture is reacted in a third solvent, and finally rotary evaporated to obtain the separated enantiomers;

[0048] In step S3, the concentration of hydrochloric acid is 1~2 mol / L;

[0049] The third solvent is selected from at least one of methanol, ethanol, and tetrahydrofuran;

[0050] The conditions are: reaction time 5-9 hours, reaction temperature 20-35℃;

[0051] The extractant is selected from at least one of ethyl acetate and dichloromethane; the drying agent is selected from at least one of anhydrous sodium sulfate and anhydrous magnesium sulfate.

[0052] S4 includes:

[0053] The separated enantiomers are dissolved in a fourth solvent to obtain a third solution;

[0054] Hydroxylamine was added to the third solution to react and obtain a fourth mixture.

[0055] The fourth mixture was cooled, washed with water, extracted with an extractant, washed with water and brine, dried with a desiccant, and concentrated by vacuum distillation to obtain the chiral oxime intermediate.

[0056] In step S4, the cooling temperature of the fourth mixture is 20~35℃;

[0057] The fourth solvent is selected from at least one of methanol, ethanol, and tetrahydrofuran;

[0058] The reaction conditions are: reaction time 12-16 h, reaction temperature 65-80 °C;

[0059] The mass-to-volume ratio of the separated enantiomer to the fourth solvent is 0.18~0.2 g / ml;

[0060] The molar ratio of the separated enantiomer to the hydroxylamine is 1:2.5~3.5;

[0061] The extractant is selected from at least one of ethyl acetate and dichloromethane; the drying agent is selected from at least one of anhydrous sodium sulfate and anhydrous magnesium sulfate.

[0062] Further, S5 includes:

[0063] The chiral oxime intermediate was dissolved in a fifth solvent under the protection of an inert gas, then iron powder was added, and after cooling, a mixture of acetic anhydride and acetic acid was added to react and obtain a fifth mixture.

[0064] After cooling the fifth mixture, the pH value was neutralized to neutral by neutralizing alkali, followed by extraction with extractant, washing with water and brine, drying with desiccant, and concentration by vacuum distillation to obtain the second crude residue.

[0065] The second crude residue was subjected to chromatography on a silica column to obtain the chiral acetamide;

[0066] In step S5, the mass-to-volume ratio of the chiral oxime intermediate to the fifth solvent is 0.06~0.07 g / ml;

[0067] The molar ratio of the chiral oxime intermediate, the iron powder, the acetic anhydride, and the acetic acid is 1:5.5~6.5:2.5~3.5:2.5~3.5;

[0068] The fifth solvent is toluene;

[0069] The reaction conditions are: reaction time 4-8 hours, reaction temperature 20-35°C; and cooling temperature 0°C.

[0070] The silica column chromatography ratio is petroleum ether: ethyl acetate = 4:1 to 1:1;

[0071] The extractant is selected from at least one of ethyl acetate and dichloromethane; the drying agent is selected from at least one of anhydrous sodium sulfate and anhydrous magnesium sulfate.

[0072] Further, S6 includes:

[0073] Under inert gas protection, the chiral acetamide was added to N,N-dimethylformamide, and after cooling, phosphorus oxychloride was added dropwise to react and obtain the sixth mixture.

[0074] The sixth mixture was diluted with a sixth solvent, cooled, and then neutralized to neutral pH with a neutralizing alkali. It was then extracted with an extractant, washed with water and brine, dried with a drying agent, and concentrated by vacuum distillation to obtain a first crude mixture. The first crude mixture was then subjected to chromatography on a silica column to obtain the chiral chloropyridine.

[0075] In step S6, the cooling temperature is 0°C;

[0076] The reaction conditions are: reaction time 12-16 h, reaction temperature 98-108 °C;

[0077] The sixth solvent is selected from at least one of ethyl acetate and dichloromethane;

[0078] The mass-to-volume ratio of the chiral acetamide to the sixth solvent is 0.04~0.06 g / ml;

[0079] The molar ratio of the chiral acetamide, the N,N-dimethylformamide, and the phosphorus oxychloride is 1:3.5~3.7:7.4~7.6;

[0080] The silica column chromatography ratio is petroleum ether: ethyl acetate = 5:1 to 1:1;

[0081] The extractant is selected from at least one of ethyl acetate and dichloromethane; the drying agent is selected from at least one of anhydrous sodium sulfate and anhydrous magnesium sulfate.

[0082] The S7 includes: adding CH2Cl2 to the chiral chloropyridine under inert gas protection, cooling, adding Tf2O and PPh3 dropwise to react and obtain a ninth mixture, and then adding an organic base to obtain a tenth mixture;

[0083] The tenth mixture was quenched, extracted, dried, and concentrated to obtain a concentrated solution;

[0084] Et2O was added to the concentrated solution, and the solution was cooled and recrystallized to obtain phosphate.

[0085] Under an inert gas atmosphere, the phosphate, arylboronic acid, Ni(COD)₂, SlPr·HCl, and NaO are... t The mixture of Bu, K3PO4, 4Å active molecular sieve and THF was reacted, quenched, extracted, dried and concentrated to obtain the chiral chloropyridine with R1.

[0086] Further, S8 includes:

[0087] Under the protection of an inert gas, the chiral chloropyridine with R1, Ar1-B(OH)2, Pd catalyst, and 2-bicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were dissolved in a fourth solution, and then a first alkaline additive was added to react and a seventh mixture was obtained.

[0088] The seventh mixture was cooled, washed with water, extracted with an extractant, washed with water and brine, dried with a desiccant, and concentrated by vacuum distillation to obtain the second crude mixture.

[0089] The second crude mixture was subjected to chromatography on a silica column to obtain the chiral triterpenoid-substituted arylpyridine;

[0090] In step S7, the fourth solution is a mixture of the seventh solvent and water. The seventh solvent is selected from at least one of toluene, ethanol, methanol, and tetrahydrofuran, and the volume ratio of the seventh solvent to water is 3~5:1.

[0091] The molar ratio of the chiral chloropyridine with R1, the Ar1-B(OH)2, the Pd catalyst, the 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl, and the basic additive is 1:1.0~3.0:0.1~0.5:0.12~0.6:1.0~2.0;

[0092] The mass-to-volume ratio of the chiral chloropyridine with R1 to the fourth solution is 0.02~0.03 g / ml;

[0093] The reaction conditions are as follows: reaction time is 12-16 hours, and reaction temperature is 65-110°C.

[0094] The cooling temperature is 20~35℃;

[0095] The first alkaline additive is at least one of cesium hydroxide, sodium hydroxide, cesium carbonate, and sodium carbonate;

[0096] The Pd catalyst is selected from palladium acetate, [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, tetra(triphenylphosphine)palladium, and tridibenzylacetone dipalladium;

[0097] The silica column chromatography ratio is petroleum ether: ethyl acetate = 6:1 to 1:1, or petroleum ether: dichloromethane = 2:1 to 1:2;

[0098] The extractant is selected from at least one of ethyl acetate and dichloromethane; the drying agent is selected from at least one of anhydrous sodium sulfate and anhydrous magnesium sulfate.

[0099] Further, S9 includes:

[0100] Under inert gas protection, the chiral triterpenoid-substituted arylpyridine and the potassium tetrachloroplatinate were added to the fifth solution to react and obtain the eighth mixture.

[0101] The eighth mixture was cooled, washed with water, extracted with an extractant, washed with water and brine, dried with a desiccant, and concentrated by vacuum distillation to obtain chiral platinum dimer.

[0102] In step S9, the fifth solution is a mixture of the eighth solvent and water. The eighth solvent is selected from at least one of toluene, ethanol, methanol, and tetrahydrofuran, and the volume ratio of the eighth solvent to water is 2 to 4:1.

[0103] The molar ratio of the chiral triterpenoid-substituted arylpyridine to the potassium tetrachloroplatinate is 1:1 to 1.2;

[0104] The mass-to-volume ratio of the chiral triterpenoid-substituted arylpyridine to the fifth solution is 0.03~0.04 g / ml;

[0105] The cooling temperature is 20~35℃;

[0106] The reaction conditions are as follows: reaction time is 2.5~3.5h, and reaction temperature is 65~110℃.

[0107] The extractant is selected from at least one of ethyl acetate and dichloromethane; the drying agent is selected from at least one of anhydrous sodium sulfate and anhydrous magnesium sulfate.

[0108] S10 includes:

[0109] Under inert gas protection, the second basic additive and acetylacetone were added to the ninth solvent and stirred. Then, the chiral dimer platinum was added to react, and the mixture was concentrated by vacuum distillation to obtain the third crude mixture.

[0110] The third crude mixture was subjected to chromatography on a silica column to obtain the triptene platinum complex;

[0111] In step S10, the ninth solvent is at least one of dichloromethane and 1,2-dichloroethane;

[0112] The second alkaline additive is potassium tert-butoxide;

[0113] The reaction conditions are: reaction time 12~18h, reaction temperature 25~35℃;

[0114] The molar ratio of the chiral dimer platinum, the second basic additive, and the acetylacetone is 1:2~3:2~4;

[0115] The mass-to-volume ratio of the chiral platinum dimer to the ninth solvent is 0.015~0.017 g / ml;

[0116] The silica column chromatography ratio is petroleum ether: dichloromethane = 6:1 to 1:1.

[0117] The beneficial effects of the technical solution provided by the embodiments of the present invention are as follows: Compared with existing chiral structures applied in the optoelectronic field, the triterpenoid skeleton is not easily twisted and bent, has good rigidity, and can suppress nonradiative transitions of molecules; at the same time, its stereoconfiguration is stable and does not easily racemize, and it maintains high optical activity under light or heating conditions such as separation and device fabrication, thus possessing advantages such as circularly polarized light emission (CPL), high fluorescence quantum yield, and good thermal stability; from a synthetic perspective, it is stable and easy to operate, has a variety of functional groups, and can easily degenerate and prepare a series of compounds, and optically pure isomers can be obtained through asymmetric synthesis or chiral resolution.

[0118] The thin film fluorescence quantum efficiency of the chiral metal complex based on the novel chiral triterpenoid framework provided by this invention is as high as 95.88%, and the asymmetry factor g is as high as 3×10⁻⁶. -3 .

[0119] The chiral metal complexes based on novel chiral triterpenoid frameworks provided by this invention can be used as sensitizing host materials or luminescent materials in the light-emitting layer of OLED devices. They can also be widely applied in asymmetric catalysis, drug development, materials science and other fields. When applied to organic electroluminescent devices, these materials can improve the defects of existing chiral frameworks in terms of stereoscopic stability, structural tunability, chiral self-assembly ability, etc., and can significantly improve the luminescence performance of organic electroluminescent devices. Attached Figure Description

[0120] To more clearly illustrate the technical solutions in the embodiments of the present invention, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0121] Figure 1 This is the 1H NMR spectrum of chiral triterpenoid-substituted arylpyridine (+)-6a in Example 1;

[0122] Figure 2 This is the carbon NMR spectrum of chiral triterpenoid-substituted arylpyridine (+)-6a in Example 1;

[0123] Figure 3 This is the 1H NMR spectrum of the triterpenoid platinum complex (+)-8a in Example 1;

[0124] Figure 4This is the carbon NMR spectrum of the triterpenoid platinum complex (+)-8a in Example 1;

[0125] Figure 5 This is the mass spectrum of chiral triterpenoid-substituted arylpyridine (+)-6a in Example 1;

[0126] Figure 6 This is the mass spectrum of the triterpenoid platinum complex (+)-8a from Example 1;

[0127] Figure 7 These are the circular dichroism chromatograms of the triterpenoid platinum complexes (+)-8a and (-)-8a in Example 1;

[0128] Figure 8 These are the (+)-8a and (-)-8a circular polarization spectra of the triterpenoid platinum complex in Example 1;

[0129] Figure 9 These are the (+)-8a and (-)-8a circular polarization spectra of the triterpenoid platinum complex in Example 1;

[0130] Figure 10 These are the (+)-8a and (-)-8a circular polarization spectra of the triterpenoid platinum complex in Example 1. Detailed Implementation

[0131] To make the objectives, technical solutions, and advantages of the present invention clearer, the embodiments of the present invention will be described in further detail below with reference to the accompanying drawings.

[0132] Example 1

[0133] A type of tripterene platinum complex, the general structural formula of which is shown in formulas (I) and (II) below:

[0134]

[0135] (I) (II)

[0136] Ar1 is independently selected from one of a substituted or unsubstituted aryl group with 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group with 6 to 12 carbon atoms; R1 and R2 are each independently selected from one of H, an alkyl group with 1 to 5 carbon atoms, or an aryl group with 6 to 12 carbon atoms; L1 is a bidentate chelate anion ligand. Ar1 is independently selected from one of phenylene, biphenylene, or dibenzothiophene; R1 and R2 are each independently selected from one of H, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, or biphenyl; the substituent in Ar1 is independently selected from one of cyano, methoxy, halogen group, or an alkyl group with 1 to 4 carbon atoms.

[0137] Example 2

[0138] A method for preparing a platinum-like triterpenoid complex, the method comprising the following steps:

[0139] Step (101): Under argon protection, AlCl3 (10 g, 41 mmol) was cooled to 0 °C and dissolved in DCM (75 mL). After stirring until the raw material was completely dissolved, the mixture was brought back to room temperature. Anthracene (8.9 g, 50 mmol) and 2-cyclopenten-1-one (8.2 g, 100 mmol) were added. The mixture was heated to 40 °C and stirred for 3 days. The reaction was stopped after the anthracene compound was completely consumed by TLC monitoring, and the first mixture was obtained. The first mixture was cooled to 0 °C, and AlCl3 was quenched with H2O (20 mL). The aqueous layer was extracted with DCM (50 mL), washed with water and brine, dried with anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude residue was recrystallized from ethanol to obtain the enantiomer (11.9 g, 92%), which was a colorless solid.

[0140] Step (102): Under nitrogen protection, enantiomer (+)-1 (3.9 g, 15 mmol) was dissolved in THF (75 mL) and stirred until the starting material was completely dissolved. Then, R / S-tert-butylsulfinamide (1.81 g, 15 mmol) and Ti(OEt)4 (6.8 g, 30 mmol) were added, and the mixture was heated to 60 °C and stirred for 14 h. The reaction was stopped after the enantiomers were completely consumed by TLC monitoring. The reaction mixture was cooled to 30 °C, treated with saturated NH4Cl (20 mL), and the aqueous layer was extracted with EA (50 mL). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude residue was chromatographically analyzed on a silica column to obtain a pair of diastereomers (+)-2 (2.62 g, 48%), wherein the silica column chromatography ratio was petroleum ether: ethyl acetate = 10:1.

[0141] Step (103): Hydrolyze a pair of diastereomers (+)-2 with HCl (20 mL, 2 mol / L in H2O), neutralize the pH to 7.5 with sodium hydroxide, extract with ethyl acetate, and dry with anhydrous sodium sulfate to obtain a third mixture. Add the third mixture to methanol and react at 30 °C for 7 h. Rotary evaporation yields the separated enantiomer (+)-1.

[0142] Step (104): The separated enantiomer (3.9 g, 15 mmol) was added to ethanol (20 ml) and stirred until the raw material was completely dissolved. Then, NH2OH (1.5 g, 45 mmol) was added, and the mixture was refluxed at 70 °C for 14 h. After cooling to 30 °C, the mixture was washed with H2O (20 ml), and the aqueous layer was extracted with DCM (50 ml). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, and concentrated by vacuum distillation to obtain the chiral oxime intermediate (+)-3 (3.71 g, 88%).

[0143] Step (105): Under nitrogen atmosphere, chiral oxime intermediate (+)-3 (2.77 g, 10 mmol) was added to toluene (42 mL) and stirred until the starting material was completely dissolved. Then, Fe powder (3.35 g, 60 mmol) was added, and the mixture was cooled to 0°C. A mixture of Ac2O (3.1 g, 30 mmol) and AcOH (1.8 g, 30 mmol) was slowly added, and the mixture was heated to 30°C for 6 h. The reaction was stopped after complete consumption of the chiral oxime intermediate by TLC monitoring. The reaction mixture was cooled to 0°C, neutralized to neutral with saturated sodium bicarbonate, and the aqueous layer was extracted with EA (100 mL). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude residue was chromatographically analyzed on a silica column to obtain chiral acetamide (+)-4 (1.72 g, 40%). The silica column chromatography ratio was petroleum ether (n-hexane): ethyl acetate = 3:1.

[0144] Step (106): Under nitrogen atmosphere, chiral acetamide(+)-4 (1 g, 3.3 mmol) was added to DMF (0.8 g, 12 mmol), stirred until homogeneous, and cooled to 0°C. Then, POCl3 (3.8 g, 25 mmol) was added dropwise, and the mixture was heated to 100°C and reacted for 14 h. The reaction was stopped after complete consumption of chiral acetamide by TLC monitoring. The mixture was diluted with EA (20 mL), cooled to 0°C, neutralized to pH 7.5 with saturated sodium bicarbonate, and the aqueous layer was extracted with EA (100 mL). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude mixture was chromatographically analyzed on a silica column to obtain chiral chloropyridine(+)-5 (0.765 g, 70%), wherein the silica column chromatography ratio was petroleum ether (n-hexane): ethyl acetate = 3:1.

[0145] Step (107): Under a nitrogen atmosphere, add chiral chloropyridine(+)-5 (1.0 equivalent), add CH2Cl2 (0.1 M), and stir until homogeneous. Cool the solution to -78°C. Add Tf2O (1.0 equivalent) dropwise, stirring for 30 minutes. Then add PPh3 (1.1 equivalent), and stir for another 30 minutes at -78°C. Add an organic base (NEts or DBU, 1.0 equivalent) dropwise, allowing the reaction to return to room temperature (approximately 15-30 minutes) while stirring. Quench the reaction mixture with the same volume of H2O as CH2Cl2, extract three times with CH2Cl2, combine the organic layers, dry with anhydrous MgSO4, filter, and concentrate under vacuum to approximately 2-10 mL (depending on the scale of the reaction). Add excess frozen Et2O (0°C) to the concentrated solution, then recrystallize it in a -20°C freezer for approximately 1 hour, filtering to obtain the phosphate. Under a nitrogen atmosphere, phosphate (1.0 mol%) and arylboronic acid (2.0 mol%) were added, and the mixture was placed in a glove box. Ni(COD)₂ (5-10 mol%), SlPr·HCl (5-10 mol% mol%), NaOtBu (5.5-11 mol% mol%), K₃PO₄ (2.0 mol%), 4Å activated molecular sieve (4Å MS) (750 mg / mmol), and THF (0.1 M) were added, and the mixture was sealed and removed from the glove box. The reaction mixture was stirred at room temperature for 20 minutes, then heated at 50-70 °C for 12-24 hours. The reaction was quenched with H₂O, extracted three times with CH₂Cl₂, and the combined organic layers were dried over anhydrous MgSO₄, filtered, and concentrated under vacuum. The crude mixture was separated on a silica column to obtain the target compound.

[0146] Step (108): Under nitrogen protection, the target compound obtained in step (107) (0.7 g, 2.12 mmol), phenylboronic acid (0.78 g, 6.36 mmol), palladium acetate (0.048 g, 0.212 mmol), and 2-bicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.12 g, 0.254 mmol) were added to a mixture of ethanol (20 mL) and water (5 mL) and stirred until the starting material was completely dissolved. Then, cesium hydroxide (0.54 g, 3.60 mmol) was added, and the mixture was heated to 80°C and stirred for 14 h. The reaction was stopped after the chiral chloropyridine was completely consumed by TLC monitoring. The mixture was cooled to 30°C, washed with H2O (20 mL), and DCM was used. (100ml) The aqueous layer was extracted, then washed with water and brine, dried with anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude mixture was subjected to chromatography on a silica column to obtain chiral triterpenoid-substituted arylpyridine (+)-6a (0.708g, 90%), wherein the column chromatography ratio was petroleum ether (n-hexane): ethyl acetate = 3:1.

[0147] Step (109): Under nitrogen atmosphere, chiral triterpenoid-substituted arylpyridine(+)-6a (0.7 g, 1.95 mmol) and potassium tetrachloroplatinate (0.81 g, 2.145 mmol) were added to a mixture of tetrahydrofuran (15 mL) and water (5 mL). The mixture was stirred until the raw materials were completely dissolved. The mixture was heated to 75 °C and stirred in the dark for 3 h. The reaction was stopped when the solution turned black. The mixture was cooled to 30 °C, washed with H2O (10 mL), and the aqueous layer was extracted with DCM (50 mL). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, and concentrated by vacuum distillation to obtain chiral dimer platinum(+)-7a (1.05 g, 90%).

[0148] Step (110): Under nitrogen atmosphere, potassium tert-butoxide (0.116 g, 1.04 mmol) and acetylacetone (0.125 g, 1.245 mmol) were added to dichloromethane (30 mL) and stirred until the raw materials were completely dissolved. The mixture was stirred at room temperature for 0.5 h, and then chiral dimer platinum(+)-7a (0.5 g, 0.415 mmol) was added. The mixture was stirred at 30 °C for 16 h, concentrated by vacuum distillation, and the crude mixture was chromatographically analyzed on a silica column to obtain triptene-like platinum complex(+)-8a (0.270 g, 49%). The column chromatography ratio was petroleum ether (n-hexane): dichloromethane = 4:1.

[0149] Example 3

[0150] A method for preparing a platinum-like triterpenoid complex, the method comprising the following steps:

[0151] Step (201): Under argon protection, 10g of AlCl3 was cooled to 0℃ and dissolved in 1,2-dichloroethane (100mL). After stirring until the raw material was completely dissolved, the mixture was brought back to room temperature. 10.7g of anthracene and 5g of 2-cyclopenten-1-one were added. The mixture was heated to 35℃ and stirred for 2 days. The reaction was stopped after the anthracene compound was completely consumed by TLC monitoring, and the first mixture was obtained. The first mixture was cooled to 0℃, and AlCl3 was quenched with H2O (20 mL). The aqueous layer was extracted with ethyl acetate (50 mL), washed with water and brine, dried over anhydrous magnesium sulfate, concentrated by vacuum distillation, and the crude residue was recrystallized from ethanol to obtain the enantiomer, which was a colorless solid.

[0152] Step (202): Under argon protection, 3.9 g of the enantiomer was dissolved in 1,2-dichloroethane (78 mL) and stirred until the raw material was completely dissolved. Then, 2.7 g of R / S-tert-butylsulfinamide and 45.2 g of Ti(OEt) were added, and the mixture was heated to 55 °C and stirred for 12 h. The reaction was stopped after the enantiomer was completely consumed by TLC monitoring. The reaction mixture was cooled to 20 °C, treated with saturated NH4Cl (20 mL), and the aqueous layer was extracted with EA (50 mL). The mixture was then washed with water and brine, dried over anhydrous magnesium sulfate, concentrated by vacuum distillation, and the crude residue was chromatographically analyzed on a silica column to obtain a pair of diastereomers. The silica column chromatography ratio was petroleum ether: ethyl acetate = 15:1.

[0153] Step (203): A pair of diastereomers were hydrolyzed with HCl (20 mL, 1 mol / L in H2O), the pH was neutralized to 7 with potassium hydroxide, then extracted with ethyl acetate and dried with anhydrous magnesium sulfate to obtain a third mixture. The third mixture was added to ethanol and reacted at 20 °C for 5 h. The distilled mixture was then used to obtain the separated enantiomers.

[0154] Step (204): The separated enantiomer (3.9 g, 15 mmol) was added to methanol (25 ml) and stirred until the raw material was completely dissolved. Then, 1.3 g of NH2OH was added, and the mixture was refluxed at 65 °C for 12 h. After cooling to 30 °C, the mixture was washed with H2O (20 ml), and the aqueous layer was extracted with DCM (50 ml). The mixture was then washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated by vacuum distillation to obtain the chiral oxime intermediate.

[0155] Step (205): Under argon atmosphere, 2.77 g (10 mmol) of the chiral oxime intermediate was added to 45 mL of toluene and stirred until the starting material was completely dissolved. Then, 3.07 g of Fe powder was added, and the mixture was cooled to 0 °C. A mixture of 2.6 g of Ac₂O and 1.5 g of AcOH was slowly added, and the mixture was heated to 20 °C for 4 h. The reaction was stopped after the chiral oxime intermediate was completely consumed by TLC monitoring. The reaction mixture was cooled to 0 °C and neutralized to neutral with saturated sodium bicarbonate. The aqueous layer was extracted with EA (100 mL), washed with water and brine, dried over anhydrous magnesium sulfate, concentrated by vacuum distillation, and the crude residue was chromatographically analyzed on a silica column to obtain chiral acetamide. The silica column chromatography ratio was petroleum ether (n-hexane): ethyl acetate = 4:1.

[0156] Step (206): Under argon atmosphere, chiral acetamide (1g, 3.3 mmol) was added to 0.85g of DMF, stirred until homogeneous, and cooled to 0℃. Then, 3.75g of POCl3 was added dropwise, and the mixture was heated to 98℃ for 12h. The reaction was stopped after complete consumption of chiral acetamide by TLC monitoring. The mixture was diluted with dichloromethane (25 mL), cooled to 0℃, neutralized to pH 7 with saturated sodium bicarbonate, and the aqueous layer was extracted with EA (100 mL). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude mixture was chromatographically analyzed on a silica column to obtain chiral chloropyridine. The silica column chromatography ratio was petroleum ether (n-hexane): ethyl acetate = 5:1.

[0157] Step (207): Under a nitrogen atmosphere, add chiral chloropyridine(+)-5 (1.0 equivalent), add CH2Cl2 (0.1 M), and stir until homogeneous. Cool the solution to -78°C. Add Tf2O (1.0 equivalent) dropwise, stirring for 30 minutes. Then add PPh3 (1.1 equivalent), and stir for another 30 minutes at -78°C. Add an organic base (NEts or DBU, 1.0 equivalent) dropwise, allowing the reaction to return to room temperature (approximately 15-30 minutes) while stirring. Quench the reaction mixture with the same volume of H2O as CH2Cl2, extract three times with CH2Cl2, combine the organic layers, dry with anhydrous MgSO4, filter, and concentrate under vacuum to approximately 2-10 mL (depending on the scale of the reaction). Add excess frozen Et2O (0°C) to the concentrated solution, then recrystallize it in a -20°C freezer for approximately 1 hour, filtering to obtain the phosphate. Under a nitrogen atmosphere, phosphate (1.0 mol%) and arylboronic acid (2.0 mol%) were added, and the mixture was placed in a glove box. Ni(COD)₂ (5-10 mol%), SlPr·HCl (5-10 mol% mol%), NaOtBu (5.5-11 mol% mol%), K₃PO₄ (2.0 mol%), 4Å activated molecular sieve (4Å MS) (750 mg / mmol), and THF (0.1 M) were added, and the mixture was sealed and removed from the glove box. The reaction mixture was stirred at room temperature for 20 minutes, then heated at 50-70 °C for 12-24 hours. The reaction was quenched with H₂O, extracted three times with CH₂Cl₂, and the combined organic layers were dried over anhydrous MgSO₄, filtered, and concentrated under vacuum. The crude mixture was separated on a silica column to obtain the target compound.

[0158] Step (208): Under argon protection, the target compound (0.7 g, 2.12 mmol) obtained in step (207), 0.26 g of phenylboronic acid, 0.734 g of tetrakis(triphenylphosphine)palladium, and 0.4 g of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl were added to a mixture of toluene (27 mL) and water (8 mL) and stirred until the raw materials were completely dissolved. Then, 0.32 g of cesium hydroxide was added, and the mixture was heated to 65°C and stirred for 12 h. The reaction was stopped after the chiral chloropyridine was completely consumed by TLC monitoring. The mixture was cooled to 20°C, washed with H2O (20 mL), and the aqueous layer was extracted with DCM (100 mL). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude mixture was chromatographically analyzed on a silica column to obtain chiral triphenylene-substituted arylpyridine. The column chromatography ratio was petroleum ether (n-hexane): ethyl acetate = 6:1.

[0159] Step (209): Under argon atmosphere, chiral triterpenoid-substituted arylpyridine (0.7 g, 1.95 mmol) and potassium tetrachloroplatinate (0.80 g) were added to a mixture of ethanol (17 mL) and water (8 mL). The mixture was stirred until the raw materials were completely dissolved. The mixture was heated to 65 °C and stirred in the dark for 2.5 h. The reaction was stopped when the solution turned black. The mixture was cooled to 20 °C, washed with H2O (10 mL), and the aqueous layer was extracted with DCM (50 mL). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, and concentrated by vacuum distillation to obtain chiral dimer platinum.

[0160] Step (210): Under argon atmosphere, 0.10 g of potassium tert-butoxide and 0.085 g of acetylacetone were added to 35 mL of 1,2-dichloroethane and stirred until the raw materials were completely dissolved. The mixture was stirred at room temperature for 0.5 h, and then chiral dimer platinum (0.5 g, 0.415 mmol) was added. The mixture was stirred at 25 °C for 12 h, concentrated by vacuum distillation, and the crude mixture was chromatographically analyzed on a silica column to obtain a platinum complex similar to triterpenesene. The column chromatography ratio was petroleum ether (n-hexane): dichloromethane = 6:1.

[0161] Example 4

[0162] A method for preparing a platinum-like triterpenoid complex, the method comprising the following steps:

[0163] Step (301): Under argon protection, 10.8 g of AlCl3 was cooled to 0°C and dissolved in DCM (67 mL). After stirring until the raw material was completely dissolved, the mixture was brought back to room temperature. Anthracene (8.9 g, 50 mmol) and 8.2 g of 2-cyclopenten-1-one were added. The mixture was heated to 45°C and stirred for 4 days. The reaction was stopped after the anthracene compound was completely consumed by TLC monitoring, and the first mixture was obtained. The first mixture was cooled to 0°C, and AlCl3 was quenched with H2O (20 mL). The aqueous layer was extracted with DCM (50 mL), washed with water and brine, dried with anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude residue was recrystallized from ethanol to obtain the enantiomer, which was a colorless solid.

[0164] Step (302): Under nitrogen protection, the enantiomer (3.9 g, 15 mmol) was dissolved in THF (65 mL) and stirred until the starting material was completely dissolved. Then, 3.5 g of R / S-tert-butylsulfinamide and 48.6 g of Ti(OEt) were added, and the mixture was heated to 65 °C and stirred for 16 h. The reaction was stopped after the enantiomer was completely consumed by TLC monitoring. The reaction mixture was cooled to 35 °C, treated with saturated NH4Cl (20 mL), and the aqueous layer was extracted with EA (50 mL). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude residue was chromatographically analyzed on a silica column to obtain a pair of diastereomers. The silica column chromatography ratio was petroleum ether: ethyl acetate = 3:1.

[0165] Step (303): A pair of diastereomers were hydrolyzed with HCl (20 mL, 2 mol / L in H2O), the pH was neutralized to 8 with potassium bicarbonate, then extracted with ethyl acetate and dried with anhydrous sodium sulfate to obtain a third mixture. The third mixture was added to methanol and reacted at 35 °C for 9 h. The distilled mixture was then used to obtain the separated enantiomers.

[0166] Step (304): The separated enantiomer (3.9 g, 15 mmol) was added to 19.5 ml of tetrahydrofuran and stirred until the starting material was completely dissolved. Then, 1.75 g of NH2OH was added, and the mixture was refluxed at 80 °C for 16 h. After cooling to 35 °C, the mixture was washed with H2O (20 ml), and the aqueous layer was extracted with DCM (50 ml). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, and concentrated by vacuum distillation to obtain the chiral oxime intermediate.

[0167] Step (305): Under nitrogen atmosphere, the chiral oxime intermediate (2.77 g, 10 mmol) was added to toluene (40 mL) and stirred until the starting material was completely dissolved. Then, 3.6 g of Fe powder was added, and the mixture was cooled to 0°C. A mixture of 3.5 g of Ac₂O and 2.1 g of AcOH was slowly added, and the mixture was heated to 35°C for 8 h. The reaction was stopped after the chiral oxime intermediate was completely consumed by TLC monitoring. The reaction mixture was cooled to 0°C and neutralized to neutral with saturated sodium bicarbonate. The aqueous layer was extracted with EA (100 mL), washed with water and brine, dried over anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude residue was chromatographically analyzed on a silica column to obtain chiral acetamide. The silica column chromatography ratio was petroleum ether (n-hexane): ethyl acetate = 1:1.

[0168] Step (306): Under nitrogen atmosphere, chiral acetamide (1g, 3.3 mmol) was added to 0.9g of DMF, stirred until homogeneous, and cooled to 0℃. Then, 3.8g of POCl3 was added dropwise, and the mixture was heated to 108℃ for 16h. The reaction was stopped after complete consumption of chiral acetamide by TLC monitoring. The mixture was diluted with EA (17 mL), cooled to 0℃, neutralized to pH 8 with saturated sodium bicarbonate, and the aqueous layer was extracted with EA (100 mL). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude mixture was chromatographically analyzed on a silica column to obtain chiral chloropyridine. The silica column chromatography ratio was petroleum ether (n-hexane): ethyl acetate = 1:1.

[0169] Step (307): Under a nitrogen atmosphere, add chiral chloropyridine(+)-5 (1.0 equivalent), add CH2Cl2 (0.1 M), and stir until homogeneous. Cool the solution to -78°C. Add Tf2O (1.0 equivalent) dropwise, stirring for 30 minutes. Then add PPh3 (1.1 equivalent), and stir for another 30 minutes at -78°C. Add an organic base (NEts or DBU, 1.0 equivalent) dropwise, allowing the reaction to return to room temperature (approximately 15-30 minutes) while stirring. Quench the reaction mixture with the same volume of H2O as CH2Cl2, extract three times with CH2Cl2, combine the organic layers, dry with anhydrous MgSO4, filter, and concentrate under vacuum to approximately 2-10 mL (depending on the scale of the reaction). Add excess frozen Et2O (0°C) to the concentrated solution, then recrystallize at -20°C for approximately 1 hour, filtering to obtain the phosphate. Under a nitrogen atmosphere, phosphate (1.0 mol%) and arylboronic acid (2.0 mol%) were added, and the mixture was placed in a glove box. Ni(COD)₂ (5-10 mol%), SlPr·HCl (5-10 mol% mol%), NaOtBu (5.5-11 mol% mol%), K₃PO₄ (2.0 mol%), 4Å activated molecular sieve (4Å MS) (750 mg / mmol), and THF (0.1 M) were added, and the mixture was sealed and removed from the glove box. The reaction mixture was stirred at room temperature for 20 minutes, then heated at 50-70 °C for 12-24 hours. The reaction was quenched with H₂O, extracted three times with CH₂Cl₂, and the combined organic layers were dried over anhydrous MgSO₄, filtered, and concentrated under vacuum. The crude mixture was separated on a silica column to obtain the target compound.

[0170] Step (308): Under nitrogen protection, the target compound (0.7 g, 2.12 mmol) obtained in step (307), phenylboronic acid (0.78 g, 6.36 mmol), tris(dibenzylacetone) dipalladium (0.97 g), and 2-biscyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.6 g) were added to a mixture of tetrahydrofuran (20 mL) and water (4 mL) and stirred until the starting material was completely dissolved. Then, cesium hydroxide (0.64 g) was added, and the mixture was heated to 110°C and stirred for 16 h. The reaction was stopped after the chiral chloropyridine was completely consumed by TLC monitoring. The mixture was cooled to 35°C, washed with H2O (20 mL), and DCM was used. (100ml) The aqueous layer was extracted, then washed with water and brine, dried with anhydrous sodium sulfate, concentrated by vacuum distillation, and the crude mixture was subjected to chromatography on a silica column to obtain chiral triterpenoid-substituted arylpyridine, wherein the column chromatography ratio was petroleum ether: dichloromethane = 2:1.

[0171] Step (309): Under nitrogen atmosphere, chiral triterpenoid-substituted arylpyridine (0.7 g, 1.95 mmol) and potassium tetrachloroplatinate (0.97 g) were added to a mixture of tetrahydrofuran (20 mL) and water (5 mL). The mixture was stirred until the raw materials were completely dissolved. The mixture was heated to 110 °C and stirred in the dark for 3.5 h. The reaction was stopped when the solution turned black. The mixture was cooled to 35 °C, washed with H2O (10 mL), and the aqueous layer was extracted with DCM (50 mL). The mixture was then washed with water and brine, dried over anhydrous sodium sulfate, and concentrated by vacuum distillation to obtain chiral dimer platinum.

[0172] Step (310): Under nitrogen atmosphere, add 0.14 g of potassium tert-butoxide and 0.16 g of acetylacetone to dichloromethane (30 mL) and stir until the raw materials are completely dissolved. Stir at room temperature for 0.5 h, then add chiral dimer platinum (0.5 g, 0.415 mmol), stir at 35 °C for 18 h, concentrate by vacuum distillation, and perform chromatography on a silica column to obtain a platinum complex similar to triterpenesene. The column chromatography ratio is petroleum ether (n-hexane): dichloromethane = 1:1.

[0173] It should be noted that the test results for the sample in Example 1 are as follows:

[0174] Figure 1 This is the 1H NMR spectrum of the chiral triterpenoid-substituted arylpyridine (+)-6a in Example 2. Figure 1 Medium, Write solid, 85% yield, PE:EtOAc = 5:1, Mp 260 – 262 ℃.1H NMR (400 MHz, CDCl3) δ 7.99 – 7.93 (m, 2H), 7.47 (t, J = 7.5 Hz, 2H), 7.44 – 7.35 (m, 2H),7.34 – 7.29 (m, 1H), 7.18 (t, J = 4.0 Hz, 3H), 7.15 – 7.10 (m, 2H), 7.07 (d,J = 7.9 Hz, 1H), 6.90 (t, J = 7.1 Hz, 2H), 6.79 – 6.73 (m, 1H), 4.95 (d, J =3.3 Hz, For C 28 H 22N+:372.1746, Found: 372.1745 (M+H+); Figure 2 This is the carbon NMR spectrum of chiral triterpenoid-substituted arylpyridine (+)-6a from Example 1. Figure 2 Medium, 13C NMR (101 MHz, CDCl3) δ 163.98, 156.29, 144.12,143.55, 141.85, 140.12, 139.84, 135.81, 132.78, 128.76, 128.51, 126.97,126.00, 125.86, 125.77, 125.28, 124.96, 124.11, 123.63, 118.70, 53.08, 49.99,48.59, 40.45, 33.58.

[0175] Figure 3 This is the 1H NMR spectrum of the triterpenoid platinum complex (+)-8a from Example 2. Figure 3 Medium, Yellowsolid, 49% yield, PE:CH2Cl2 = 3:1, Mp >250 ℃. 1H NMR (400 MHz, CDCl3) δ7.69 (dd, J = 7.7, 1.0 Hz,1H), 7.34 – 7.27 (m,3H), 7.20 – 7.05 (m, 7H), 6.93(ddd, J = 11.9, 8.6, 4.2 Hz, 2H), 6.74 (td, J = 7.5, 1.1 Hz, 1H), 5.65 (d, J= 3.0 Hz, 1H), 5.59 (s, 1H), 5.07 (dd, J = 8.9, 3.0 Hz, 1H), 4.24 (d, J = For C 33 H 28 NO2Pt+: 665.17623, Found:665.17604 (M+H+); Figure 4 This is the carbon NMR spectrum of the triterpenoid platinum complex (+)-8a from Example 1. Figure 4In the 13C NMR (101 MHz, CD₂Cl₂) values: δ 186.40, 184.14, 167.42, 167.18, 146.09, 144.33, 143.49, 142.00, 140.43, 138.49, 137.11, 134.42, 130.10, 128.20, 126.19, 126.13, 125.99, 125.68, 125.57, 124.93, 124.81, 124.06, 123.89, 122.84, 116.41, 102.36, 51.74, 50.14, 48.95, 40.26, 33.99, 28.55, 27.39.

[0176] Figure 5 This is the mass spectrum of chiral triterpenoid-substituted arylpyridine (+)-6a from Example 2. Figure 6 This is the mass spectrum of the triterpenoid platinum complex (+)-8a from Example 1; Figure 7 The (+)-8a and (-)-8a complexes of the triterpenoid platinum group in Example 1 are at a concentration of 1×10⁻⁶. -5 Circular dichroism chromatogram of mol / L Figure 8 , Figure 9 and Figure 10 In Example 1, the (+)-8a and (-)-8a of the triterpenoid platinum complex were at a concentration of 1×10⁻⁶. -5 Circular polarization spectrum of mol / L.

[0177] It should also be noted that Tables 1, 2, 3, 4, 5, 6, 7, 8 and 9 are examples of other R2-anthracene, R1-B(OH)2 and Ar1-B(OH)2, and the experimental procedures are the same as in Example 2.

[0178] Table 1

[0179]

[0180] Table 2

[0181]

[0182] Table 3

[0183]

[0184] Table 4

[0185]

[0186] Table 5

[0187]

[0188] Table 6

[0189]

[0190] Table 7

[0191]

[0192] Table 8

[0193]

[0194] Table 9

[0195]

[0196] In this invention, a chiral perturbation strategy is used to connect a chiral source to a achiral TADF molecule with a known structure via chemical bonds, resulting in a novel chiral nitrogen-containing heterocyclic small molecule that combines the excellent properties of both types of materials. This type of novel small molecule has low production cost, precise control of the synthetic route, and structural rigidity and central chirality, making it less prone to racemization and maintaining good stereochemical stability under light and heat.

[0197] The sequence numbers of the above embodiments of the present invention are for descriptive purposes only and do not represent the superiority or inferiority of the embodiments.

[0198] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A platinum-like triterpenoid complex, characterized in that, The general structural formulas of the triptene platinum complexes are shown in formulas (I) and (II) below: ； （I） （Ⅱ） Ar1 is independently selected from one of the substituted or unsubstituted phenylene, biphenylene, or dibenzothiophene group; The substituents in Ar1 are independently selected from one of cyano, methoxy, halogen groups, and alkyl groups having 1 to 4 carbon atoms; R1 is H; In formula (I), each of R2 is independently selected from H and an alkyl group having 1 to 5 carbon atoms; In formula (II), R2 is independently selected from H, alkyl groups having 1 to 5 carbon atoms, and aryl groups having 6 to 12 carbon atoms; L1 is a bidentate chelating anion ligand.

2. The triterpenoid platinum complex according to claim 1, characterized in that, In formula (I), each of R2 is independently selected from one of H, methyl, ethyl, n-propyl, isopropyl, and tert-butyl; In formula (II), each of R2 is independently selected from one of H, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, naphthyl, and biphenyl.

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