CN117551143A - Preparation method and application of aggregation-induced emission cyclometallated platinum complex - Google Patents
Preparation method and application of aggregation-induced emission cyclometallated platinum complex Download PDFInfo
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000004220 aggregation Methods 0.000 title claims abstract description 20
- 230000002776 aggregation Effects 0.000 title claims abstract description 20
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000003446 ligand Substances 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000463 material Substances 0.000 claims abstract description 7
- 150000003057 platinum Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 claims abstract description 4
- 150000005360 2-phenylpyridines Chemical class 0.000 claims abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 claims description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 239000003480 eluent Substances 0.000 claims description 5
- 239000003208 petroleum Substances 0.000 claims description 5
- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- 239000008367 deionised water Substances 0.000 claims description 3
- 229910021641 deionized water Inorganic materials 0.000 claims description 3
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 claims description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000003760 magnetic stirring Methods 0.000 claims description 2
- 229910021645 metal ion Inorganic materials 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 230000006837 decompression Effects 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 8
- 239000000178 monomer Substances 0.000 abstract description 5
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 8
- 238000004020 luminiscence type Methods 0.000 description 7
- 238000000295 emission spectrum Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 101150050192 PIGM gene Proteins 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UODINHBLNPPDPD-UHFFFAOYSA-N 2-bromo-5-fluoropyridine Chemical group FC1=CC=C(Br)N=C1 UODINHBLNPPDPD-UHFFFAOYSA-N 0.000 description 1
- YWNJQQNBJQUKME-UHFFFAOYSA-N 2-bromo-5-methylpyridine Chemical group CC1=CC=C(Br)N=C1 YWNJQQNBJQUKME-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Engineering & Computer Science (AREA)
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Abstract
A preparation method and application of cyclometalated platinum complex with aggregation-induced emission property belong to the field of phosphorescent materials. Three cyclometalated platinum complexes are prepared by taking 2-phenylpyridine derivatives as cyclometalated ligands and acetylacetone as auxiliary ligands, and the study on the photophysical properties of the cyclometalated platinum complexes shows that the cyclometalated platinum complexes prepared by the method have excellent aggregation-induced emission properties, are shown to emit orange light in a tetrahydrofuran/water system with high water content, and have the maximum emission wavelength which is more than 100nm red shift compared with the emission of monomers in tetrahydrofuran. The method for synthesizing the cyclometalated ligand by using the Suzuki cross-coupling reaction is environment-friendly, simple, convenient and efficient. The cyclometalated platinum complex prepared by the invention has important application value in the field of phosphorescent materials.
Description
Technical Field
The invention relates to a preparation method and application of three cyclometalated platinum complexes with aggregation-induced emission properties, and belongs to the field of phosphorescent materials.
Background
Conventional fluorescent molecules typically have intense fluorescence in dilute solutions, which at high concentrations can decrease or even quench. In 2001, tang Benzhong et al found that a class of small organic molecules were substantially non-fluorescent in dilute solutions and exhibited bright fluorescent Emission in the aggregated state (chem. Commun.,2001,18,1740-1741), and they referred to this phenomenon as Aggregation-Induced Emission (AIE). The proposal of aggregation-induced emission concept provides an effective thought for solving the important scientific problem of luminescence quenching caused by aggregation, and greatly promotes the application and development of high-efficiency solid-state luminescent materials. To date, the AIE molecules of all documents are mostly pure small organic molecules, and relatively few novel Aggregation-induced phosphorescent emission (AIPE) materials based on transition metal complexes. The cyclometalated platinum complex is widely used as a phosphorescent material in the fields of OLED (dye Pigm. 2021,184:108857;Dalton Trans, 2023, 52:4595-4605), cell imaging (Angew.Chem.Int.Ed., 2022,61:e202210703;Angew.Chem.Int.Ed, 2023,62:e 202310402), probe (Tetrahedron Lett. 2023,126:154663;Dyes and Pigm, 2023, 220:111719) and the like. Therefore, the preparation of the cyclometallated platinum complex with excellent aggregation-induced emission properties has important application value.
Disclosure of Invention
The invention aims to provide a preparation method of cyclometallated platinum complex Pt1-Pt3 with aggregation-induced emission property and the aggregation-induced emission property thereof.
The technical scheme adopted by the invention is as follows: the preparation method of the cyclometalated platinum complex Pt1-Pt3 comprises the steps of synthesizing a cyclometalated ligand by taking 2-bromopyridine and derivatives thereof and 2-biphenylboronic acid as reactants, and then carrying out a coordination reaction with acetylacetone and platinum metal ions simultaneously to generate the cyclometalated platinum complex, wherein the structure is as follows:
the preparation method of the cyclometalated ligand and cyclometalated platinum complex Pt1-Pt3 comprises the following specific synthesis steps:
(1) Synthesis of cyclometallated ligand: 2-bromopyridine or a derivative thereof, 2-biphenylboronic acid (1.5 equiv.), potassium carbonate (2.0 equiv.) and palladium acetate (1.5%equiv.) are sequentially added into a two-port round bottom flask, then 8mL of an ethanol/water mixed solvent (V/V, 3:1) is added, the reaction progress is tracked by thin layer chromatography under 80 ℃ magnetic stirring, 25mL of saturated saline is added, the reaction solution is extracted three times by ethyl acetate, the organic phases are combined, reduced pressure concentration is carried out, petroleum ether/ethyl acetate is taken as an eluent, and the cyclic metal ligand is obtained through column chromatography separation.
(2) Synthesis of cyclometallated platinum complexes: to a two-necked round bottom flask, a cyclometallated ligand and 1.2 equivalents of potassium tetrachloroplatinate were added, and after 3 nitrogen substitutions, 8mL of ethylene glycol monoethyl ether/water mixed solvent (V/V, 3:1) was added to remove oxygen, and the reaction was magnetically stirred at 105℃for 24 hours under nitrogen protection. After the reaction is finished, the reaction solution is concentrated under reduced pressure to obtain a dichloro bridge intermediate product. Dichloro-bridge intermediate, acetylacetone (4.0 equiv.) and potassium carbonate (2.0 equiv.) were added to a round bottom flask, 8mL of ethylene glycol monoethyl ether was added and heated to reflux at 105 ℃ under nitrogen for 24h. After the reaction is finished, cooling to room temperature, adding 25mL of deionized water, extracting the reaction liquid with dichloromethane, concentrating the collected organic phase under reduced pressure to obtain a crude product, and separating and purifying by column chromatography by taking petroleum ether/dichloromethane as an eluent to obtain a target product. Product structure passage 1 H NMR and high resolution mass spectrometry corroboration.
The cyclometallated platinum complex comprises the following derivatives:
complex Pt1: the cyclometallated ligand is selected from 2- (2-phenyl) phenylpyridine; the auxiliary ligand is acetylacetone;
complex Pt2: the cyclometallated ligand is selected from 2- (2-phenyl) phenyl-5-fluoropyridine; the auxiliary ligand is acetylacetone;
complex Pt3: the cyclometallated ligand is selected from 2- (2-phenyl) phenyl-5-methylpyridine; the auxiliary ligand is acetylacetone.
The invention has the beneficial effects that:
1. the method for synthesizing the cyclometalated ligand by using the Suzuki cross-coupling reaction is environment-friendly, simple, convenient and efficient.
2. The cyclometallated platinum complex modified by different ligands can obtain the cyclometallated platinum complex with excellent aggregation-induced emission property and obvious red shift of light emission in an aggregation state through modularized design. The complex has excellent aggregation-induced emission property, the aggregation degree of the complex is controlled by regulating and controlling the proportion of poor solvent water, and a green light emission monomer solution and an orange light emission aggregate suspension can be obtained; in the range of 0-70% water content, the complex luminescence is reduced and then enhanced with small amplitude; at the water content interval of 80-90%, with the increase of the proportion of poor solvent, the luminescence of the complex becomes weak and the maximum emission wavelength is shifted in red by a large margin; when the water content reaches 95%, the luminescence is converted from green light emission to orange light emission, the emission intensity is remarkably enhanced, and the maximum emission wavelength is red-shifted by more than 100nm compared with the monomer.
Drawings
FIG. 1 is a graph showing the emission spectrum of the complex Pt1 at various water contents (tetrahydrofuran/water as solvent, 5X 10 -5 mol/L)。
FIG. 2 is a graph showing the emission spectrum of the complex Pt2 at various water contents (tetrahydrofuran/water as solvent, 5X 10 -5 mol/L)。
FIG. 3 is a graph showing the emission spectrum of the complex Pt3 at various water contents (tetrahydrofuran/water as solvent, 5X 10 -5 mol/L)。
Detailed Description
EXAMPLE 1 Synthesis of Complex Pt1
(1) Synthesis of cyclometallated ligand:
to a 25mL two-necked round bottom flask, 2-bromopyridine (0.50 mmol,79.00 mg), 2-biphenylboronic acid (0.75 mmol,148.52 mg), potassium carbonate (1.00 mmol,138.21 mg) and palladium acetate (7.50. Mu. Mol,1.68 mg) were sequentially added, then 8mL of an ethanol/water mixed solvent with a volume ratio of 3:1 was added, followed by stirring magnetically at 80℃under an air atmosphere to carry out a Suzuki cross-coupling reaction, the reaction progress was followed by thin layer chromatography, after completion of the reaction, 25mL of saturated brine was added, extracted three times with ethyl acetate, the organic phases were combined, concentrated under reduced pressure, and separated by column chromatography with petroleum ether/ethyl acetate as eluent to obtain a cyclometalated ligand.
(2) Synthesis of cyclometallated platinum complexes:
to a 25mL two-necked round bottom flask was added cyclometallated ligand (0.20 mmol,46.26 mg) and potassium tetrachloroplatinate (0.24 mmol,99.67 mg), and after 3 nitrogen substitutions, 8mL ethylene glycol monoethyl ether/water mixed solvent (V/V, 3:1) was added and the reaction was magnetically stirred at 105℃for 24h under nitrogen. Reverse-rotationAfter the reaction was completed, the reaction solution was transferred to a 25mL single-necked round bottom flask, and the reaction solution was concentrated under reduced pressure to obtain a dichloro-bridge intermediate. To a single neck round bottom flask of the dichloro-bridged intermediate was added acetylacetone (0.40 mmol,40.05 mg), potassium carbonate (0.20 mmol,27.64 mg) and 8mL of ethylene glycol monoethyl ether and heated under nitrogen at 105℃under reflux for 24h. After the reaction is finished, cooling to room temperature, adding 25mL of deionized water, extracting the reaction liquid with dichloromethane, concentrating the collected organic phase under reduced pressure to obtain a crude product, separating by column chromatography with petroleum ether/dichloromethane as eluent, and purifying to obtain the target product with the yield of 68%. The structural characterization data are as follows: 1 H NMR(400MHz,CDCl 3 ) Delta 9.15-8.94 (t, 1H), 7.73-7.64 (d, J=6.3 Hz, 1H), 7.47-7.39 (m, 3H), 7.37-7.29 (t, J=7.6 Hz, 3H), 7.20-7.13 (t, J=7.5 Hz, 1H), 6.99-6.92 (t, J=1.4 Hz, 1H), 6.92-6.85 (d, J=1.3 Hz, 1H), 6.61-6.51 (d, J=8.4 Hz, 1H), 5.52-5.43 (s, 1H), 2.07-1.96 (d, J=8.0 Hz, 6H). HRMS (EI, m/z): calculated value C 22 H 19 NO 2 Pt[M] +· 524.1064, found 524.1075.
EXAMPLE 2 Synthesis of Complex Pt2
Example 2 was prepared in the same manner as example 1, except that: except that 2-bromopyridine used in the synthesis of cyclic metal ligands in example 1 was replaced with 2-bromo-5-fluoropyridine.
Pt2 yield 45%, structural characterization data were as follows: 1 H NMR(400MHz,CDCl 3 ) Delta 9.14-8.84 (s, 1H), 7.74-7.58 (d, J=7.6 Hz, 1H), 7.49-7.37 (d, J=7.1 Hz, 3H), 7.36-7.29 (d, J=7.5 Hz, 2H), 7.22-7.10 (m, 2H), 6.96-6.82 (d, J=7.4 Hz, 1H), 6.60-6.43 (dd, J=9.4, 5.5Hz, 1H), 5.59-5.39 (s, 1H), 2.11-1.95 (d, J=4.1 Hz, 6H) HRMS (ESI, m/z) calculated C 22 H 19 FNO 2 Pt[M+H] + 543.1042, found 543.1035.
EXAMPLE 3 Synthesis of Complex Pt3
Example 3 was prepared in the same manner as in example 1, except that: except that 2-bromopyridine used in the synthesis of cyclic metal ligands in example 1 was replaced with 2-bromo-5-methylpyridine.
Pt3 yield 55%, structural characterization data were as follows: 1 H NMR(400MHz,CDCl 3 ) Delta 8.91-8.75 (s, 1H), 7.72-7.60 (d, J=7.6 Hz, 1H), 7.45-7.36 (d, J=7.1 Hz, 3H), 7.36-7.29 (d, J=6.8 Hz, 2H), 7.18-7.11 (m, 2H), 6.91-6.83 (d, J=7.4 Hz, 1H), 6.47-6.38 (d, J=8.5 Hz, 1H), 5.50-5.44 (s, 1H), 2.32-2.26 (s, 3H), 2.05-1.97 (s, 6H) HRMS (ESI, m/z) calculated C 23 H 22 NO 2 Pt[M+H] + 539.1293, found 539.1290.
EXAMPLE 4 AIE Property test of complexes Pt1-Pt3
Dissolving Pt1-Pt3 in tetrahydrofuran to obtain a solution with concentration of 1×10 -3 mixing the above solution, tetrahydrofuran and water at different volume ratios to obtain 5×10 solution -5 The emission spectra of the mixed solutions were then measured for different mol/L water contents. The results of FIGS. 1-3 show that in tetrahydrofuran/water solutions, the complex luminescence is slightly attenuated and then enhanced with increasing poor solvent water content in the range of 0-70% water content; at the water content interval of 80-90%, with the increase of the proportion of poor solvent, the luminescence of the complex becomes weak and the maximum emission wavelength is shifted in red by a large margin; when the water content reaches 95%, the luminescence is converted from green light emission to orange light emission, the emission intensity is remarkably enhanced, and the maximum emission wavelength is red-shifted by more than 100nm compared with the monomer. The results show that the complexes Pt1-Pt3 have excellent aggregation-induced emission properties, and the aggregation degree of the complexes is controlled by regulating and controlling the proportion of poor solvent water, so that a green light-emitting monomer solution and an orange light-emitting aggregate suspension can be obtained.
Claims (3)
1. The aggregation-induced emission cyclometallated platinum complex is characterized in that: the cyclometalated platinum complex is formed by coordination of platinum metal ions with 2-phenylpyridine derivatives as cyclometalated ligands and acetylacetone as auxiliary ligands, and has the following structure:
the 2-phenylpyridine derivative is selected from the group consisting of 2- (2-phenyl) phenylpyridine, 2- (2-phenyl) phenyl-5-fluoropyridine, and 2- (2-phenyl) phenyl-5-methylpyridine.
2. The method for preparing the aggregation-induced emission cyclometallated platinum complex according to claim 1, wherein the method comprises the steps of: the synthesis steps of the cyclometallated platinum complex are as follows:
(1) Synthesis of cyclometallated ligand: taking 2-bromopyridine or a derivative thereof and 2-biphenylboronic acid as reactants, taking potassium carbonate as alkali, taking palladium acetate as a catalyst, carrying out Suzuki cross coupling reaction under the magnetic stirring of an ethanol/water mixed solvent in an air atmosphere, and separating by column chromatography after the reaction is completed to obtain a cyclometalated ligand;
(2) Synthesis of cyclometallated platinum complexes: adding a cyclometallation ligand and 1.2 equivalent of potassium tetrachloroplatinate into a two-neck round bottom flask, adding an deoxidized ethylene glycol monoethyl ether/water mixed solvent under the protection of nitrogen, and magnetically stirring at 100-120 ℃ for reaction for 22-24h; after the reaction is finished, transferring the reaction solution into a single-neck round-bottom flask, and concentrating under reduced pressure to obtain a dichloro bridge intermediate product;
adding 4.0 equivalents of acetylacetone, 2.0 equivalents of potassium carbonate and ethylene glycol monoethyl ether into a single-port bottle, and magnetically stirring at 100-120 ℃ under the protection of nitrogen for reacting for 22-24h; after the reaction is finished, deionized water is added, the crude product is obtained by decompression concentration after extraction, petroleum ether/dichloromethane is used as eluent, and the target product is obtained by column chromatography separation and purification.
3. The use of an aggregation-induced emission cyclometallated platinum complex according to claim 1, wherein: the cyclometalated platinum complex is applied to the field of phosphorescent materials.
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