CN110938096A - A platinum complex with aggregation-induced luminescence and its preparation method and application - Google Patents
A platinum complex with aggregation-induced luminescence and its preparation method and application Download PDFInfo
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- CN110938096A CN110938096A CN201910810746.1A CN201910810746A CN110938096A CN 110938096 A CN110938096 A CN 110938096A CN 201910810746 A CN201910810746 A CN 201910810746A CN 110938096 A CN110938096 A CN 110938096A
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Abstract
The invention belongs to the technical field of organic metal complexes, and discloses a platinum complex with aggregation-induced emission and a preparation method and application thereof. The complex is obtained by taking metal platinum as a center and coordinating with a tetradentate Schiff base ligand, and the structural formula is shown as the following formula (I). The compound has the advantages of simple synthesis process, mild conditions and structural general formula as shown in formula (I). The complex has a light-emitting wavelength in a red light region (620-760 nm), has an aggregation induction effect and good thermal stability, and is expected to be assembled into a single-layer light-emitting device. In addition, the synthesis process is simple, the production cost is low, large-scale production can be realized, and the method has good application in the aspects of preparing luminescent materials or luminescent devices and the likeCommercial application value and wide development prospect.
Description
Technical Field
The invention belongs to the technical field of organic metal complexes, and particularly relates to a platinum complex with aggregation-induced emission, and a preparation method and application thereof.
Background
In recent years, organic electroluminescent devices (OLEDs) have been widely used in many areas of life, and are characterized by self-luminescence, high visibility and brightness, high power saving efficiency, light weight, thin thickness, simple structure, low cost, and the like, and thus are considered as one of the most promising products in the 21 st century. Transition metal complexes have been studied intensively as materials for the light-emitting layer of OLEDs, but have drawbacks: the luminescence intensity of the complex is reduced along with the increase of the concentration of the solution, and the luminescence in an aggregation state is quenched, so that the application of the transition metal complex in a luminescent material is seriously influenced.
In 2001, the Tang Ben Kai Yao Chi Shi team proposed aggregation-induced emission effect (AIE), discovered that the silacyclopentadiene derivative in solution did not emit light basically, but emitted light gradually increased in the aggregated state due to the enhancement of light emission caused by the inhibition of intramolecular rotation, designed different kinds of organic luminophores according to the AIE mechanism, solved the low efficiency caused by concentration quenching effect, enriched in the applications of light-emitting devices, sensing, biological imaging.
The metal d orbit in the transition metal complex and the ligand with good chelating ability form a d-p conjugated system, and the electron cloud density is transferred to a greater extent on the whole molecule, so that the luminescence property can be promoted. Thompson describes a near-infrared electroluminescent material, investigating platinum (II) porphyrin derivatives with extended pi-conjugation, with an emission maximum at 765 nm. However, the long excited state lifetime (53 μ s) of the complex adversely affects the performance of the material due to saturation of the active emitter in the active layer. In addition, the production of porphyrins requires complex synthetic processes and is difficult to produce on a large scale in industrial applications.
The Schiff base compound has the advantages of simple synthesis and easily adjustable structure, is a good ligand for constructing the metal organic complex, and is easy to realize industrialization of mass production. The ligand has better chelating property on transition metal, non-transition metal and rare earth complex, so the Schiff base compound with good conjugated structure has important application value in luminescent materials.
Disclosure of Invention
In order to overcome the disadvantages and shortcomings of the prior art, it is a primary object of the present invention to provide a platinum complex having aggregation-induced emission.
The invention aims to provide a preparation method of the platinum complex with aggregation-induced emission. The method takes triphenylethylene as a starting material to synthesize tetraphenylethylene with hydroxyl coordination sites; then acetic acid is used as a solvent, and an aldehyde compound is obtained through the Daff reaction under the conditions of heating and stirring; finally, taking ethanol as a solvent, and reacting with micromolecular diamine under the condition of heating and stirring to obtain Schiff base ligand; and the coordination reaction is that under the protection of inert gas, potassium chloroplatinite is dissolved in a small amount of DMSO, a ligand is dissolved in a DMF solvent, sodium acetate is added, the mixed solution is refluxed at high temperature, and then column chromatography purification and vacuum drying are carried out, thus finally obtaining the platinum complex.
It is a further object of the present invention to provide the use of the above platinum complexes with aggregation-induced emission.
The purpose of the invention is realized by the following technical scheme:
a platinum complex with aggregation-induced emission is a complex obtained by taking metal platinum as a center and coordinating with tetraphenyl ethylene Schiff base ligands, and the structural formula of the complex is shown as the following formula (I):
wherein R is any one of the following groups:
the preparation method of the platinum complex with aggregation-induced emission is characterized by comprising the following operation steps:
(1) preparation of intermediate TPE-OH: dissolving triphenylbromoethylene and 4-hydroxyphenylboronic acid in a solvent, and adding sodium carbonate, zinc powder and tetrakis (triphenylphosphine) palladium, N2Heating and stirring for 20-24 h in the atmosphere, extracting after the raw materials are consumed, and purifying the crude product by column chromatography to obtain an intermediate TPE-OH (4- (1,2, 2-triphenylethylene) phenol) with a structure shown in a formula (II);
(2) preparation of intermediate TPE-CHO: dissolving the intermediate TPE-OH and Hexamethylenetetramine (HMTA) obtained in the step (1) in a solvent at room temperature, wherein the mass ratio of the intermediate TPE-OH to the hexamethylenetetramine is 1: 1-5, heating and stirring for 3-5 h, removing the solvent under reduced pressure to obtain a crude product, and purifying by column chromatography to obtain the intermediate TPE-CHO (2-hydroxy-5- (1,2, 2-triphenylethylene)) with the structure shown in the formula (III);
(3) preparation of Schiff base ligand: adding the intermediate TPE-CHO into absolute ethyl alcohol, stirring slightly under heating, adding an ethanol solution of diamine, heating at high temperature and refluxing for 5-8h, carrying out vacuum filtration on a reaction solution after the reaction is stopped to obtain a colored precipitate, and recrystallizing the residue with ethanol to obtain a Schiff base ligand with the structure shown in the formula (IV); the diamine has the structure of
Wherein R is any one of the following groups:
(4) preparation of platinum complexes: under the protection of inert gas, 1 equivalent of potassium chloroplatinate is dissolved in DMSO, 1.2 equivalents of ligand is dissolved in DMF solvent, and sodium acetate is added; mixing the two solutions, refluxing at high temperature for 6-8h, purifying by column chromatography, and vacuum drying to obtain platinum complex with aggregation-induced emission.
The solvent in the step (1) is degassed toluene; the temperature of the heating and stirring is 90 ℃.
The solvent in the step (2) is glacial acetic acid; the temperature of the heating and stirring is 100 ℃.
The mass ratio of the intermediate TPE-CHO to the diamine in the step (3) is 2: 1; the temperature of the slightly heated stirring was 80 ℃.
And (4) the high-temperature reflux temperature in the step (4) is 60-90 ℃.
The temperature of the high-temperature reflux in the step (4) is 80 ℃; the high-temperature reflux time is 6 hours.
And (4) the inert gas in the step (4) is nitrogen, argon or helium.
The temperature of the vacuum drying can be adjusted according to actual needs.
The reaction formula of the step (1) is as follows:
the reaction formula of the step (2) is as follows:
the reaction formula of the step (3) is as follows:
the reaction formula of the step (4) is as follows:
the platinum complex with aggregation-induced emission is applied to the preparation of luminescent materials or luminescent devices.
Compared with the prior art, the invention has the following advantages and effects:
according to the invention, platinum is successfully used as a metal center, and a ligand with a four-tooth ligand is constructed to form a complex, so that platinum elements are well developed and utilized, and a platinum complex with aggregation-induced luminescence is successfully synthesized; the compound has the luminescent wavelength in a red light region (620-760 nm), has high luminescent intensity and good thermal stability when compounded, meets the requirement of preparing a luminescent device by a vapor deposition film forming method, and can be assembled into a single-layer luminescent device; in addition, the preparation method of the complex has the advantages of simplified process, simple equipment and low production cost, can realize large-scale production, and has good commercial application prospect in the application aspects of preparing luminescent materials or luminescent devices and the like.
Drawings
FIG. 1 is a diagram of fluorescence spectra of Schiff base ligands prepared in example in THF solution.
FIG. 2 shows the luminescence spectrum of a THF solution of a platinum complex prepared in example.
FIG. 3 shows the luminescence spectra of the platinum complexes prepared in the examples in different aggregation states.
FIG. 4 is a graph showing phosphorescence lifetimes of platinum complexes prepared in examples.
FIG. 5 is a thermogravimetric analysis chart of the platinum complex prepared in the example.
Detailed description of the invention
The invention is further described with reference to the drawings and the following detailed description, which are not intended to limit the invention in any way. Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated.
Unless otherwise indicated, reagents and materials used in the following examples are commercially available.
Example 1 preparation of Schiff base ligands and platinum complexes
1. The preparation method of the intermediate product 4- (1,2, 2-triphenylvinyl) phenol comprises the following steps:
adding triphenylbromoethylene, 4-hydroxyphenylboronic acid (molar ratio is 1: 1.2), sodium carbonate (5 equivalents) and tetratriphenylphosphine palladium into degassed toluene, and heating and refluxing for 24h under the protection of nitrogen; after the reaction is finished, cooling to room temperature, addingAdding hydrochloric acid, extracting, removing the solvent under reduced pressure, and performing column chromatography to obtain a white solid with the yield: 71.7 percent;1H NMR(400MHz,DMSO)δ9.39(d,J＝10.4Hz,1H),7.17(m,9H),7.00(m,5H),6.80(m,3H),6.55(d,J＝8.6Hz,2H).
the reaction equation is as follows:
2. the preparation method of the intermediate product 2-hydroxy-5- (1,2, 2-triphenylethenyl) comprises the following steps:
dissolving 4- (1,2, 2-triphenylethenyl) phenol in 40ml acetic acid, adding hexamethylenetetramine (molar ratio 1: 1.5) under vigorous stirring, refluxing for 3h, cooling to room temperature, extracting with dichloromethane to obtain organic phase, removing solvent under reduced pressure, and purifying by column chromatography to obtain yellow solid with yield: 55.5 percent.1H NMR(400MHz,DMSO)δ10.68(s,1H),10.11(s,1H),7.44(t,J＝5.9Hz,1H),7.23(s,1H),7.11(m,9H),6.98(dd,J＝
12.8,8.0Hz,6H),6.74(m,1H).
The reaction equation is as follows:
3. the preparation method of the Schiff base ligand comprises the following steps:
dissolving the prepared 2-hydroxy-5- (1,2, 2-triphenylethylene) in absolute ethanol, adding 1, 3-propanediamine (molar ratio of 2: 1) under stirring, and heating under reflux for 3 h; after the heating reflux reaction is finished, cooling the reaction solution to room temperature, filtering the reaction solution, collecting precipitate, and recrystallizing the ethanol to obtain yellow solid with the yield: 61.1 percent.1H NMR(400MHz,DMSO)δ13.48(s,2H),8.30(s,2H),7.12(m,19H),6.95(m,15H),6.61(d,J＝8.5Hz,2H),3.54(t,J＝6.6Hz,4H),1.91(s,2H).
The reaction equation is as follows:
the obtained Schiff base ligand is subjected to fluorescence spectrum measurement, and the result is shown in figure 1, and under the irradiation of light of 320nm, the ligand has a maximum emission peak at 536nm and shows yellow light.
4. The preparation method of the platinum complex with aggregation-induced emission comprises the following steps:
weighing a certain amount of Schiff base ligand, dissolving in a DMF solvent, and adding sodium acetate; adding a DMSO solution of potassium chloroplatinate into the solution, wherein the molar ratio of the Schiff base ligand to the potassium chloroplatinate is 1.2: 1; and (3) refluxing at high temperature for 6h, filtering, purifying by using column chromatography, and drying in vacuum to finally obtain the platinum complex, wherein the yield is as follows: 39.3 percent.1H NMR(400MHz,DMSO)δ＝8.04(s,2H),7.12(dd,J＝15.1,8.5,18H),6.98(dd,J＝18.9,6.8,16H),6.53(d,J＝9.4,2H),3.80(s,4H),1.84(s,2H).
The reaction equation is as follows:
5. results
(1) The platinum complex obtained was measured by luminescence spectroscopy, and the results are shown in fig. 2.
(2) The prepared platinum complex was tested for luminescence spectra in different aggregation states (mixed solution of tetrahydrofuran and water), and the results are shown in fig. 3, where the enhancement of the emission peak at 690nm of the compound molecule is attributed to the formation of aggregates, and in the aggregation state, intramolecular rotation is suppressed, thus preventing non-radiative relaxation of the excited state. Thus, the excited state energy can be efficiently released as photons, demonstrating that the compounds are indeed AIE active.
(3) The prepared platinum complex was subjected to a solid phosphorescence lifetime test in a 77K state, and the results thereof are shown in fig. 4.
(4) Under the protection of nitrogen, the temperature rise rate is 10 ℃/min, and the measurement temperature is 20-800 ℃, the prepared platinum complex is further subjected to thermogravimetric analysis, and the result is shown in fig. 5.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (9)
1. A platinum complex having aggregation-induced emission characterized by: the complex is obtained by taking metal platinum as a center and coordinating with tetraphenyl ethylene Schiff base ligand, and the structural formula of the complex is shown as the following formula (I):
wherein R is any one of the following groups:
2. the method for preparing a platinum complex with aggregation-induced emission according to claim 1, comprising the following steps:
(1) preparation of intermediate TPE-OH: dissolving triphenylbromoethylene and 4-hydroxyphenylboronic acid in a solvent, and adding sodium carbonate, zinc powder and tetrakis (triphenylphosphine) palladium, N2Heating and stirring for 20-24 h in the atmosphere, extracting after the raw materials are consumed, and purifying the crude product by column chromatography to obtain an intermediate TPE-OH with a structure shown in a formula (II);
(2) preparation of intermediate TPE-CHO: dissolving the intermediate TPE-OH and hexamethylenetetramine obtained in the step (1) in a solvent at room temperature, wherein the mass ratio of the intermediate TPE-OH to the hexamethylenetetramine is 1: 1-5, heating and stirring for 3-5 h, removing the solvent under reduced pressure to obtain a crude product, and purifying by column chromatography to obtain an intermediate TPE-CHO with a structure shown in a formula (III);
(3) preparation of Schiff base ligand: adding the intermediate TPE-CHO into absolute ethyl alcohol, stirring slightly under heating, adding an ethanol solution of diamine, heating at high temperature and refluxing for 5-8h, carrying out vacuum filtration on a reaction solution after the reaction is stopped to obtain a colored precipitate, and recrystallizing the residue with ethanol to obtain a Schiff base ligand with the structure shown in the formula (IV); the diamine has the structure of
Wherein R is any one of the following groups:
(4) preparation of platinum complexes: under the protection of inert gas, 1 equivalent of potassium chloroplatinate is dissolved in DMSO, 1.2 equivalents of ligand is dissolved in DMF solvent, and sodium acetate is added; mixing the two solutions, refluxing at high temperature for 6-8h, purifying by column chromatography, and vacuum drying to obtain platinum complex with aggregation-induced emission.
3. The method of claim 2, wherein: the solvent in the step (1) is degassed toluene; the temperature of the heating and stirring is 90 ℃.
4. The method of claim 2, wherein: the solvent in the step (2) is glacial acetic acid; the temperature of the heating and stirring is 100 ℃.
5. The method of claim 2, wherein: the mass ratio of the intermediate TPE-CHO to the diamine in the step (3) is 2: 1; the temperature of the slightly heated stirring was 80 ℃.
6. The method of claim 2, wherein: and (4) the high-temperature reflux temperature in the step (4) is 60-90 ℃.
7. The method of claim 2, wherein: the temperature of the high-temperature reflux in the step (4) is 80 ℃; the high-temperature reflux time is 6 hours.
8. The method of claim 2, wherein: and (4) the inert gas in the step (4) is nitrogen, argon or helium.
9. Use of the platinum complex with aggregation-induced emission according to claim 1 for the preparation of a luminescent material or a luminescent device.
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| CN109574872A (en) * | 2019-01-08 | 2019-04-05 | 福建师范大学 | A kind of fluorescence probe and the preparation method and application thereof for detecting copper ion |
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| US20050233167A1 (en) * | 2004-04-16 | 2005-10-20 | Chi-Ming Che | System and method for producing light with organic light-emitting devices |
| CN109406474A (en) * | 2018-11-14 | 2019-03-01 | 河南工业大学 | A kind of aggregation-induced emission-molecular engram fluorescent optical sensor preparation method and application detecting rhodamine B |
| CN109438267A (en) * | 2018-11-29 | 2019-03-08 | 首都医科大学 | A kind of bi-functional complexing agent and its preparation method and application containing tetraphenylethylene |
| CN109574872A (en) * | 2019-01-08 | 2019-04-05 | 福建师范大学 | A kind of fluorescence probe and the preparation method and application thereof for detecting copper ion |
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