CN111233936B - Phosphorescence aggregation-induced luminescent material of platinum (II) complex containing nitrogen monodentate ligand and C ^ N bidentate ligand - Google Patents
Phosphorescence aggregation-induced luminescent material of platinum (II) complex containing nitrogen monodentate ligand and C ^ N bidentate ligand Download PDFInfo
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Abstract
The phosphorescence aggregation inducing luminescent material of platinum (II) complex containing nitrogen monodentate ligand and C ^ N bidentate ligand has a molecular framework general formula as follows:
Description
Technical Field
The invention relates to the technical field of organic metal complex luminescent materials, in particular to a phosphorescence aggregation induced luminescent material of a platinum (II) complex based on nitrogen-containing monodentate ligands and C ^ N bidentate ligands with different sizes.
Background
In 2001, Tangben faith et al discovered a phenomenon of aggregation-induced emission (AIE) of organic molecules. The organic luminescent molecules show the characteristic of enhanced luminescence in a solid state, and the problem of luminescence aggregation quenching which troubles the luminescent molecules is solved to a great extent. Organic light emitting diode devices require organic light emitting molecules to have strong light emitting properties in the solid state. Aggregation-induced emission of organic molecules therefore represents a great advantage in organic light emitting diodes. However, most of organic light-emitting molecules are fluorescent materials, and the prepared light-emitting diode can only emit light by utilizing a singlet state, so that the efficiency is low. The organic metal complex phosphorescent material can emit light by utilizing singlet excitons and triplet excitons at the same time, so that the device efficiency is higher. It is expected that the development of a phosphorescent aggregation-inducing luminescent material is a very important measure for improving the efficiency of an organic light emitting diode if the AIE characteristics are combined with the organometallic complex phosphorescent material. However, to date, phosphorescent AIE emissive materials have been less studied and the electroluminescent efficiency has a significant gap from conventional phosphorescent materials. Therefore, it is important to develop a novel phosphorescent AIE luminescent molecule and study the relationship between its structure and AIE performance.
Disclosure of Invention
In order to develop a novel phosphorescent AIE molecule and research the structural performance relationship thereof, the invention aims to provide a phosphorescent aggregation-induced luminescent material of a platinum (II) complex based on nitrogen-containing monodentate ligands and C ^ N bidentate ligands with different sizes, wherein a planar platinum (II) complex is used as a framework to design and synthesize a Pt (C ^ N) NCl type phosphorescent AIE molecule, wherein C ^ N is a 2-phenylpyridine bidentate ligand, N is a nitrogen-containing monodentate ligand, and Cl is a chlorine monodentate ligand; on the basis, the sizes of the C ^ N bidentate ligand and the nitrogen-containing monodentate ligand are regulated to regulate the phosphorescent AIE behavior, and the phosphorescent AIE characteristic is realized by utilizing the blocked transformation of a basic state plane coordination framework to a tetrahedral framework in an excited state in an aggregation state; in addition, through intermolecular action, group rotation on the ligand is hindered, non-radiative decay of a phosphorescent complex excited state can be inhibited, the aggregation state luminous capacity is increased, the AIE property is realized, and then the two ligands are functionally modified, so that the property regulation space of the platinum (II) complex is remarkably improved.
In order to achieve the above purpose, the technical scheme of the invention is as follows:
the phosphorescence aggregation inducing luminescent material of platinum (II) complex containing nitrogen monodentate ligand and C ^ N bidentate ligand has a molecular framework general formula as follows:
in the above general structural formula:
ar1 represents organic nitrogen heteroaromatic rings of different sizes and is any one of the following organic groups:
ar2 represents an organic aromatic system of varying sizes, being any one of the following organic groups:
ar3 represents nitrogen-containing organic aromatic systems of different sizes and is any one of the following organic groups:
wherein n represents the number of aromatic rings of 0 to 2 in the same molecule.
It can be seen from the above general molecular architecture that the material molecule provided by the invention has a platinum metal center and two functionalized ligands, the size of which is regulated and controlled by different structures, and the regulation and control of the phosphorescence AIE performance of the organic metal platinum (II) complex can be improved to a great extent, thus providing good performance for the application of the material in the field of organic light emitting diodes. Therefore, the organic ligands with different sizes provided by the invention provide a very unique design idea in the aspect of developing metal luminescent materials with AIE properties, and have very important application value.
Drawings
FIG. 1 is a schematic diagram of the synthesis of an organometallic platinum (II) complex phosphorescent material Pt1 according to the invention.
FIG. 2 is a schematic diagram of the synthesis of organometallic platinum (II) complex phosphorescent material Pt2 according to the invention.
FIG. 3 is a schematic diagram of the synthesis of organometallic platinum (II) complex phosphorescent material Pt3 according to the invention.
FIG. 4 is an AIE property emission spectrum of Pt1 as a phosphorescent material for synthesizing organometallic platinum (II) complex according to the invention.
FIG. 5 is an AIE property emission spectrum of Pt2 as a phosphorescent material for synthesizing organometallic platinum (II) complex according to the invention.
FIG. 6 is an AIE property emission spectrum of Pt3 as a phosphorescent material for synthesizing organometallic platinum (II) complex according to the invention.
FIG. 7 is a graph showing the luminescence spectra of organometallic platinum (II) complex phosphorescent materials Pt1-Pt3 synthesized according to three selected examples of the invention.
Detailed Description
The invention is further described with reference to the following figures and specific examples.
Example one
The phosphor aggregation induced emission material Pt1 of the platinum (II) complex containing nitrogen monodentate ligand and C ^ N bidentate ligand of the embodiment has the chemical formula C20H15ClN2Pt, the molecular structural formula is:
referring to fig. 1, the synthesis steps are as follows:
the first step is as follows: 0.2g of organic ligand
And 0.39g K2PtCl4Putting the mixture into a reaction vessel, adding 24mL of mixed solvent of ethylene glycol ethyl ether and water into a nitrogen atmosphere, wherein the volume ratio of the ethylene glycol ethyl ether to the water in the mixed solvent is 3:1, heating the mixture to 85 ℃ in the nitrogen atmosphere, stirring the mixture for 8 hours, cooling the mixture to room temperature, adding 50mL of deionized water into the reaction vessel, performing chromatography to obtain a solid, filtering the solid, taking a filter cake, and drying the filter cake to obtain an intermediate product;
the second step is that: the intermediate product and 0.07g pyridine were put into a reaction tube, 15mL chloroform was added under nitrogen atmosphere, heated to 45 ℃ under nitrogen atmosphere, stirred for 12 hours, cooled to room temperature, evaporated to remove the solvent to give a crude product, which was then purified with a homemade thin layer silica gel chromatography plate to give 0.22 g Pt1 with a yield of 44%.
The nuclear magnetic characterization data are as follows:1H NMR(400MHz,CDCl3,δ):9.83(d,J＝4.70Hz,1H),9.00(d,J＝5.00Hz,2H),8.43(d,J＝8.70Hz,1H),7.93(t,J＝7.30Hz,1H),7.87(t,J＝7.10Hz,1H),8.32(d,J＝8.20Hz,1H),7.76(d,J＝3.50Hz,1H),7.54-7.38(m,5H),7.16(t,J＝6.0Hz,1H),6.50(d,J＝8.4Hz,1H).13C NMR(100MHz,CDCl3,δ):168.20,154.10,152.40,145.47,138.85,138.54,138.07,132.09,130.63,130.22,129.75,129.23,127.48,126.30,123.88,122.35,121.80,121.06.
based on the above data, the synthesized organometallic platinum (II) complex phosphorescent material Pt1 is illustrated.
Example two
The phosphor aggregation induced emission material Pt2 of the platinum (II) complex containing nitrogen monodentate ligand and C ^ N bidentate ligand of the embodiment has the chemical formula C32H23ClN2Pt, the molecular structural formula is:
referring to fig. 2, the synthesis steps are as follows:
the first step is as follows: 0.2g of organic ligand
And 0.39g K2PtCl4Putting the mixture into a reaction vessel, adding 24mL of mixed solvent of ethylene glycol ethyl ether and water into a nitrogen atmosphere, wherein the volume ratio of the ethylene glycol ethyl ether to the water in the mixed solvent is 3:1, heating the mixture to 85 ℃ in the nitrogen atmosphere, stirring the mixture for 8 hours, cooling the mixture to room temperature, adding 50mL of deionized water into the reaction vessel, performing chromatography to obtain a solid, filtering the solid, taking a filter cake, and drying the filter cake to obtain an intermediate product;
the second step is that: the intermediate product is mixed with
0.2g of the crude product was placed in a reaction tube, 20mL of chloroform was added under nitrogen, the mixture was heated to 45 ℃ under nitrogen, stirred for 12 hours, cooled to room temperature, evaporated to remove the solvent to give a crude product, and the crude product was purified by a home-made thin layer silica gel chromatography plate to give 0.30 g of Pt2 in 46% yield.
The nuclear magnetic characterization data are as follows:1H NMR(400MHz,CDCl3,δ):9.83(d,J＝5.60Hz,1H),9.10(d,J＝6.80Hz,2H),8.01(s,1H),7.92-7.68(m,11H),7.50(d,J＝4.40Hz,3H),7.43(t,J＝7.20Hz,1H),7.35(t,J＝3.60Hz,2H),7.22(t,J＝3.20Hz,1H),6.84(s,1H).13C NMR(100MHz,CDCl3,δ):166.37,154.02,151.45,149.62,143.26,139.84,138.52,136.40,135.07,134.84,130.78,130.33,129.54,129.01,128.70,128.19,128.09,127.52,127.15,127.10,126.66,124.56,123.58,123.34,123.20,122.58,118.90.
based on the above data, the synthesized organometallic platinum (II) complex phosphorescent material Pt2 is illustrated.
EXAMPLE III
The phosphor aggregation induced emission material Pt3 of the platinum (II) complex containing nitrogen monodentate ligand and C ^ N bidentate ligand of the embodiment has the chemical formula C45H36ClN3Pt, the molecular structural formula is:
referring to fig. 3, the synthesis steps are as follows:
the first step is as follows: 0.2g of organic ligand
And 0.31g K2PtCl4Putting the mixture into a reaction vessel, adding 24mL of mixed solvent of ethylene glycol ethyl ether and water into a nitrogen atmosphere, wherein the volume ratio of the ethylene glycol ethyl ether to the water in the mixed solvent is 3:1, heating the mixture to 85 ℃ in the nitrogen atmosphere, stirring the mixture for 8 hours, cooling the mixture to room temperature, adding 50mL of deionized water into the reaction vessel, performing chromatography to obtain a solid, filtering the solid, taking a filter cake, and drying the filter cake to obtain an intermediate product;
the second step is that: the intermediate product is mixed with
0.23g was put into a reaction tube, 20mL of chloroform was added under nitrogen, and the mixture was heated to 45 ℃ under nitrogen, stirred for 12 hours, cooled to room temperature, evaporated to remove the solvent to give a crude product, which was then purified by a home-made thin layer silica gel chromatography plate to give 0.35 g of Pt3 with a yield of 61%.
The nuclear magnetic characterization data are as follows:1H NMR(400MHz,CDCl3,δ):9.77(d,J＝4.90Hz,1H),9.21(d,J＝6.80Hz,2H),8.21(d,J＝7.70Hz,2H),8.05(d,J＝8.50Hz,2H),7.89-7.77(m,6H),7.57(d,J＝8.20Hz,2H),7.50(t,J＝6.40Hz,3H),7.41-7.30(m,5H),7.24(t,J＝5.60Hz,1H),7.17(t,J＝5.90Hz,1H),6.89(s,1H),2.07(q,J＝7.30Hz,4H),0.38(t,J＝7.40Hz,6H).13C NMR(100MHz,CDCl3,δ):167.44,154.32,151.50,150.77,149.11,145.39,143.64,143.47,141.04,140.52,140.42,139.93,138.72,134.81,128.70,127.80,127.49,126.62,126.24,123.78,123.42,122.92,121.71,121.48,120.54,120.52,119.71,118.24,109.75,55.86,32.76,8.61.
based on the above data, the synthesized organometallic platinum (II) complex phosphorescent material Pt3 is illustrated.
The AIE performance of the organic metal platinum (II) complex phosphorescent material Pt1-Pt3 synthesized according to the invention is tested: respectively dissolving organic metal platinum (II) complex phosphorescent materials Pt1-Pt3 in a tetrahydrofuran/water system, and configuring the materials to have the concentration of 1.0 multiplied by 10 under the same conditions along with the constant change of the volume ratio of water-5Different solutions in mol/L. Wherein when fwWhen the concentration is 0%, the volume ratio of water is 0%, and the AIE emission spectra of the organometallic platinum (II) complex phosphorescent material Pt1-Pt3 are respectively shown in FIG. 4, FIG. 5 and FIG. 6 under the excitation of ultraviolet light with the wavelength of 400 nm. From the trend that the intensity of the phosphorescence changes along with the volume of the added water in the graph, the sizes of the two organic ligands have very obvious influence on the phosphorescence signal enhancement process, and the larger the sizes of the C ^ N bidentate ligand and the nitrogen monodentate ligand are, the more easily the AIE behavior occurs. Therefore, these results provide valuable information for modulating phosphorescent AIE behavior.
The luminescent properties of the organic metal platinum (II) complex phosphorescent material Pt1-Pt3 synthesized according to the invention are tested: respectively dissolving organic metal platinum (II) complex phosphorescent materials Pt1-Pt3 in dichloromethane to be prepared into a concentration of 1.0 × 10-5The luminescence spectrum of the organometallic platinum (II) complex phosphorescent material Pt1-Pt3 measured by the mol/L solution under the excitation of ultraviolet light with the wavelength of 400nm is shown in FIG. 7.
While the invention has been described in connection with specific embodiments thereof, it will be understood that it is not intended to limit the scope of the invention, which is defined by the appended claims, but rather by any variation of the claims.
Claims (3)
1. The phosphorescence aggregation inducing luminescent material of platinum (II) complex containing nitrogen monodentate ligand and C ^ N bidentate ligand has a molecular framework general formula as follows:
in the above general structural formula:
ar1 represents organic nitrogen heteroaromatic rings of different sizes and is any one of the following organic groups:
ar2 represents an organic aromatic system of varying sizes, being any one of the following organic groups:
ar3 represents nitrogen-containing organic aromatic systems of different sizes and is any one of the following organic groups:
wherein n represents the number of aromatic rings of 0 to 2 in the same molecule.
2. The phosphorescence aggregation induced luminescent material of platinum (II) complex containing nitrogen monodentate ligand and C ^ N bidentate ligand is characterized in that the chemical formula is C20H15ClN2Pt, the molecular structural formula is:
3. the phosphorescence aggregation induced luminescent material of platinum (II) complex containing nitrogen monodentate ligand and C ^ N bidentate ligand is characterized in that the chemical formula is C32H23ClN2Pt, the molecular structural formula is:
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