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Bipyrazine macrocyclic compound, preparation method and application of bipyrazine macrocyclic compound in construction of fluorescent powder

A technology of macrocyclic compounds and phosphors, which is applied in the cross field of organic materials and coordination chemistry, can solve the problems of high cost, insufficient supply, complex synthesis steps, etc., and achieve the effect of low cost, low industrial cost and simple synthesis method

Active Publication Date: 2022-04-05
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the commercial phosphors on the market at this stage are inorganic materials doped with rare earth metals. They are very dependent on rare earth metals, especially metals such as europium, terbium and yttrium, and there are problems such as insufficient supply and high cost, and most of them need High temperature production, complex synthesis steps

Method used

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  • Bipyrazine macrocyclic compound, preparation method and application of bipyrazine macrocyclic compound in construction of fluorescent powder
  • Bipyrazine macrocyclic compound, preparation method and application of bipyrazine macrocyclic compound in construction of fluorescent powder
  • Bipyrazine macrocyclic compound, preparation method and application of bipyrazine macrocyclic compound in construction of fluorescent powder

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: Synthesis of double pyrazine macrocyclic compound 1,3-OBP

[0047]

[0048]Under nitrogen atmosphere, 1,3-dihydroxynaphthalene (1.60g, 10mmol), 2,6-dichloropyrazine (1.49g, 10mmol), cesium carbonate (6.5g, 20mmol) were added to DMSO (100mL) in a round bottom flask. After vigorously stirring at 120° C. for 18 h, the reaction mixture was poured into 200 mL of water, extracted three times with 100 mL of ethyl acetate, and the organic phase was recovered. Wash the organic phase with saturated brine, reclaim the organic phase; wash with anhydrous Na 2 SO 4 The organic phase was dried, filtered and concentrated in vacuo to give crude product. Using petroleum ether and ethyl acetate (volume ratio of 5:1) as a developing solvent, the crude product was purified by column chromatography (using a 200-mesh silica gel column) to obtain the bispyrazine macrocyclic compound 1,3- OBP, yield: 51.7% (calculated as 2,6-dichloropyrazine).

[0049] 1,3-OBP (C 28 h 16...

Embodiment 2

[0056] Embodiment 2: Synthesis of double pyrazine macrocyclic compound 2,3-OBP

[0057]

[0058] The preparation method of 2,3-OBP is the same as that of 1,3-OBP, except that 1,3-dihydroxynaphthalene is replaced by 2,3-dihydroxynaphthalene (1.60g, 10mmol), yield: 23.1% (with 2, 6-dichloropyrazine calculation).

[0059] 2,3-OBP (C 28 h 16 N 4 o 4 ), theoretical value of high resolution mass spectrometry: [M+H] + :473.1172, experimental value: 473.1242( Figure 8 ). Elemental analysis theoretical value: C 71.18%; H 3.41%; N 11.86%, experimental value: C 70.91%; H 3.52%; N 31.66%.

[0060] The phosphor powder with high luminous efficiency is prepared by using the above bispyrazine macrocyclic compound 2,3-OBP. 2,3-OBP (4.7mg, 0.01mmol) and cuprous iodide (3.8mg, 0.02mmol) were completely dissolved in acetonitrile (2mL), respectively, and the two clear solutions were mixed together, and placed in a dark room at room temperature for 1 days, the MOFs obtained after part ...

Embodiment 3

[0063] Embodiment 3: Synthetic double pyrazine macrocyclic compound OFP

[0064]

[0065] The preparation method of OFP is the same as that of 1,3-OBP, except that 1,3-dihydroxynaphthalene is replaced by fluorescein (3.32g, 10mmol), the yield: 19.3% (calculated as 2,6-dichloropyrazine).

[0066] OFP(C 48 h 24 N 4 o 10 ), theoretical value of high resolution mass spectrometry: [M+H] + :817.1492, experimental value: 817.0638( Figure 14 ). Elemental analysis theoretical value: C 70.59%; H 2.96%; N 6.86%, experimental value: C 70.37%; H 3.11%; N 6.49%.

[0067] The phosphor powder with high luminous efficiency is prepared by using the bispyrazine macrocyclic compound. OFP (8.2mg, 0.01mmol) and cuprous iodide (3.8mg, 0.02mmol) were completely dissolved in acetonitrile (2mL), respectively, and the two clear solutions were mixed together, left standing in a dark room at room temperature for 1 day, and part of the solvent After volatilization, MOFs 3( Figure 15 is the sc...

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Abstract

The invention provides a bispyrazine macrocyclic compound, a preparation method and application of the bispyrazine macrocyclic compound in construction of fluorescent powder. The preparation method comprises the following steps: mixing a raw material with a bisphenol structure with a 2, 6-dichloropyrazine raw material, and obtaining the dipyrazine macrocyclic compound, namely oxygen bridge [2] calixarene [2] pyrazine (ORP) under an alkaline heating condition. The compound is rich in structure, simple in synthesis method and low in cost. The prepared dipyrazine macrocyclic compound has a pyrazine unit, is easy to coordinate, and can be used as a novel bridging ligand for constructing MOFs (Metal-Organic Frameworks). The fluorescent powder is prepared by using the bispyrazine macrocyclic compound as a bridging ligand and performing MOFs crystal growth with a copper source, the prepared MOFs crystal can be excited by a blue wave band to emit strong yellow light, the preparation method is simple, the preparation method is independent of large-scale instruments, the industrial cost is low, and the bispyrazine macrocyclic compound can be used as the fluorescent powder of a white-light LED and can be applied to industrial production.

Description

technical field [0001] The invention relates to a class of bispyrazine macrocyclic compounds, a preparation method and the application thereof in the construction of fluorescent powder, and belongs to the cross field of organic materials and coordination chemistry. Background technique [0002] Pyrazine is a six-membered heterocyclic compound containing two nitrogen heteroatoms at the 1 and 4 positions. It is weakly basic and widely exists in natural products and pharmaceutical preparations; its aromaticity is similar to that of pyridine, and it is often used as a nitrogen-containing heterocyclic compound. Neutral bridging ligands are used to construct crystalline materials. Pyrazine derivatives have various structures, and their synthesis methods are relatively mature. However, cyclic derivatives containing pyrazine units are rarely reported because the synthesis process of cyclic compounds is relatively complicated. The development of pyrazine cyclic compounds with simpl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/14C07D498/22C09K11/06H01L33/50
CPCY02B20/00
Inventor 李恺刘园园李媛媛汪婷彭秋晨
Owner ZHENGZHOU UNIV
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