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Tetraphenylpyrazine small molecule derivatives, tetraphenylpyrazine polymers and aggregation-induced luminescent materials

A technology of aggregation-induced luminescence and tetraphenylpyrazine, which is applied in luminescent materials, compounds of group 4/14 elements of the periodic table, organic chemistry, etc., can solve the problems of cumbersome synthesis steps, harsh conditions, and structural damage of HPS. Achieve the effect of good stability, easy derivation and clear mechanism

Active Publication Date: 2017-07-07
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] HPS and TPE derivatives have undoubtedly promoted the rapid development of AIE materials, but the problems they face cannot be ignored: (1) The synthesis steps of HPS are cumbersome and the conditions are harsh, and its structure is easily destroyed under alkaline conditions; (2) ) The internal double bond in TPE is easy to degrade under the action of heat or ultraviolet light, and its stability needs to be improved; (3) Whether the double bond structure in TPE is suitable for AIE (Z / E isomerism and intramolecular rotation restriction) Contributions are controversial

Method used

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  • Tetraphenylpyrazine small molecule derivatives, tetraphenylpyrazine polymers and aggregation-induced luminescent materials
  • Tetraphenylpyrazine small molecule derivatives, tetraphenylpyrazine polymers and aggregation-induced luminescent materials
  • Tetraphenylpyrazine small molecule derivatives, tetraphenylpyrazine polymers and aggregation-induced luminescent materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Synthesis of tetraphenylpyrazine (compound shown in formula 1-1)

[0071]

[0072] Method one: synthetic method references (D.Davidson, M.Weiss and M.Jelling, J.Org.Chem.1937,2,328), in 50mL round bottom flask, add 2.12g benzoin (10mmol), 1.45ml acetic anhydride ( 15mmol), 2.32g ammonium acetate (10mmol) and 10mL acetic acid. The reaction was refluxed in acetic acid for 3.5 hours, the temperature was lowered and suction filtered, and the filter residue was recrystallized in acetic acid to obtain white needle-like crystals, yield: 33.9%. The characterization data of the product are as follows:

[0073] 1 H NMR (500MHz CDCl 3 ): δ(TMS,ppm)7.65(m,8H),7.33(m,12H).

[0074] 13 C NMR (125MHz, CDCl 3 ): δ (TMS, ppm) 148.5, 138.5, 129.9, 128.7, 128.3.

[0075] HRMS (MALDI-TOF): m / z 384.1664 ([M] + ), calcd for C 28 h 20 N 2 384.1626.

[0076] Method 2: Synthetic method References (J.A.Katzenellenbogen, et al., Bioorg.Med.Chem., 2003, 11, 629): In a 50mL round bot...

Embodiment 2

[0079] Synthesis of Tetraphenylpyrazine Derivatives (Compounds Shown in Formula 1-2)

[0080]

[0081] The synthesis method is similar to the method 1 in Example 1 of this patent, the difference is that the raw materials are changed accordingly, white needle-like crystals, yield: 20%. Product characterization data are as follows:

[0082] 1 H NMR (500MHz CDCl 3 ): δ(TMS,ppm)7.61(d,8H),6.86(d,8H),3.82(s,12H).

[0083] 13 C NMR (125MHz, CDCl 3 ): δ (TMS, ppm) 159.9, 146.8, 131.1, 113.7, 55.3.

[0084] HRMS (MALDI-TOF): m / z 504.2039 ([M] + ), calcd for C 32 h 28 N 2 o 4 504.2049.

[0085] The AIE performance of the compound obtained in this example is similar to that of the compound in Example 1.

Embodiment 3

[0087] Synthesis of Tetraphenylpyrazine Derivatives (Compounds Shown in Formula 2-2)

[0088] (1) Synthesis of 1-(4-bromophenyl)-2-acetophenone

[0089]

[0090] Synthetic method reference (C.Cheng, et al., Org.Lett.2010,12,1736): 10g 4-bromophenylboronic acid (50mmol), 1.32g Ni(dppe)Cl were added to a 250mL round bottom flask 2 (2.5mmol) and 5.1gZnCl 2 (37.5 mmol). The reaction system was vacuumed and replaced with nitrogen three times, and then 75mL of 1,4-dioxane, 2.9mL of phenylacetonitrile (25mmol) and 0.45ml of water (25mol) were injected into it, and the reaction was maintained at 80°C for 8h. After the reaction was completed, the filter residue was washed three times with tetrahydrofuran, and the filtrate was spin-dried. The crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 20:1) to obtain a white solid with a yield of 74.4%. The characterization data of the product are as follows:

[0091] 1 H NMR (500MHz DMSO-d 6...

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Abstract

The invention discloses a tetrapherylpyrazine low-molecular-weight derivate, a tetrapherylpyrazine polymer and an aggregation-induced emission material. The tetrapherylpyrazine low-molecular-weight derivate is of a structure as shown in a formula (1), wherein R1, R2, R3 and R4 are independently selected from hydrogen, alkoxy, substituted or unsubstituted phenyl, halogen or acetenyl; the substituent of phenyl is aromatic group. The tetrapherylpyrazine derivate is basically prepared by two methods, namely, (1) the method for preparing by the cyclization reaction of a benzoin derivative, and (2) preparing by the cyclization reaction of dibenzoyl derivate and 2-diphenyl diaminoethane; the synthesized diyne derivate can be derived by clicking polymerizing through an AIE (Aggregation Induced Emission) polymer. In light of the simple and convenient synthesis, tetrapherylpyrazine can be used as a novel AIE mother nucleus following after hexaphenyl silole and tetraphenyl ethylene and is wide in applicable scope. The formula is described in the specification.

Description

technical field [0001] The invention belongs to the field of organic / polymer light-emitting materials, and in particular relates to the preparation and performance of a tetraphenylpyrazine-based small molecule with aggregation-induced light-emitting performance and a polymer. Background technique [0002] In the research of traditional organic light-emitting materials, the aggregation fluorescence quenching of organic molecules has always been a problem that needs to be solved urgently. For example, in an organic light-emitting diode (OLED), the organic molecules contained in the film as the light-emitting layer are in an aggregated state, and the fluorescence concentration quenching of traditional molecules is inevitable. Although aggregation can be avoided by doping and introducing bulky groups on molecules to increase steric hindrance, the negative effects and increased costs cannot be ignored. [0003] In 2001, Professor Tang Benzhong of the Hong Kong University of Scie...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/12C07F7/10C08G73/06C09K11/06
CPCC07D241/12C07F7/0812C08G73/0638C09K11/06C09K2211/1007C09K2211/1014C09K2211/1044C09K2211/1425C09K2211/1466
Inventor 陈明秦安军唐本忠孙景志
Owner ZHEJIANG UNIV
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