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D-sigma-A configuration compound, synthetic method and application

A synthesis method and compound technology, applied in the field of fluorescent materials, can solve the problems of cumbersome reaction steps, few synthesis methods, and restrictions on the application of D-σ-A type spiro ring molecular frameworks, and achieve the effect of simple synthesis method and good stability

Pending Publication Date: 2021-10-26
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the D-σ-A type spirocyclic molecular skeleton is rarely reported in the literature, and the traditional construction method has the disadvantages of cumbersome reaction steps and fewer synthesis methods in organic synthesis, which greatly limits the ability of D-σ-A Applications of Type Spiral Molecular Frameworks

Method used

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  • D-sigma-A configuration compound, synthetic method and application
  • D-sigma-A configuration compound, synthetic method and application
  • D-sigma-A configuration compound, synthetic method and application

Examples

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Embodiment 1

[0049] This embodiment provides a kind of synthetic method of D-σ-A configuration compound, and this method comprises the following steps:

[0050] Step 1, in the glove box, add Pd(OAc) sequentially into the sealed tube 2 (13.5mg, 0.06mmol), P(p-F-C 6 h 4 ) 3 (22.8mg, 0.072mmol), CsOPiv (42.1mg, 0.18mmol), Cs 2 CO 3 (560mg, 1.8mmol) and 60mL DMF were first stirred in the glove box for 5-10min, then compound 1 (320.6mg, 0.72mmol) and compound 2 (133.8mg, 0.6mmol) were added into a sealed tube. After the addition was complete, the sealed tube was taken out of the glove box and reacted at 130° C. for 20 h. After the reaction was completed, the reaction liquid was returned to room temperature, extracted with DCM and saturated ammonium chloride solution, back extracted three times and the organic phase was collected. The organic phase was washed with anhydrous MgSO 4 Dry, filter with Celite, and spin dry. Separation by column chromatography (PE / EA=10:1, R f =0.30), a yello...

Embodiment 2

[0059] This embodiment provides a kind of synthetic method of D-σ-A configuration compound, and this method comprises the following steps:

[0060] Step 1, in the glove box, add Pd(OAc) sequentially into the sealed tube 2 (135mg, 0.6mmol), P(p-F-C 6 h 4 ) 3 (228mg, 0.72mmol), CsOPiv (421mg, 1.8mmol), Cs 2 CO 3 (5.6g, 18mmol) and 60mL DMF were first stirred in the glove box for 5-10min, and then compound 1 (3.2g, 7.2mmol) and compound 2 (1.3g, 6mmol) were added into a sealed tube. After the addition was complete, the sealed tube was taken out of the glove box and reacted at 130° C. for 20 h. After the reaction was completed, the reaction liquid was returned to room temperature, extracted with DCM and saturated ammonium chloride solution, back extracted three times and the organic phase was collected. The organic phase was washed with anhydrous MgSO 4 Dry, filter with Celite, and spin dry. Separation by column chromatography (PE / EA=10:1, R f =0.30), a yellow solid was o...

Embodiment 3

[0066] This example presents the application of the D-σ-A configuration compound as a fluorescent material. The D-σ-A configuration compound in this example uses the D-σ-A configuration compound obtained in Example 1.

[0067] The D-σ-A configuration compound obtained in Example 1 has carried out the determination of the fluorescence emission spectrum, and found that it has better spectroscopic properties, such as figure 1 shown. It can be seen from its fluorescence emission spectrum that there are two fluorescence emission peaks in toluene and n-hexane solutions, respectively in the blue and yellow light regions, while in other solvents there is only a single peak in the blue light region. We consider that the reason why there are two fluorescence emission peaks in toluene and n-hexane solutions may be that the previous fluorescence emission peaks in n-hexane and toluene solutions come from phenylcarbazole, also called LE state (that is, locally excited state) , the latter f...

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Abstract

The invention provides a D-sigma-A configuration compound, a synthesis method and application. The D-sigma-A configuration compound has a structural formula shown in the specification. The D-sigma-A configuration compound disclosed by the invention has better spectroscopic properties. A tested fluorescence emission spectrum shows that the emission peak in tetrahydrofuran, ethyl acetate, dichloromethane and acetonitrile solvents is 451 nm, and two fluorescence emission peaks exist in toluene and n-hexane solutions and are respectively in blue light and yellow light regions.

Description

technical field [0001] The invention belongs to the field of fluorescent materials and relates to fluorescent probes, in particular to a D-σ-A configuration compound, a synthesis method and an application. Background technique [0002] Spiro ring skeleton has three main characteristics: ① Two rings share one carbon atom; ② Rigid three-dimensional structure; ③ Potential central chirality or axial chirality, for example, the most common spiro ring skeleton-spiro [4.5] is as follows Show: [0003] [0004] In addition, because the spiro ring connects two diconjugated systems through a special cross configuration, it effectively inhibits the stacking effect between molecules and reduces fluorescence quenching, making it a useful luminescent material. Building blocks. And most of the materials with spiro ring as the core skeleton have a high glass transition temperature (Tg), excellent thermal stability and color stability, in addition, the spiro ring structure has excellent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06
CPCC07D209/86C09K11/06C07B2200/07C09K2211/1029C09K2211/1011
Inventor 谭博军刘宁卢先明汪伟葛忠学陈劭力
Owner XIAN MODERN CHEM RES INST
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