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D-A spiro spiro skeleton configuration compound, synthetic method and application

A synthesis method and compound technology, applied in the field of fluorescent materials, can solve the problems of limiting the application of D-A type spirocyclic skeleton molecular frameworks, few synthesis methods, cumbersome reaction steps, etc., and achieve simple synthesis methods, simple reaction conditions and wide application foreground effect

Pending Publication Date: 2021-11-12
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, there are few reports of D-A type spirocyclic skeleton molecules in the literature, and the traditional construction methods have disadvantages such as cumbersome reaction steps and fewer synthesis methods in organic synthesis, which greatly limit the D-A type spirocyclic skeleton structure. Application of Molecular Framework

Method used

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  • D-A spiro spiro skeleton configuration compound, synthetic method and application
  • D-A spiro spiro skeleton configuration compound, synthetic method and application
  • D-A spiro spiro skeleton configuration compound, synthetic method and application

Examples

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Effect test

Embodiment 1

[0053] This embodiment provides a kind of synthetic method of D-A spirocyclic skeleton structure compound, and this method comprises the following steps:

[0054] 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 the 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, and the extraction was repeated 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...

Embodiment 2

[0075] This embodiment provides a kind of synthetic method of D-A spirocyclic skeleton structure compound, and this method comprises the following steps:

[0076] 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, 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, and the extraction was repeated 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), t...

Embodiment 3

[0083] This example presents the application of the D-A spirocyclic skeleton compound as a fluorescent material. The D-A spirocyclic skeleton compound in this example uses the D-A spirocyclic skeleton compound obtained in Example 1.

[0084] The D-A spiro ring skeleton type compound that obtains in embodiment 1 has carried out the mensuration of fluorescence emission spectrum, finds that it has better spectroscopic property, as figure 1 shown. It can be seen from its fluorescence emission spectrum that its peaks are all in the blue light region in different solutions. As the polarity of the solvent changes, the position of the emission peak does not change, but the emission intensity changes. Among them, the emission intensity is the largest in dichloromethane, and the emission intensity is the smallest in acetonitrile. It has broad application prospects.

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Abstract

The invention provides a D-A spiro skeleton configuration compound as well as a synthesis method and application thereof. The D-A spiro skeleton configuration compound has a structural formula shown in the specification. The D-A spiro skeleton configuration compound disclosed by the invention has better spectroscopic properties. From a tested fluorescence emission spectrum, peaks in different solutions are all in a blue light region. Along with the change of the polarity of the solvent, the emission peak position is not changed, and the emission intensity is changed.

Description

technical field [0001] The invention belongs to the field of fluorescent materials and relates to a fluorescent probe, in particular to a D-A spirocyclic skeleton 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 exc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06
CPCC07D209/86C09K11/06C09K2211/1029C07B2200/07
Inventor 谭博军刘宁徐明辉莫洪昌段秉蕙
Owner XIAN MODERN CHEM RES INST
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