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Bifluorene-containing helicene-like compound and synthesis method thereof

A synthesis method and compound technology, applied in the directions of hydrocarbons, hydrocarbons, chemical instruments and methods, etc., can solve the problems of long reaction route, dangerous conditions, difficult to control, etc., to avoid dangerous conditions but difficult to control, high fluorescence The effect of quantum efficiency

Pending Publication Date: 2022-02-25
TIANJIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention aims to solve the related technical problems in the synthesis method of the helicoid compound containing monofluorene, and provides a helicoid compound containing bisfluorene and its synthesis method, which uses naphthalene substituted with diarylic acid as the raw material for the first time , using the intramolecular Friedel-Crafts acylation reaction strategy to construct a new type of helicene-like compound containing bisfluorene; the synthesis method is simple and easy to operate, avoiding the problems of dangerous conditions that are difficult to control, long and uneconomical reaction routes, etc. in previous methods. And by adjusting different aryl substituent groups to obtain conjugated extended helicoid molecules

Method used

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  • Bifluorene-containing helicene-like compound and synthesis method thereof
  • Bifluorene-containing helicene-like compound and synthesis method thereof
  • Bifluorene-containing helicene-like compound and synthesis method thereof

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Embodiment 1

[0046] The compound IIa of embodiment 1 is prepared, and the reaction formula is:

[0047]

[0048] Embodiment 1 is prepared according to the following steps:

[0049] (1) Synthesis of intermediate IVa: In a 25mL dry three-neck flask that has been placed in a magnet, place a reflux condenser, and add diaryl-substituted naphthalene Va (308mg, 1mmol), NBS (1.068g, 6mmol), BPO (0.14g, 0.6mmol), then add anhydrous CCl 4(10mL), stirred and refluxed for 24h. The resulting reaction solution was spin-dried in vacuo, followed by extraction with dichloromethane and washed with distilled water. After the collected organic phase was dried over anhydrous sodium sulfate, the solvent was spin-dried, and the obtained crude product was placed in a 100 mL three-necked flask. Add ethanol (30mL) and silver nitrate solution (7.5mL), stir and reflux for 24h. After the reaction is complete, filter while hot to remove the green precipitate. The obtained filtrate was spin-dried to obtain a crud...

Embodiment 2

[0066] Steps (1)-(3) of Example 2 are the same as in Example 1; the difference is only in the preparation of compound Ib, and the chemical reaction formula is as follows:

[0067]

[0068] In a 25 mL reaction tube protected by an argon atmosphere, 2-bromo-1,1'-biphenyl (3 equiv, 52 μL) was added, and then tetrahydrofuran (2.0 mL) was added and stirred to dissolve. The reaction solution was frozen to -78°C, n-butyl lithium in n-hexane (1.6M, 0.19 mL) was added dropwise, and the reaction was stirred at -78°C for 30 min. Next, a tetrahydrofuran solution (2 mL) of IIa (0.1 mmol, 33 mg) was added to the previously prepared lithium reagent solution, and the reaction was continued to stir and slowly returned to room temperature. The reaction was quenched by adding saturated ammonium chloride solution, extracted with ethyl acetate, washed with distilled water, dried over anhydrous sodium sulfate, and the obtained solid was placed in a 25 mL reaction tube after being spin-dried. Un...

Embodiment 3

[0071] Steps (1)-(3) of Example 3 are the same as in Example 1; the difference is only in the preparation of compound Ic, and the chemical reaction formula is as follows:

[0072]

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Abstract

The invention belongs to the technical field of carbocyclic compounds, and discloses a difluorene-containing helicene-like compound and a synthesis method thereof. Diaryl acid substituted naphthalene is used as a raw material, and an intramolecular Friedel-Crafts acylation ring formation reaction is adopted to successfully prepare a class of helicene-like compounds with spiral chirality and photoelectric functional properties. The method has the advantages of being short in synthesis route, high in yield, easy to operate and the like, and is different from a traditional helicene synthesis ring formation method, and the novel Friedel-Crafts acylation ring formation strategy is low in preparation cost and easy to popularize. Based on a new cyclization strategy, different aryl functional groups such as a benzene ring, a naphthalene ring and a phenanthrene ring can be changed to correspondingly obtain the [6]-[10] helicene-like compound. Based on the luminescence property of fluorene and the inherent spiral chirality of helicene, the compound is expected to be widely applied in the fields of circular polarization luminescence, organic electroluminescence, nonlinear optics and the like.

Description

technical field [0001] The invention belongs to the technical field of carbocyclic compounds, and in particular relates to a bifluorene-containing helicoid compound and a synthesis method thereof. Background technique [0002] Helicene is a class of polycyclic aromatic compounds with a helical structure formed by at least four aromatic rings condensed at the ortho position. Due to the steric repulsion between the aromatic rings at the end of the backbone, this type of molecule exhibits a special P / M helical chirality, and thus can exhibit unique physicochemical and optical properties. However, helicene molecules usually exhibit poor luminescent properties. As a widely reported blue chromophore, fluorene has been successfully introduced into planar conjugated molecular systems, such as small molecules and polymers, and the resulting fluorene-containing compounds have strong luminescent properties, which can be used as luminescent materials used in organic optoelectronic dev...

Claims

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Application Information

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IPC IPC(8): C07C13/62C07C13/72C07C1/32
CPCC07C13/62C07C13/72C07C1/326C07C45/46C07C2603/54C07C2603/94C07C49/665
Inventor 孙哲徐站强龚宗丞
Owner TIANJIN UNIV
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