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Ortho-carborane-tetraphenylethylene compound, and preparation method and application thereof

A technology of tetraphenylethylene and o-carborane, which is applied in the field of o-carborane-tetraphenylethylene compounds and their preparation, can solve the problems of complex synthesis steps and lack of synthesis methods, and achieve simple reaction operations and mild conditions , the effect of broad application prospects

Active Publication Date: 2019-03-01
UNIV OF JINAN
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] By introducing tetraphenylethylene units into the carborane structure, research and obtain new aggregation-induced luminescent materials, which can not only further expand the application field of carborane compounds, but also obtain new aggregation-induced luminescent materials. On the other hand, The synthesis steps of the few existing carborane-tetraphenylethylene compounds are relatively complicated, and there is currently a lack of simpler synthesis methods for these compounds

Method used

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  • Ortho-carborane-tetraphenylethylene compound, and preparation method and application thereof
  • Ortho-carborane-tetraphenylethylene compound, and preparation method and application thereof
  • Ortho-carborane-tetraphenylethylene compound, and preparation method and application thereof

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preparation example Construction

[0060] The preparation method of thin-layer chromatography in the embodiment of the present invention is a conventional method, and the single crystal cultivation method is also a conventional method in the art.

[0061] Preferably, the thin-layer chromatography preparation method is as follows: take GF-254 silica gel, pour it into a prepared 0.5% sodium carboxymethylcellulose solution, stir and grind it thoroughly, spread the silica gel evenly on a square glass plate, vibrate the glass plate to make the silica gel Flatten it, place it in a cool place to dry, then place it in an oven to dry, cool to room temperature, and take it out. Among them, the volume-to-weight ratio of 0.5% sodium carboxymethylcellulose solution to silica gel is 2.5:1; the drying temperature in the shade is 20-30°C; the oven drying temperature is 100-120°C; the oven drying time is 2 ~3h; the cooling temperature in the oven is 40~50°C.

[0062] Preferably, the single crystal cultivation method is: dissol...

Embodiment 1

[0064]

[0065] In this embodiment, the reaction process and the addition process were all carried out under the protection of argon.

[0066] Add o-carborane (77.1mg, 0.54mmol), 1-(4-formylphenyl)-1,2,2-triphenylethylene (217.4mg, 0.60mmol) successively in the reaction flask, add 20mL to dry 1 mol / L tetrabutylammonium fluoride tetrahydrofuran solution (1 mol / L, 1.6 mL, 1.6 mmol) was added dropwise under stirring, and stirred at room temperature for 1 h.

[0067] The reaction was quenched by adding 15 mL of saturated aqueous ammonium chloride solution, and stirring was continued for 10 min. The reaction system was transferred to a separatory funnel for liquid separation, the aqueous phase was extracted with dichloromethane (15 mL×3), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to dryness to obtain a crude product. Thin-layer chromatography was used to separate and purify the crude product. The developer w...

Embodiment 2

[0074]

[0075] In this embodiment, the reaction process and the addition process were all carried out under the protection of argon.

[0076] Add o-carborane (72.3mg, 0.50mmol), 1,1-bis(4-formylphenyl)-2,2-diphenylethylene (116.6mg, 0.30mmol) successively in the reaction flask, add 10mL Dry tetrahydrofuran was added dropwise with 1 mol / L tetrabutylammonium fluoride tetrahydrofuran solution (1 mol / L, 1.5 mL, 1.5 mmol) under stirring, and stirred at room temperature for 65 min.

[0077] The reaction was quenched by adding 10 mL of saturated aqueous ammonium chloride solution, and stirring was continued for 10 min. The reaction system was transferred to a separatory funnel for liquid separation, the aqueous phase was extracted with dichloromethane (15 mL×3), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to dryness to obtain a crude product. Use thin-layer chromatography to separate and purify the crude produc...

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Abstract

The invention discloses an ortho-carborane-tetraphenylethylene compound, and a preparation method and application thereof, and belongs to the field of organic synthesis and luminescent materials. Theortho-carborane-tetraphenylethylene compound has the following structure, wherein R1 is selected from H, CHO or a structure shown in the description (the unlabeled vertices in the carborane structureare BH). The ortho-carborane-tetraphenylethylene compound has the advantages that an ortho-carborane system structure is combined with tetraphenylethylene to form a new compound system; by the preparation method, the defect that boron in ortho-carborane is easy to remove under the similar conditions in the prior art is avoided; the reaction operations are simple, and the conditions are moderate; the obtained ortho-carborane-tetraphenylethylene compound has the aggregation-inducing luminescence property and the force-induced fluorescence discoloration property, thereby being a good photo-functional material; the ortho-carborane-tetraphenylethylene compound can be applied to the fields of luminescent materials, biological probes and chemical sensing, and has a broad application prospect.

Description

technical field [0001] The invention relates to the field of organic synthesis and luminescent materials, in particular to an o-carborane-tetraphenylethylene compound and a preparation method and use thereof. Background technique [0002] With the discovery and research of the aggregation-induced emission (AIE) phenomenon, researchers have synthesized a large number of compounds with AIE properties, and began to involve the synthesis and application of new AIE materials in different high-tech fields. [0003] Aggregation-induced luminescent materials have a wide range of applications in the fields of chemistry, materials, and life sciences, covering biological probes, chemical sensors, optoelectronic devices, and stimuli-responsive materials. At present, the AIE organic compound systems that have been studied more mainly include tetraphenylethylene (TPE), silole (silole) and 9,10-distyryl anthracene. Among them, TPE, as a typical molecule with AIE properties, is mainly used...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/05C09K9/02C09K11/06G01N21/64
CPCC07F5/05C09K9/02C09K11/06C09K2211/1007C09K2211/1096G01N21/64
Inventor 聂永张昊苗金玲孙国新李业新
Owner UNIV OF JINAN
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