O-carborane-tetraphenylethylene compound and its preparation method and use

Abstract

The invention discloses an o-carborane-tetraphenylethylene compound, a preparation method and an application thereof, and belongs to the field of organic synthesis and luminescent materials. The o-carborane-tetraphenylethylene compound includes the following structure: wherein, R 1 Selected from H, CHO or (wherein, the vertices not marked in the carborane structure are all BH). The invention provides an ortho-carborane-tetraphenylethylene compound, which combines the ortho-carborane system structure with tetraphenylethylene to form a new compound system. Carborane has the disadvantage of being easy to deboron under similar conditions, and the reaction operation is simple and the conditions are mild. The o-carborane-tetraphenylethylene compound obtained in the present invention not only has aggregation-induced luminescent properties, but also has mechanofluorescent discoloration properties, and is a better optical functional material, which can be used for luminescent materials, biological probes and In the field of chemical sensing, it has broad application prospects.

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...

Examples

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...

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...

Examples

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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