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Non-conjugated aniline bridged tetraphenylethylene donor-acceptor Stehausen adduct as well as preparation method and application of non-conjugated aniline bridged tetraphenylethylene donor-acceptor Stehausen adduct

A technology of tetraphenylethylene and conjugated aniline bridges, which is applied in the field of synthesis of new compounds, can solve the problems of insignificant fluorescence intensity, weak fluorescence intensity, and no strong fluorescent groups, etc., and achieve excellent photochromic performance and fast photoresponse rate , The effect of the simple synthesis method

Active Publication Date: 2022-07-01
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But its disadvantages are: ① ultraviolet light excitation, high-energy light damages a lot; ② weak fluorescence intensity, no strong fluorescent group, the effect of controlling fluorescence intensity is not obvious; ③ poor applicability, and the effect of applying to information storage is not good

Method used

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  • Non-conjugated aniline bridged tetraphenylethylene donor-acceptor Stehausen adduct as well as preparation method and application of non-conjugated aniline bridged tetraphenylethylene donor-acceptor Stehausen adduct
  • Non-conjugated aniline bridged tetraphenylethylene donor-acceptor Stehausen adduct as well as preparation method and application of non-conjugated aniline bridged tetraphenylethylene donor-acceptor Stehausen adduct
  • Non-conjugated aniline bridged tetraphenylethylene donor-acceptor Stehausen adduct as well as preparation method and application of non-conjugated aniline bridged tetraphenylethylene donor-acceptor Stehausen adduct

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preparation example Construction

[0047] The preferred preparation method of the compound of formula is exemplarily provided below, which should not be construed as a limitation of the present invention by those skilled in the art.

[0048] The synthetic route and preparation method of existing known compounds A1, A2 are as follows:

[0049]

[0050] Preparation of compound A1:

[0051] 1,3-Diethyl-2-thiobarbituric acid (2.00 g, 10.0 mmol) and furfural (830 μL, 10.0 mmol) were added sequentially to 30 mL of H 2 O was stirred at 70°C for 2.5 hours. After the reaction was complete (monitored by TLC), the formed yellow precipitate was collected by vacuum filtration and washed with cold H 2 O wash twice. The resulting solid was dissolved in dichloromethane (75 mL) and washed with 30 mL saturated sodium chloride solution, 30 mL saturated sodium bicarbonate solution, 30 mL H 2 O wash. with MgSO 4 After drying to remove water, the solid was separated by filtration, and the filtrate was collected and concentr...

Embodiment 1

[0057] (1) Preparation of 4-(1,2,2-triphenylvinyl)benzaldehyde

[0058] Take a 250mL three-necked flask, under the protection of nitrogen, 3-bromostyrene (3.340g, 10mmol), 4-formylbenzeneboronic acid (1.500g, 10mmol), potassium carbonate (4.150g, 30mmol), four (tri Phenylphosphine) palladium (0.100g, 0.1mmol) and tetrahydrofuran 80mL were successively added to the there-necked flask, heated to 70° C., refluxed for 12 hours, and the reaction process was monitored by TCL (petroleum ether: ethyl acetate=20:1, v / v). After completion of the reaction, heating was stopped, the mixture was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. 40 mL of dichloromethane was added, followed by extraction with water (30 mL) and saturated sodium chloride solution (30 mL) three times. The organic layers were combined and dried over anhydrous magnesium sulfate to remove water. After the magnesium sulfate solid was removed by filtration, dich...

Embodiment 2

[0067] (1) Preparation of 4-(1,2,2-triphenylvinyl)benzaldehyde

[0068] Take a 250mL three-necked flask, under the protection of nitrogen, 3-bromostyrene (3.340g, 10mmol), 4-formylbenzeneboronic acid (3.000g, 20mmol), potassium carbonate (4.150g, 30mmol), four (tri Phenylphosphine) palladium (0.200g, 0.2mmol) and tetrahydrofuran 80mL were successively added to the there-necked flask, heated to 80°C, refluxed for 24 hours, and the reaction process was monitored by TCL (petroleum ether: ethyl acetate=20:1, v / v). After completion of the reaction, heating was stopped, the mixture was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. 40 mL of dichloromethane was added, followed by extraction with water (30 mL) and saturated sodium chloride solution (30 mL) three times. The organic layers were combined and dried over anhydrous magnesium sulfate to remove water. After the magnesium sulfate solid was removed by filtration, dichlo...

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Abstract

The invention relates to the field of synthesis of new compounds, in particular to a donor-acceptor Steulcuus adduct of non-conjugated aniline bridged tetraphenyl ethylene as well as a preparation method and application of the donor-acceptor Steulcuus adduct. The compound has any one structural formula of a formula (I) and a formula (II). The non-conjugated aniline bridged tetraphenyl ethylene donor-acceptor Steiner hausen adduct DASAs prepared by the preparation method disclosed by the invention has excellent photochromic performance and fluorescence control capability under visible light, and has certain potential in the aspect of fluorescent material application.

Description

technical field [0001] The invention relates to the field of new compound synthesis, in particular to a donor-acceptor Steinhaus adduct of a non-conjugated aniline bridged tetraphenylene and a preparation method and application thereof. Background technique [0002] Molecular switches are one of the important components in the construction of photosensitive materials. They usually contain organic functional groups that can absorb light energy. Photochromic molecules can reversibly switch from one state to another under excitation of light of different wavelengths. Compared with other stimuli such as temperature, pH, redox, etc., light can achieve cross-spatial control, which has unique advantages. Donor-Acceptor Stenhouse Adducts (DASAs) compounds are a new type of visible light photochromic compounds. Such molecules can freely switch between circular and linear shapes under different illumination conditions, accompanied by changes in molecular size and polarity. Under v...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/60C07D319/06C09K11/06C09K9/02
CPCC07D239/60C07D319/06C09K11/06C09K9/02C09K2211/1007C09K2211/1014C09K2211/1044C09K2211/1088Y02E10/549
Inventor 曹德榕符鹏王胜
Owner SOUTH CHINA UNIV OF TECH
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