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Diarylethene fluorescent molecular switch and preparation method and application thereof

A technology of diarylethene and fluorescent molecules, which is applied in the fields of fluorescence/phosphorescence, chemical instruments and methods, and material analysis through optical means, and can solve problems such as low fluorescence quenching efficiency, no visible light response, and high fluorescence switching ratio. , to achieve high quantum yield, rich molecular switch system, and simple synthesis

Active Publication Date: 2018-02-02
HUAZHONG UNIV OF SCI & TECH
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  • Description
  • Claims
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Problems solved by technology

[0008] In view of the above defects or improvement needs of the prior art, the present invention provides a tetraarylethene-based diarylethene fluorescent molecular switch with aggregation-induced luminescence, its preparation method and application, the purpose of which is to adopt two Arylethylene quenches one or more fluorescent groups, and introduces a chromogenic group into the molecule or increases the degree of conjugation of the molecule to promote the red shift of its absorption spectrum; through the introduction of AIE (aggregation-induced emission) The group enables it to obtain strong luminescence in a solid state or in an aggregated state. Under the irradiation of ultraviolet light or visible light, multiple diarylethenes can quickly quench the fluorescence of the fluorescent groups gathered in the surrounding, so as to achieve the purpose of high fluorescence switch ratio. , so as to solve the technical problems that the fluorescent molecular switch in the prior art can only respond to ultraviolet light but not visible light, the switch ratio is small, and the fluorescence quenching efficiency is low

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  • Diarylethene fluorescent molecular switch and preparation method and application thereof
  • Diarylethene fluorescent molecular switch and preparation method and application thereof
  • Diarylethene fluorescent molecular switch and preparation method and application thereof

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preparation example Construction

[0059] The preparation method of the above fluorescent molecular switch comprises the following steps:

[0060] (1) Utilize Mcmurry reaction to couple intramolecular or intermolecular ketone carbonyls into olefinic bonds, and then Miyaura reaction occurs to generate boronic acid ester or boronic acid by halogen group to obtain tetraarylethene nucleus;

[0061] (2) For an aryl group containing two active sites, use Suzuki reaction to modify the active site at one end of the aryl group to obtain a diarylethene nucleus that retains the active site at the other end;

[0062] (3) Suzuki coupling reaction is performed between the tetraarylethene core obtained in step (1) and the diarylethene core obtained in step (2) which retains the active site at the other end.

[0063] Specifically, in the structure of formula (II), R 1 and R 2 for R 3 When it is a methoxy group, the preparation method of the corresponding fluorescent molecular switch includes the following steps:

[0064]...

Embodiment 1

[0082] A diarylethene fluorescent molecular switch shown in formula (2), whose name is abbreviated as Di(C 8 H 17 O-DTE)-TPE, where R 1 and R 2 for R 3 is methoxy. Its synthetic route is as figure 1 shown, including the following steps:

[0083] (1) ethylene glycol dimethyl ether was pretreated with nitrogen for 30 minutes to remove dissolved oxygen, and the raw materials were p-n-pentoxyphenylboronic acid (0.90 g, 3.6 mmol), 1,2-bis(5-bromo-2methylthiophene) -3-yl) perfluorocyclopentene (DTE-2Br) (1.58g, 3mmol) and sodium carbonate (1.59g, 15mmol) were uniformly dispersed in a mixture of ethylene glycol dimethyl ether and water according to the feeding ratio of 1:1.2:5 In the mixed solution of 4:1, the catalyst tetrakis (triphenylphosphine) palladium (0.17 g, 0.15 mmol) was added under nitrogen atmosphere, and the mixture was pumped 3 to 4 times. The reaction temperature was 90° C. and the reaction time was 20 hours. After completion of the reaction, the organic laye...

Embodiment 2

[0089] A diarylethene fluorescent molecular switch as shown in formula (1), whose name is abbreviated as Di(C 8 H 17 O-DTE)-OTPE, R 1 and R 2 for R 3 is H and X is O. Its synthetic route is as Figure 7 shown, including the following steps:

[0090] (1) Mix zinc powder with anhydrous tetrahydrofuran, slowly inject titanium tetrachloride (2.639 mL, 23.52 mmol) at 0°C under nitrogen atmosphere, reflux for 3 to 5 hours, cool down to room temperature, and add the raw material 2,2'-dichloromethane Bromobenzophenone (2g, 5.88mmol) and Zhanxanthone (1.154g, 5.88mmol) were dissolved in THF at a charging ratio of 1:1 and were added to the system quickly, and the system was pumped for 3 to 4 times. The reaction temperature was 80°C, and the reaction time for 5 hours. Use 10% K after the reaction 2 CO 3 The reaction was quenched and the organic layer was collected and purified by column chromatography to give the product OTPE-2Br.

[0091] (2) Potassium acetate (0.934g, 9.54m...

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Abstract

The invention discloses an aggregation-induced emission type diarylethene fluorescent molecular switch and a preparation method and application thereof. The aggregation-induced emission type diarylethene fluorescent molecular switch is characterized in that an AIE radical is introduced to gain solid or aggregation strong emission capacity; two diarylethene can be used for quickly quenching fluorescence of fluorescent radicals which aggregate in the surrounding under the irradiation of ultraviolet rays or visible light, thus achieving the purpose of high fluorescent switch ratio. According to the light control type AIE-effect fluorescent molecular switch, the limitation that traditional fluorescent chromophore leads to fluorescence quenching is broken; in addition, the fluorescent molecularswitch in solid and aggregation state has the advantages of being high in switch ratio and high in fluorescence quenching efficiency by being compared with the fluorescent molecular switch in solution state; the fluorescent molecular switch is applicable to information storage under solid state and photoelectric devices and has potential application in biosensing and fluorescence imaging.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and more specifically relates to a diarylethene fluorescent molecular switch with aggregation-induced luminescence, its preparation method and application. Background technique [0002] Aggregation-induced emission (AIE) materials, whether in solid state, nanoparticles, or in polymer media, can exhibit stronger fluorescence emission than in solution, which is of great help to realize the practical application of fluorescent materials. [0003] Wei-Hong Zhu's research group reported a fluorescent molecular switch that combines the AIE group quinoline malononitrile with diarylethene. The conversion rate of the photocyclization reaction is 57.6%. The tetrahydrofuran mixture has a fluorescence on-off ratio of about 5. Due to its low fluorescence intensity and low fluorescence quantum yield, it has not been used. [0004] Park's group reported for the first time a fluorescent molecular switch that co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14C07D333/16C09K11/06G01N21/64
CPCC07D333/16C07D409/14C09K11/06C09K2211/1007C09K2211/1088C09K2211/1092G01N21/6428
Inventor 李冲陈颖朱明强叶欢谢诺华
Owner HUAZHONG UNIV OF SCI & TECH
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