Visible-light-regulated dithienyl ethylene fluorescent molecular switch and preparation method and application thereof

A technology of dithienylethylene and fluorescent molecules, which is applied in the direction of fluorescence/phosphorescence, material analysis through optical means, and luminescent materials, etc., can solve the problem of low fluorescent switch ratio, achieve high fluorescent switch ratio, good fatigue resistance, The effect of high fluorescence quenching efficiency

Active Publication Date: 2021-02-02
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In view of the defects or improvement needs of the prior art, the purpose of the present invention is to provide a dithienylethylene fluorescent molecular switch that is fully regulated by visible light and ha

Method used

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  • Visible-light-regulated dithienyl ethylene fluorescent molecular switch and preparation method and application thereof
  • Visible-light-regulated dithienyl ethylene fluorescent molecular switch and preparation method and application thereof
  • Visible-light-regulated dithienyl ethylene fluorescent molecular switch and preparation method and application thereof

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preparation example Construction

[0068] The invention provides the preparation method of the said dithienylethylene derivative, comprising the following preparation steps:

[0069](1) First, use 3,5-dibromo-2-methylthiapan, n-butyllithium and trimethylchlorosilane as raw materials to obtain 3-bromo-2-methyl-5-trimethyl through substitution reaction base silylthiophene; then use 3-bromo-2-methyl-5-trimethylsilylthiophene, n-butyllithium and perfluorocyclopentene as raw materials to prepare 1,2-bis(2-methyl base-5-trimethylsilylthiophen-3-yl)perfluorocyclopentene, and finally 1,2-bis(2-methyl-5-trimethylsilylthiophen-3-yl)perfluorocyclopentene Pentene, anhydrous tetrahydrofuran and NBS were used as raw materials, and reacted at room temperature for 16 hours in the dark to obtain a compound, 1,2-bis(5-bromo-2-methylthiophen-3-yl) perfluorocyclopentene, namely Br -DTE-Br.

[0070] (2) With Br-DTE-Br, with R 1 and R 2 The aniline compound and triphenylphosphine of the group are the main reaction raw materials,...

Embodiment 1

[0087] A kind of diarylethene fluorescent molecular switch shown in formula (three), wherein R 1 and R 2 for Its name is abbreviated as TPA-AC-DTE-Ph-O-PMI (or DTE-PMI-1), and its synthetic route is as follows figure 1 shown, including the following steps:

[0088] (1) References for the synthesis process of Br-DTE-Br (Li Chong, Synthesis, properties and applications of diarylethene fluorescent molecular switches [D]. Wuhan, Huazhong University of Science and Technology Wuhan Optoelectronics National Research Center, 2015: 28- 32).

[0089] (2) Under nitrogen protection, Br-DTE-Br (1.5g, 4.75mmol), triphenylphosphine (0.015g, 0.095mmol), 4-ethynyltriphenylamine (0.77g, 4.75mmol), redistilled 25mL of triethylamine and 120mL of redistilled tetrahydrofuran were quickly poured into a 250mL two-necked flask, and Pd(PPh 3 ) 2 Cl 2 (0.01g, 0.238mmol) and copper iodide (0.108g, 0.095mmol), carefully evacuate nitrogen several times to remove oxygen, and react at 90°C for 24h. A...

Embodiment 2

[0098] A kind of diarylethene fluorescent molecular switch shown in formula (four), its name is abbreviated as TPA-AC-DTE-PMI (or DTE-PMI-2), wherein R 1 and R 2 for Its synthetic route is as follows Image 6 shown, including the following steps:

[0099] (1) The synthesis of Br-DTE-Br is shown in Example 1;

[0100] (2) The synthesis process of TPA-AC-DTE-Br is shown in Example 1;

[0101] (3) PMI-Br (0.80g, 1.42mmol), bis-boronic acid pinacol ester (0.54g, 2.2mmol) and potassium acetate (0.36g, 3.6mmol), divalent palladium catalyst were added to a 50mL two-necked flask PdCl 2 (dppf) (50mg, 0.072mmol) and redistilled 1,4-dioxane (50mL), stirred and mixed evenly, evacuated nitrogen three times to remove oxygen, heated to 90°C for 16h. Quench the reaction solution, after cooling to room temperature, use CH 2 Cl 2 Extraction, the organic phases were combined and washed three times with distilled water, washed with anhydrous MgSO 4 After drying, suction filtration, spin...

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Abstract

The invention belongs to the field of new materials, and particularly relates to a visible-light-regulated dithienyl ethylene fluorescent molecular switch and a preparation method and application thereof. The dithienyl ethylene derivative takes aniline alkynyl as a photosensitization group and perylene monoimide (PMI) as a fluorescent group, and comprises a structural unit shown as a formula (I) or a formula (II), wherein R1 and R2 are respectively and independently alkyl of C1-C10, alkyl alcohol of C1-C10 or aryl of C6-C20. When the derivative is used as a fluorescent molecular switch, the introduction of an aniline alkynyl group enables the fluorescence response wavelength of the molecular switch to be redshifted to a visible light region, and the derivative has the advantages of good thermal stability, good fatigue resistance, high cyclization rate, high fluorescence switch ratio and the like.

Description

technical field [0001] The invention belongs to the field of new materials, and more specifically relates to a dithienylethylene fluorescent molecular switch regulated by visible light, its preparation and application. Background technique [0002] Dithienylethylene fluorescent molecular switch has high fluorescent quantum yield, high fluorescent switch ratio, good fatigue resistance and thermal stability, and can still maintain good optical switching performance in thin films, which is very important for realizing ultra-high density Optical storage and super-resolution imaging have great research significance. [0003] After the first report of fully visible light-regulated diarylethene molecular switch 20 years ago, Lehn and his colleagues successfully red-shifted the DAEs for the first time by introducing two additional thiophene units at the 5-position and 5'-position of dithiophene. absorb. Then Irie et al. synthesized a class of compounds with perfluorocyclopentadith...

Claims

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Application Information

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IPC IPC(8): C07D409/14C09K11/06G01N21/64
CPCC07D409/14C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1092G01N21/6428G01N21/6458
Inventor 朱明强骆鹏飞李冲熊凯
Owner HUAZHONG UNIV OF SCI & TECH
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