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Diarylethene organic photochromic material based on furan as well as preparation method and application thereof

A photochromic material, diarylethene technology, applied in the field of materials science, can solve the problems of high cost and complex synthesis route, and achieve the effects of excellent fatigue resistance, high yield and good thermal stability

Inactive Publication Date: 2017-09-01
SHANGHAI UNIVERSITY OF ELECTRIC POWER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a furan-based organic photochromic material and its preparation method and application. The described organic photochromic material and its preparation method and application can solve the problem of The organic photochromic materials in the prior art have complex synthetic routes and high cost technical problems, and at the same time can realize the application in biological imaging, biological sensing and environmental protection materials

Method used

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  • Diarylethene organic photochromic material based on furan as well as preparation method and application thereof
  • Diarylethene organic photochromic material based on furan as well as preparation method and application thereof
  • Diarylethene organic photochromic material based on furan as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1 (the synthesis of organic photochromic material DFC):

[0031] Synthesis of compound DFC

[0032]

[0033] The preparation method of 4-bromo-5-methylfuran-2-carbaldehyde (compound 2) can be found in literature (Sysoiev D, Fedoseev A, Kim Y, et al.Synthesis and Photoswitching Studies of Difurylperfluorocyclopentenes with Extendedπ‐Systems[J].Chemistry–A European Journal, 2011, 17(24):6663-6672.)

[0034] Preparation method of 5-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde (compound 3). 250ml three-necked bottle with N 2 Replace gas three times, N 2 Under protection, 9.45g compound 2 (50mmol), 19.05g biboronic acid pinacol ester (75mmol), 14.7g potassium acetate (150mmol) and 1.83g PdCl were added successively. 2 dppf (2.5 mmol). Finally, DMF after strict deoxygenation was added. The reaction was stirred at 80°C for 48 hours. Chromatography (eluent PE:EA=10:1) gave 9.8 g of a light yellow solid with a yield of 83%. 1 H...

Embodiment 2

[0036] Embodiment 2 (photochromic performance of organic photochromic material DFC):

[0037] The compound DFC obtained above was dissolved in acetonitrile to make a concentration of 10 μmol L -1 acetonitrile solution. Add 2.5mL of the solution to be tested into a 1cm×1cm×4cm quartz cuvette with stirring, and use a 365nm monochromatic light source according to different time lengths (1min, 2min, 3min, 4min, 5min, 6min, 7min, 8min, 9min , 10min, 11min, 12min, 13min, 14min, 15min, 16min, 17min, 18min, 19min, 20min, 21min, 22min) to irradiate the solution to be tested, and adopt a UV-visible spectrophotometer to measure the absorption spectrum, the result is as follows figure 1 shown. Under the irradiation of 365nm ultraviolet light, a new absorption peak appeared in the absorption spectrum at 520nm, and gradually increased to reach the photostable state with the prolongation of time, and the color of the solution also changed from colorless to pink. Under the irradiation of v...

Embodiment 3

[0038] Embodiment 3 (biological application of organic photochromic material DFC):

[0039] Compounds DFC (1,2-bis(5-formyl-2-methyl-3-furyl)cyclopentene) and DTC (1,2-bis(5-formyl-2-methyl-3-thiophene base) Cytotoxicity of cyclopentene was quantitatively determined by Cell Counting Kit-8 (CCK-8). In the experiment, MC3T3-E1 cells (from the Cell Bank of Shanghai Branch of the Chinese Academy of Sciences) were cultured in MEM-α medium at 1.0×10 4 Cells / well were seeded into 96-well plates. After 12 hours of cell growth, the medium was replaced with new medium (200 μL / well) containing various concentrations of the compounds DFC and DTC. Before performing the CCK-8 assay, replace the medium from the previous step with 200 μL of new medium containing 20 μL of CCK-8 solution, and incubate the cells for a further 48 h. After incubation for 3 hours, the absorbance at 450 nm in each well was measured using a microplate reader (Multiskan Mk 3). Quantitative cytotoxicity was calcula...

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Abstract

The invention provides a diarylethene organic photochromic material based on furan. The structural formula of the diarylethene organic photochromic material is of formula I as shown in the specification. The invention further provides a preparation method of the photochromic material. The preparation method comprises the following steps: in a reaction container, performing reaction on a substituted aldehyde compound based on diarylethene, dibromocyclopentene, potassium phosphate, a palladium catalyst, N,N-dimethylformamide or dioxane or tetrahydrofuran or methylbenzene for 1-24 hours at 20 DEG C to backflow temperature, cooling, filtering, extracting, performing spinning drying, and passing through a column, thereby obtaining a diarylethene compound of formula I. The photochromic material is simple and efficient in preparation method, high in yield, good in economy, high in on-scale production value and good in environmental-friendliness. The photochromic material has very good spectral properties, can be used for preparing multihoming photoelectric molecule switches, molecular lead elements, photochromic light emitting devices and the like.

Description

technical field [0001] The invention belongs to the field of materials science, and relates to a green organic photochromic material, in particular to a furan-based diarylethene organic photochromic material and its preparation method and application. Background technique [0002] Since Masahiro Irie first proposed the theory of bistable diarylethenes in 1988, diarylethenes have attracted extensive research interest. After nearly 30 years of development, diarylethene has shown great application value in various fields such as optoelectronic devices, information storage, bioimaging, sensing, anti-counterfeiting, and display. For organic photochromic materials, the reading and writing of information all adopts the all-photon mode, so designing and preparing high-performance organic photochromic materials has always been the goal pursued by researchers. Photochromic phenomenon means that when a compound is irradiated by a certain wavelength of light, it can undergo a specific ...

Claims

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Application Information

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IPC IPC(8): C09K9/02C09K11/06C07D307/46G01N21/64A61K49/00
CPCC09K9/02A61K49/0021C07D307/46C09K11/06C09K2211/1007C09K2211/1088G01N21/643G01N2021/6432
Inventor 陈文博王上上邹祺朱亮亮
Owner SHANGHAI UNIVERSITY OF ELECTRIC POWER
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