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Triarylethene photochromic material containing furan derivatives and its synthesis method and application

A photochromic material, triarylethylene technology, applied in the direction of color-changing fluorescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of high material cost, easy oxidation cycle times, complicated design and synthesis, etc. Excellent rewritability, excellent development potential

Active Publication Date: 2022-06-07
SUN YAT SEN UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

However, most traditional organic photochromic materials have problems such as complex design and synthesis, high material cost, easy oxidation, and poor cycle times.
The structure of triarylethene compounds is simple and easy to modify, and has the advantages of excellent chemical and physical stability and good fatigue resistance. Triphenylethylene derivatives with excellent photochromic properties (Ou D, et.al.Chemical Science, 2016, 7(8):5302-5306), however, this type of emerging materials has great potential in real-time regulation and long-term memory storage. There are still some deficiencies that need further improvement

Method used

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  • Triarylethene photochromic material containing furan derivatives and its synthesis method and application
  • Triarylethene photochromic material containing furan derivatives and its synthesis method and application
  • Triarylethene photochromic material containing furan derivatives and its synthesis method and application

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preparation example Construction

[0029] The above-mentioned synthetic method of the triarylethylene-based photochromic material containing furan derivatives, comprising the following methods:

[0030] Method (1): Synthesize the dibromo-substituted product of the furan ring or its derivative containing a formaldehyde substituent at one end through the Corey-Funchs reaction; The target product is obtained by Suzuki reaction. Preferably, the method (1) includes the following steps: 1. providing a furan ring containing a formaldehyde substituent at one end or a derivative thereof, in a dichloromethane solution, under the action of triphenylphosphine and carbon tetrabromide, at room temperature The reaction obtains its dibromo substituted product; ② the dibromo substituted product obtained in step 1 is combined with an aromatic compound or heterocyclic compound containing boronic acid or pinacol boronate group in a tetrahydrofuran solution, under the action of potassium carbonate, through tetratriphenylene The ta...

Embodiment 1

[0035] (1) Synthesis of intermediate [2-(2,2-dibromoethylene)furan]

[0036]

[0037] In a 250ml single-necked flask, add 60ml of dichloromethane, 4.76g of carbon tetrabromide (20mmol) and 10.49g of triphenylphosphine (40mmol), place in an ice-water bath, and add 0.96g of 2-furan after reacting on a magnetic stirrer for 1h Formaldehyde (10mmol) was reacted at room temperature for 16h. A black solution was obtained, and the excess solvent was evaporated in a rotary evaporator to obtain an oily mixed product. Then, it is purified by silica gel column chromatography, and the eluent is n-hexane. 2.28 g of white solid were obtained, and the yield was 91.31%.

[0038] (2) Synthesis of target product Example 1

[0039]

[0040] Add 1.25g 2-(2,2-dibromoethylene) furan (5mmol) and 1.68g phenylboronic acid (15mmol) in a 250mL there-necked flask, add an appropriate amount of THF in a nitrogen atmosphere, add 3.45g K 2 CO 3 (15.00mmol) in 2mol / L aqueous solution, add 5‰ catalys...

Embodiment 2

[0042]

[0043] Referring to the step (2) of Example 1, 4-fluorophenylboronic acid was used to synthesize the target product Example 2, and the yield was 88.24%. 1 H NMR (500MHz, DMSO-d 6 )δ7.52(d,J=1.4Hz,1H),7.35-7.27(m,4H),7.26-7.19(m,2H),7.19-7.12(m,2H),7.01(s,1H),6.37 –6.31(m,1H),5.55(d,J=3.4Hz,1H).

[0044] The product of this example is formulated to a concentration of 1.0×10 -3 M tetrahydrofuran solution, under the irradiation of 365nm LED ultraviolet light source, gradually turned yellow from a colorless and transparent solution, and measured the comparison of ultraviolet absorption spectra before and after photochromic figure 1 shown.

[0045] Under the irradiation of 365nm LED ultraviolet light source, the product of this example gradually turned yellow from white crystal powder. The comparison of ultraviolet absorption spectra before and after photochromic was measured. figure 2 shown.

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Abstract

The invention discloses a triarylethene photochromic material containing furan derivatives and its synthesis method and application. On the basis of the traditional triphenylethylene photochromic material, furan and its Derivative groups, and optimize the synthetic route, greatly expand the controllable range of the material, the synthesis method is simple, easy to purify, greatly improve its photochromic performance, and focus on improving the color stability and controllability of this series of materials And it effectively reduces the production cost of materials, so it is suitable as memory storage materials, smart wearable devices, etc. In addition, since the raw materials used are all chemical raw materials with mature technology, and the simple synthesis and purification steps provide great potential for the large-scale market application of this system material.

Description

technical field [0001] The invention relates to the field of new materials, in particular to a furan derivative-containing triarylethylene photochromic material, a synthesis method thereof, and applications in the fields of optical information storage, wearable devices, optical control materials, security and anti-counterfeiting, biological detection and the like . Background technique [0002] In recent years, photochromism refers to the reversible color change of a chemical substance under the condition of absorbing electromagnetic radiation. In the process of interconversion between two states, compounds are usually accompanied by a series of changes in chemical and physical properties such as refractive index, dielectric constant, solubility, luminescence, surface wettability or mechanical performance. Therefore, photochromic materials have great potential in the fields of anti-counterfeiting, detection, nonlinear optics, information storage, single-molecule logic gates...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/36C07D307/38C07D405/14C09K9/02
CPCC09K9/02C07D307/36C07D307/38C07D405/14C09K2211/1029C09K2211/1088
Inventor 于涛王乐宇詹天涯谢宗良杨志涌郑世昭赵娟刘四委张艺池振国许家瑞
Owner SUN YAT SEN UNIV
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