Trihalogen substituted triphenylethylene photochromic material and its synthesis method and application

A technology of photochromic materials and triphenylene, which is applied in the fields of color-changing fluorescent materials, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc. Limit the application prospects of high-speed information storage and other issues, and achieve the effects of easy and easy purification after post-processing, hydrophobic performance, and fast color-changing response.

Active Publication Date: 2021-06-11
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the response speed of this kind of compound to ultraviolet light is slow, and it takes 10s to complete under the irradiation of 365LED ultraviolet lamp. Application prospect of information storage

Method used

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  • Trihalogen substituted triphenylethylene photochromic material and its synthesis method and application
  • Trihalogen substituted triphenylethylene photochromic material and its synthesis method and application
  • Trihalogen substituted triphenylethylene photochromic material and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Synthesis of intermediate [diethyl 4-fluorophenylphosphate]

[0032]

[0033] 2.51 g of 4-fluorobenzyl chloride (0.01 mol) and 6.85 mL of triethyl phosphite (0.04 mol) were added to a 50 ml one-necked flask. Heat to 190°C and stir. After refluxing for 6 h, the reaction was cooled to room temperature, and excess triethyl phosphite was distilled off under reduced pressure. After cooling, n-hexane was added to the system to produce a white precipitate which was filtered and dried to obtain 2.21 g of a white solid with a yield of 90%. (2) synthesis of target product embodiment 1

[0034]

[0035] Add 4,4'-difluorobenzophenone (0.502g, 0.002mol), diethyl 4-fluorophenylphosphate (0.456g, 0.002mol) and dry THF solvent (30mL) into a 100mL three-neck round bottom flask, Stir under the protection of argon atmosphere and cool to 0°C with an ice bath, add potassium tert-butoxide (0.224 g, 0.002 mol), keep the ice bath for 0.5 h, then rise to room temperature and contin...

Embodiment 2

[0038] (1) Synthesis of intermediate [diethyl 4-chlorophenylphosphate]

[0039]

[0040] Referring to the step (1) of Example 1, 4-chlorobenzyl chloride was used instead of 4-fluorobenzyl chloride to synthesize diethyl 4-chlorophenylphosphate, and the yield was 93%.

[0041] (2) synthesis of target product embodiment 2

[0042]

[0043] Referring to step (2) of Example 1, use 4,4'-dichlorobenzophenone to replace 4,4'-difluorobenzophenone, and 4-chlorophenylphosphate diethyl ester to replace 4-fluorophenylphosphate diethyl The target product Example 2 was synthesized with an ester yield of 85%. 1 H NMR (400MHz, Chloroform-d) δ7.32(s,1H),7.30(d,J=2.1Hz,2H),7.27(s,1H),7.20(d,J=8.6Hz,2H),7.15 –7.07(m,4H),6.94(d,J=8.5Hz,2H),6.87(s,1H).

[0044] Under the irradiation of 365nm LED ultraviolet light source, the product of this example gradually turns red from white crystal powder, and the comparison of ultraviolet absorption spectra before and after photochromism is measured ...

Embodiment 3

[0046] (1) Synthesis of intermediate [diethyl 4-iodophenylphosphate]

[0047]

[0048] Referring to the step (1) of Example 1, 4-iodophenyl phosphate diethyl was synthesized by using 4-iodobenzyl bromide instead of 4-fluorobenzyl chloride, and the yield was 81%.

[0049] (2) synthesis of target product embodiment 3

[0050]

[0051] Referring to step (2) of Example 1, 4,4'-dibromobenzophenone is used to replace 4,4'-difluorobenzophenone, and 4-iodophenylphosphate diethyl ester is used to replace 4-fluorophenylphosphate diethyl Ester synthesis target product Example 3, yield 83%. 1 H NMR (400MHz, Chloroform-d) δ7.53–7.41(m,6H),7.14(d,J=8.6Hz,2H),7.03(d,J=8.4Hz,2H),6.84(s,1H) ,6.75(d,J=8.4Hz,2H).

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Abstract

The invention discloses a trihalogen substituted triphenylethylene photochromic material and its synthesis method and application. It has ultra-fast discoloration response speed, simple synthesis steps, low raw material prices, easy and easy purification of products after treatment, and high color purity. , good rewritability and other advantages, suitable for high-speed optical information storage, high-precision chemical and biological detection, and rapid biological imaging materials. In addition, using this photochromic reaction, the amorphous film of this series of materials is irradiated with ultraviolet light. Microcrystalline surfaces with different morphologies can be obtained, and the surface morphology can be controlled by light, thereby realizing the hydrophobicity of the surface by light control, which is suitable for anti-counterfeiting and light control materials and other fields.

Description

technical field [0001] The invention relates to the technical field of organic luminescent materials, in particular to a class of trihalogen-substituted triphenylethylene photochromic materials, a synthesis method thereof, and applications in the fields of chemical and biological detection, biological imaging, optical information storage, and the like. Background technique [0002] Photochromism refers to the reversible color change of chemical substances under the condition of absorbing electromagnetic radiation or heating (H. Diirr, H. Bouas-Lament. Pure and Applied Chemistry, 2001). Photochromic materials have great application potential in the fields of anti-counterfeiting, biological detection, chemical sensing, information storage, and molecular machines. With the development of basic scientific theory and analytical detection technology in recent decades, people have been able to achieve precise regulation of various physical and chemical properties at the molecular s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C25/24C07C1/34C07F9/40C09K9/02
CPCC07C1/34C07C25/24C07C2531/24C07F9/4056C09K9/02
Inventor 王乐宇于涛许锐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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