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Spiropyran derivative, photochromic material and preparation method of photochromic material

A technology of photochromic materials and spiropyran derivatives, applied in color-changing fluorescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of reduced detection accuracy and interference, and achieve low equipment investment and stable luminescent properties , The effect of easy access to raw materials

Active Publication Date: 2021-06-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the currently studied photochromic materials all emit light with a short lifetime (such as nanoseconds), and are easily interfered by the short-lived background fluorescence in the organism during the detection process, resulting in a decrease in detection accuracy.

Method used

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  • Spiropyran derivative, photochromic material and preparation method of photochromic material
  • Spiropyran derivative, photochromic material and preparation method of photochromic material
  • Spiropyran derivative, photochromic material and preparation method of photochromic material

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preparation example Construction

[0058] [Preparation method of photochromic material]

[0059] The present invention also provides a preparation method of a photochromic material as shown above, which includes the following steps:

[0060] (1), dissolving the host material in the first solvent to obtain the first mixture; dissolving the guest material in the second solvent to obtain the second mixture;

[0061] (2) Mix the first mixture and the second mixture, then remove the first solvent and the second solvent, and obtain the photochromic material after drying. Preferably, a vacuum distillation method can be used to remove the first solvent and the second solvent in the mixture system.

[0062] Optionally, the preparation method of the photochromic material may also be: dissolving the host material and the guest material in the same solvent at the same time, then removing the solvent, and drying to obtain the photochromic material. Similarly, vacuum distillation can also be used to remove the solvent in t...

Embodiment 1

[0066] This embodiment provides a photochromic material, which includes a host material and a guest material.

[0067] Wherein, the host material is polymethyl methacrylate, the structural formula is shown in the above formula (II-3), and n=10000.

[0068] The guest material is a chemical structure (abbreviated as compound 3) shown in formula (I), and the group R is

[0069] The synthetic method of compound 3 is: under reflux state, join following compound 1 (1.67g, 10mmol) in the ethanol solution (30mL) of following compound 2 (2.91g, 10mmol), reflux reaction 12 hours, then cooling After reaching room temperature, the solid was collected by filtration and finally recrystallized in ethanol to obtain compound 3 (1.3 g).

[0070]

[0071] The H NMR spectrum parameters of compound 3 are as follows: 1 H NMR (400MHz, CDCl 3 )δ8.06–7.98(m,2H),7.67(d,J=7.5Hz,1H),7.52–7.47(m,2H),7.35–7.32(m,1H),7.23–7.18(m,1H) ,6.93(d,J=10.4Hz,1H),6.88(s,1H),6.77(d,J=8.4Hz,1H),5.92(d,J=10.4Hz...

Embodiment 2

[0078] This embodiment provides a photochromic material, which includes a host material and a guest material.

[0079] Wherein, the host material is polyvinylpyrrolidone, the structural formula is shown in the above formula (II-6), and n=60000.

[0080] The guest material is a chemical structure (abbreviated as compound 6) shown in formula (I), and the group R is

[0081] The synthetic method of compound 6 is: under reflux state, join following compound 3 (1.67g, 10mmol) in the ethanol solution (30mL) of following compound 4 (3.05g, 10mmol), reflux reaction 12 hours, then cooling After reaching room temperature, the reaction solution was concentrated and purified by column to obtain compound 6 (0.81 g).

[0082]

[0083] The proton nuclear magnetic resonance spectrum parameters of compound 6 are as follows: 1 H NMR (400MHz, CDCl 3 )δ8.08–8.00(m,2H),7.56(d,J=7.3Hz,1H),7.44–7.33(m,2H),7.21(s,1H),7.16(td,J=7.3,1.0Hz ,1H),6.95(t,J=5.2Hz,2H),6.78(d,J=8.8Hz,1H),5.90(d,J=10....

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Abstract

The invention provides a spiropyran derivative, a photochromic material and a preparation method of the photochromic material. The photochromic material includes a host material and a guest material. The host material is a high-molecular polymer, and the guest material is the spiropyran derivative. The preparation method comprises the steps: dissolving the host material and the guest material in a solvent, and then removing the solvent to obtain the photochromic material. The photochromic material disclosed by the invention has the characteristic of long-life luminescence, and can be applied to the aspects of photoelectric devices, display materials, information storage materials or anti-counterfeiting materials and the like. In addition, interference of nanosecond-level short-service-life background fluorescence can be avoided during biological imaging experiment detection, so that the detection accuracy is improved.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, and relates to a spiropyran derivative, a photochromic material and a preparation method thereof. Background technique [0002] Photochromic materials have a unique stimuli-responsiveness to light. Therefore, they are currently used in many fields such as fluorescent probes, biological imaging, ultra-high resolution microscopic imaging, and smart materials. The significant change of the fluorescent signal of the photochromic material before and after the color change can greatly improve the signal-to-noise ratio of the detection signal. However, the currently studied photochromic materials are all short-lived (such as nanosecond) luminescent, which are easily interfered by the short-lived background fluorescence in the organism during the detection process, resulting in a decrease in detection accuracy. Contents of the invention [0003] The purpose of this application is to prov...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K9/02C08L33/12C08K5/3417C08J5/18C08L39/06
CPCC07D491/107C09K9/02C08J5/18C08K5/3417C09K2211/1033C08J2333/12C08L39/06
Inventor 马骧马良伟田禾
Owner EAST CHINA UNIV OF SCI & TECH
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