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Photochromic compounds, preparation method thereof and photochromic products

A technology of photochromic compounds, applied in the preparation of carbon-based compounds, organic compounds, color-changing fluorescent materials, etc. With problems such as chirality, it can achieve the effects of large molecular energy level changes, large structural changes, and large dipole changes

Active Publication Date: 2018-08-03
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the existing photochromic moieties themselves do not have chirality. The introduction of chirality often requires additional modification of chiral groups or the introduction of other groups to increase steric hindrance to increase the racemization energy barrier. In addition to the difficulty of synthesis, it often changes the properties of photochromic molecules uncontrollably

Method used

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  • Photochromic compounds, preparation method thereof and photochromic products
  • Photochromic compounds, preparation method thereof and photochromic products
  • Photochromic compounds, preparation method thereof and photochromic products

Examples

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preparation example Construction

[0052] The present invention also provides a preparation method of the photochromic compound, comprising:

[0053] The compound M shown in the general formula M and the compound N shown in the general formula N are heated to reflux in an alkaline solution to obtain the photochromic compound I shown in the general formula I-I and the compound N shown in the general formula I - the photochromic compound II described in II:

[0054]

[0055] The preparation method of the photochromic compound can be completed in one pot, hereinafter referred to as one pot method. The preparation method has simple process and easy operation. The following is the synthetic mechanism of the photochromic compound:

[0056]

[0057] It is worth noting that the inventors found in the process of preparing the photochromic compound that when R 2 When it is a hydrogen atom, the compound of exo form cannot be obtained by the above-mentioned preparation method. The reason is that when the naphthale...

Embodiment 1

[0093] Compound 1 (1.5 g, 7.1 mmol), 3-pentanone (2.46 g, 28.6 mmol) and 15 mL of methanol were added to a round bottom flask. KOH (3.18g, 56.7mmol) was dissolved in 5mL of methanol, and slowly dropped into the above dispersion, then heated to reflux and reacted for 24h. After the reaction was completed, a solid was obtained by filtration, and the solid was washed 3 times with methanol. The crude product was separated by column chromatography and recrystallized with dichloromethane / methanol to obtain 853 mg of a light yellow solid, which was compound A, and the yield of compound A was 57%.

[0094] The synthetic route of described compound A is:

[0095]

[0096] The measurement result of compound A nuclear magnetic resonance (NMR) and high-resolution mass spectrum is:

[0097] 1 H NMR (500MHz, CD 2 Cl 2 )δ7.42(d, J=8.3Hz, 1H), 7.33(d, J=8.3Hz, 1H), 7.27(d, J=8.2Hz, 1H), 7.24(d, J=8.3Hz, 1H) ,7.18(d,J=8.3Hz,1H),7.13(d,J=8.3Hz,1H),6.78(d,J=8.2Hz,1H),6.69(d,J=8.3Hz,1H),...

Embodiment 2

[0103]Add compound 1 (1g, 4.76mmol) and chloroform (30ml) into a 100ml three-necked flask. Liquid bromine (1.13ml, 22.0mmol) and chloroform (15ml) were added to the dropping funnel. At room temperature, the liquid bromine solution was slowly added dropwise. After the drop, the reaction solution was heated to 85° C. for 3 hours, and then the temperature was lowered. Anhydrous sodium sulfite solution was added in an ice bath to quench excess bromine. The reaction solution was diluted with dichloromethane, washed three times with water, dried over anhydrous sodium sulfate, filtered and the solvent was removed. The crude product was recrystallized from chloroform and methanol to obtain 1.02 g of a yellow solid, which was compound 3, and the yield of compound 3 was 73%.

[0104] Weigh compound 3 (1.00g, 3.46mmol) into a round bottom flask, add 3-pentanone (1.46ml, 14.0mmol) and methanol (14.6ml). Slowly add a solution of potassium hydroxide (1.5g, 27mmol) in methanol (7.4ml) to t...

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Abstract

The invention provides photochromic compounds. The structure of the photochromic compounds is shown as general formula I-I or general formula I-II in the description, wherein R1 is H or an alkyl groupwith 1-10 carbon atoms; R2 is an alkyl group with 1-10 carbon atoms, an alkoxy group with 1-10 carbon atoms, halogen or nitro group; R3, R4, R5 and R6 are independently selected from hydrogen, alkylgroups, alkoxy groups, cyano groups,-B(OH)2, groups shown in the description, halogen or other chromophores. The invention further provides a preparation method of the photochromic compounds and an application of the photochromic compounds to photochromic products.

Description

technical field [0001] The invention relates to the field of organic photochromic materials, in particular to a photochromic compound, a preparation method thereof and a photochromic product. Background technique [0002] Photochromic molecules refer to molecules that undergo isomerization after light absorption accompanied by changes in the absorption spectrum, and this process is reversible under the action of heating or another wavelength of light. Photochromic molecules have been widely used in electronics, medicine, molecular machines, and nanotechnology. At present, the photochromic moieties that are relatively mature and widely used mainly include azobenzene, diarylethene, and spiropyran (Chem.Rev.2013, 113, 6114, Angew.Chem.Int.Ed.2015 , 54, 11338, Adv. Mater. 2010, 22, 3348)). The mechanism of reversible photoisomerization mainly includes cis-trans isomerization, ring-opening-ring-closing isomerization, and free radical-free radical bond formation due to single bo...

Claims

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Application Information

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IPC IPC(8): C09K9/02C07C201/12C07C45/74C07C49/665C07C205/45C07D333/22
CPCC07C49/665C07C205/45C07C2602/30C07C2603/54C07D333/22C09K9/02
Inventor 曹晓宇陆如强鲍粤华杨琳琳严笑云瞿航
Owner XIAMEN UNIV
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