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High-solubility photochromic compound and preparation method thereof

A photochromic, high-solubility technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of lack of flexible substituents, affect product quality, poor compatibility, etc., and achieve easy processing Film-forming, no background color, excellent solubility effects

Active Publication Date: 2021-11-05
TIANJIN UVOS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there have been invention patent reports on the preparation and application of naphthopyran photochromic compounds, such as CN105008373A, CN102532088A, and CN1671699A. These reported naphthopyran compounds generally have rigid conjugated groups such as benzene rings , naphthalene ring, etc., lack of flexible substituents, so the solubility of these compounds in organic solvents such as toluene, ethanol, acetone is low, and the compatibility in polymer systems is not good, affecting product quality

Method used

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  • High-solubility photochromic compound and preparation method thereof
  • High-solubility photochromic compound and preparation method thereof
  • High-solubility photochromic compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] The synthesis of embodiment 1 photochromic compound Ia

[0063] Step 1: Synthesis of Compound C1

[0064]

[0065] To a 100 mL Shrek tube at 0°C, sodium hydride (0.2 g, 64 mmol) was added, followed by 30 mL of anhydrous tetrahydrofuran. 4,4'-Dihydroxybenzophenone A1 (2.1 g, 10 mmol) was dissolved in 30 ml of anhydrous DMF, and slowly added into the reaction vial with a syringe, and stirred for 1 h. B1 (1.5 g, 64 mmol) was added to the reaction system, heated to 60° C. for 72 h. Cool to room temperature, add saturated NH to the reaction system 4 Cl solution was extracted three times with ethyl acetate (3×50ml), and the organic phases were combined and washed once with brine (50mL) and water (50mL) respectively. Dry over anhydrous sodium sulfate and filter. The solvent was removed by a rotary evaporator to obtain a crude product, which was separated and purified by silica gel column chromatography (eluent: dichloromethane / methanol = 40:1) to obtain a yellow oil C1 ...

Embodiment 2

[0077] The synthesis of embodiment 2 photochromic compounds Ib

[0078] Step 1: Synthesis of Benzophenone Derivative C2

[0079]

[0080] Weigh sodium hydride powder (1.9 g, 80 mmol), add it into a 250 mL Shrek bottle, and add 50 mL of anhydrous tetrahydrofuran under nitrogen protection. Dissolve A (25.71g, 25mmol) in 25mL of anhydrous N,N-dimethylformamide, and drop it into the reaction flask after fully dissolved. Ice bath, stirring for one hour, B1 (13.7g, 50mmol) was added to the reaction flask. Heated to 60°C and reacted for 72 hours. Cool to room temperature, add saturated NH to the reaction system 4 Cl solution was extracted three times with ethyl acetate (3×50ml), and the organic phases were combined and washed once with brine (50mL) and water (50mL) respectively. Dry over anhydrous sodium sulfate and filter. The solvent was removed by a rotary evaporator to obtain a crude product, which was separated and purified by silica gel column chromatography (eluent: di...

Embodiment 3

[0092] Embodiment 3: the synthesis of photochromic compound Ic

[0093] D3 synthetic reference embodiment 1 and 2 steps, no longer repeat

[0094]

[0095] Add D3 (320mg, 1mmol), E2 (300mg, 1mmol) and 20mL toluene to a 100mL single-necked bottle, and stir. Add 2 drops of dodecylbenzenesulfonic acid with a rubber dropper and heat to 40°C for 3h. Cool to room temperature, extract three times with dichloromethane (3×20ml), combine the organic phases, and wash once with saturated brine (20ml) and distilled water (20ml) respectively. Dry over anhydrous magnesium sulfate, filter, and remove the solvent with a rotary evaporator. The residue is separated and purified by silica gel column chromatography (eluent: dichloromethane / methanol = 100:1) to obtain a light yellow solid Ic with a yield of 79%.

[0096] H NMR spectrum of Ic: 1 H NMR (400MHz, CDCl 3 )δ(ppm)8.52(d,J=8.0Hz,1H),8.07(d,J=8.0Hz,1H),7.75(d,J=8.0Hz,1H),7.54–7.42(m,4H), 7.30–7.24(m,2H),7.05–7.02(m,1H),6.95–6.90(m,1...

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Abstract

The invention relates to a high-solubility photochromic compound and a preparation method thereof. The high-solubility photochromic compound has a structure as shown in a formula I. In the formula, R1, R2, R3 and R4 are the same or different and independently represent hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkyl alcohol, halogen, trifluoromethyl, phenyl, morpholine, piperidine or indole, R5 represents an alkyl group of C1 to C6, an alkoxy group of C1 to C6 or an alkyl alcohol of C1 to C6. R < 6 >, R < 7 > and R < 8 > are the same or different, at least one of theR < 6 >, R < 7 > and R < 8 > is-O-(CH2CH2O) m-Z, and the rest of theR < 6 >, R < 7 > and R < 8 > is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, halogen, trifluoromethyl, phenyl, morpholine, piperidine or indole; m represents an integer of 0-6; z represents hydrogen or-(CH2) p-CH3; and p represents an integer of 0-6. The invention also provides a preparation method of the compound, and the prepared compound shows excellent compatibility in an organic solvent system or a polymer system, has the characteristics of rapid photoresponse, fast fading rate, good fatigue resistance and the like, and has a good application prospect.

Description

technical field [0001] The invention relates to the field of organic optical functional materials, in particular to a highly soluble photochromic compound and a preparation method thereof. Background technique [0002] Photochromism refers to the structural change of a certain compound under the irradiation of light of a certain intensity wavelength to form a new compound. Under the action of another wavelength of light or heat, it can return to its original state. There are obvious differences in the ultraviolet absorption spectra of these two isomers, and the most intuitive performance is a color change. Therefore, this type of material is usually called a photochromic material. Photochromic materials have wide application value in information storage, optical switches, color-changing glasses, smart windows, color-changing clothing, ink paint and anti-counterfeiting materials. [0003] According to the composition of materials, photochromic materials mainly include inorg...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/94C09K9/02
CPCC07D311/94C09K9/02C09K2211/1088
Inventor 席志强杨俊生辛金菲刘宗
Owner TIANJIN UVOS TECH CO LTD
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