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Photochromic compound and preparation method thereof

A photochromic and compound technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of uneven dispersion, weak adhesion, low photochromic efficiency, etc., and achieve obvious photochromic phenomenon Effect

Inactive Publication Date: 2018-12-21
ZHONGSHAN HAIHONG MEDICINE CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 1. Inorganic photochromic materials: The photochromic effect of typical inorganic systems is accompanied by a reversible oxidation-reduction reaction, which has good reversibility and fatigue resistance; the disadvantages are low photochromic efficiency, weak adhesion, and poor dispersion. Uniform, undertone and opaque

Method used

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  • Photochromic compound and preparation method thereof
  • Photochromic compound and preparation method thereof
  • Photochromic compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The photochromic compound 3-phenyl-3-(4-methoxyphenyl)-13-methyl-13-methoxy-3,13-dihydrobenzo[h]indene[2,1-f ] Preparation of pyran:

[0049] (1) Preparation of HF-2

[0050]

[0051]In a 10L three-necked flask, add compound HF-1 (300g, 1.14mol), xylene (3000mL) and 800g methanesulfonic acid, heat to 120°C, react for 4h, pour the reaction solution into 500mL water, filter, filter the residue with 100mL water After washing and drying in an air blast oven, 260 g of an earthy gray solid was obtained, with a yield of 92.6%.

[0052] ESI-MS:[M+H] + =247.2

[0053] NMR data: 1 H NMR (400MHz, CDCl 3 )δ7.99–7.92(m,1H),7.79(s,1H),7.63(dd,J=11.2,4.5Hz,1H),7.55–7.43(m,1H),7.36–7.27(m,1H) ,3.65(s,1H),2.54(s,1H).

[0054] (2) Preparation of HF-3

[0055]

[0056] Add HF-2 (246.2g, 1.0mol), 1-(4-methoxyphenyl)-2-propyn-1-ol (333g, 1.4mol), toluene 2.5L, methanesulfonate in sequence to the reaction flask 30g of acid; the reaction temperature is 90-100°C, stirred for 8-1...

Embodiment 2

[0068] Photochromic test of photochromic compounds

[0069] Make the styrene resin monomer of the photochromic compound prepared in Example 1 into a transparent solution, add an appropriate amount of V65, pour it, heat and cure it, and turn it into a colorless and transparent resin lens, and then irradiate it with ultraviolet light for about 2 seconds The solution gradually turns red, and the intensity of the absorption peak increases with the prolongation of the irradiation time, and the coloring depth of the liquid after discoloration gradually becomes darker. After the ultraviolet rays disappeared, the color of the solution faded to colorless rapidly, and the time was about 90s. This illustrates that the photochromic compound has undergone a photochromic reaction under the action of ultraviolet light, and the reaction formula is as follows:

[0070]

[0071] After 10,000 color-changing and fading cycles, there is no significant decline in its color-changing performance....

Embodiment 3

[0073] High temperature test

[0074] Put 10 g of the solid photochromic compound prepared in Example 1 into a crucible, then transfer the crucible to a muffle furnace, raise the temperature to 350° C., and keep the temperature at this temperature for 1 hour. Take out the solid, take 30mg and dissolve it in 100mL styrene resin monomer to make a transparent solution, add an appropriate amount of V65, pour it, heat and cure it, and turn it into a colorless and transparent resin lens, and then irradiate it with ultraviolet light, and the resin lens changes rapidly The red becomes darker, and then the solution is transferred to visible light, and it basically fades to colorless in about 90s. Thus, the compound can withstand high temperatures of 350°C.

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Abstract

The invention discloses a photochromic compound. The photochromic compound is characterized by having a basic structure represented by a structural formula (I), wherein R1 is substituted or unsubstituted C1-C6 alkyl; R2 is substituted or unsubstituted C1-C6 alkyl. The invention discloses a preparation method of the photochromic compound. According to the photochromic compound and the preparation method thereof, the photochromic compound can change into red from colorless under ultraviolet irradiation and can change into colorless from red after ultraviolet rays disappear, and the photochromismis obvious. Main discoloration color tones displayed by different structures of the compound are all red, and discolorations are all in a range from light red to dark red; after 10,000 times of discoloration-fade circles, the discoloration property of the photochromic compound is not lowered obviously; meanwhile, proven by a high-temperature experiment, the compound can endure the high temperature of 350 DEG C and can be used as a photochromic material.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a photochromic compound and a preparation method thereof. Background technique [0002] Photochromism refers to the change of the molecular structure of certain compounds under the action of light of a certain wavelength and intensity, resulting in a corresponding change in the color of the light absorption peak, and this change is generally reversible. Photochromic materials are classified as follows: [0003] 1. Inorganic photochromic materials: The photochromic effect of typical inorganic systems is accompanied by reversible oxidation-reduction reactions, which have good reversibility and fatigue resistance; the disadvantages are low photochromic efficiency, weak adhesion, and poor dispersion. Even, with undertones and opaque. Inorganic photochromic compounds mainly include transition metal oxides, metal halides and rare earth complexes. [0004] 2. Organic photoch...

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 杨青海李吉昌华高松吴玉芳
Owner ZHONGSHAN HAIHONG MEDICINE CO LTD
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