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Chromene compound and preparation method thereof

A technology of chromene compound and alkyl group, applied in the field of chromene compound and its preparation, can solve the problems of uneven dispersion, weak adhesion, low photochromic efficiency, etc., and achieve the effect of obvious photochromic phenomenon

Pending Publication Date: 2019-01-18
ZHONGSHAN HAIHONG MEDICINE CO LTD +1
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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 a typical inorganic system is accompanied by a reversible oxidation-reduction reaction, which has good reversibility and fatigue resistance; the disadvantage is that the photochromic efficiency is low, the adhesion is weak, and the dispersion is not good. Uniform, undertone and opaque

Method used

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  • Chromene compound and preparation method thereof
  • Chromene compound and preparation method thereof
  • Chromene compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Chromene compound 6,10-dimethoxy-3-phenyl-3-(4-methoxyphenyl)-13-pentyl-13-methoxy-3,13-dihydrobenzo[h ]Indene[2,1-f]pyran preparation:

[0050] (1) Preparation of QF-2

[0051]

[0052]In a 10L three-necked flask, add compound QF-1 (300g, 0.93mol), toluene (3000mL) and 700g methanesulfonic acid, heat to 110°C, react for 4h, pour the reaction solution into 5000mL water, filter, and wash the filter residue with 1000mL water , and dried in a blast oven to obtain 266 g of an earthy gray solid, with a yield of 93.4%. used directly in the next reaction.

[0053] ESI-MS:[M+H] + =307.3

[0054] NMR data: 1 H NMR (400MHz, DMSO) δ10.64 (d, J = 28.2Hz, 1H), 7.88 (t, J = 24.2Hz, 1H), 7.66–7.35 (m, 4H), 7.32–7.11 (m, 1H) ,6.88(d,J=22.3Hz,1H),4.19–3.99(m,3H),3.93(s,3H).

[0055] (2) Preparation of QF-3

[0056]

[0057] Add QF-2 (260g, 0.85mol), 1-(4-methoxyphenyl)-2-propyn-1-ol (300g, 1.26mol), toluene 2.5L, methanesulfonic acid 30g; the reaction temperature is 90-10...

Embodiment 2

[0069] Chromene compound 6,10-dimethoxy-3-phenyl-3-(4-methoxyphenyl)-13-methyl-13-methoxy-3,13-dihydrobenzo[h ]Indene[2,1-f]pyran preparation:

[0070] (1) Preparation of QF-2

[0071]

[0072] In a 10L three-necked flask, add compound QF-1 (300g, 0.93mol), toluene (3000mL) and 700g methanesulfonic acid, heat to 110°C, react for 4h, pour the reaction solution into 5000mL water, filter, and wash the filter residue with 1000mL water , and dried in a blast oven to obtain 266 g of an earthy gray solid, with a yield of 93.4%. used directly in the next reaction.

[0073] ESI-MS:[M+H] + =307.3

[0074] NMR data: 1 H NMR (400MHz, DMSO) δ10.64 (d, J = 28.2Hz, 1H), 7.88 (t, J = 24.2Hz, 1H), 7.66–7.35 (m, 4H), 7.32–7.11 (m, 1H) ,6.88(d,J=22.3Hz,1H),4.19–3.99(m,3H),3.93(s,3H).

[0075] (2) Preparation of QF-3

[0076]

[0077] Add QF-2 (260g, 0.85mol), 1-(4-methoxyphenyl)-2-propyn-1-ol (300g, 1.26mol), toluene 2.5L, methanesulfonic acid 30g; the reaction temperature is 90-1...

Embodiment 3

[0091] Photochromic test of chromene compounds

[0092] Prepare the chromene compound styrene and other resin monomers prepared in Example 1 into a transparent solution, add an appropriate amount of V65, pour, heat and cure to make it a colorless and transparent resin lens, and then irradiate it with ultraviolet light for about 2 seconds The solution gradually turns blue, 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 compound I has undergone a photochromic reaction under the action of ultraviolet light, and the reaction formula is as follows:

[0093]

[0094] After 10,000 color-changing and fading cycles, there is no significant decline in its color-changing performance.

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Abstract

The invention discloses a chromene compound, the chromene compound is characterized by being provided with a basic structure shown as in a structural formula (I), wherein R1 is substituted or unsubstituted C1-C6 alkyl; and R2 is substituted or unsubstituted C1-C6 alkyl. The invention discloses a preparation method of the chromene compound. The chromene compound becomes cyan from colorless, and becomes colorless from cyan again after the ultraviolet ray disappears, and the photochromic phenomenon is obvious. The main color change tones displayed by different structures of the compound are cyan,the color is within the range from light cyan and ultramarine, the color change performance is not obviously reduced after the circulation of color change and fading for 10000 times, and meanwhile, the high-temperature test shows that the compound can tolerate the high temperature of 350 DEG C and can be applied as a photochromic material.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a chromene 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. The classification of photochromic materials is as follows: [0003] 1. Inorganic photochromic materials: The photochromic effect of a typical inorganic system is accompanied by a reversible oxidation-reduction reaction, which has good reversibility and fatigue resistance; the disadvantage is that the photochromic efficiency is low, the adhesion is weak, and the dispersion is not good. Even, with undertones and opaque. Inorganic photochromic compounds mainly include transition metal oxides, metal halides and rare earth comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/94C09K9/02C08F112/08G02B1/04
CPCG02B1/04C09K9/02C07D311/94C08F112/08C09K2211/1088
Inventor 杨青海华高松吴玉芳
Owner ZHONGSHAN HAIHONG MEDICINE CO LTD
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