Chromene compound

一种色烯化合物、键合的技术，应用在有机化学、变色荧光材料、化学仪器和方法等方向，能够解决未获知色烯化合物等问题

Active Publication Date: 2014-01-15
TOKUYAMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] In order to improve the above-mentioned environmental dependence and temperature dependence, a chromene compound whose photoresponse is several times faster than the conventional chromene compound, that is, the fading half-life is a fraction of that of the conventional chromene compound, is required. No such chromene compound is known

Method used

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Examples

Experimental program
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Effect test

preparation example Construction

[0156]

[0157] The preparation method of the chromene compound of the present invention is not particularly limited, and any synthesis method can be used.

[0158] The chromene compound represented by the above formula (1) can be efficiently produced, for example, by the following method.

[0159] That is, it can be produced by a method of reacting a naphthol compound represented by the following formula (6) with a propargyl alcohol compound represented by the following formula (7) in the presence of an acid catalyst.

[0160]

[0161] In the formula, R 1 ,X,A,C * and a are the same as defined in the above formula (1).

[0162]

[0163] (where, R 2 and R 3 Same definition as in formula (1) above).

[0164] The reaction ratio of the naphthol compound and the propargyl alcohol compound can be used in a wide range, and is preferably selected from the range of 1:10 to 10:1 (molar ratio). In addition, as the acid catalyst, for example, sulfuric acid, benzenesulfonic ...

Embodiment 1

[0209] Embodiment 1 (synthesis of chromene compound E1)

[0210] (Synthesis of naphthol compounds)

[0211] Add 50.0g (172mmol) of 3-bromo-4-methoxybenzophenone and 28.7g (189mmol) of 4-methoxyphenylboronic acid into 250ml of 1,2-dimethoxyethane, and add 25 ml of ethanol, 400 g of a 10% aqueous sodium carbonate solution, and 0.05 g (0.043 mmol) of tetrakis(triphenylphosphine)palladium were added and reacted at 78°C. After 3 hours, 1,000 ml of toluene was added to the reaction solution, the organic layer was washed with water, and the solvent was removed, followed by recrystallization with 200 ml of methanol to obtain the following formula as a white solid:

[0212]

[0213] The indicated 4-methoxy-3-(4-methoxyphenyl)benzophenone was 51.6 g (162 mmol, yield 94%).

[0214] This benzophenone compound and 32.5 g (186 mmol) of diethyl succinate were dissolved in 150 ml of tetrahydrofuran. A tetrahydrofuran solution of 23.6 g (211 mmol) of potassium tert-butoxide was dropped i...

Embodiment 2

[0243] Example 2 (Evaluation of Photochromic Properties in Solution)

[0244] The chromene compound (E1) obtained in Example 1 was dissolved in tetrahydrofuran to prepare a concentration of 0.5 mM. The solution was added to a quartz colorimetric cell with an optical path length of 1 mm as a sample. The temperature of the sample is 23°C ± 1°C, and the UV-LED irradiator manufactured by Omron Corporation (ZUV-C20H for the controller part, ZUV-H20MB for the irradiation head unit part, and ZUV-L8H for the lens unit part) is used as the light source. The distance between the sample and the light source is 50mm, irradiate 365nm ultraviolet light to make it color, and measure the photochromic characteristics. The photochromic properties were evaluated by the following items.

[0245] [1] Maximum absorption wavelength (λmax): It is the maximum absorption wavelength after color development obtained by a spectrophotometer (momentary multi-channel photodetector MCPD2000M) manufactured b...

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Abstract

Specifically provided is a chromene compound represented by formula (1), which has a short fading half-life even at low temperatures in a common polymer solid matrix. (In formula (1), R1 represents a hydroxyl group or the like; each of R2 and R3 represents an aryl group or the like; X represents a divalent group such as an arylene group; C* represents a spirocarbon atom; a spiroring A represents a saturated hydrocarbon ring having 4-12 ring member carbon atoms, or the like; and at least one ring member carbon atom constituting the ring A is a group that is represented by formula (4) (wherein each of R7 and R8 represents a cycloalkyl group or the like).)

Description

technical field [0001] The present invention relates to a new chromene compound and the use of the chromene compound. Background technique [0002] Photochromism refers to the change of color (called color development) when some compounds are irradiated with ultraviolet light such as sunlight or mercury lamp light, and return to the original color when the light is stopped and placed in a dark place ( A phenomenon of reversible action known as fading). Compounds with this property are known as photochromic compounds. One of the uses of this photochromic compound is a light-adjusting material for sunglasses. For a long time, as this photochromic compound, chromene compounds, spiro oxazine compounds, spiropyran compounds, etc. [0003] In particular, since chromene compounds are excellent in light resistance and various color hues can be obtained by optimizing substituents, many studies have been conducted so far. For example, a chromene compound having an indeno(2,1-f)na...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/78C07C39/17C07C43/23C07C323/21C07D295/08C07D327/06C07D407/04C07D497/10C09K9/02G02B5/23
CPCC07C39/17C07C43/23C07C323/21C07D295/096C07D311/94C07D327/04C07D407/04C07D497/10C08G77/38C09K9/02G02B5/23C07C2601/14C07C2603/94C09K2211/1037C09K2211/1033C09K2211/1088C09K2211/1425C09K2211/145C09K2211/1007C09K2211/1011C07C39/23C08L83/04C07D311/92C07C2601/04C07C2601/08C07C2601/16Y10T428/31504C07D311/78C07D413/04
Inventor 和泉忍寺西一浩大黑裕介三道光喜
Owner TOKUYAMA CORP
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