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Photochromic compound and application thereof

A photochromic and photochromic material technology, applied in the direction of color-changing fluorescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of lens color change, different anti-UV aging characteristics, etc., and achieve high color sensitivity and excellent color rendering Durability, Effect of Short Fade Half-Life

Pending Publication Date: 2022-02-11
JIANGSU SHIKEXINCAI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In fact, dyes of different colors may have different anti-UV aging properties, different fading kinetics or different thermal dependencies, leading to changes in the tint of the lens during use

Method used

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  • Photochromic compound and application thereof
  • Photochromic compound and application thereof
  • Photochromic compound and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0053] Preparation of intermediates:

[0054] 1. Preparation of intermediate A-5: 10-fluoro-2,2-bis(4-methoxyphenyl)-2H-benzo[h]chromen-5-ol

[0055]

[0056] (1) A-3: Preparation of 1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol

[0057] 4,4'-dimethoxybenzophenone A-1 (500mg, 2.06mmol) was dissolved in 10mL of ethylenediamine, and acetylene lithium ethylenediamine complex A-2 (558mg, 6.20mmol) was added. Stir at room temperature for 2 hours under nitrogen atmosphere. After the reaction was completed, it was quenched with ice water, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride, and dried over anhydrous sodium sulfate. After concentration, the crude product was purified by silica gel column chromatography to obtain 1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol A-3 (450 mg, white solid), yield: 81%. ESI-MS m / z: 269[M+H] + .

[0058] (2) A-5: Preparation of 10-fluoro-2,2-bis(4-methoxyphenyl)-2H-benzo[h...

Embodiment 1

[0073] Example 1: Preparation of 5,5'-oxybis(10-fluoro-2,2-bis(4-methoxyphenyl)-2H-benzo[h]chromene)

[0074]

[0075] 10-Fluoro-2,2-bis(4-methoxyphenyl)-2H-benzo[h]chromen-5-ol A-5 (200 mg, 0.47 mmol) was dissolved in tetrahydrofuran (5 mL), Add diethyl azodicarboxylate (DEAD, 35mg, 0.2mmol) and triphenylphosphine (52mg, 0.2mmol) and react for 16 hours. After the reaction is completed, concentrate and separate through silica gel preparation plate to obtain 5,5'-oxo Bis(10-fluoro-2,2-bis(4-methoxyphenyl)-2H-benzo[h]chromene) (75 mg, white solid), yield: 38%. ESI-MS m / z: 839[M+H] + .

[0076] 1 H-NMR (400MHz, DMSO-d 6 ): δ7.83-7.62(m, 2H), 7.47-7.32(m, 10H), 7.30-7.15(m, 2H), 6.88-6.70(m, 10H), 6.58(d, J=7.2Hz, 2H ), 6.39 (d, J=7.2Hz, 2H), 3.52 (s, 12H).

Embodiment 2

[0077] Example 2: Preparation of 5,5'-oxybis(10-trifluoromethyl-2,2-bis(4-methoxyphenyl)-2H-benzo[h]chromene)

[0078]

[0079] 10-Trifluoromethyl-2,2-bis(4-methoxyphenyl)-2H-benzo[h]chromen-5-ol A-7 (200 mg, 0.42 mmol) was dissolved in tetrahydrofuran (5 mL ), add diethyl azodicarboxylate (DEAD, 31mg, 0.18mmol) and triphenylphosphine (47mg, 0.18mmol) and react for 16 hours. '-Oxybis(10-trifluoromethyl-2,2-bis(4-methoxyphenyl)-2H-benzo[h]chromene) (50 mg, white solid), yield: 23%. ESI-MSm / z: 939[M+H] + .

[0080] 1 H-NMR (400MHz, DMSO-d 6 ): δ8.12-7.65 (m, 2H), 7.55-7.37 (m, 10H), 7.32-7.12 (m, 2H), 6.89-6.72 (m, 10H), 6.57 (d, J=7.2Hz, 2H ), 6.41 (d, J=7.2Hz, 2H), 3.55 (s, 12H).

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Abstract

The invention discloses a photochromic compound and application thereof. The structural formula of the compound is shown as a formula (I), wherein R1, R2, R5 and R6 are respectively selected from hydrogen, methyl, methoxyl, methylthio, aryl, halogen, CN, NO2, CF3 or CF2H; R3, R4, R7 and R8 are respectively selected from hydrogen, methyl, methoxyl, methylthio, halogen, CN, NO2, CF3 or CF2H, and at least one of R3, R4, R7 and R8 is an electron withdrawing group; and A is a C1-C8 straight chain alkyl group, a C1-C8 branched chain alkyl group, a C1-C8 cyclic alkyl group, an aryl group, a heteroatom or a C1-C8 heteroatom-containing alkyl group. The compound has the advantages of high color developing sensitivity, excellent durability and extremely short fading half-life period. The compound can be used as a memory material, a dimming material, a photochromic lens material, an optical filter material, a display material, an optical information device, an optical switch element, a photoresist material, a photometer or a decorative material.

Description

technical field [0001] The invention relates to the field of photochromic materials and provides a multi-substituted benzochromene photochromic compound. Background technique [0002] Photochromism refers to a reversible phenomenon in which the color of certain compounds changes rapidly when irradiated with light containing ultraviolet rays, and returns to the original color when the light is stopped and placed in a dark place. Compounds with this property are called photochromic compounds. Photochromic materials have broad application prospects in the fields of color-changing glasses, optical information storage, molecular switches, and defense identification technology, and have always been one of the research hotspots in the fields of chemistry and material science. . [0003] Naphthopyrans are known to be reported as photochromic compounds capable of changing color under the influence of poly- or monochromatic light, such as UV light. When the irradiation is stopped, o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/92C09K9/02
CPCC07D311/92C09K9/02C09K2211/1088
Inventor 范为正王明华张鹤军宋化灿朱国勋宋森川赵毅杰司云凤刘洋
Owner JIANGSU SHIKEXINCAI CO LTD
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