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Indene-fused 2H-naphtho-[2,1-b]pyran photochromic compound and preparation method thereof

A compound, a color-causing technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problem of insufficient color and achieve the effect of fast fading rate, wide application prospect and high reaction yield

Pending Publication Date: 2019-10-01
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of material has good fatigue resistance and optical density value, but the color body is generally blue, and the color is not rich enough, especially the lack of yellow material

Method used

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  • Indene-fused 2H-naphtho-[2,1-b]pyran photochromic compound and preparation method thereof
  • Indene-fused 2H-naphtho-[2,1-b]pyran photochromic compound and preparation method thereof
  • Indene-fused 2H-naphtho-[2,1-b]pyran photochromic compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation of embodiment 1 photochromic compound Ia

[0028] The first step: the preparation of compound M1, the reaction formula is as follows:

[0029]

[0030] To a 100 mL Shrek tube add 4-bromo-2-naphthol (0.50 g, 2.20 mmol), 2-methoxycarbonylphenylboronic acid pinacol ester (0.82 g, 2.64 mmol), tetrakis(triphenyl)phosphine Palladium (0.25 g, 0.22 mmol) and anhydrous sodium carbonate (1.12 g, 10.56 mmol). Close it, vacuum it, N 2 For protection, inject THF / H with a needle 2 O (20mL / 8mL) solution was stirred at 80°C for 12h (monitored by TLC). After the reaction was completed, it was washed with brine, washed with water and extracted with ethyl acetate (50 mL×2). The organic phase was collected and washed with anhydrous Na 2 SO 4 Drying, concentration, and separation by silica gel column chromatography gave the product M1 as a white solid. Yield 72%.

[0031] The H NMR spectrum characterization data of M1 is: 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 8.02 ...

Embodiment 2

[0048] The preparation of embodiment 2 photochromic compound Ib, reaction formula is as follows:

[0049]

[0050] To a 100ml round bottom flask was added M3 (0.17g, 0.60mmol), toluene (20mL), 1,1-bis(4-fluorophenyl)prop-2-yn-1-ol (0.18g, 0.75mmol) And 1-2 drops of dodecylbenzenesulfonic acid. Heated to 40°C for 3h. After the reaction was completed, the reaction solution was distilled under reduced pressure to remove the solvent, and the residue was separated by silica gel column chromatography to obtain a yellow solid product Ib with a yield of 52%.

[0051] The proton nuclear magnetic resonance spectrum characterization data of 1b is: 1 H NMR (400MHz, CDCl 3 )δ(ppm)8.70(d,J=8.8Hz,1H),8.27(d,J=8.0Hz,1H),8.08(d,J=8.8Hz,1H),7.54–7.42(m,7H), 7.41–7.36(m,3H),6.99(t,J=8.8Hz,4H),5.94(d,J=10.0Hz,1H),1.58(s,6H).

[0052] The carbon nuclear magnetic resonance spectrum characterization data of Ib is: 13 C NMR (100MHz, CDCl 3 ):δ(ppm)163.45,160.99,155.35,147.67,140.74,140.02,1...

Embodiment 4

[0053] The preparation of embodiment 4 photochromic compound Ic, reaction formula is as follows:

[0054]

[0055] Into a 100 mL round bottom flask was added M3 (0.19 g, 0.73 mmol), toluene (20 mL), 1-(4-methoxyphenyl)-1-phenylprop-2-yn-1-ol (0.22 g , 0.91mmol) and 1-2 drops of dodecylbenzenesulfonic acid. Heated to 40°C for 3h. After the reaction was completed, the reaction solution was distilled under reduced pressure to remove the solvent, and the residue was separated by silica gel column chromatography to obtain a yellow viscous oily product Ic with a yield of 79%.

[0056] The H NMR spectrum characterization data of Ic are: 1 H NMR (400MHz, CDCl 3 )δ(ppm)8.70(d,J=8.0Hz,1H),8.29(d,J=7.6Hz,1H),8.13(d,J=8.0Hz,1H),7.59–7.31(m,12H), 7.29(d, J=7.6Hz, 1H), 6.84(d, J=8.8Hz, 2H), 6.06(d, J=10.0Hz, 1H), 3.76(s, 3H), 1.67(s, 3H), 1.57(s,3H).

[0057] The carbon nuclear magnetic resonance spectrum characterization data of Ic are: 13 C NMR (100MHz, CDCl 3 )δ(ppm)157.87,154...

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Abstract

The invention provides an indene-fused 2H-naphtho-[2,1-b]pyran photochromic compound and a preparation method thereof. The molecular formula of the compound is shown in a formula I, wherein R1 and R2are hydrogen, straight-chain or branched-chain alkyl groups containing 1-6 carbon atoms, straight-chain or branched-chain alkoxy groups containing 1-6 carbon atoms, straight-chain or branched-chain halogenated alkyl groups or halogenated alkoxy groups, substituted by at least one halogen atom, corresponding to the alkyl groups and the alkoxy groups respectively, phenyl groups or substituted phenylgroups, halogen, NH2 and <->NHR. The preparation method of the compound comprises the steps that 2-methoxycarbonylphenylboronic acid pinacol ester and 4-bromine-2-naphthol are subjected to a couplingreaction, a Grignard reagent addition reaction and a cyclization reaction to obtain an intermediate 7,7-dialkyl-7H-benzo-[c]fluorene-6-phenol, and then the intermediate and 1,1-(diaryl)-2-allylene-1-ol generate I under the acid catalysis. The synthesis of the photochromic compound I has the advantages that the steps are few, the reaction conditions are mild, the operation is simple, and the reaction yield is high, a color body of the photochromic compound I is yellow or orange, and the photochromic compound I has the advantages of good fatigue resistance and high color ratio.

Description

technical field [0001] The invention relates to the field of organic photochromic materials, in particular to a preparation method of an indene-fused ring 2H-naphtho[2,1-b]pyran photochromic compound Background technique [0002] Photochromism means that the molecular structure of certain compounds will change under the irradiation of light of a certain wavelength, resulting in obvious changes in their absorption spectrum, accompanied by color changes. Under the irradiation of another wavelength of light or heat, it will return to its original state. Photochromism is a reversible chemical change. Photochromic materials have a wide range of applications in optical information storage materials, anti-counterfeiting identification, photochromic paint inks, color-changing clothing, and color-changing glasses. [0003] Organic photochromic compounds mainly include azobenzene, fulgid anhydride, diarylethene, spirooxazine, spiropyran, and naphthopyran. Among them, the photochrom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K9/02C07D311/94
CPCC09K9/02C07D311/94C09K2211/1007C09K2211/1088
Inventor 韩杰孙娟娟
Owner NANKAI UNIV
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