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Double-condensed-ring naphthopyran 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 insufficient light response, low color rate of chromophores, and limited application range, etc., to achieve rapid response, The effect of high color ratio and wide application prospects

Active Publication Date: 2019-10-18
TIANJIN UVOS TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of material still has some disadvantages, such as the low color rate of the chromophore, and the light response is not fast enough, which limits its application range.

Method used

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  • Double-condensed-ring naphthopyran photochromic compound and preparation method thereof
  • Double-condensed-ring naphthopyran photochromic compound and preparation method thereof
  • Double-condensed-ring naphthopyran photochromic compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation of embodiment 1 photochromic compound Ia

[0033] The first step: the preparation of compound M1, the reaction formula is as follows:

[0034]

[0035] In a 100mL three-necked flask, add 2.4g (8.45mmol) of 4-methoxynaphthalene-1-ylboronic acid pinacol ester, 1.75g ​​(6.4mmol) of dimethyl 2-bromoisophthalate, tetrakistriphenylphosphine Palladium 890mg (0.768mmol), anhydrous sodium carbonate 3.9g (36.86mmol), the device was evacuated and filled with nitrogen. Inject 1,4-dioxane / water (V 二氧六环 / V 水 =5:2) mixed solvent 56mL, reacted at 80°C for 12h, and stopped the reaction after the disappearance of the raw material point as monitored by TLC. Cool to room temperature, filter with celite, wash the organic phase three times with water, and extract with ethyl acetate. Combined organic layers, anhydrous MgSO 4 dry. The crude product obtained by distillation under reduced pressure was separated by column chromatography (petroleum ether / ethyl acetate=20:1...

Embodiment 2

[0052] The photochromic property test of embodiment 2 compound Ia

[0053] Take compound Ia, configure 8×10 -5 mol / L ethyl acetate solution. The solution was colorless before light irradiation, and the solution changed from colorless to purple rapidly when irradiated with ultraviolet light.

[0054] attached figure 1 It is the discoloration phenomenon of the toluene solution of compound Ia irradiated with ultraviolet light for 10 seconds.

[0055] attached figure 2 is compound Ia ethyl acetate solution (8×10 -5 mol / L) UV-Vis absorption spectrum when illuminated. Depend on figure 2 Calculated by the fitting formula, when the absorbance reaches half of the saturation value, the time is 3.6s, and when it reaches full saturation, the time is 12.6s, indicating that the compound changes color rapidly. Dilute to 8 x 10 in concentration -5 When mol / L, its saturated absorbance still reaches 0.7, shows that the color rate of compound Ia is high.

[0056] The ethyl acetate sol...

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Abstract

The invention relates to the field of organic functional materials. The invention provides a double-condensed-ring naphthopyran photochromic compound shown as a formula I and a preparation method thereof. The preparation method comprises the following steps: 4-methoxynaphthalen-1-ylboronic acid pinacol ester reacts with 2-bromoisophthalic acid dimethyl ester under the condition of a palladium catalyst to obtain 2-(4-methoxynaphthalen-1-yl)isophthalic acid dimethyl ester M1; the M1 and methylmagnesium bromide are subjected to addition, acidification cyclization and demethylation reactions to obtain 1,1,5,5-tetramethyl-1,5-dihydrobenzo[mno]aceanthrylene-9-ol M4; and then the compound M4 and 1,1-diaryl-2-propyn-1-ol react to generate the target compound I under acid catalysis. The compound Ican be changed from colorless to purple or blue under ultraviolet irradiation, the process is reversible, and the compound I has the characteristics of quick light response, excellent fatigue resistance, high color rate and the like. In the formula I, R<1> and R<2> are the same or different and separately represent hydrogen, straight-chain or branched-chain alkyl containing 1-6 carbon atoms, straight-chain or branched-chain alkoxy containing 1-6 carbon atoms, aryl, halogens, NH2 and -NRR.

Description

technical field [0001] The invention relates to the field of organic photochromic materials, in particular to a bis-condensed ring naphthopyran photochromic compound and a preparation method thereof. Background technique [0002] The photochromic properties of natural pyran compounds were first discovered by Becker in the 1960s, but as photochromic materials, their stability and cycle performance are poor, and their use value is low. In the 1990s, 2,2-diphenylnaphthopyran compounds with better performance were developed and used in commercial color-changing resin lenses. This has attracted people's attention, and a large number of photochromic compounds such as naphthopyrans, aromatic heterocyclic pyrans, and indene-fused ring naphthopyrans have been synthesized. Among them, indene-fused naphthopyran compounds have good photoresponsiveness, fast fading speed and good fatigue resistance, and are a kind of photochromic materials with practical application value, especially in...

Claims

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Application Information

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IPC IPC(8): C07D311/94C09K9/02
CPCC07D311/94C09K9/02C09K2211/1088
Inventor 韩杰席志强孙娟娟孟继本刘宗
Owner TIANJIN UVOS TECH CO LTD
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