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Synthetic method of dual-furan substituted fulgide photochromic compound

A technology of fugitive anhydride and photochromism, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of harsh synthesis conditions, low yield of target compounds, and difficulty in synthesis

Active Publication Date: 2013-02-06
浙江阿克迈新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the Stobbe condensation reaction is not only ketone-ester condensation, but also side reactions such as ester-ester condensation and ketone-ketone condensation, the reaction is more complicated, and the yield of the target compound is low, generally 5% to 30%.
[0006] Compared with the monoheterocyclic substituted fulgide, there is a substituted heterocycle on each methylene carbon in the biheterocyclic substituted fulgide molecule. Theoretically, it is possible to form 2 electrocyclization reactions. system (similar to all-cis-hexatriene structure), which is more conducive to the photochromic reaction, however, this type of molecule has greater steric hindrance, which brings difficulties in synthesis
In 1999, Kiji et al. [Kiji J, et al.A convenient and general synthetic method for photochromic fulgides by palladium-catalyzed carbonylation of 2-butyne-1,4-diols.Mol.Cryst.Lig.Cryst.,2000,344 : 235-240] have reported the method for the carbonylation of butyne-1,4-diol to synthesize biheterocyclic fulgid anhydride compound, reaction is under Pa catalysis, carries out under high temperature and high pressure, and this method is biheterocyclic The synthesis of fulgid anhydride has opened up a new path, but the synthesis conditions are harsh and difficult to promote

Method used

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  • Synthetic method of dual-furan substituted fulgide photochromic compound

Examples

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Effect test

Embodiment 1

[0027] Add 15mL of anhydrous tert-butanol to a dry 250mL three-necked bottle, and then dissolve 5g of potassium metal in it to obtain a potassium tert-butoxide solution. Add 9g of 2,5-dimethyl-3-acetylfuran and 28g of butanedi Diethyl acetate and 55mL of tert-butanol were mixed to obtain a mixed solution, and the above mixed solution was added dropwise to the above-mentioned potassium tert-butoxide solution for 1 hour under stirring at 20°C. After the addition was completed, reflux was continued for 24 hours, and then cooled to room temperature, acidify with 5mol / L hydrochloric acid to pH 5-6, then distill off the solvent under reduced pressure, dissolve the residue in 200-400mL water, extract twice with ether (2×50mL), and wash the water layer with Acidify with hydrochloric acid (6mol / L) to strong acidity (PH = 1), and after static separation, the reddish-brown organic phase monoester is extracted with ether for 3 times (3×100mL), dried and filtered with anhydrous sodium sulfa...

Embodiment 2

[0034] Same as Example 1, but the consumption of step (1) 2,5-dimethyl-3-acetylfuran is changed from 9g to 11.5g, the consumption of diethyl succinate is changed from 28g to 33.6g, other Change.

Embodiment 3

[0036] Same as Example 1, but the consumption of step (1) 2,5-dimethyl-3-acetylfuran is changed from 9g to 8.2g, the consumption of diethyl succinate is changed from 28g to 23.8g, other Change.

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Abstract

The invention relates to a synthetic method of dual-furan substituted fulgide photochromic compound, the method comprises the steps of taking potassium tert-butoxide as organic alkali; enabling 2, 5-dimethyl-3-acetylfuran and diethyl succinate to generate monoacid ester by Stobbe condensation reaction; then generating diester by methanol and acetylchloride; enabling diester and 2, 5-dimethyl-3-acetylfuran to generate monoacid ester by Stobbe condensation reaction; finally, saponifying the monoacid ester in alcohol solution of potassium hydroxide to obtain dual-acid; dewatering the dual-acid, obtaining dual-furan substituted fulgide. The dual-furan substituted fulgide photochromic compound can change into pink (closed loop body) from yellow (open loop body) in a solid or liquid state under irradiation of the ultraviolet light with wavelength of 360-370nm. Compared with the mono-furan substituted fulgide photochromic compound, the molecule of the furan substituted fulgide photochromic compound has two functional groups capable of cyclization reaction, which better facilitates photochromism.

Description

technical field [0001] The invention belongs to the field of chemical industry, and specifically relates to photochromic material technology, in particular to a method for synthesizing difuran-substituted fulginic anhydride photochromic compounds. Background technique [0002] Photochromic compounds are a new class of functional organic materials. The photochromic phenomenon means that the compound undergoes a specific chemical reaction to produce another product when it is irradiated by light of a certain wavelength, and its absorption spectrum changes significantly. Under the irradiation of light or heat, it returns to its original form. The specificity of photochromic compounds brings broad application prospects, which can be used as optical information recording materials, molecular wires, and molecular switches. Wait. [0003] At present, most of the research on photochromic compounds is concentrated on azochromic compounds, azobenzenes, spiropyrans, spirooxazines, thi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/36C09K9/02
Inventor 王锐兰周安安
Owner 浙江阿克迈新材料有限公司
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