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Azobenzene photochromicsm compound containing L-ethyl lactate chiral carbon and synthesis thereof

An ethyl lactate, photochromic technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of insignificant discoloration, limited application, low storage stability, etc., and achieve obvious photochromic phenomenon. , the effect of stable storage and wide application prospects

Inactive Publication Date: 2009-07-29
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The general azobenzene compounds have little difference in the absorption spectrum between the cis and trans states, the color change is not obvious, and the storage stability at room temperature is low, and the practicability is not good, which limits its application in many aspects.

Method used

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  • Azobenzene photochromicsm compound containing L-ethyl lactate chiral carbon and synthesis thereof
  • Azobenzene photochromicsm compound containing L-ethyl lactate chiral carbon and synthesis thereof
  • Azobenzene photochromicsm compound containing L-ethyl lactate chiral carbon and synthesis thereof

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Experimental program
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Embodiment 1

[0029] Embodiment 1: the synthesis of the azobenzene photochromic compound containing L-ethyl lactate chiral carbon with the following structure:

[0030]

[0031] The first step, pour 40.35g (15 parts by weight) of thionyl chloride into a three-necked flask, cool to 0°C in an ice bath and feed, and weigh 2.69g (1 part by weight) of 4-carboxy-4'-N , N-dimethylazobenzene was added to the three-necked flask in batches, and the reaction temperature in the bottle was kept at 0°C. After all the dyes were added, 0.05g (0.02 parts by weight) of N,N-dimethylformazol was added. Amide as catalyst, react at room temperature for 0.5h, then add an oil bath to slowly raise the temperature for reaction, keep stirring at 30°C for 1h, then raise the temperature to 70°C for another 2h, vacuum distill off all unreacted thionyl chloride, cool to Standby at room temperature;

[0032] In the second step, add 13.45g (5 parts by weight) of N,N-dimethylformamide to the above-mentioned three-necked...

Embodiment 2

[0033] Embodiment 2: the synthesis of the azobenzene photochromic compound containing L-ethyl lactate chiral carbon with the following structure:

[0034]

[0035] The first step, pour 48.42g (18 parts by weight) of thionyl chloride into a three-necked flask, cool to 3°C in an ice bath and feed, and weigh 2.69g (1 part by weight) of 4-carboxy-4'-N , N-dimethylazobenzene was added to the three-necked flask in batches, and the reaction temperature in the bottle was kept at 3°C. After all the dyes were added, 0.08g (0.03 parts by weight) of N,N-dimethylformazol was added. Amide as a catalyst, react at room temperature for 1 hour, then add an oil bath to slowly heat up the reaction, keep stirring at 40°C for 2 hours, then raise the temperature to 80°C for another 4 hours, vacuum distill off all unreacted thionyl chloride, and cool to room temperature stand-by;

[0036] In the second step, add 18.83g (7 parts by weight) of N,N-dimethylformamide to the above-mentioned three-neck...

Embodiment 3

[0037] Embodiment 3: the synthesis of the azobenzene photochromic compound containing L-ethyl lactate chiral carbon with the following structure:

[0038]

[0039] The first step, pour 53.80g (20 parts by weight) of thionyl chloride into a three-necked flask, cool to 5°C in an ice bath and feed, and weigh 2.69g (1 part by weight) of 4-carboxy-4'-N , N-dimethylazobenzene was added to the three-necked flask in batches, and the reaction temperature in the bottle was kept at 5°C. After all the dyes were added, 0.11g (0.04 parts by weight) of N,N-dimethylformazol was added. Amide as catalyst, react at room temperature for 2 hours, then add an oil bath to slowly raise the temperature to react, keep stirring at 50°C for 3 hours, then raise the temperature to 90°C and react for 6 hours, vacuum distill off all unreacted thionyl chloride, and cool to room temperature stand-by;

[0040] In the second step, add 26.90g (10 parts by weight) of N,N-dimethylformamide to the above-mentione...

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Abstract

The invention relates to an azobenzene photochromic compound containing L-ethyl lactate chiral carbon and a synthetic method thereof. L-ethyl lactate chiral carbon groups are introduced into the azobenzene compound, therefore, the photochromic property is changed obviously. Before and after the inducing, the absorption spectrum of UV-Vis changes greatly, which means the absorption spectrum difference of cis and trans states is large, and the reservation at the room temperature is stable. Therefore, the application field of azobenzene photochromic material is enlarged, and the azobenzene photochromic material has wide potential application prospect in fields of data storing material, liquid crystal displaying material, nonlinear material, optical molecular switches, chiral recognition, and the like. The structure of the photochromic compound which contains chiral carbon and is synthesized by the invention has the general formula as is shown above.

Description

technical field [0001] The invention relates to an azobenzene photochromic compound containing L-ethyl lactate chiral carbon and a synthesis method thereof, belonging to the field of azo photochromic materials. Background technique [0002] Photochromism (Photochromism) means that compound A is subjected to a wavelength of λ 1 When exposed to light, compounds B with different structures and spectral properties can be generated through specific chemical reactions, and at a wavelength of λ 2 Under the action of light or heat, compound B reversibly generates compound A, and the change process is shown in the following formula: [0003] [0004] Photochromic materials are a new class of functional materials that have been studied in recent years, and have received extensive attention in the high-tech field. The discoloration mechanism of azobenzene compounds is due to the presence of -N=N-, two isomers of cis (cis) and trans (trans), which have unique optical properties and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08C09K9/02
Inventor 谢孔良陈思侯爱芹于艳红
Owner DONGHUA UNIV
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