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Azobenzol photochromic compound of fluorine-containing end group chiral carbon and method for synthesizing the same

A technology of photochromism and synthesis method, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problems of inconspicuous discoloration, low storage stability, limited application, etc., and achieve wide application prospects, photochromic Obvious discoloration and stable storage

Inactive Publication Date: 2009-08-12
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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  • Azobenzol photochromic compound of fluorine-containing end group chiral carbon and method for synthesizing the same
  • Azobenzol photochromic compound of fluorine-containing end group chiral carbon and method for synthesizing the same
  • Azobenzol photochromic compound of fluorine-containing end group chiral carbon and method for synthesizing the same

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: Synthesis of the azobenzene photochromic compound containing fluorine-terminated 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-salt 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-dimethylazobenzene was added. Formamide was used as a catalyst, reacted at room temperature for 0.5h, then added an oil bath to slowly raise the temperature for reaction, kept stirring at 30°C for 1h, then raised the temperature to 70°C for another 2h, vacuum filtered all unreacted thionyl chloride, Cool to room temperature for later use;

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

Embodiment 2

[0033] Embodiment 2: The synthesis of the azobenzene photochromic compound of the fluorine-containing terminal 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-salt 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-dimethylazobenzene was added. Formamide was used as a catalyst, reacted at room temperature for 1 hour, then added an oil bath to slowly raise the temperature for reaction, kept stirring at 40°C for 2 hours, then raised the temperature to 80°C for another 4 hours, vacuum filtered all unreacted thionyl chloride, cooled to room temperature for use;

[0036] In the second step, add 18.83g (7 parts by weight) of N,N-dimethylfo...

Embodiment 3

[0037] Embodiment 3: The synthesis of the azobenzene photochromic compound of the fluorine-containing terminal 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-salt 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-dimethylazobenzene was added. Formamide was used as a catalyst, reacted at room temperature for 2 hours, then added an oil bath to slowly raise the temperature for reaction, kept stirring at 50°C for 3 hours, then raised the temperature to 90°C and reacted for 6 hours, vacuum filtered all unreacted thionyl chloride, cooled to room temperature for use;

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

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Abstract

The invention relates to an azobenzol photochromism compound containing fluorine terminal group chiral carbon, and a synthesizing method thereof. As a fluorine terminal group chiral carbon group is introduced into an azobenzol compound, the photochromism property of the azobenzol compound undergoes obvious change, UV-Vis absorption spectrum changes greatly before and after inducement, i.e the absorption spectrum changes greatly in the two statuses of cis-form and trans-form, and the storage is stable at the room temperature. Hereby, the application scope of azobenzol-type photochromism materials is enlarged, and the azobenzol-type photochromism materials have wide and potential application prospect in the fields such as the data storage material field, the liquid crystal display material field, the non-linear material field, the optical molecular switch field, the chiral identification field, and the like. The synthesized azobenzol photochromism compound containing chiral carbon has a general formula shown in the drawing.

Description

technical field [0001] The invention relates to an azobenzene photochromic compound containing fluorine terminal 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 a...

Claims

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Application Information

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IPC IPC(8): C07C245/08C09K9/02
Inventor 谢孔良于艳红陈思侯爱芹
Owner DONGHUA UNIV
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