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Photochromic compound and its preparation method and application

A compound and selected technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve problems such as photochemical side reactions, limit the application of r-spiropyran, and affect the number of reversible conversion cycles

Active Publication Date: 2016-08-24
湖州佳灏信息技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, merocyanine will automatically transform into a colorless spiro ring structure after being stored at room temperature for a few minutes to a few hours. In addition, photochemical side reactions will occur during the sting process, thereby affecting the number of cycles of reversible transformation. These limitations limit r Application of Spiropyran in Photomolecular Switch

Method used

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  • Photochromic compound and its preparation method and application
  • Photochromic compound and its preparation method and application
  • Photochromic compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Add 2.5g (62.4mmol) NaOH and 100ml water into a four-neck flask, stir to dissolve at 60°C, then add 10g (62.4mmol) 2,7-dihydroxynaphthalene, stir at 60°C for 30min, and wait for dissolution After adding 5.2g (74.80mmol) NaNO 2 , stirred for 20 min, cooled to 0° C. in an ice-salt bath, slowly added dropwise a mixture of 8 mL of concentrated sulfuric acid and 15 mL of water at this temperature, and continued to react for 3 h after the addition was complete. After the reaction was completed, 11.33 g of a reddish-brown solid was obtained after suction filtration, and the yield was 96.2%. Elemental Analysis, C 10 h 7 o 3 N: found value (theoretical value) / %: C 63.49 (63.52); H 3.71 (3.70); H 7.43 (7.41).

[0034]

[0035] (2) Under a nitrogen atmosphere, add 9.45g (0.05mol) of 1-nitroso-2,7-dihydroxynaphthalene and 600mL of anhydrous methanol to a 1000mL four-neck flask, reflux and stir for 1h, and then add 2 times the equivalent of indole Dole, stirred at reflux...

Embodiment 2

[0043] Using the same method as in Example 1, replacing indole with pyrrole and p-phenylbenzoyl chloride with p-naphthylbenzoyl chloride, 1,3-dimethyl-6'-pyrrolyl-9 '-[p-naphthylbenzoyloxy]-1,3 dihydrospiro[benzimidazole-2,3'-naphtho[2,1-b][1,4]oxazine. The yield was 53.1%.

[0044] The photochromic substance is configured into 1×10 with chloroform -5 mol / L dilute solution, and then irradiated with 365nm ultraviolet light, it can be observed that the color of its chloroform solution changes from colorless to blue-green, and at the same time, it can be observed with an ultraviolet spectrophotometer (U.S. after 623nm -1 The maximum absorption peak appears.

Embodiment 3

[0046] Using the same method as in Example 1, replacing indole with imidazole, and p-phenylbenzoyl chloride with p-anthracenylbenzoyl chloride, 1,3-dimethyl-6'-imidazolyl-9 '-[p-Anthracenylbenzoyloxy]-1,3 dihydrospiro[benzimidazole-2,3'-naphtho[2,1-b][1,4]oxazine. The yield was 51.8%.

[0047] The photochromic substance is configured into 1×10 with chloroform -5 mol / L dilute solution, and then irradiated with 365nm ultraviolet light, it can be observed that the color of its chloroform solution changes from colorless to pink purple, and at the same time, it can be observed with a UV spectrophotometer (Varian UV1101, USA). after 620nm -1 The maximum absorption peak appears. The above-mentioned embodiments only illustrate the principles and effects of the present invention, but are not intended to limit the present invention. Anyone skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Th...

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Abstract

The invention discloses a photochromic compound 6'-azacyclo substituted-9'-acyloxy esterified spirooxazine and a preparation method thereof. R1 is chosen from substituent or unsubstituent imidazolyl, pyrazolyl, pyrryl, indolyl, indazolyl or purinyl, and the substituent is halogen or C1-6 alkyl; R2 is chosen from C1-10 alkyl benzoyl, phenyl benzoyl, naphthyl benzoyl or anthryl benzoyl. The invention tries to take substituent naphthalene nucleus as a substrate, the novel oxazine compound is synthesized through modification of 6'-bit azacyclo and esterification reaction of 9'-bit, and the type of the oxazine compound is expanded. The performance of the photochromic compound is researched under the ultraviolet condition to obtain the oxazine compound with favorable photochromic property. A foundation is expected for developing the photochromic material with excellent performance, and meanwhile, reference is provided for further research on the spirooxazine compound in future.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a photochromic compound and its preparation method and application. Background technique [0002] Photochromic materials refer to a class of materials that can change color after being excited by a light source. Photochromism refers to the change of the molecular structure of certain compounds under the action of light of a certain wavelength and intensity, resulting in a corresponding change in the color of the light absorption peak, and this change is generally reversible. It has been more than 100 years since human beings discovered the phenomenon of photochromism. The first successful commercial application began in the 1960s. Two material scientists, Amistead and Stooky, from the Corning Studio in the United States first discovered the reversible photochromic properties of silver-halide (AgX) glasses, and then people identified the mechanism. He applied a lot of research a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/10C09K9/02
CPCC07D498/10C09K9/02C09K2211/1022C09K2211/1048
Inventor 杨宝杰张舒
Owner 湖州佳灏信息技术有限公司