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6íõ-heterocycle substituted spirooxazine photochromic compound and method for preparing same

A technology of photochromism and compounds, applied in the direction of chemical instruments and methods, color-changing fluorescent materials, etc., to achieve the effect of less dosage, bright colors and good fatigue resistance

Inactive Publication Date: 2005-06-22
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at the same time, a halogen is introduced at the 5-position of the benzene ring, and a spirooxazine photochromic material substituted with a heterocycle at the 6'-position of the naphthalene ring has not yet been reported.

Method used

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  • 6íõ-heterocycle substituted spirooxazine photochromic compound and method for preparing same
  • 6íõ-heterocycle substituted spirooxazine photochromic compound and method for preparing same
  • 6íõ-heterocycle substituted spirooxazine photochromic compound and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The first step, synthesis of nitrosonaphthol

[0029] Dissolve 5.7g (0.04mol) of 2-naphthol in 68mL of hot water containing 1.6g (0.04mol) of NaOH, place in an ice-salt bath, cool to 0°C, add 2.8g (0.04mol) of sodium nitrite, Add 9.5 mL of sulfuric acid with a concentration of 5.6 mol / mL dropwise under stirring, keeping the temperature at about 0°C. After the addition, continue stirring at 0°C for 1 hour, and then add a small amount of (NH 4 ) 2 SO 4 to remove excess sodium nitrite. Suction filtration, the solid was fully washed with water, and dried to obtain a yellow solid, which was recrystallized from petroleum ether (60-90° C.) to obtain 5.4 g of reddish-brown needle-like crystals with a yield of 79%, m.p.106-107° C. (lit. 106°C).

[0030]

[0031] The second step, synthesis of 5-chloro-1,3,3-trimethyl-2-methylidene indoline

[0032] Dissolve 8.39g (0.025mol) of 5-chloro-1,2,3,3-tetramethylindoline iodide in 25mL of water, add 8mL of aqueous solution contai...

Embodiment 2

[0041] The first step, synthesis of 1,3,3-trimethyl-2-methyleneindoline

[0042] Dissolve 7.5g (0.025mol) of 1,2,3,3-tetramethylindoline iodide in 25mL of water, add 8mL of aqueous solution containing 1.6g (0.04mol) of NaOH, stir at room temperature for 30 minutes, and wash with chloroform extraction, the organic phase was washed with water, and washed with anhydrous MgSO 4 After drying, the solvent was distilled off to obtain 3.9 g of a colorless liquid with a yield of 90%, which would rapidly turn red when placed in air.

[0043]

[0044] The second step, synthesis of 1,3,3-trimethyl-6'-decahydroisoquinoline-spiroindoline-2,3'-[3H]naphtho[2,1-b][1,4 ] Synthesis of oxazines

[0045]

[0046] 1.73g (0.01mol) of nitrosonaphthol, 2.78g (0.02mol) of decahydroisoquinoline, 50mL of trichlorethylene as a solvent, heated to reflux for 30 minutes, slowly added dropwise 1.73g of indoline, and continued to reflux for 3 -4 hours, spin-dried, and performed column chromatography w...

Embodiment 3

[0050] The first step, synthesis of 5-chloro-1,3,3-trimethyl-6′-hexamethyleneimine-spiroindoline-2,3′[3H]naphtho[2,1-b] [1,4]oxazine

[0051]

[0052] 2g (0.011mol) of nitrosonaphthol and 1.13mL of hexamethyleneimine were introduced into N in 30mL of anhydrous methanol 2 , heated to reflux for 30 minutes, added dropwise 1.3g (0.006mol) 5-chloro-1,3,3-trimethyl-2-methyleneindoline and continued to heat and reflux overnight to obtain 0.23g of photochromic product, producing The rate is 8.42%.

[0053] image 3 Example 3 Synthetic Compound Mass Spectrum.

[0054] The second step, detection:

[0055]Photochromic substances can be observed to change the color of the solution to blue-purple under the irradiation of ultraviolet light or sunlight. At the same time, the maximum absorption peak of ultraviolet absorption wavelength can be observed at 589nm after irradiation with ultraviolet spectrophotometer -1 place.

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Abstract

The invention discloses a 6íõ-heterocycle substituted spirooxazine photochromic compound and method for preparation, wherein the compound has the structural formula disclosed in the specification, the advantages of the synthesized photochromic compound include bright color, better antifatigue property, thus can be widely applied to the field of optical information material, false proof identification material, textile printing and dyeing.

Description

technical field [0001] The invention relates to a photochromic compound, in particular to a 6'-heterocyclic substituted spirooxazine photochromic compound and a preparation method thereof. Background technique [0002] In the research on spirooxazine photochromic compounds, most of them focus on changing the parent ring and changing various substituents, such as introducing various electron-donating groups or electron-withdrawing groups on the benzene ring, and introducing various electron-donating groups or electron-withdrawing groups on the naphthalene ring. Various substituent groups are introduced at the 6'-position or 9'-position, such as patents JP07,132,667, EP0316,980, EP0245,020, organic photochromic chemistry (edited by the Japanese Chemical Society, published in 1996, P70-88), etc. , they are widely used in optical information storage, optical recording materials, optical disc materials and decorative materials, while Nankai University is also used in anti-counter...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K9/02
Inventor 孟继本黄华鸣陈培丽高用彬付亿方
Owner NANKAI UNIV
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