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Double functional photochromism compound with stable nitrogen-oxygen free radical group and spiro oxazinyl and synthetic method and use thereof

A photochromic and compound technology, used in chemical instruments and methods, organic chemistry, color-changing fluorescent materials, etc., can solve the problem of unreported organic photochromic molecules, and achieve simple and stable synthesis and purification methods. Good, easy-to-obtain raw materials

Inactive Publication Date: 2007-08-08
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Spirooxazine compounds, as a very important class of many organic photochromic compounds, have attracted widespread attention, and have been extensively studied and applied. However, the introduction of paramagnetic The stable nitroxide radical functional group makes the molecule possess paramagnetism in addition to the typical photochromic properties, and the organic photochromic molecules with bifunctional integration have not been reported yet.

Method used

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  • Double functional photochromism compound with stable nitrogen-oxygen free radical group and spiro oxazinyl and synthetic method and use thereof
  • Double functional photochromism compound with stable nitrogen-oxygen free radical group and spiro oxazinyl and synthetic method and use thereof
  • Double functional photochromism compound with stable nitrogen-oxygen free radical group and spiro oxazinyl and synthetic method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of 2,2,6,6-tetramethyl-1-oxopiperidin-4-2-chloroacetate:

[0042]

[0043] Add 10mmol of 4-hydroxy-2,2,6,6-tetramethyl-piperidine-1-oxygen, 10mmol of chloroacetic acid to 30ml of dichloromethane, and add an equimolar amount of Dicyclohexylcarbodiimide (DCC) and 0.6 mg of p-dimethylaminopyridine (DMAP) were reacted at room temperature for 12 hours. The formed urea was removed by filtration. The filtrate was successively washed with 10ml of 1M hydrochloric acid, 10ml of NaHCO 3saturated solution and 10ml of saturated brine for washing. Anhydrous Mg 2 SO 4 Dry overnight, filter, concentrate the filtrate, separate and purify with a silica gel column [v (ethyl acetate) / v (petroleum ether) = 3 / 5], and then recrystallize with petroleum ether to obtain red needle crystals with a yield of 89%.

Embodiment 2

[0045] Synthesis of 6-bromohexanoic acid 2,2,6,6-tetramethyl-1-oxopiperidin-4-ester:

[0046]

[0047] Add 10mmol of 4-hydroxy-2,2,6,6-tetramethyl-piperidine-1-oxygen, 10mmol of 6-bromohexanoic acid to 30ml of dichloromethane, add at 0°C under nitrogen protection Equimolar amounts of dicyclohexylcarbodiimide (DCC) and 0.6 mg of p-dimethylaminopyridine (DMAP) were reacted at room temperature for 12 hours. The formed urea was removed by filtration. The filtrate was successively washed with 10ml of 1M hydrochloric acid, 10ml of NaHCO 3 saturated solution and 10ml of saturated brine for washing. Anhydrous Mg 2 SO 4 Dry overnight, filter, concentrate the filtrate, separate and purify with a silica gel column [v (ethyl acetate) / v (petroleum ether) = 3 / 5], and recrystallize with petroleum ether to obtain a red solid with a yield of 80%.

Embodiment 3

[0049]

[0050] 0.5mmol 1,3-dihydro-1,3,3-trimethyl-9'-hydroxy-spiro-[2H-indole-2,3'-[3H]naphtho[2,1-b][1 , 4] oxazine, 0.5mmol 2-chloroacetic acid 2,2,6,6-tetramethyl-1-oxopiperidine-4-ester (Example 1) and 6g anhydrous potassium carbonate, 25ml acetone, heated to reflux , reacted for 12 hours, filtered, the filtrate was concentrated, and silica gel column chromatography [v (ethyl acetate) / v (petroleum ether) = 2 / 5], the product was obtained with a yield of 30%.

[0051] 1 HNMR (CDCl 3 ): 7.87(1H, s), 7.72(2H, m), 7.63(1H, d, J=8.8Hz), 7.18(1H, d, J=8.8Hz), 7.12(1H, d, J=8.8Hz ), 6.94 (3H, m), 6.61 (1H, d, J=8, 8Hz), 4.88 (2H, s), 2.79 (3H, s), 1.39 (6H, s).

[0052] MS: m / z 556.8 [M + ].

[0053] Paramagnetic (ESR) (CH 2 Cl 2 , X-band, room temperature): triplet (1:1:1), g=2.007, a=15.34G.

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PUM

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Abstract

The invention discloses a dysfunctional photoproduced color bleeding compound and synthesizing method and application with stable nitrogen-oxygen free radical and spiral oxazine radical, which is characterized by the following: adopting substituted 9'-hydroxy indole oxazine and stable nitrogen-oxygen free radical as raw material; obtaining the product with structural formul as right formula (R1 is C1-C18 alkyl; R2 is hydrogen, C1-8 alkyl, C1-8 alkoxy, halogen or condensed benzene ring; L is connecting arm - (CH2) m-; m is between 1 and 9).

Description

technical field [0001] The invention belongs to the field of spirooxazine organic photochromic materials, in particular to a bifunctional photochromic compound with a stable nitroxide free radical group and a spirooxazine group, a synthesis method and an application thereof. Background technique [0002] The principle of photochromism can be described as follows: [0003] [0004] Photochromic substance A, in a certain wavelength of light (hv 1 ) under the irradiation, can change its molecular structure to form compound B, and change color. Compound B can be used at another wavelength of light (hv 2 ) or heat (△) to restore the original color, this reversible process is called photochromism. [0005] Organic photochromic materials have broad application prospects. Compared with inorganic materials, they have the advantages of wide selection range, fast response speed, easy processing, and low cost. Organic photochromic systems mainly include spirooxazine compounds, sp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K9/02C07D498/10G02F7/00H03K17/94
Inventor 闫文鹏张长瑞樊美公
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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