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Thiodiene nickel complex and its preparation method and use

A technology of thiodiene nickel and complexes, applied in chemical instruments and methods, instruments, organic chemistry, etc., can solve the problems of low filtering efficiency, poor solubility and compatibility, and difficult processing of optical filters, etc. problem, to achieve the effect of high light absorption coefficient, easy processing, and good light absorption characteristics

Inactive Publication Date: 2016-02-17
佛山市顺德区骐奥塑料实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Few of the thiodiene complex filters currently available for laser protection can meet the requirements of high absorption coefficient at 1064nm, and the solubility and compatibility of thiodiene complexes that have been developed Generally not good, therefore, the processing of related filters is more difficult, and the filtering efficiency is not high

Method used

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  • Thiodiene nickel complex and its preparation method and use
  • Thiodiene nickel complex and its preparation method and use
  • Thiodiene nickel complex and its preparation method and use

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Thiodiene nickel complexes, the structural formula is:

[0039] ...compound 3(I) wherein (2-Ethylhexyl).

[0040] The preparation method of compound 3 (I), comprises the following steps:

[0041]

[0042] (1) Synthesis of Compound 1 (I) (N-ethylhexylcarbazole)

[0043] In a 250ml single-necked bottle, add carbazole (15.05g, 90mmol) and 130mL DMF. After the carbazole is completely dissolved, slowly add NaH (2.59g, 108mmol), while cooling down in an ice-water bath, stir for 30min, and then add bromo Isooctane (20.86g, 108mmol), stirred overnight at room temperature. After the reaction was complete, the reaction mixture was poured into 300 mL of distilled water, extracted three times with n-hexane (100 ml / time), washed once with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, and purified by column chromatography (n-hexane was Eluent) to obtain 22.68 g of a colorless violet oily liquid with a yiel...

Embodiment 2

[0049] Thiodiene nickel complexes, the structural formula is:

[0050] .....Compound 3(II) where (2-Ethylhexyl).

[0051] The preparation method of complex 3 (II), comprises the following steps:

[0052]

[0053] (1) Synthesis of Compound 1 (II) (N-ethylhexylphenothiazine)

[0054] In a 250ml single-necked bottle, add phenothiazine (18g, 90.33mmol) and 100mL DMF, after the phenothiazine is completely dissolved, slowly add NaH (2.80g, 117.4mmol), while cooling down in an ice-water bath, stir for 30min, and then dropwise Bromoisoctane (22.68 g, 117.4 mmol) was added and stirred overnight at room temperature. After the reaction is complete, the reaction is poured into 300mL distilled water to stop the reaction, extracted three times with n-hexane (100ml / time), washed once with saturated saline water, anhydrous MgSO 4 Dry overnight, remove the solvent by rotary evaporation, and purify by column chromatography (n-hexane as eluent) to obtain a blue-yellow oily liquid with ...

Embodiment 3

[0060] Thiodiene nickel complexes, the structural formula is:

[0061]  …3(III) where (2-Ethylhexyl).

[0062] The preparation method of complex 3 (III), comprises the following steps:

[0063]

[0064] (1) Synthesis of compound (4-[(2-ethylhexyl) oxygen]-1-iodobenzene)

[0065] In a 250mL round bottom flask, add 4-iodophenol (28.00g, 127.27mmol), K 2 CO 3 (26.32g, 190.40mmol), bromoisoctane (26.62g, 135.00mmol) and DMF (100mL), under argon protection, react at 100°C for 51h. After the reaction, the mixture was poured into 100 mL of distilled water, extracted three times with n-hexane, washed once with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, and purified by column chromatography (eluent was n-hexane) to obtain a colorless Liquid compound 32.43g, yield 76.68%. 1 H-NMR (400MHz, CDCl 3 ,δ):7.51(d,J=8.96Hz,2H),6.67(d,J=8.96Hz,2H),3.78(d,J=5.84Hz,2H),1.69(m,1H),1.23-1.52 (m,8H),0.90(m,6H).IR,υ max (K...

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Abstract

The invention relates to a sulfo-diene nickel complex as well as a preparation method and applications thereof and belongs to the field of organic synthesis. According to the adopted technical scheme, the general formula of the sulfo-diene nickel complex is shown in the specification, wherein the R is straight chain or branched chain alkyl of C6-C20 or straight chain or branched chain alkoxy of C6-C20. The preparation method of the complex comprises the following steps: dissolving a compound with the structural formula as shown in the specification in an organic solvent, carrying out acylation reaction with oxalyl chloride (C2O2Cl2) to obtain an o-diketone compound and continuing reacting under the action of P2S5 and nickel chloride to obtain the sulfo-diene nickel complex. The preparation method disclosed by the invention is simple and mild in condition; the prepared complex is good in heat stability and difficult in separating and has very high light absorption coefficient in a near-infrared region; the light filter prepared by adopting the complex is very good in effect on near-infrared laser protection and is particularly suitable for 1064nm laser protection; in the meantime, the complex has the double characteristics of visibility and laser protection compatible in a visible light region.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a thiodiene nickel complex, as well as its preparation method and application. Background technique [0002] With the popularization of near-infrared lasers in biomedicine, optical communications, and military applications, the protection of near-infrared lasers will receive more and more attention. For the 1064nm laser, its wavelength is just in the range of 800-1300nm in the biological optical window, which has good permeability to organisms, and has a wide range of applications in biological imaging, drug controlled release, diagnosis and treatment, etc. prospect. Accordingly, research on biological protection against 1064nm lasers has become an urgent problem to be solved, especially the protection of the eyes of operators has been put on the agenda. [0003] 1064nm laser is also one of the wavelengths of commonly used military lasers. With the continu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07D279/22C07C325/02C09B57/10G02B5/20G02B1/04
CPCC07C325/02C07D209/86C07D279/22C09B57/10G02B1/04G02B5/208G02B5/223
Inventor 刘应良曹少魁张真如许慎刚
Owner 佛山市顺德区骐奥塑料实业有限公司
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