Method for preparing optically active poly(alkyl-aryl) silane

An alkylarylsilane and optically active technology, which is applied in the field of preparation of polyalkylarylsilane, can solve the problems of difficulty in preparation, limited synthesis method, and high synthesis cost of dichlorosilane monomer, and achieves simple operation method and low cost low effect

Inactive Publication Date: 2012-01-04
HANGZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Due to the current limited synthesis methods of optically active polysilanes, the dichlorosilane monomers used in the existing synthesis methods have high synthesis cost and difficulty in preparation, chiral amines must be equivalent, and cannot be recycled and reused. The invention proposes a preparation method of optically active polyalkylarylsilane, the preparation method is easy to operate and low in cost

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  • Method for preparing optically active poly(alkyl-aryl) silane
  • Method for preparing optically active poly(alkyl-aryl) silane
  • Method for preparing optically active poly(alkyl-aryl) silane

Examples

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Embodiment 1

[0029] Under the protection of argon, the non-optically active polysilane poly-4-methylphenylmethylsilane (134 mg, the molar number of repeating units is 1 mmol), the chiral diamine compound (-)-sparteine(a) (23 mg, 0.1 mmol) dissolved in 20ml tetrahydrofuran. The solution was cooled to -78 0 C, slowly drop tert-butyllithium (0.1mmol), at -78 0 C for 1 hour. The reaction was quenched by adding saturated ammonium chloride solution (1 ml) dropwise, extracted with toluene three times (3×10 mL), and the organic layer was washed three times with saturated saline solution (3×10 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, evaporated the solvent, dissolved in anhydrous tetrahydrofuran (1 mL), and reprecipitated with absolute ethanol to obtain 124 mg of optically active poly-4-methylphenylmethylsilane. The result is an average molecular weight distribution of M w / M n = 1.3, the average molecular weight is M n = 13000 of methylphenyl polysilane,...

Embodiment 2

[0032] Under nitrogen protection, the non-optically active polysilane poly-4-ethylphenylmethylsilane (148 mg, the molar number of repeating units is 1 mmol), the chiral diamine compound (-)-sparteine ​​(a) (2.3 mg , 0.01mmol) dissolved in 20ml 1,2-dimethoxyethane. The solution was cooled to -100 0 C, slowly drop n-butyllithium (0.1mmol), at -100 0 C was reacted for 0.5 hours. The reaction was quenched by adding saturated ammonium chloride solution (1 ml) dropwise, extracted with dichloromethane (3×10 mL), and the organic layer was washed three times with saturated saline solution (3×10 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was distilled off, dissolved in anhydrous chloroform (1 mL), and reprecipitated with anhydrous methanol to obtain 127 mg of optically active poly-4-ethylphenylmethylsilane. The result is an average molecular weight distribution of M w / M n = 1.2, the average molecular weight is M n = 12908 of methylp...

Embodiment 3

[0034] Under the protection of argon, the non-optically active polysilane poly-4-methylphenylethylsilane (148 mg, the molar number of repeating units is 1 mmol), the chiral diamine compound (-)-sparteine ​​(a) (230 mg, 1mmol) dissolved in 20ml benzene. The solution cools down to 0 0 C, slowly drop sec-butyllithium (0.1mmol), at 0 0 C for 1 hour. The reaction was quenched by adding saturated ammonium chloride solution (0.5 ml) dropwise, extracted twice with chloroform (2×10 mL), and the organic layer was washed three times with saturated saline solution (3×10 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, evaporated the solvent, dissolved in anhydrous benzene (1 mL), and reprecipitated with anhydrous ethanol to obtain 127 mg of optically active poly-4-methylphenylethylsilane. The result is an average molecular weight distribution of M w / M n = 1.4, the average molecular weight is M n = 12963 of methylphenylpolysilane, the yield is 89%.

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Abstract

The invention relates to an organic high molecular compound, in particular to a method for preparing optically active poly(alkyl-aryl) silane. As the traditional method for synthesizing optically active poly(alkyl-aryl) silane is extremely limited, the invention provides a novel method for preparing optically active poly(alkyl-aryl) silane. Polysilane which is not optically active is used as a raw material in an organic solvent A, alkyl lithium is a reactant, chiral diamine is used as a chiral inductor, and saturated ammonium chloride is used for quenching reaction to prepare the optically active poly(alkyl-aryl) silane. The preparing method has the advantages of convenience for operation and low cost.

Description

technical field [0001] The present invention relates to organic macromolecular compounds, in particular to a preparation method of optically active polyalkylaryl silanes. Background technique [0002] Optically active polysilane is a kind of polymer with a stable unidirectional helical structure composed of a helical main chain constructed by Si-Si single bonds and chiral or achiral substituent groups connected to the main chain. Due to the σ-conjugation effect in the molecule, the electrons can be widely delocalized along the main chain, so this kind of polysilane has special physical and chemical properties that other carbon-based and siloxane-based polymers do not have, and is ideal for preparing chiral sensors. , chiral analyzers, chiral amplifiers, chiral optical switches and chiral optical memory ideal materials. At the same time, optically active polysilanes also have broad application prospects in molecular recognition and as chiral stationary phases. [1] . Howeve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G77/60
Inventor 陈巍峰来国桥蒋剑雄李志芳王秋红
Owner HANGZHOU NORMAL UNIVERSITY
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