Silolene compound, as well as preparation method and application thereof

A technology for silacyclopentene and silacyclopentene, which is applied to silacyclopentene compounds and the fields of their preparation and application, can solve the problems that silacyclopentene research is rarely reported in literature, has no synthetic method, and the like, To achieve the effect of simple and feasible experimental equipment and operation, wide application range and high separation efficiency

Active Publication Date: 2014-08-20
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Silacyclopentene is a novel compound. Since 1959, Japanese scholar Brave (Braye E H, Hubel W.Chem.Ind. (Lond.), 1959: 1250-1251) synthesized silacyclopentadiene. , the research on silacyclopentadiene derivatives is constantly emerging, but there are few literature reports on the research on silacyclopentadiene, and there is no general synthetic method

Method used

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  • Silolene compound, as well as preparation method and application thereof
  • Silolene compound, as well as preparation method and application thereof
  • Silolene compound, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Preparation of 1,1 dialkyl(aryl)yl-3,4-diphenyl-2,5-dilithium silole.

[0046] Taking 1,1 dimethyl-3,4-diphenyl-2,5-dilithium silole as an example, prepared according to the method disclosed in the literature (J Am Chem Soc, 1994, 116:11715211722.), under nitrogen atmosphere Under protection, metal lithium (0.14 g, 0.02 mol) was reacted with naphthalene (2.56 g, 0.02 mol) dissolved in 12 ml THF in a 50 ml reaction flask at room temperature for 3 hours. Add dropwise dimethyldiphenylethynylsilane (1.30 g, 0.005 mol) dissolved in 5 ml THF to the above solution, and react for 1 hour to generate 1,1 dimethyl-3,4-diphenyl-2,5 - Dilithium silole. It was directly used in the next reaction without separation.

[0047] The 1,1-position substituents in 1,1 dialkyl (aryl)-3,4-diphenyl-2,5-dilithium silole include: hydrogen, methyl, ethyl, propyl, iso Propyl, n-butyl, isobutyl, tert-butyl, hexyl, phenyl, etc., but not limited thereto.

Embodiment 2

[0048] Example 2: Preparation of 1,1-dimethyl-3,4-diphenyl-2,2,5,5-tetrakis(dimethylsilyl)yl-3-silacyclopentene.

[0049]

[0050] R 1

R 2

R 3

R 4

R 5

Methyl

Methyl

Methyl

Methyl

---

[0051] At room temperature, under the protection of nitrogen, metal lithium (0.28g, 0.04mol) reacted with naphthalene (5.12g, 0.04mol) dissolved in 24mlTHF for 3 hours at room temperature, and then added 2.6g of dimethyl dissolved in 10mlTHF Diphenylethynylsilane (0.01mol), reacted for 1 hour to obtain a reaction solution containing 0.01mol 1,1-dimethyl-3,4-diphenyl-2,5-dilithium silole, and then added 4.0ml Dimethylchlorosilane (0.04mol), reacted for 10 hours, extracted the aqueous phase with 25ml ether three times after the reaction was completed, combined the organic phases, washed with saturated sodium chloride solution, and dried for half an hour with anhydrous MgSO4 after separation, under normal pressure Filtrate, conc...

Embodiment 3

[0054] Example 3: Preparation of 1,1,3,4-tetraphenyl-2,2,5,5-tetrakis(methylphenylsilyl)yl-3-silacyclopentene.

[0055]

[0056] R 1

R 2

R 3

R 4

R 5

Phenyl

Phenyl

Methyl

Phenyl

---

[0057] At room temperature, under the protection of nitrogen, lithium metal (0.28g, 0.04mol) reacted with naphthalene (5.12g, 0.04mol) dissolved in 24mlTHF for 3 hours at room temperature, and then added 3.92g diphenyl diphenylene dissolved in 10mlTHF Diphenylethynylsilane (0.01mol), reacted for 1 hour to prepare a reaction solution containing 0.01mol 1,1,3,4-tetraphenyl 2,5-dilithium silole, and then added 5.0ml methylphenyl Chlorosilane (0.05mol), reacted for 10 hours, extracted the aqueous phase with 25ml ether three times after the reaction was completed, combined the organic phases, washed with saturated sodium chloride solution, dried with anhydrous MgSO for half an hour after liquid separation, filtered under normal press...

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PUM

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Abstract

The invention discloses a silolene compound shown in formula I, and discloses a method for preparing the silolene compound and application of the silolene compound in serving as a luminescent material.

Description

(1) Technical field [0001] The invention relates to a synthesis method of a derivative with a silacyclopentene structure, which belongs to an important organic synthesis intermediate. (2) Background technology [0002] Silacyclopentene is a novel compound. Since 1959, Japanese scholar Brave (Braye E H, Hubel W.Chem.Ind. (Lond.), 1959: 1250-1251) synthesized silacyclopentadiene. , the research on silacyclopentadiene derivatives is emerging continuously, but there are few literature reports on the research on silacyclopentadiene, and there is no general synthetic method. (3) Contents of the invention [0003] The object of the present invention is to provide a series of compounds containing silacyclopentene structure. [0004] Another object of the present invention is to provide a method for synthesizing such compounds. [0005] The silacyclopentene compounds provided by the present invention are shown in formula I: [0006] [0007] In formula I, [0008] R 1 , R ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08C09K11/06
Inventor 赵祖金郭延举邱化玉其他发明人请求不公开姓名
Owner HANGZHOU NORMAL UNIVERSITY
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