Preparation method and application of 7-position vinyl substituted osmapentalyne

A technology of osmopentyne and vinyl, which is applied in the field of preparation of osmopentyne substituted by vinyl at the 7th position, and can solve problems such as limited synthesis methods and limited structures of final products

Active Publication Date: 2020-01-14
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, although the osmopentyne series compounds have shown many unique properties that other materials do not have in the field of optics and electricity, the current synthesis methods of this type of compounds are very limited, and the structures of the final products are also very limited.

Method used

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  • Preparation method and application of 7-position vinyl substituted osmapentalyne
  • Preparation method and application of 7-position vinyl substituted osmapentalyne
  • Preparation method and application of 7-position vinyl substituted osmapentalyne

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121]

[0122] [Os] in the above formula is OsCl(PPh 3 ) 2 . Among them, HCl·Et 2 O is diethyl ether hydrochloride (purchased from Sarn Chemical Technology (Shanghai) Co., Ltd., the brand name is A01W8101821000), (Phenylacetylene, purchased from Bailingwei Technology Co., Ltd., the trade name is 445058), and the DCM used is dichloromethane redistilled solvent.

[0123] Preparation of compound III-1

[0124] Under a nitrogen atmosphere, under magnetic stirring, dissolve osmalpentyne compound I-4 (0.5mmol) and phenylacetylene II-1 (0.5mmol) in 50mL of dichloromethane, and quickly add 2mol / L hydrochloric acid Diethyl ether solvent 3mL, reacted at room temperature for 2h, concentrated, neutral alumina column chromatography (eluent: dichloromethane / methanol = 20 / 1 volume ratio), obtained 0.48mmol purple solid compound III-1, yield: 96%. (The yield of compound III-1 is the molar amount of compound III-1 / molar amount of ospentyne compound I-4×100%).

[0125] The NMR and h...

Embodiment 2

[0128] Method A.

[0129]

[0130] [Os] in the above formula is OsCl(PPh 3 ) 2 . Among them, HCl·Et 2 O is diethyl ether hydrochloride (purchased from Sarn Chemical Technology (Shanghai) Co., Ltd., the brand name is A01W8101821000), (Phenylacetylene, purchased from Bailingwei Technology Co., Ltd., the trade name is 445058), and the DCM used is dichloromethane redistilled solvent.

[0131] Preparation of Compound III-2

[0132] Under nitrogen atmosphere, under magnetic stirring, dissolve osmalpentyne compound IV-5 (0.5mmol) and phenylacetylene II-1 (0.5mmol) in 50mL of dichloromethane, and quickly add 2mol / L hydrochloric acid Diethyl ether solvent 3mL, reacted at room temperature for 2h, concentrated, neutral alumina column chromatography (eluent: dichloromethane / methanol = 20 / 1 volume ratio), obtained 0.48mmol purple solid compound III-2, yield: 96%. (The yield of compound III-2 is the molar amount of compound III-2 / the molar amount of osmalpentyne compound IV-5×100...

Embodiment 3

[0142]

[0143] [Os] in the above formula is OsCl(PPh 3 ) 2 . Among them, HCl·Et 2 O is diethyl ether hydrochloride (purchased from Sarn Chemical Technology (Shanghai) Co., Ltd., the brand name is A01W8101821000), (p-thiomethylphenylacetylene, reference RSC Advances, 6(95), 92845-92851, 2016 synthesis), the DCM used is dichloromethane redistilled solvent.

[0144] Preparation of Compound III-3

[0145] Under nitrogen atmosphere, under magnetic stirring, dissolve osmalpentyne compound I-88 (0.5mmol) and p-thiomethylphenylacetylene II-5 (0.5mmol) in 50mL of dichloromethane, and quickly add 2mol 3mL of diethyl ether hydrochloride solvent per L, reacted at room temperature for 2h, concentrated, neutral alumina column chromatography (eluent: dichloromethane / methanol=20 / 1 volume ratio), and obtained 0.49mmol purple solid compound III-1 , Yield: 98%. (The yield of Compound III-3 is the molar amount of Compound III-3 / the molar amount of Ospentyne Compound I-88×100%).

[014...

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Abstract

The invention discloses a preparation method of 7-position vinyl substituted osmapentalyne. The reaction formula is as follows: the 7-position vinyl substituted osmapentalyne prepared by the inventionhas high solubility, good stability, very high molar absorption coefficient and better electrochemical performance, and can be widely applied to dye sensitized solar cells, organic solar cells, photodynamic therapy, photolysis of water and lithium-air batteries and other fields. The reaction of the preparation method prepared by the invention has the characteristics of high efficiency and specificity, mild reaction conditions and good functional group tolerance.

Description

technical field [0001] The invention belongs to the technical field of organometallic chemistry, and in particular relates to a preparation method and application thereof for osmopentyne substituted with a vinyl group at the 7th position. Background technique [0002] Metal-organic chemistry intersects between inorganic and organic chemistry, and is closely related to energy, materials, environment and life sciences. In recent years, with the rapid development of metal-organic chemistry, two traditional branches have been formed: one is traditional metal-organic chemistry, that is, designing and synthesizing new metal-organic compounds, studying their structure, reactivity and application prospects; the other is oriented to organic synthesis Metal-organic chemistry, that is, the development of metal-promoted highly selective catalytic reactions, provides new methods for the synthesis of drugs and new materials. As an important subject, organometallic chemistry has become on...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00B01J31/12H01L51/46
CPCC07F15/002B01J31/122B01J2531/825H10K85/615H10K85/655H10K85/657Y02E10/549
Inventor 夏海平陈仕焰张颖朱永发刘亚南高翔林祖樟蔡亚鹏欧阳普凡卓庆德何旭敏
Owner XIAMEN UNIV
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