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Selenophene vinyl compounds and organic conjugated material thereof, and preparation method of organic conjugated material

A technology of selenophene vinyl and compound, applied in the field of selenophene vinyl compound and organic conjugated material and preparation thereof, can solve the problems of complex synthesis steps and high material production cost, achieve fewer synthesis steps, low production cost and wide application Foreground effect

Inactive Publication Date: 2016-08-17
UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the synthesis steps are complicated and the production cost of the material is high

Method used

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  • Selenophene vinyl compounds and organic conjugated material thereof, and preparation method of organic conjugated material
  • Selenophene vinyl compounds and organic conjugated material thereof, and preparation method of organic conjugated material
  • Selenophene vinyl compounds and organic conjugated material thereof, and preparation method of organic conjugated material

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Experimental program
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Embodiment 1

[0036] This embodiment provides a kind of selenophene compound, the general structural formula is as shown in formula (I);

[0037]

[0038] The Et is ethyl.

[0039] The present embodiment provides the method for preparing the selenophene compound shown in the above formula (I) as follows:

[0040]

[0041] Utilize olefin metathesis reaction, in organic solvent, first prepare the intermediate product shown in formula (Z) by the compound shown in formula (Y), hereinafter referred to as intermediate product Z, then prepare formula (X) by intermediate product Z The selenophenol vinyl compound shown, wherein Et is ethyl.

[0042] The first step: prepare the intermediate product Z from the compound represented by formula (Y).

[0043] First, under nitrogen protection at -78°C, n-butyllithium (1.8mmol; 0.72ml) was slowly dropped into a solution of selenophene (194mg; 1.5mmol) in anhydrous THF (20mL), then warmed to 0°C and stirred React for 30 minutes; then add Cr(CO) at -...

Embodiment 2

[0046] The present embodiment provides monomer M, and its structural formula is as follows:

[0047]

[0048] The preparation method of monomer M is as follows:

[0049]

[0050] Under the protection of nitrogen at -78°C, n-butyllithium solution (0.38mL, 0.94mmol) was slowly dropped into a solution of compound I (160mg, 0.43mmol) in anhydrous THF (50mL), and the mixture was reacted at -78°C 30 minutes, raised to room temperature and reacted for 1 hour; then cooled to -78°C, Me 3 SnCl (0.94mL, 0.94mmol) was slowly added dropwise to the reaction system, slowly raised to room temperature, and stirred for 8 hours. Add KF aqueous solution to quench the reaction, CH 2 Cl 2 Extract (3×50mL), wash with water (3×50mL), organic phase MgSO 4 Dry and concentrate to obtain a crude product, which is recrystallized from methanol to obtain 211 mg of a red crystalline solid with a yield of 70%.

Embodiment 3

[0052] This embodiment provides a structure of the conjugated polymer material PNDISVSOET as follows:

[0053]

[0054] The preparation method of the conjugated polymer material PNDISVSOET is as follows:

[0055] in N 2 Under gas protection, monomer a (128.1 mg, 0.13 mmol), monomer M (91 mg, 0.13 mmol), Pd 2 (dba) 3 (8mg), P(O-Tol) 3 (11mg), added anhydrous toluene (7mL), heated to 130°C for 48 hours. Add 2-(tributyltin)thiophene, react at 130°C for 6 hours; add 2-iodothiophene, react at 130°C for 6 hours, and cool to room temperature. The reactant solution was poured into methanol (500ml) for coagulation, and the crude product was obtained by filtration. The crude product was sequentially extracted with acetone, n-hexane, THF and chloroform with a Soxhlet extractor. The chloroform extract was concentrated and precipitated in methanol to obtain 106.1 mg of a dark green solid with a yield of 67.9%.

[0056] Gained copolymer PNDISVSOET has wider absorption at 350-1000nm...

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Abstract

The embodiment of the invention relates to selenophene vinyl compounds and an organic conjugated material thereof, and a preparation method of the organic conjugated material. The structural general formula of the selenophene vinyl compounds is disclosed in the specification, wherein Et is ethyl. The structural general formula of the organic conjugated material of the selenophene vinyl compounds is disclosed in the specification, wherein A is an aromatic conjugated unit with different electron donating and receiving capacities, n is polymerization degree and is any whole number ranging from 2 to 100. The selenophene vinyl compounds are prepared from selenophene, n-butyllithium, hexacarbonyl chromium, triethoxytetrafluoro borate and tetra(triphenylphosphine) palladium by olefin double-decomposition reaction in an organic solvent. The corresponding organic conjugated material is prepared by still coupled reaction. The preparation method provided by the invention has the advantages of simple route, fewer steps and low production cost.

Description

technical field [0001] The invention relates to a selenophene compound, in particular to a selenophene compound, an organic conjugated material and a preparation method thereof. Background technique [0002] Conjugated organic semiconductor materials have broad application prospects in organic optoelectronics and other fields, and the study of their synthesis methodology is very important for the design and synthesis of high-performance conjugated organic semiconductor materials. In terms of organic solar cell research, the synthesis of organic polymer donor materials with narrow bandgap, wide absorption, and high hole mobility is one of the main challenges in designing and synthesizing high-performance conjugated organic semiconductor materials. Selenium in selenol has a large atomic radius, small electronegativity, and strong polarizability. Using selenol to construct a conjugated organic semiconductor material is conducive to the delocalization of charges, and an organic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D345/00C08G61/12
CPCC07D345/00C08G61/123C08G2261/124C08G2261/1412C08G2261/1424C08G2261/18C08G2261/3225C08G2261/3327C08G2261/344C08G2261/414C08G2261/512C08G2261/91
Inventor 黄辉董涛吕磊王小芬
Owner UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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