Preparation method of monobromothiophenyl derivatives

A thienyl and derivative technology, applied in the field of chemistry, can solve the problems of high consumption time and cost, low yield of mono-bromothienyl derivatives, difficulty in separation and purification, etc., to simplify subsequent purification and post-treatment processes, avoid The effect of separating and purifying the form and improving the reaction yield

Inactive Publication Date: 2019-03-22
盐城锦明药业有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Funct.Mater, Lett.2017,10,1750085 also reported that the preparation of monobrominated thienyl derivatives is not only low in yield, but also separated by column chromatography or recrystallization due to disubstitution, monosubstitution and similarity in raw material structure Purification is very difficult, time-consuming and costly

Method used

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  • Preparation method of monobromothiophenyl derivatives
  • Preparation method of monobromothiophenyl derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Add 100mL of chloroform solution with a concentration of 5mmol / L compound TDPP into a 250mL round bottom flask, keep the reaction system at -20°C, add 10mmol / L N-bromosuccinimide at a rate of 1.0mL / min 50mL of trichloromethane solution, reacted for 8 hours after the addition, and separated the solvent. The crude product was purified by column chromatography with n-hexane and dichloromethane solution with a volume ratio of 5:1 to obtain the isolated product TDPP- Br, the yield was 84%, and the disubstituted TDPP content was zero.

Embodiment 2

[0025] In a 250mL round bottom flask, add 100mL of a chloroform solution with a concentration of 10mmol / L compound TDPP, keep the reaction system at -20°C, and add 10mmol / L of N-bromosuccinimide at a rate of 1.0mL / min 100mL of trichloromethane solution, reacted for 8 hours after the addition, and separated the solvent. The crude product was purified by column chromatography with n-hexane and dichloromethane solution with a volume ratio of 5:1 to obtain the isolated product TDPP- Br, the yield is 95%, and the disubstituted TDPP content is zero.

Embodiment 3

[0027] Add 50mL of chloroform solution with a concentration of 20mmol / L compound TDPP into a 250mL round bottom flask, keep the reaction system at -20°C, add 10mmol / L N-bromosuccinimide at a rate of 1.0mL / min 100mL of trichloromethane solution, reacted for 8 hours after the addition, and separated the solvent. The crude product was purified by column chromatography with n-hexane and dichloromethane solution with a volume ratio of 5:1 to obtain the isolated product TDPP- Br, the yield was 86%, and the disubstituted TDPP content was zero.

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Abstract

The invention provides a preparation method of monobromothiophenyl derivatives. In particular, thienyl diketopyrrolopyrrole reacts with N-bromo-succinimide, and monosubstituted thienyl derivatives areobtained by controlling the concentration, the molar ratio, the reaction temperature, the charging speed and the reaction time of the reactants, so that polysubstituted products are avoided, and thewhole process is simple, convenient, efficient and suitable for large-scale production.

Description

technical field [0001] The invention relates to a preparation method of an organic conjugated small molecule monobrominated thienyl derivative, belonging to the field of chemistry. Background technique [0002] Organic optoelectronic materials have a π-conjugated molecular structure and excellent electron delocalization performance, diverse structural composition and performance adjustment space, and can adjust the light absorption performance, optical band gap, and orbital energy level of the material through different combinations of donor and acceptor units. etc., thus being widely used in fields such as organic light emitting diodes, field effect transistors and solar cells. For example, the polymer P3HT of thiophene can be used as a P-type organic semiconductor and donor material due to its good electron donating effect. The α-position of thiophene derivatives has high activity and is easily prepared by substitution reaction with N-bromosuccinimide. Bromide can further...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06H01L51/30H01L51/46H01L51/54
CPCC09K11/06C07D487/04C09K2211/1029C09K2211/1092H10K85/655H10K85/6572
Inventor 孙世新陈阳王彦卿任天华方东邢蓉杨锦明
Owner 盐城锦明药业有限公司
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