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Conjugated micromolecule material based on bithiophene dipyrrole and derivatives thereof, and preparation method and application thereof

An alkyl and aryl technology, applied in the field of conjugated small molecule materials, can solve the problems of reporting, no devices, etc.

Active Publication Date: 2014-03-26
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its energy level and electrochemistry are very suitable as semiconductor materials, but no practical devices have been reported so far

Method used

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  • Conjugated micromolecule material based on bithiophene dipyrrole and derivatives thereof, and preparation method and application thereof
  • Conjugated micromolecule material based on bithiophene dipyrrole and derivatives thereof, and preparation method and application thereof
  • Conjugated micromolecule material based on bithiophene dipyrrole and derivatives thereof, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Embodiment 1: Synthesis of dibromobis (ethylhexyl) bithienylidene dipyrrole shown in formula II

[0087] chemical reaction flow chart image 3 As shown, the specific reaction conditions are as follows:

[0088] At low temperature (-78°C), in a nitrogen atmosphere, dissolve 0.89 mmol of bithiophenylidene dipyrrole (reported and synthesized by Tyler B. Norsten, published in the journal Chem. Eur. J. 2012, 18, 695-708) in 20 mL of tetrahydrofuran , add organic base lithium diisopropylamide (2.25mmol) for substitution reaction for 1 hour, then add 1,2-dibromotetrachloroethane (2.76mmol) for substitution reaction for 5 hours, then add water, use dichloro Methane was extracted three times, and the organic phases were combined and dried over anhydrous sodium sulfate. After removing the solvent, the product (0.41 mmol, 46%) was obtained by column separation with silica gel. The structural confirmation data are as follows: 1 H NMR (300MHz, CDCl 3 )δ7.17(d,2H,J=3.9Hz),7.08(d...

Embodiment 2

[0089] Embodiment 2: Synthesis of dibromobis(ethylhexyl)bithienylidene dipyrrole derivatives shown in formula III

[0090]chemical reaction flow chart Figure 4 Shown, concrete reaction step condition is as follows:

[0091] Step 1: At 0°C, dissolve 25 mmol of 5-bromothiophene 2-carboxylic acid (synthesized by Shih, Chuan, published in Journal of Medicinal Chemistry, 1992, 36, 1109-1116) in 50 mL of dichloromethane, add Active agent dicyclohexylcarbodiimide 30mmol, then add R-NH 2 (R is ethylhexyl) 0.275mmol, carried out amidation reaction at room temperature for 5 hours, filtered, washed with hydrochloric acid and potassium carbonate solution, dried with anhydrous sodium sulfate, and separated by silica gel column to obtain the product (16.7mmol 70% ). The structural confirmation data are as follows: elemental analysis: the calculated value is C 13 h 20 BrNOS: C, 49.06; H, 6.33; N, 4.40; S, 10.07; actual value: C, 49.26; H, 6.36; N, 4.20; S, 10.28.

[0092] Step 2: At r...

Embodiment 3

[0097] Example 3: Synthesis of dibenzofuran bis(ethylhexyl)bithienylidene dipyrrole shown in formula I

[0098] chemical reaction flow chart Figure 5 As shown, the specific reaction conditions are as follows:

[0099] At room temperature, the product synthesized in Example 1 (0.14mmol) was dissolved in 50mL of tetrahydrofuran, then 2(tributyltin)benzofuran (0.36mmoL) was added, and tetrakis(triphenylphosphine)palladium 0.007mmol was added, and heated at 60° C was stirred for 10 hours, the reaction was stopped, and the product (0.12 mmol 89%) was obtained by separation with a silica gel column after removing the solvent. The structural confirmation data are as follows: 1 H NMR (300MHz, CDCl 3 )δ7.59(d,2H,J=7.5Hz),7.53-7.49(m,6H),7.32-7.28(m,4H),7.23(m,2H),6.97(s,2H),3.89-3.87 (m, 4H), 1.72(m, 2H), 1.35-1.26(m, 16H), 0.89-0.84(m, 12H); elemental analysis: the calculated value is C 48 h 50 N 2 o 4 S 2 :C,73.62;H,6.44;N,3.58;S,8.19;actual value:C,73.44;H,6.43;N,3.56;S,8....

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Abstract

The invention discloses a conjugated micromolecule material based on bithiophene dipyrrole and derivatives thereof, and a preparation method and application thereof. The molecular structure is disclosed as Formula I, wherein R1 and R2 independently represent C1-C50 alkyl group, C1-C50 alkoxy group, aralkyl group or heteroalkyl group; X1 and X2 independently represent carbon or nitrogen; and Ar1 and Ar2 independently represent an unsubstituted or substituted group: monocycloaryl group, bicycloaryl group, tricycloaryl group and above, monocyclo heteroaryl group, bicyclo heteroaryl group, tricyclo heteroaryl group and above, and 1-3 groups above connected by bonding (including single bond, double bond and triple bond) or condensing. The micromolecule material has excellent current carrier transmission performance and solubility, and can be used in organic field-effect transistors and organic solar cells in the field of photoelectricity. Formula I.

Description

technical field [0001] The invention relates to a conjugated small molecule material based on bithiophenylidene dipyrrole and its derivatives, a preparation method and application thereof. Background technique [0002] Organic molecular materials, also known as organic solids (Zhu Daoben, Wang Fosong. Organic solids. Shanghai: Shanghai Science and Technology Press, 1999), usually refer to organic optoelectronic materials with π-electronic structures and special optical, electrical, and magnetic properties, commonly known as organic semiconductors Material. Compared with inorganic materials, organic semiconductor materials have their own unique advantages. The properties of organic semiconductor materials are easy to control, the preparation process is simple, the cost is low, and organic flexible circuits can be prepared in large areas. At this stage, organic semiconductor materials can be divided into two categories: polymers and small molecule materials. Compared with po...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14H01L51/30H01L51/46
CPCC07D409/14H10K85/654H10K85/655H10K85/6574H10K85/6576Y02E10/549
Inventor 张德清刘子桐蔡政旭王建国张关心
Owner INST OF CHEM CHINESE ACAD OF SCI
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