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Stille cross-coupling room-temperature polymerization method based on aryl dihalide and aryl distannane

An aryldihalide and aryldistanane technology, which is applied in the field of organic semiconductor active layer donor-acceptor conjugated polymer synthesis, can solve the problem of reduced charge mobility, increased energy consumption, and copolymerization of D-A copolymers. structural defects and other problems, to achieve the effect of reducing synthesis cost, safety assurance, and reducing structural defects

Pending Publication Date: 2021-11-05
UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

Under this condition, not only the energy consumption required for the reaction is increased, but also the structural defects of the copolymer are more likely to occur.
The generation of structural defects will reduce the charge mobility of the D-A copolymer

Method used

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  • Stille cross-coupling room-temperature polymerization method based on aryl dihalide and aryl distannane
  • Stille cross-coupling room-temperature polymerization method based on aryl dihalide and aryl distannane
  • Stille cross-coupling room-temperature polymerization method based on aryl dihalide and aryl distannane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] Under nitrogen protection, 2,5-bis(trimethyltin-based)selenophene (23.0 mg, 0.05 mmol), 3,6-bis(5-bromothienyl)-2,5-bis(2-decyl Tetradecyl)pyrrolo[3,4-c]pyrrole-1,4-dione (56.4mg, 0.05mmol), P(t-Bu) 3 Pd G3 (2.9 mg, 0.005 mmol) and potassium phosphate (10.6 mg, 0.05 mmol) were placed in a reaction vial. After adding 1.0 mL of tetrahydrofuran, the mixture was stirred at room temperature for 24 hours. After adding 20.0 mL of methanol, the resulting precipitate was filtered. Then the precipitated polymer was subjected to Soxhlet extraction with acetone, n-hexane and chloroform, respectively. The solution obtained after extraction with chloroform was concentrated, and then the polymer was precipitated with 20.0 mL of methanol, filtered and dried to obtain a black-green polymer solid (52.2 mg, 95%). 1 H NMR (500MHz, CDCl 3 ): δ9.27-8.86(br,2H),7.49-6.73(br,4H),4.62-3.47(br,4H),2.07-1.96(br,2H),1.85-0.98(br,80H),0.99 -0.68(br,12H). GPC: M n 39.4kDa, M w 8...

Embodiment 2

[0035]

[0036] Under nitrogen protection, 2,5-bis(trimethyltin-based)selenophene (23.0 mg, 0.05 mmol), 3,6-bis(5-bromothiophen-2-yl)-2,5-bis( 2-octyldodecyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (50.8mg, 0.05mmol), P(t-Bu) 3Pd G3 (2.9 mg, 0.005 mmol) and potassium phosphate (10.6 mg, 0.05 mmol) were placed in a reaction vial. After adding 1.0 mL of tetrahydrofuran, the mixture was stirred at room temperature for 24 hours. After adding 20.0 mL of methanol, the resulting precipitate was filtered. Then the precipitated polymer was subjected to Soxhlet extraction with acetone, n-hexane and chloroform, respectively. The solution obtained after extraction with chloroform was concentrated, and then the polymer was precipitated with 20.0 mL of methanol, filtered and dried to obtain a black-green polymer solid (46.5 mg, 94%). 1 H NMR (500MHz, CDCl 3 ):δ9.26-8.82(br,2H),7.58-6.72(br,4H),4.34-3.65(br,4H),2.09-1.80(br,2H),1.53-0.98(br,64H),0.93 -0.74(br,12H). GPC: M n 32....

Embodiment 3

[0038]

[0039] Under nitrogen protection, 2,5-bis(trimethyltin-based)selenophene (23.0mg, 0.05mmol), 3,6-bis(5-bromothiophene[3,2-b]thiophen-2-yl )-2,5-bis(2-octyldodecyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione (56.4mg, 0.05mmol), P (t-Bu) 3 Pd G3 (2.9 mg, 0.005 mmol) and potassium phosphate (10.6 mg, 0.05 mmol) were placed in a reaction vial. After adding 1.0 mL of tetrahydrofuran, the mixture was stirred at room temperature for 24 hours. After adding 20.0 mL of methanol, the resulting precipitate was filtered. Then the precipitated polymer was subjected to Soxhlet extraction with acetone, n-hexane and chloroform, respectively. The solution obtained after extraction with chloroform was concentrated, and then the polymer was precipitated with 20.0 mL of methanol, filtered and dried to obtain a black-green polymer solid (51.5 mg, 89%). 1 H NMR (500MHz, CDCl 3 ):δ9.51-8.63(br,2H),7.51-5.82(br,4H),4.55-3.50(br,4H),2.49-2.11(br,2H),2.09-1.00(br,64H),1.00 -0.65(br,12H...

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Abstract

The invention provides a methodology for preparing an organic semiconductor material based on a universal Stille cross-coupling copolymerization reaction of an aryl system at room temperature. The method comprises the following steps of: under the protection of inert gas and under the catalyst action of methanesulfonic acid (tri-tert-butylphosphino) (2'-amino-1, 1'-biphenyl-2-yl) palladium (II) (namely P (t-Bu) 3Pd G3), adding potassium phosphate as an additive, putting aryl dihalide and aryl distannane into tetrahydrofuran or methylbenzene, and reacting at room temperature to obtain a mixture; and dropwise adding the mixture into methanol, precipitating and filtering, respectively extracting the precipitate through acetone, normal hexane and trichloromethane by adopting a Soxhlet extractor, concentrating a polymer solution extracted by trichloromethane, and dropwise adding the concentrated polymer solution into methanol to obtain a high-molecular-weight D-A conjugated polymer. The conjugated polymer prepared by the method can be applied to the fields of organic field effect transistors, organic solar cells, cell imaging, photo-thermal and photodynamic therapy and the like.

Description

Technical field: [0001] The invention relates to the technical field of synthesis of organic semiconductor active layer donor-acceptor (D-A) conjugated polymers, in particular to a Stille cross-coupling room-temperature polymerization method based on aryl dihalides and aryl distannanes. Background technique: [0002] Organic conjugated polymers have attracted much attention due to their great potential in plastic electronics, such as tunable chemical structure, tunable band gap and light absorption, excellent charge transport mobility, flexible preparation and solution processability, etc. advantage. The π-conjugated D-A copolymer with no defects and perfect alternating structure has better charge transport performance than the D-A copolymer with structural defects. [0003] The traditional preparation method of D-A conjugated polymer is based on tris(dibenzylideneacetone) dipalladium and bis(tri-o-tolylphosphine)palladium(0) system (i.e. Pd 2 (dba) 3 / P(o-tol) 3 system)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
CPCC08G61/126C08G61/124C08G61/123C08G2261/414C08G2261/124C08G2261/3243C08G2261/3241C08G2261/3225C08G2261/3223C08G2261/3222
Inventor 黄辉史钦钦马博维
Owner UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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