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Conjugated small molecule based on nona fused heterocycle, preparation method and applications thereof

A technology of small molecules and fused heterocyclic rings, which is applied in the field of organic solar material preparation to achieve strong absorption, good thermal stability, and high charge transport performance

Active Publication Date: 2019-04-23
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

From the perspective of device results, it is difficult to have both high open-circuit voltage and high short-circuit current. How to design an acceptor material with an appropriate band gap (~1.4eV) is still the focus of organic solar cell research.

Method used

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  • Conjugated small molecule based on nona fused heterocycle, preparation method and applications thereof
  • Conjugated small molecule based on nona fused heterocycle, preparation method and applications thereof
  • Conjugated small molecule based on nona fused heterocycle, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Synthesis of 4-n-octyl-4H-dithieno[3,2-b:2',3'-d]pyrrole (1):

[0057]

[0058] In a 50mL two-neck flask, 3,3'-dibromo-2,2'-bithiophene (2.5g, 7.71mmol) and sodium tert-butoxide (1.85g, 19.29mmol) were dissolved in 15mL of toluene, and a nitrogen drum After soaking for 10 minutes, quickly add tris(dibenzylideneacetone)dipalladium (211.94mg, 0.231mmol) and 1,1'-binaphthyl-2,2'-bisdiphenylphosphine (480.40mg, 0.771mmol) ), under the protection of nitrogen, slowly dropwise add n-octylamine (997.13 mg, 7.71 mmol) to the mixed solution, and heat to 110° C. to react overnight. Stop the reaction, cool to room temperature, pour the reaction mixture into deionized water, extract with ethyl acetate, wash twice with water, wash once with saturated brine, dry the organic phase with anhydrous magnesium sulfate, spin dry the organic solvent, and chromatographic column chromatography After separation, the eluent was petroleum ether / dichloromethane (volume ratio 9:1) to obtain pale yello...

Embodiment 2

[0072] Synthesis of compound INTC

[0073]

[0074] Under the protection of nitrogen, in a 25mL reaction tube, compound 5 (150.0mg, 108.85μmol), 3-(dicyanomethylene)indigo (211.37mg, 1.09mmol) and β-alanine (1.94mg, 21.77 μmol) is dissolved in a dry 1,2-dichloroethane / absolute ethanol (8ml / 4ml) mixed solvent. After the reaction was heated to reflux for 24 hours, it was cooled to room temperature. It was extracted three times with chloroform, the organic phase was washed twice with water, and dried with anhydrous magnesium sulfate. The solvent was removed, and the residue was separated by column chromatography. The eluent was petroleum ether / dichloromethane (volume ratio 2:1) to obtain a black-green solid INTC (128 mg, 68%). The hydrogen nuclear magnetic spectrum, carbon spectrum and high resolution mass spectrum of this compound are attached respectively. figure 1 , Attached figure 2 , Attached image 3 . 1 H NMR(500MHz, CDCl 3 )δ (ppm) = 8.88 (s, 2H), 8.64 (d, J = 6.7 Hz, 2H)...

Embodiment 3

[0076] Synthesis of compound INTC

[0077]

[0078] Add compound 5 (150.0 mg, 108.85 μmol), 3-(dicyanomethylene) indigo (211.37 mg, 1.09 mmol), 30 mL of chloroform into a 50 mL two-necked flask, and blow nitrogen for 30 minutes to remove the air in the flask After adding 1 mL of pyridine, stirring and reacting at 65°C for 24 hours, and then cooling to room temperature, the resulting reaction solution was poured into 200 mL of methanol, and the precipitate obtained by filtration was dried and separated by silica gel column chromatography. The eluent was petroleum ether / Dichloromethane (volume ratio 2:1), the product is a black-green solid INTC (120 mg, 64%). The hydrogen nuclear magnetic spectrum, carbon spectrum and mass spectrum are the same as in Example 2.

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Abstract

The invention relates to a conjugated small molecule based on nona fused heterocycle, a preparation method and applications thereof. According to the preparation method, 2,5-dibromoterephthalic acid diethyl ester is used as a raw material, and a series of coupling, ring forming, condensation and other reaction steps are performed to synthesize a small molecule having a large planar structure. According to the present invention, the A-D-A conjugated small molecule based on the nona fused heterocycle unit of pyrrolodithiophene has characteristics of good thermal stability, good solubility and good film forming property; the results of ultraviolet-visible light absorption spectrum and electrochemical tests show that the compound has moderate optical band gap, and has good absorption in visible and near-infrared regions; and the obtained product has low HOMO level and low LUMO level, and is the potential organic solar cell receptor material or perovskite battery electron transport layer material.

Description

Technical field [0001] The invention relates to a class of A-D-A conjugated molecules with a nona fused ring of pyrrolodithiophene and a preparation method thereof, and the application of small molecules as electron acceptors in organic solar cells (OPV), belonging to the field of organic solar material preparation. Background technique [0002] The promotion of renewable energy is regarded as the best solution to the greenhouse effect and environmental pollution in the 21st century. Solar energy is widely distributed and has a long radiation time. It directly converts radiant energy into electrical energy, avoiding the energy loss caused by mechanical energy that traditional power generation technology must pass through. At present, silicon-based inorganic photovoltaic devices have formed mature industrial applications. Due to the large power consumption during the silicon reduction process and the complex production process, the unit power cost during its life cycle is much hig...

Claims

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Application Information

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IPC IPC(8): C07D495/22H01L51/46
CPCC07D495/22H10K85/657Y02E10/549
Inventor 唐卫华孙佳周杰俞江升尹新星张倬涵冯豪豪
Owner NANJING UNIV OF SCI & TECH
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