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A-D-A conjugated molecules based on hepta-condensed ring units and preparation method for A-D-A conjugated molecules and application of A-D-A conjugated molecules

A technology of A-D-A and conjugated molecules, which is applied in the fields of electrical components, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc., to achieve the effects of strong visible light absorption, good thermal stability, and high charge transport performance

Active Publication Date: 2016-02-10
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no literature or patent report on the application of A-D-A conjugated small molecules

Method used

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  • A-D-A conjugated molecules based on hepta-condensed ring units and preparation method for A-D-A conjugated molecules and application of A-D-A conjugated molecules
  • A-D-A conjugated molecules based on hepta-condensed ring units and preparation method for A-D-A conjugated molecules and application of A-D-A conjugated molecules
  • A-D-A conjugated molecules based on hepta-condensed ring units and preparation method for A-D-A conjugated molecules and application of A-D-A conjugated molecules

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The synthetic route of A-D-A conjugated molecule 1 based on hepta-fused ring unit is as follows:

[0061]

[0062] Add compound a (200mg, 0.19mmol) in the three-necked round-bottomed flask, compound b (279mg, 1.4mmol), chloroform (50mL), add 1mL pyridine after logical argon 30 minutes to remove the air in the three-necked round-bottomed flask; Stir the reaction at 65°C for 12 hours, then cool to room temperature; pour the resulting reaction solution into 200mL of methanol, filter the precipitate obtained and dry it with silica gel (200-300 mesh) column chromatography for separation, the eluent is petroleum Ether / dichloromethane (volume ratio 1:1), the product was a dark blue solid (57 mg, 21%), which was the A-D-A conjugated molecule 1 based on hepta-fused ring units. 1 HNMR (400MHz, CDCl 3 ):δ8.87(s,2H),8.70(d,J=7.6Hz,2H),8.22(s,2H),7.93(d,J=6.4Hz,2H),7.79(m,4H),7.63 (s,2H),7.23(d,J=8.4Hz,8H),7.15(d,J=8.4Hz,8H),2.58(m,8H),1.61(m,8H),1.33(m,24H) ,0.87(m,12H). 13 ...

Embodiment 2

[0065] The synthetic route of A-D-A conjugated molecule 2 based on hepta-fused ring unit is as follows:

[0066]

[0067] Add compound c (165mg, 0.11mmol), compound b (219mg, 1.1mmol), chloroform (50mL) in the three-necked round-bottomed flask, and add 0.5mL of pyridine after argon flow for 30 minutes to remove the air in the three-necked round-bottomed flask; Stir the reaction at a temperature of 65°C for 12 hours, then cool to room temperature; pour the resulting reaction solution into 200mL of methanol, filter the precipitate obtained and dry it with silica gel (200-300 mesh) column chromatography, the eluent is Petroleum ether / dichloromethane (volume ratio 1:1), the product was a dark green solid (152 mg, 74%), which was the A-D-A conjugated molecule 2 based on hepta-fused ring units. 1 HNMR (400MHz, CDCl 3 ):δ8.78(s,2H),8.70(d,J=7.2Hz,2H),7.93(d,J=7.2Hz,2H),7.77(m,4H),7.69(s,2H),7.60 (s,2H),7.56(s,2H),7.21(d,J=8.0Hz,8H),7.14(d,J=8.0Hz,8H),2.78(d,J=7.2Hz,4H),2.60 (m,...

Embodiment 3

[0070] The synthetic route of A-D-A conjugated molecule 3 based on hepta-fused ring unit is as follows:

[0071]

[0072] Add compound d (200mg, 0.148mmol), compound e (100mg, 0.345mmol) and 20mL toluene in the three-necked round-bottomed flask, pass argon gas 15 minutes to remove the air in the three-necked round-bottomed flask, add Pd (PPh 3 ) 4 (40mg, 0.034mmol), stirred at a temperature of 110 ° C for 48 hours; cooled to room temperature; added 40mL (0.1gmL -1 ) KF aqueous solution, stirring overnight at room temperature, to remove tin impurities; add 150mL water in the resulting reactant, CH 2 Cl 2 (2 × 150mL) for extraction, the resulting organic phase with anhydrous MgSO 4 Carry out drying; After filtering and spinning to remove the solvent, use petroleum ether / dichloromethane mixed solvent (volume ratio 1:1) as eluent, silica gel (200~300 mesh) column chromatography separation and purification to obtain a blue-black solid ( 30 mg, 14.1%), which is the A-D-A conj...

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Abstract

The invention relates to A-D-A conjugated molecules by taking hepta-condensed ring units as cores and oligomerized five-membered aromatic rings as bridging units, wherein the tail ends are electron withdrawing units, a preparation method for the A-D-A conjugated molecules and an application of the molecules as active layer electron donors or electron acceptor materials in organic solar batteries (OPV). The A-D-A conjugated molecules based on hepta-condensed ring units can be processed by a solution method, have a proper energy level and have a relatively good sunlight capturing ability and heat stability, so that the molecules are an ideal material for the electron donors or electron acceptors in the organic solar batteries. The molecules have the structure as shown in the formula.

Description

technical field [0001] The invention relates to a class of A-D-A conjugated molecules based on a seven-fused ring unit as a core, an oligomerized five-membered aromatic heterocycle as a bridging unit, and an electron-withdrawing unit at the end and a preparation method thereof, and the electron donor of this type of molecule as an active layer Applications of Bulk or Electron Acceptor Materials in Organic Solar Cells (OPVs). Background technique [0002] Due to the advantages of low cost, light weight, bendability, solution processability and large area preparation, organic solar cells have received extensive attention in academia. In recent years, polymer and small molecule solar cells have developed rapidly and achieved remarkable results (X.Zhan, D.Zhu, Conjugated polymers for high-efficiency organic photovoltaics, Polym.Chem., 2010, 1,409; Y.Chen, X.Wan, G .Long,Highperformancephotovoltaicapplicationsusingsolution-processedsmallmolecules,Acc.Chem.Res.,2013,46,2645; 109...

Claims

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Application Information

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IPC IPC(8): C07D495/22H01L51/46
CPCY02E10/549
Inventor 占肖卫林禹泽白会涛王嘉宇张明煜
Owner INST OF CHEM CHINESE ACAD OF SCI
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