Conjugated molecular compound based on asymmetric selenium fused heterocycle and preparation method thereof

A conjugated molecule, asymmetric technology, used in organic chemistry, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc., can solve the problems of difficult synthesis of central core structure and no literature reports, and achieve novel molecular structure and thermal stability. The effect of good, high charge transport properties

Active Publication Date: 2019-05-17
GUILIN UNIVERSITY OF TECHNOLOGY
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Problems solved by technology

[0005] Multi-component fused-ring fluorene small molecule electron acceptor materials (Adv.Mater.2016, DOI: 10.1002 / adma.201604964; Chem.Mater.2017, 29, 18, 7908; Adv.Energy Mater. 2018, 1702870; Adv.Mater. 2018,1707508; Adv.Energy Mater.2018,1802021; J. Mater.Chem.A,2018,6,20313.), has a very good rigid planar structure, strong π-π interaction between molecules and relatively High carrier mobility, showing broad spectral absorption and high molar absorptivity, based on its small molecule acceptor material solar cells show a photoelectric conversion efficiency of 9 to 14%, but the modification of its small molecular structure The modification mainly focuses on the replacement of the terminal electron-withdrawing group, and the modification of the central core structure has not been reported in the literature due to the difficulty of the synthesis method.

Method used

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  • Conjugated molecular compound based on asymmetric selenium fused heterocycle and preparation method thereof
  • Conjugated molecular compound based on asymmetric selenium fused heterocycle and preparation method thereof
  • Conjugated molecular compound based on asymmetric selenium fused heterocycle and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0036] The synthetic route of embodiment 1. compound 3 is as follows:

[0037]

[0038] Asymmetric bis-nitrated fluorene (5.20 g, 8.93 mmol) and tributyltin-based thiophene (8.33 g, 22.32 mmol) with a molar ratio of 1:2.5 in 5% mol of Pd[PPh 3 ] 2 Cl 2 (313.4mg, 0.446mmol) was catalyzed by coupling reaction in 50mL of anhydrous tetrahydrofuran solution to obtain compound 1 (4.0g, 6.79mmol). Compound 1 (2.54g, 4.32mmol) and Se (6.83g, 86.45mmol) with a molar ratio of 1:20 were closed in 80mL N-methylpyrrolidone solution to obtain an asymmetric fused ring compound 2 (2.18g, 3.34 mmol ). Compound 2 (0.884g, 1.35mmol) was reacted with phosphorus oxychloride (4.15g, 27.09mmol) and 5mL of N,N-dimethylformamide to obtain asymmetric fused ring dialdehyde compound 3 (767mg, 1.08mmol ). 1 H NMR(500MHz,DMSO)δ9.91(s,1H),9.88(s,1H),8.11(s,1H),8.08(s,1H),8.05(d,J=3.9Hz,1H),7.83 (d,J=3.9Hz,1H),7.43(s,1H),7.33(s,1H), 2.12-1.99(m,4H),1.09-0.93(m,12H),0.68(t,J=6.9 Hz,6H),0.55(s,4H).MS(M...

Embodiment 2

[0039] Embodiment 2. The synthetic route of compound FSe-IC is as follows:

[0040]

[0041] The asymmetric fused ring dialdehyde compound 3 (100mg, 0.141mmol) and the electron-withdrawing unit 3-(dicyanomethylene)inden-1-one (134mg, 0.691mmol) at a molar ratio of 1:5 were prepared in the absence of In an oxygen-free reaction vessel, use chloroform as a solvent, add 0.2 mL of pyridine, heat and reflux for 6 hours, pour the product into methanol solution after the reaction, and purify the filtered solid product by column chromatography to obtain an asymmetric selenium complex Ring Conjugated Molecular Compound FSe-IC (109mg, 0.103mmol). 1 HNMR (500MHz, CDCl3) δ8.94 (s, 1H), 8.90 (s, 1H), 8.74 (d, J = 7.3Hz, 1H), 8.70 (d, J = 7.3Hz, 1H), 8.10 (s, 2H), 7.94-7.88(m,4H),7.83-7.78(m,4H),7.64(s,1H),7.45(s,1H),2.07(m,4H), 1.16-1.01(m,12H) ,0.79-0.66(m,10H).MS(MALDI):m / z 1060.56.Anal.Calcd for C 59 h 42 N 4 o 2 S 2 Se 2 : C, 66.79; H, 3.99. Found: C, 66.56; H, 4.04%.

[004...

Embodiment 3

[0043] Embodiment 3. The synthetic route of compound FSe-IC is as follows:

[0044]

[0045] The asymmetric fused ring dialdehyde compound 3 (150mg, 0.212mmol) with a molar ratio of 1:5 and the electron-withdrawing unit 5,6-difluoro-3-(dicyanomethylene)inden-1-one ( 239mg, 1.04mmol) in an oxygen-free anhydrous reaction vessel, with chloroform as solvent, add 0.2mL of pyridine, heat and reflux for 6 hours, pour the product into methanol solution after the reaction, and filter the solid product obtained by column chromatography The asymmetric selenium heterofused ring conjugated molecular compound FSe-2FIC (191mg, 0.168mmol) was obtained after purification. MS(MALDI):m / z 1133.56.Anal.Calcd for C 59 h 38 f 4 N 4 o 2 S 2 Se 2 : C, 62.55; H, 3.38. Found: C, 62.96; H, 3.24%.

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Abstract

The invention belongs to the technical field of conjugated molecular compounds, and discloses a conjugated molecular compound based on an asymmetric selenium fused heterocycle and a preparation methodthereof. The preparation method for the conjugated molecular compound based on the asymmetric selenium fused heterocycle comprises the following steps that asymmetric double nitrated fluorene servesas a raw material and is coupled with thiophene, and after closed-loop reaction and formylation are carried out, the tail end is connected to different electron-deficient units so as to form an A-D-Atype conjugated molecule. According to the conjugated molecular compound and the preparation method thereof provided by the invention, the molecular structure is novel, the synthesis steps are few, aproduct is easy to separate and purify, the solubility and the stability are relatively good, the spectral absorption range and a molecular energy level orbit are proper, and therefore the conjugatedmolecular compound and the preparation method thereof have huge application potential in organic solar cell electronic receptor materials.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic technology, and specifically relates to a class of A-D-A conjugated molecular compounds based on an asymmetric selenium heterofused ring as the mother nucleus, and the terminal is connected to an electron-deficient unit, and a preparation method thereof, and this type of molecule is used as a compound in a blended active layer. Applications of electron acceptor materials in organic solar cells. Background technique [0002] Organic solar cells have the advantages of thinness, cheapness, flexibility, solution processing, and large-area preparation, and have attracted extensive attention from researchers in academia and industry. In recent years, polymer and small molecule acceptor material solar cells have developed rapidly, and breakthroughs have been made (Nature Communications, 2018, 9, 4645; Energy & Environmental Science, 2018, 11, 3275; ACS Energy Letters, 2018, 2566; J. Mater.Chem.A, 201...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D517/22H01L51/46
CPCY02E10/549
Inventor 海杰峰李玲冯程
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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