Novel 2,6-site-substituted BODIPY organic dye sensitizer and preparation method therefor

A technology of organic dyes and sensitizers, which is applied in the field of dye-sensitized solar cell materials, can solve the problems of limited resources and high prices, and achieve the effects of simple product purification, low production costs, and increased yields

Active Publication Date: 2016-01-13
邳州市润宏实业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, ruthenium dyes have disadvantages such as limited resources and high prices, which limit its application.

Method used

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  • Novel 2,6-site-substituted BODIPY organic dye sensitizer and preparation method therefor
  • Novel 2,6-site-substituted BODIPY organic dye sensitizer and preparation method therefor
  • Novel 2,6-site-substituted BODIPY organic dye sensitizer and preparation method therefor

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] (1) Synthesis of Dye1:

[0106] Intermediate 14 (180mg, 0.3mmol), cyanoacetic acid (50mg, 0.6mmol), acetonitrile (20mL), chloroform (20mL) and piperidine (0.2mL) were sequentially added to a 100mL three-necked flask, under argon protection, Reflux at 80°C for 24h. After cooling to room temperature, the reaction solution was poured into 50 mL of dichloromethane for dilution, washed with water 3 times (3×50 mL), and the organic phase was dried with anhydrous MgSO4. The solvent was removed by rotary evaporation, and the crude product was subjected to silica gel column chromatography (dichloromethane: methanol = 10:1) to obtain 156 mg of dark red solid powder with a yield of 80%. 1 HNMR(400MHz, CDCl 3 )δ10.15(s,1H), 8.17(d,J=7.4Hz,2H), 7.70(d,J=7.2Hz,2H), 7.51(s,2H),7.46(d,J=6.5Hz, 4H), 7.32(s, 2H), 3.17(t, 2H), 2.83(s, 3H), 2.81(s, 3H), 2.63(s, 3H), 2.50(s, 3H), 1.74(s, 2H) ), 1.54(d,J=4.6Hz,2H),1.43(d,J=6.5Hz,2H),0.96(t,3H). 13 CNMR(101MHz, CDCl 3 )δ:186.34,158.42,149.58,1...

Embodiment 2

[0108] (2) Synthesis of Dye2:

[0109] A method similar to synthetic dye 1 was used to obtain 150 mg of purple-red solid powder with a yield of 78%. 1 HNMR(600MHz,DMSO)δ: 8.21(d,J=7.7Hz,2H), 8.12(s,1H), 7.67-7.69(d,J=7.7Hz,2H), 7.62(d,J=7.7Hz, 2H), 7.47(d,J=9.8Hz,2H),7.36(d,J=7.2Hz,2H),7.19-7.24(t,J=7.3Hz,2H),3.12(s,2H),2.47( s, 3H), 2.46(s, 3H), 2.43(s, 3H), 2.41(s, 3H), 1.79(m, 2H), 1.65(m, 2H), 1.49(m, 2H), 0.90(t ,J=7.0Hz,3H). 13 CNMR (151MHz, DMSO) δ: 174.83, 172.89, 140.75, 140.49, 137.63, 133.49, 132.47, 131.41, 131.32, 130.12, 126.81, 126.68, 126.48, 123.29, 123.07, 120.93, 120.32, 110.29, 110.23, 32.94, 31.75, 29.49,22.56,15.43,14.49,14.42,13.64,13.22.MALDI-TOF-MS,m / z:calcdforC 42 H 49 BF 2 N 4 O 2 [M] + :690.400,found:690.251.

Embodiment 3

[0111] Synthesis of Dye3

[0112] A method similar to synthetic dye 1 was used to obtain 145 mg of purple-red solid powder with a yield of 75%. 1 HNMR (600MHz, DMSO) δ: 8.20 (d, J = 6.5 Hz, 1H), 8.17 (d, J = 6.8 Hz, 1H), 7.91 (s, 1H), 7.60-7.55 (m, 2H), 7.46 ( t,J=7.3Hz,1H), 7.21(t,J=7.1Hz,1H), 7.09(d,J=6.7Hz,1H), 4.41(s,2H), 3.09(s,2H), 2.48( s,6H),2.41(s,6H),1.76(s,2H),1.65(s,2H),1.48(s,2H),1.37(d,J=6.6Hz,2H),1.23-1.13(m ,10H),0.90(t,J=6.8Hz,3H),0.78(t,J=6.6Hz,3H). 13 CNMR (151MHz, DMSO) δ: 155.41,151.10,148.38,140.81,140.66,139.06,137.58,135.96,132.25,131.06,130.20,126.32,126.03,122.34,121.75,121.27,120.83,120.72,119.31,111.52,109.77, 51.60,32.81,32.35,31.57,29.26,29.23,29.11,29.08,27.05,22.50,22.29,15.40,14.77,14.35,14.32,13.92,13.13.MALDI-TOF-MS, m / z:calcdforC 42 H 49 BF 2 N 4 O 2 [M] + :690.400,found:690.612.

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Abstract

The present invention relates to a novel 2,6-site-substituted BODIPY organic dye sensitizer and a preparation method therefor. The organic dye sensitizer is organic photovoltaic materials with a D-pi-A structure. By taking a meso-site-substituted BODIPY core as a pi bridge framework, the sites 2 and 6 of the BODIPY core is respectively substituted by an electron donor and an electron acceptor. The present invention further discloses a preparation method for the above the dye sensitizer. The preparation method obtains a dye molecule having a general structural formula I by taking 2,4-dimethylpyrrole as an initial reaction raw material, performing a serials of simple synthesis reactions, and finally performing classical Suzuki coupling and Knoevenagel condensation reactions. The dye sensitizer synthesis method is simple, easy to control and high in yield, and has general applicability. When the method is applied to dye sensitized solar cell preparation, a dye sensitized solar cell material with a high fill factor and an ideal photoelectric conversion efficiency can be obtained. The formula I is shown in the description.

Description

Technical field: [0001] The present invention relates to the field of dye-sensitized solar cell materials, in particular to a novel 2,6-position substituted BODIPY organic dye sensitizer. Background technique: [0002] Switzerland since 1991 The team used ruthenium bipyridine as a dye and nanoporous TiO for the first time 2 Since the thin film has prepared dye-sensitized solar cells (DSSCs), dye-sensitized nanocrystalline TiO 2 Solar cells have become a research hotspot in the field of solar photoelectric conversion in the past two decades due to their low manufacturing cost and high photoelectric conversion efficiency. Photosensitive dyes mainly include metal complexes and pure organic dyes. At present, metal complexes based on polypyridine ruthenium complexes have been extensively and intensively studied due to their good stability and high energy conversion efficiency. However, ruthenium dyes have disadvantages such as limited resources and high prices, which limit its appli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/04C07F5/02H01G9/20
CPCY02E10/542
Inventor 赵鸿斌周伟男彭敏张文涛廖俊旭宗乔徐晓林谢泽川
Owner 邳州市润宏实业有限公司
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