A kind of 2,6-position substituted bodipy organic dye sensitizer and preparation method thereof

An organic dye and sensitizer technology, applied in the field of dye-sensitized solar cell materials, can solve the problems of high price and limited resources, and achieve the effects of low production cost, simple purification and improved yield

Active Publication Date: 2017-06-23
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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  • A kind of 2,6-position substituted bodipy organic dye sensitizer and preparation method thereof
  • A kind of 2,6-position substituted bodipy organic dye sensitizer and preparation method thereof
  • A kind of 2,6-position substituted bodipy organic dye sensitizer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] (1) Synthesis of Dye 1:

[0111] 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-neck flask, and 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 3 times with water (3×50 mL), and the organic phase was dried over 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 H NMR (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 C NMR (101MHz, CDCl 3 )δ:186.34,158.42,149.58,1...

Embodiment 2

[0113] (2) Synthesis of Dye 2:

[0114] 150 mg of purple-red solid powder was obtained by a method similar to that of dye 1, and the yield was 78%. 1 H NMR (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 C NMR(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: calcd for C 42 h 49 BF 2 N 4 o 2 [M] + :690.400,found:690.251.

Embodiment 3

[0116] Synthesis of Dye 3

[0117] 145 mg of purple-red solid powder was obtained by a method similar to that of dye 1, and the yield was 75%. 1 H NMR (600MHz, DMSO) δ: 8.20 (d, J = 6.5Hz, 1H), 8.17 (d, J = 6.8Hz, 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 C NMR(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: calcd for C 42 h 49 BF 2 N4 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

[0001] Technical field: [0002] The invention relates to the field of dye-sensitized solar cell materials, in particular to a 2,6-substituted BODIPY organic dye sensitizer. [0003] Background technique: [0004] Switzerland since 1991 The group first used bipyridyl ruthenium as a dye with nanoporous TiO 2 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 preparation cost and high photoelectric conversion efficiency. Photosensitive dyes mainly include metal complexes and pure organic dyes. At present, metal complexes mainly based on polypyridine ruthenium complexes have been extensively and deeply studied because of their good stability and high energy conversion efficiency. However, ruthenium dyes have disadvantages such as limited resources and high price, which limit its application. Compared with ruthenium dyes, pure organic dyes have become a hot res...

Claims

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Application Information

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Patent Type & Authority Patents(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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