A kind of organic dye sensitizer containing bodipy type conjugated unit and preparation method thereof

A technology of organic dyes and sensitizers, applied in the field of dye-sensitivity solar cell materials, can solve the problems of non-planar three-dimensional structure weakening the absorption of light, and achieve easier control of reaction conditions, low production cost, and common and readily available raw materials. Effect

Inactive Publication Date: 2017-10-13
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its non-planar three-dimensional structure weakens the absorption of light, so we combined the BODIPY unit with triphenylamine derivatives of different rigidity, hoping to improve the light absorption and light harvesting efficiency of the dye, thereby improving the performance of the battery

Method used

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  • A kind of organic dye sensitizer containing bodipy type conjugated unit and preparation method thereof
  • A kind of organic dye sensitizer containing bodipy type conjugated unit and preparation method thereof
  • A kind of organic dye sensitizer containing bodipy type conjugated unit and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Synthesis of Dye 1:

[0088] Intermediate 12 (0.16 g, 0.2 mmol), cyanoacetic acid (0.04 g, 0.4 mmol), 20 mL of chloroform and 20 mL of acetonitrile were sequentially added into a 100 mL three-neck flask. Install a reflux condenser, vacuumize, replace the argon protection, quickly add 2 drops of piperidine, and heat up to 80°C for reflux reaction for 24h. Stop the reaction, cool to room temperature, add 100 mL of dichloromethane to dilute the reaction solution, wash the organic phase with saturated brine three times (100 mL×3), and dry over anhydrous magnesium sulfate overnight. The filtrate was collected by filtration, the solvent was removed under reduced pressure, and the crude product was purified by silica gel (300-400 mesh) column chromatography [eluent, V (dichloromethane): V (methanol) = 10:1] to obtain a dark green solid powder Dye1 (0.14 g), 80% yield. 1 H NMR (400MHz, DMSO-d 6 )δ: 8.74(d, J=4.4Hz, 2H), 7.94–7.88(m, 5H), 7.73(d, J=8.5Hz, 2H), 7.63(d, J=8.6Hz...

Embodiment 2

[0090] Synthesis of Dye 2:

[0091] Intermediate 13 (0.16g, 0.2mmol) and cyanoacetic acid (0.04g, 0.4mmol) were sequentially added into a 100mL three-neck flask. A green solid powder Dye2 (0.13 g) was obtained by a method similar to the synthesis of Dye1 with a yield of 78%. 1 H NMR (400MHz, DMSO-d 6 )δ: 8.69(d,J=17.6Hz,1H),7.94–7.86(m,3H),7.78(d,J=8.2Hz,1H),7.74–7.69(m,1H),7.65(dd,J =10.0,4.4Hz,2H),7.56–7.38(m,7H),7.35–7.27(m,4H),7.18(dd,J=11.7,3.0Hz,3H),7.09–7.02(m,2H), 6.27(d, J=4.0Hz, 1H), 6.22(d, J=9.0Hz, 1H), 4.12(t, J=8.1Hz, 2H), 3.77(d, J=7.3Hz, 3H), 1.81– 1.76(m,2H),1.46–1.28(m,10H),0.88(s,3H). 13 C NMR (100MHz, DMSO-d 6 )δ:163.74,161.36,155.86,149.96,147.29,143.78,142.28,140.98,140.15,137.41,135.99,135.06,134.22,133.33,131.61,130.71,130.11,129.94,128.27,127.95,127.64,126.02,125.83,124.14 ,115.36,110.97,102.87,68.39,55.94,31.72,29.50,29.18,29.05,26.01,22.57,14.43.MALDI-TOF-MS,m / z:calcd.forC 54 h 47 BF 2 N 4 o 4 :864.370,found:864.212[M] + .

Embodiment 3

[0093] Synthesis of Dye3:

[0094] Intermediate 14 (0.16g, 0.2mmol) and cyanoacetic acid (0.04g, 0.4mmol) were sequentially added into a 100mL three-neck flask. A green solid powder Dye3 (0.13 g) was obtained by a method similar to the synthesis of Dye1 with a yield of 75%. 1 H NMR (400MHz, DMSO-d 6 )δ:8.82(s,1H),8.28–8.22(m,2H),8.02–7.93(m,4H),7.78(d,J=8.6Hz,1H),7.72–7.69(m,1H),7.56 (d, J=8.8Hz, 1H), 7.49(s, 1H), 7.42(t, J=7.8Hz, 4H), 7.31(d, J=7.8Hz, 4H), 7.27–7.21(m, 4H) ,7.06–7.03(m,1H),4.14(t,J=6.3Hz,2H),3.97–3.79(m,3H),1.85–1.71(m,2H),1.52–1.28(m,10H),0.91 (t,J=6.9Hz,3H). 13 C NMR (100MHz, DMSO-d 6 )δ:163.47,162.03,159.03,146.70,143.85,141.84,141.62,139.42,139.14,135.38,133.47,132.46,132.06,130.76,130.12,129.93,128.87,126.25,125.86,124.06,122.80,122.51,121.45,120.92 ,120.43,118.67,115.83,115.45,110.04,106.82,68.38,55.90,31.74,29.48,29.17,29.10,26.02,22.58,14.45. 52 h 45 BF 2 N 4 o 4 :838.350,found:838.991[M] + .

[0095] The relevant data of the UV absorptio...

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Abstract

The invention discloses a BODIPY-containing organic dye sensitizer and a preparation method thereof. The organic dye sensitizer is a kind of organic photosensitive dye with D-π-π-A structure, the BODIPY nuclear bridging biphenyl substituted by meso-position is the π bridge skeleton, the triphenylamine derivative is the electron-donating unit, and the cyanide Acetic acid is the electron acceptor unit. The invention also discloses a preparation method of the above-mentioned organic dye sensitizer. The organic dye sensitizer molecules are all prepared by two-step Suzuki coupling reaction and one-step Knoevenagel condensation reaction, and the general structure formula is shown in I. The molecular synthesis method of the organic dye sensitizer is simple, easy to control, high in yield and universally applicable, and the dye-sensitized solar cell material with excellent performance can be obtained by applying it to the preparation of the dye-sensitized solar cell.

Description

Technical field: [0001] The invention relates to the field of dye-sensitized solar cell materials, in particular to an organic dye sensitizer containing BODIPY-type conjugated units. Background technique: [0002] 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. The BODIPY core has multiple active sites, which can be appropriately modified and functionalized according to thermal, optical and electrical performance requirements. People have synthesized many new BODIPY dyes with excellent performance by modifying each site of the BODIPY core. Researchers usually choose to modify the two pyrrole rings of the BODIPY parent. By introducing functional groups with different properties, the conjugated chai...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/14C07F5/02H01G9/20
CPCY02E10/542
Inventor 赵鸿斌廖俊旭徐勇军韩利芬周伟男李钧华肖永招兆林
Owner DONGGUAN UNIV OF TECH
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