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Novel organic dye sensitizer containing BODYPY type conjugate units and preparation method of sensitizer

A technology of organic dyes and sensitizers, applied in the field of dye-based solar cell materials, can solve the problem of non-planar three-dimensional structures that weaken the absorption of light, and achieve easier control of reaction conditions, low production costs, and common and easy-to-obtain raw materials Effect

Inactive Publication Date: 2016-12-14
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Novel organic dye sensitizer containing BODYPY type conjugate units and preparation method of sensitizer
  • Novel organic dye sensitizer containing BODYPY type conjugate units and preparation method of sensitizer
  • Novel organic dye sensitizer containing BODYPY type conjugate units and preparation method of sensitizer

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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 CNMR (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 ultraviolet absorption spectra and...

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Abstract

The invention discloses a novel organic dye sensitizer containing BODYPY type conjugate units and a preparation method of the sensitizer. The novel organic dye sensitizer is an organic light-sensitive dye of a D-pi-pi-A structure, a BODYPY nuclear bridging phenyl group substituted at the meso- site serves as the pi bridge framework, a triphenylamine derivative serves as the electron giver unit, and cyanoacetic acid serves as the electron receptor unit. The invention further discloses a preparation method of the organic dye sensitizer. Organic dye sensitizer molecules are obtained through the two-step Suzuki coupling reaction and the one-step Knoevenagel condensation reaction, and the structural general formula is seen in the formula I (please see the formula I in the description). The organic dye sensitizer is simple in molecule synthesis method, easy to control and high in yield and has general applicability, and a dye sensitive solar cell material with excellent performance can be obtained after the organic dye sensitizer is applied to preparation of a dye sensitive solar cell.

Description

Technical field: [0001] The invention relates to the field of dye-sensitized solar cell materials, in particular to a novel 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/14C07F5/02H01G9/20
CPCY02E10/542C09B23/143C07F5/022C09B23/0058H01G9/2059
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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