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Porphyrin organic small molecular photovoltaic material and preparation method thereof

A photovoltaic material and small molecule technology, applied in photovoltaic power generation, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problems of low photoelectric conversion efficiency of organic solar cells, improve carrier mobility, optimize solubility, increase Effects of large π conjugated systems

Inactive Publication Date: 2014-04-16
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the photoelectric conversion efficiency of organic solar cells based on porphyrin and its derivatives is very low

Method used

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  • Porphyrin organic small molecular photovoltaic material and preparation method thereof
  • Porphyrin organic small molecular photovoltaic material and preparation method thereof
  • Porphyrin organic small molecular photovoltaic material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of 5,15-bis(3,5-bis(dodecyloxy)benzene)porphyrin

[0037]

[0038] In a 1000mL two-neck round bottom flask, add 3,5-bis(dodecyloxy)benzaldehyde (2.304g, 4.86mmol), bipyrromethane (700mg, 4.86mmol) and 500mL of dichloromethane, and ventilate with nitrogen 30 minutes, then add 0.25mL of trifluoroacetic acid, stir the reaction at room temperature for 12 hours, then add 1.8g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), continue stirring After reacting for 12 hours, 5 mL of triethylamine was added to quench the reaction. After the reaction, the crude product was obtained by silica gel / (dichloromethane as eluent) column chromatography and spin-dried, and then recrystallized by chloroform / methanol to obtain a dark red solid. 1 H NMR (300MHz, CDCl 3 ):δ10.30(s,2H),9.39(d,J=4.6Hz,4H),9.18(d,J=4.6Hz,4H),7.42(s,4H),6.91(s,2H),4.15 (t,J=6.6Hz,8H),1.93(m,8H),1.47(m,8H),1.24(m,64H),0.83(m,12H),-3.2(s,2H). 13 C NMR (75MHz, CDCl 3 ):δ158.67,147.02,145.31,143.16...

Embodiment 2

[0040] Synthesis of 5,15-bisbromo-10,20-bis(3,5-bis(dodecyloxy)phenyl)zinc porphyrin

[0041]

[0042] Dissolve 5,15-bis(3,5-bis(dodecyloxy)benzene)porphyrin (840mg, 0.7mmol) in 700mL of chloroform, add 35mL of pyridine, avoid light, and then add bromobutylene Imide (NBS) (274mg, 1.54mmol), reacted at 0°C for 30 minutes, then continued to react at room temperature for 4 hours, and finally quenched the reaction with acetone. After the reaction is complete, add water, extract with chloroform, dry over anhydrous sodium sulfate, spin dry the solvent and dissolve in 50mL of chloroform solution, then add 12mL of zinc acetate methanol solution (243mg, 1.2mmol of zinc acetate dissolved in 12mL of methanol solvent ), and reflux for 2 hours in the dark. After the reaction was completed, it was washed with water, dried with anhydrous sodium sulfate, spin-dried to dry the solvent, and purified by silica gel column chromatography to obtain a bright red solid. 1H NMR (300MHz, CDCl 3 )...

Embodiment 3

[0044] Synthesis of 5,15-bis(trimethylsilylacetylene)-10,20-bis(3,5-bis(dodecyloxy)phenyl)zinc porphyrin

[0045]

[0046] In a 100mL two-neck round-bottomed flask, add 5,15-bisbromo-10,20-bis(3,5-bis(dodecyloxy)benzene)zinc porphyrin (710mg, 0.5mmol), 25mL tetrahydrofuran and 12.5mL triethylamine, nitrogen gas for 30 minutes, then added bis (triphenylphosphine) palladium dichloride (17.5mg, 0.025mmol), copper iodide (CuI) (5mg, o.o25mmol) and trimethyl Silicon acetylene (200mg, 2mmol), protected from light, the reaction was stirred at room temperature for three days. After the reaction was completed, it was washed with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and then subjected to column chromatography on silica gel / (dichloromethane / petroleum ether=1:1 as eluent), and spin-dried to obtain a green solid. 1 H NMR (300MHz, CDCl 3 ):δ9.68(d,J=4.6Hz,4H),9.04(d,J=4.6Hz,4H),7.33(s,4H),6.89(s,2H),4.10(t,J=6.4Hz ,8H),1.82(m,8H),1.50(m,8H),1.23(...

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Abstract

The invention discloses a porphyrin organic small molecular photovoltaic material and a preparation method thereof. The disclosed porphyrin organic small molecular photovoltaic material adopts a porphyrin ring as a framework, one radical is in each of four meso-position positions of the porphyrin ring, wherein two radicals are acceptor units, and the other two radicals are aromatic substituted radicals. The invention further discloses the preparation method of the above porphyrin organic small molecular photovoltaic material. Pyrrole is used as a primary reaction material, then subjected to a series of simple reactions, and finally coupled with different acceptor units under the catalysis of palladium to obtain the porphyrin organic small molecular photovoltaic material. Compared with the prior art, the porphyrin organic small molecular photovoltaic material, disclosed by the invention, is improved in the ability to absorb light, intramolecular electric charge transmission performance and Pi-Pi stacking of molecules in a film forming state; the film forming performance of the material is improved, an organic photovoltaic battery prepared by using the material and adopting a solution processing method has better device performance, and the highest conversion rate of solar energy reaches 7.2 percent, so that the porphyrin organic small molecular photovoltaic material has a very important application prospect in solar batteries.

Description

technical field [0001] The invention relates to the field of organic small molecule photovoltaic materials, in particular to a porphyrin organic small molecule photovoltaic material and a preparation method thereof. Background technique [0002] Solar energy is a renewable clean energy and a huge energy treasure house. The development and utilization of solar energy has attracted more and more attention from human beings. However, the energy density of solar energy is low, and it is not easy to use it directly. It needs to be converted into other energy sources to be well utilized. In the effective use of solar energy, the use of photovoltaic cells to convert solar energy into electrical energy is the fastest growing and most dynamic research field in recent years. [0003] Solution-processable organic polymers and organic small molecule solar cells have potential advantages such as low cost, easy processing (such as spin coating, inkjet printing, etc.), and are suitable fo...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07D519/00H01L51/46
CPCY02E10/549C07D487/22C07D519/00H10K85/30
Inventor 彭小彬李立胜黄玉英秦红梅曹镛
Owner SOUTH CHINA UNIV OF TECH
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