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Synthesis method and application of branched porphyrin-perylene diimide small molecule receptor

A perylene diimide and small molecule technology, which is applied in the field of synthesis of branched porphyrin-perylene diimide small molecule receptors, can solve the problems of cumbersome preparation process, low absorption rate and high preparation cost, and achieve High light absorption performance, increase utilization efficiency, and improve the effect of photogenerated current

Active Publication Date: 2019-08-20
XIANGTAN UNIV
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Problems solved by technology

[0006] Existing photovoltaic acceptor materials have a low light absorption rate and do not improve the morphology of perylene diimide film formation, resulting in poor performance in the prepared organic photovoltaic solar cells and other devices.
Moreover, the preparation cost of the prior art is high, and the preparation process is loaded down with trivial details

Method used

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  • Synthesis method and application of branched porphyrin-perylene diimide small molecule receptor
  • Synthesis method and application of branched porphyrin-perylene diimide small molecule receptor
  • Synthesis method and application of branched porphyrin-perylene diimide small molecule receptor

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preparation example Construction

[0062] The present invention provides a preparation method of porphyrin-perylene diimide organic small molecule solar cell acceptor material, including the following steps:

[0063] Prepared by the [2+2] synthesis method: Under inert gas atmosphere, organic solvent is used as the reaction medium, and pyrrole is reacted with aldehyde through a catalytic system, and subsequent treatment is used to obtain porphyrin-perylene diimide organic small molecules Acceptor material for solar cells.

[0064] In the embodiment of the present invention, the structural formula of pyrrole is Formula II:

[0065] Formula II:

[0066] The structural formula of the aldehyde is formula III:

[0067] Formula Ⅲ: A-π-CHO;

[0068] Among them: Ar in the structure of pyrrole is the same as Ar in the structure of porphyrin organic small molecule photovoltaic acceptor material; π and A in the structure of aldehyde are the same as those in the structure of porphyrin organic small molecule photovoltaic acceptor mat...

Embodiment 1

[0076] For the synthesis of compound C provided in the embodiment of the present invention, the reaction equation is as follows:

[0077]

[0078] Compound B (514 mg, 0.29 mmol), compound A (77 mg, 0.35 mmol), 37.5 mL of dichloromethane were added to a 100 mL two-necked flask, bubbling under argon for 20 minutes, and then adding trifluoroacetic acid (3.31 mg, 0.029 mmol), stirred overnight at room temperature in the dark. Then add 2,3-dichloro-5,6-dicyanobenzene (77mg, 0.339mmol) and stir for 1 hour, spin off the solvent under reduced pressure and purify it on a chromatographic column. The developing solvent is petroleum ether: three Chloromethane (v:v=1:3), the resulting product was recrystallized in dichloromethane / methanol, and a dark brown solid was obtained as compound C (66.9 mg, 11.7%).

[0079] 1 H NMR (400MHz, Chloroform-d) δ 9.19-8.84 (m, 8H), 8.66 (m, 20H), 8.28 (m, 16H), 7.93-7.69 (m, 10H), 7.64 (m, 16H), 6.26--4.79(m,8H), 2.19m,16H), 2.05-1.67(m,16H), 1.43-1.02(m,128...

Embodiment 2

[0081] For the synthesis of compound D provided in the embodiment of the present invention, the reaction equation is as follows:

[0082]

[0083] Add compound C (61mg, 0.015mmol), zinc acetate (33mg, 0.15mmol), 15mL chloroform into a 100mL two-necked flask, stir at room temperature for 4 hours, spin dry the solvent under reduced pressure, and chromatograph on silica gel. Purify in the plate, the developing agent is petroleum ether: chloroform (v:v=1:3). The resulting product was recrystallized in dichloromethane / methanol to obtain a dark brown solid as compound D (56 mg, 91%).

[0084] 1 H NMR (400MHz, Chloroform-d) δ9.28-8.89(m,8H), 8.86-8.53(m,20H), 8.44-8.16(m,16H), 7.86-7.69(m,10H), 7.70-7.55 (m,16H),5.27-4.83(m,8H),2.51-2.02(m,16H),2.04-1.69(m,16H),1.47-0.98(m,128H),1.02-0.46(m,48H) . 13 C NMR (101MHz, Chloroform-d) δ147.86,146.21,145.15,142.86,142.41,141.40,138.71,137.39,136.01,135.03,134.87,134.83,134.58,133.90,132.49,132.22,132.09,131.96,130.05,129.73,129.33 ,128.56,128...

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Abstract

The invention belongs to the technical field of photovoltaic materials, and discloses a synthesis method and an application of a branched porphyrin-perylene diimide small molecule receptor. The porphyrin-perylene diimide small molecule solar cell receptor material has a structure represented by formula I, and pi in the formula I is benzene connected with a plurality of perylene diimides, triphenylamine, N-phenyloxazole, tetraphenylmethane or a tetraphenylsilane pi bridge. The branched porphyrin-perylene diimide organic small molecule photovoltaic acceptor material of the invention has an improved light-trapping ability, and can achieve good absorption complementation and energy level matching after being combined with a narrow bandgap polymer donor material PTB7-Th; and the small moleculereceptor can obtain a highest open-circuit voltage of 0.84 V and a highest photoelectric conversion efficiency of 7.7% when applied to an organic solar cell, so the porphyrin-perylene diimide small molecule receptor has a broad application prospect in the field of organic photovoltaics.

Description

Technical field [0001] The invention belongs to the technical field of photovoltaic materials, and in particular relates to a synthesis method and application based on a branched porphyrin-perylene diimide small molecule receptor. Background technique [0002] With the rapid development of society, people's energy demand for production and life has risen exponentially, and traditional energy sources such as coal, oil, and natural gas are consumed hugely and increasingly depleted. At the same time, with the use of chemical energy, environmental problems have become increasingly serious. As the source of the formation of part of the energy on the earth, solar energy has the characteristics of renewable, huge total, wide distribution, and pollution-free. It has always been the most dynamic research field that has received wide attention. [0003] Industrial civilization is based on electricity. Solar cells can directly convert solar energy into electrical energy, which has always bee...

Claims

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Application Information

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IPC IPC(8): C07D519/00H01L51/42H01L51/46
CPCC07D519/00H10K85/381H10K30/30Y02E10/549Y02P70/50
Inventor 王行柱陈煜卓闫磊谢柳平刘志鑫
Owner XIANGTAN UNIV
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