Synthesis method of a-d-a type organic optoelectronic small molecules based on perylene diimide and pentacene

A technology of perylene diimide and A-D-A, which is applied in the field of synthesis of A-D-A type organic optoelectronic small molecules, can solve the problems of lack of application and principle, and achieve the effect of optimizing efficiency and simple preparation method

Active Publication Date: 2020-04-10
SHANGHAI NORMAL UNIVERSITY
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Problems solved by technology

The application of this intramolecular singlet fission in the field of organic solar cells was not reported until 2015, and reports on specific applications and principles are still lacking.

Method used

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  • Synthesis method of a-d-a type organic optoelectronic small molecules based on perylene diimide and pentacene
  • Synthesis method of a-d-a type organic optoelectronic small molecules based on perylene diimide and pentacene
  • Synthesis method of a-d-a type organic optoelectronic small molecules based on perylene diimide and pentacene

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Experimental program
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Effect test

Embodiment 1

[0030] The synthetic method of the A-D-A type organic optoelectronic small molecule based on perylene diimide adopts the following steps:

[0031] (1) Take substrates 1 (50mg, 0.056mmol) and 2 (95.67mg, 0.123mmol), dissolve them in a mixed solvent composed of 10mL toluene, 2mL ethanol, and 2mL water, and quickly add tetrakis(triphenylene) after nitrogen bubbles for 40min. Phosphine) palladium (6.47mg, 0.0056mmol) and potassium carbonate (46.44mg, 0.336mmol), and then blow nitrogen for 20min. Heated to 110°C and reacted for 24 hours. After the reaction was completed, concentrated and spin-dried, separated by column chromatography to obtain 3 and 3'.

[0032] (2) Take substrate 3 (200.00mg, 0.0984mmol) and 3' (200.00mg, 0.0984mmol) respectively in two Schlenk tubes, add 50mL anhydrous and oxygen-free toluene solvent, iodine element (750mg, 2.94mmol) , using the method of freezing-pumping-thawing to remove oxygen, under the light condition of LED lamp (power 150W, luminous flux ...

Embodiment 2

[0034] The synthetic method of the A-D-A type organic optoelectronic small molecule based on perylene diimide adopts the following steps:

[0035] (1) Take substrates 1 (75mg, 0.084mmol) and 2 (156.81mg, 0.202mmol), dissolve them in a mixed solvent composed of 20mL toluene, 5mL ethanol, and 5mL water, and quickly add tetrakis(triphenylene) after nitrogen bubbles for 40min. Phosphine) palladium (7.765mg, 0.0067mmol) and potassium carbonate (58.00mg, 0.420mmol), and then blow nitrogen for 20min. Heated to 80°C and reacted for 12 hours. After the reaction, concentrated and spin-dried, separated by column chromatography to obtain 3 and 3'.

[0036](2) Take substrate 3 (100.00mg, 0.0492mmol) and 3' (100.00mg, 0.0492mmol) respectively in two Schlenk tubes, add 25mL anhydrous and oxygen-free toluene solvent, iodine simple substance (187.45mg, 0.738mmol ), using the method of freezing-pumping-thawing to remove oxygen, under the light condition of LED lamp (power 150W, luminous flux 1...

Embodiment 3

[0038] The synthetic method of the A-D-A type organic optoelectronic small molecule based on perylene diimide adopts the following steps:

[0039] (1) Take substrates 1 (150mg, 0.168mmol) and 2 (313.62mg, 0.404mmol), dissolve them in a mixed solvent composed of 40mL toluene, 8mL ethanol, and 8mL water, and quickly add tetrakis (triphenyl) after bubbling nitrogen gas for 40min. Phosphine) palladium (29.12mg, 0.0252mmol) and potassium carbonate (139.32mg, 1.008mmol), and then blow nitrogen for 20min. Heated to 140°C and reacted for 36 hours. After the reaction, concentrated and spin-dried, separated by column chromatography to obtain 3 and 3'.

[0040] (2) Take substrate 3 (50.00mg, 0.0246mmol) and 3' (100.00mg, 0.0246mmol) respectively in two Schlenk tubes, add 15mL anhydrous and oxygen-free toluene solvent, iodine element (200mg, 0.787mmol) , use the method of freezing-pumping-thawing to remove oxygen, and react for 40 hours under the light condition of LED lamp (power 150W, ...

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Abstract

The present invention involves the synthesis method of A‑D‑A organic optoelectronics small molecules based on bonamine and parallel benzene. In an inert atmosphere, 6,13‑ double (silicon aceteraceae)Benzal 2,9频 two -frequency two -frequency alcohol or 6,13‑ double (triangular acenenethyl) and pentazide 2,10‑ binary alcohol and 1‑ bromacide amine dissolved inIn the solvent, under the action of a catalyst, 2,10‑ ‑ two -苝 diimide ‑ 6,13‑ (silicon acetethite group) is obtained through the coupling reaction.Diablytic 1 6,13‑ double (silicon aceteraceae group) and five benzene, then under the action of iodine single, use LED light photos to prepare the final product through a halo reaction.For the first time, the invention has assembled the model molecules of electronic receptor materials and single -line state fission for the first time as a molecule, which can be applied in the fields of organic solar cells, field effect transistors, photoelectric detectors, and organic light diode.

Description

technical field [0001] The invention relates to the synthesis of a class of materials based on the covalent connection of perylene diimide and pentacene, in particular to a synthesis method of A-D-A type organic optoelectronic small molecules based on perylene diimide and pentacene. Background technique [0002] Perylenediimide (PDI) materials, as a kind of promising organic receptor materials, have come into the sight of scientists. So far, perylene diimide receptor materials are the most in-depth and thorough research on small molecule receptor materials. The PCE value of organic solar cells based on PDI materials has developed from 0.95% of C.W.Tang in 1985 to 9.28% of Zhaohui Wang et al. [0003] At present, research on solar cells mainly focuses on: 1) reducing manufacturing cost; 2) improving energy conversion efficiency (Power Conversion Efficiency, PCE). However, in the 1960s, William Shockley and Hans-Joachim Queisser theoretically proposed that the PCE of single-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08C09K11/06H01L51/46H01L51/54H01L51/00
CPCC09K11/06C07F7/0812C09K2211/1029H10K85/621H10K85/40Y02E10/549
Inventor 肖胜雄屈扬坤黄悦毕萌叶雨萌刘一高磊刘泰峰
Owner SHANGHAI NORMAL UNIVERSITY
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