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Synthetic method of A-D-A organic photoelectric micro-molecule based on perylene diimide and pentacene

A perylene diimide and perylene diimide-based technology, which is applied in the fields of silicon organic compounds, chemical instruments and methods, and photovoltaic power generation, can solve problems such as lack of application and principles, and achieve optimal efficiency and simple preparation methods Effect

Active Publication Date: 2018-03-13
SHANGHAI NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Synthetic method of A-D-A organic photoelectric micro-molecule based on perylene diimide and pentacene
  • Synthetic method of A-D-A organic photoelectric micro-molecule based on perylene diimide and pentacene
  • Synthetic method of A-D-A organic photoelectric micro-molecule based on perylene diimide and pentacene

Examples

Experimental program
Comparison scheme
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 invention relates to a synthetic method of an A-D-A organic photoelectric micro-molecule based on perylene diimide and pentacene. The synthetic method includes the steps: dissolving 6, 13-bi (triisopropyl silicon acetenyl) pentacene-2, 9-bi-pinacol ester or 6, 13-bi (triisopropyl silicon acetenyl) pentacene-2, 10-bi-pinacol ester and 1-bromine perylene diimide in solvents under inert atmosphere; performing coupled reaction under the action of catalysts to obtain 2, 10-biperylene diimide-6, 13-bi (triisopropyl silicon acetenyl) pentacene or 2, 9-biperylene diimide-6, 13-bi (triisopropyl silicon acetenyl) pentacene; performing LED (light-emitting diode) lamp illumination and photocycloaddition reaction under the action of iodine elementary substances to prepare the micro-molecule. According to the method, electron acceptor materials with excellent performances and singlet-state fission model molecules are firstly assembled into one molecule, and the molecule is applied to fields suchas organic solar cells, field effect transistors, photoelectric detectors and organic light emitting diodes.

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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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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