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Thiophene polycyclic organic semiconductor material synthesis based on pyrene

An organic semiconductor, thiophene technology, applied in the field of photoelectric conversion materials, can solve the problem of non-fluorescence and so on

Inactive Publication Date: 2015-12-02
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, as an organic fluorescent material, π-π stacking can quench the fluorescence caused by molecular aggregation, and there is basically no fluorescence in solid state or solution.

Method used

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  • Thiophene polycyclic organic semiconductor material synthesis based on pyrene
  • Thiophene polycyclic organic semiconductor material synthesis based on pyrene
  • Thiophene polycyclic organic semiconductor material synthesis based on pyrene

Examples

Experimental program
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Effect test

Embodiment 1

[0062] The preparation method of thiophene polycyclic organic semiconductor material compound TM-1 based on pyrene, comprises the steps:

[0063] (1) Synthesis of 1,3,6,8-tetrabromopyrene

[0064] Add 6g of pyrene and 100mL of nitrobenzene to a 250mL three-necked round-bottom flask in sequence, and add 6.8mL of liquid bromine using a syringe while stirring at room temperature; heat, stir and reflux at 220°C for 4 hours; Wash and dry overnight in vacuum to obtain a gray-green solid that is 1,3,6,8-tetrabromopyrene;

[0065] (2) Synthesis of 1,3,6,8-tetraoctynepyrene

[0066] Add 6.12g of 1,3,6,8-tetrabromopyrene, 120mL of dry tetrahydrofuran and 120mL of diisopropylamine to a 500mL three-necked round-bottomed flask; then vacuumize, fill with nitrogen twice, and add 252mg of Cuprous iodide and 852mg bis(triphenylphosphine)palladium dichloride, vacuumize and fill with nitrogen twice; then inject 12mL of 1-octyne with a syringe under stirring conditions, vacuumize and fill with ...

Embodiment 2

[0082] The preparation method of thiophene polycyclic organic semiconductor material compound TM-2 based on pyrene, comprises the steps:

[0083] (1) Synthesis of 1,3,6,8-tetrabromopyrene

[0084] Add 6g of pyrene and 100mL of nitrobenzene to a 250mL three-necked round-bottom flask in sequence, and add 6.8mL of liquid bromine using a syringe while stirring at room temperature; heat, stir and reflux at 220°C for 4 hours; Wash and dry overnight in vacuum to obtain a gray-green solid that is 1,3,6,8-tetrabromopyrene;

[0085] (2) Synthesis of 1,3,6,8-tetraoctynepyrene

[0086] Add 6.12g of 1,3,6,8-tetrabromopyrene, 120mL of dry tetrahydrofuran and 120mL of diisopropylamine to a 500mL three-necked round-bottomed flask; then vacuumize, fill with nitrogen twice, and add 252mg of Cuprous iodide and 852mg bis(triphenylphosphine)palladium dichloride, vacuumize and fill with nitrogen twice; then inject 12mL of 1-octyne with a syringe under stirring conditions, vacuumize and fill with ...

Embodiment 3

[0106] The preparation method of thiophene polycyclic organic semiconductor material compound TM-3 based on pyrene, comprises the steps:

[0107] (1) Synthesis of 1,3,6,8-tetrabromopyrene

[0108] Add 6g of pyrene and 100mL of nitrobenzene to a 250mL three-necked round-bottom flask in sequence, and add 6.8mL of liquid bromine using a syringe while stirring at room temperature; heat, stir and reflux at 220°C for 4 hours; Wash and dry overnight under vacuum to obtain a gray-green solid that is 1,3,6,8-tetrabromopyrene;

[0109] (2) Synthesis of 1,3,6,8-tetraoctynepyrene

[0110]Add 6.12g of 1,3,6,8-tetrabromopyrene, 120mL of dry tetrahydrofuran and 120mL of diisopropylamine to a 500mL three-necked round-bottomed flask; then vacuumize, fill with nitrogen twice, and add 252mg of Cuprous iodide and 852mg bis(triphenylphosphine)palladium dichloride, vacuumize and fill with nitrogen twice; then inject 12mL of 1-octyne with a syringe under stirring conditions, vacuumize and fill wit...

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Abstract

The invention discloses thiophene polycyclic organic semiconductor material synthesis based on pyrene and belongs to the field of photoelectric conversion materials. The molecular formulas of compounds are C<76>H<86>N<4>S<4> and C<62>H<80>N<2>S<2>, and the structural formula can be seen in the Application of the invention. A synthesis method comprises the steps of making the pyrene react with liquid bromine, and obtaining 1,3,6,8-tetrabromo pyrene; making the 1,3,6,8-tetrabromo pyrene react with 1-octyne, obtaining a product, and then using palladium / carbon for conducting catalytic reaction,and obtaining 1,3,6,8-quadri-octane pyrene; using ruthenium trichloride for catalyzing the 1,3,6,8-quadri-octane pyrene, adjusting the using amount of sodium periodate, and obtaining tetrone and diketone; then making o-phenylenediamine and sulfoxide chloride react with liquid bromine, and obtaining 4,7-dibromo-2,1,3-diazosulfide; making thiophene react with thiadiazole, and obtaining diazosulfide; then making o-phenylenediamine and paratoluensulfonyl chloride react with liquid bromine, subsequently, making the mixture react with concentrated sulfuric acid, then making the mixture react with thionyl chloride, and obtaining 5,6-dibromo-2,1,3-diazosulfide; conducting operation same with the reaction process, and obtaining another type of diazosulfide; making a thiadiazole product to be subjected to ring-opening reaction, and obtaining two types of o-phenylenediamine products; making the tetrone and the diketone react with the two types of o-phenylenediamine respectively, and obtaining the compounds.

Description

technical field [0001] The invention relates to a pyrene-based thiophene polycyclic organic semiconductor material compound and a preparation method, belonging to the field of photoelectric conversion materials. Background technique [0002] Photosensitive material molecules made of thiophene derivatives can efficiently convert the energy of absorbed sunlight into electrical energy. Organic semiconducting molecules and polymers offer feasibility for developing new electronics, and polycyclic aromatic hydrocarbon n-acene is one of the most promising organic semiconducting materials. Although n-acenes with higher ring numbers (n>5) are unstable, there are some well-established methods to prepare more stable acenes with higher ring numbers (5≤n≤9). In addition, the test results of photoelectric properties of macrocyclic acene are good, which further proves the necessity of in-depth research in this area. Moreover, azacenes are more stable and easier to prepare than pure ac...

Claims

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Application Information

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IPC IPC(8): C07D487/06C07D409/14
CPCC07D487/06C07D409/14
Inventor 黄学斌赵菲阳
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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