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Thiophene-containing conjugate organo-boron polymer and preparation method therefor

A technology of organic boron and polymers, applied in the field of functional organic semiconductor materials, can solve the problems of reducing application value, and achieve the effects of cheap medicines, short production cycles, and easy post-processing

Inactive Publication Date: 2019-08-30
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the sensitivity of most boron to water and oxygen reduces the practical application value of these compounds

Method used

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  • Thiophene-containing conjugate organo-boron polymer and preparation method therefor
  • Thiophene-containing conjugate organo-boron polymer and preparation method therefor
  • Thiophene-containing conjugate organo-boron polymer and preparation method therefor

Examples

Experimental program
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Effect test

Embodiment 1

[0035] A preparation method of a thiophene-containing conjugated organic boron polymer, comprising the following steps:

[0036] (1) Synthesis of raw material A, 1,4-bis(trimethylsilylacetylene)-2,5-dibromobenzene

[0037] Under anaerobic conditions, weigh 30 mmol of 1,4-dibromo-2,5-diiodobenzene, 1.5 mmol of bis(triphenylphosphine)palladium chloride, and 3 mmol of cuprous iodide in 150 In a mixed solution of degassed toluene and 75 mL of degassed diisopropylamine, 63 mmol of trimethylsilylacetylene was added to the above reaction solution, and stirred for 24 hours. After the reaction was complete, quenched by adding 150 mL of water, extracted with dichloromethane (3 x 50 mL), combined organic phase, Mg 2 SO 4 Dry, spin to dry the solvent, and purify by column chromatography (n-hexane) to give a light yellow solid (yield: 25.5 mmol, 85%), 1 H NMR (400 MHz, CDCl 3 ): δ7.67 (s, 2H), 0.27 (s,18H).

[0038] (2) Synthesis of raw material B, 1,4-bis(bis(trimethylphenylboron))-2...

Embodiment 2

[0052] A preparation method of a thiophene-containing conjugated organic boron polymer, comprising the following steps:

[0053] (1) Synthesis of raw material A, 1,4-bis(trimethylsilylacetylene)-2,5-dibromobenzene

[0054] Under anaerobic conditions, weigh 40 mmol of 1,4-dibromo-2,5-diiodobenzene, 2 mmol of bis(triphenylphosphine)palladium chloride, and 4 mmol of cuprous iodide in 200 In a mixed solution of mL degassed toluene and 100 mL degassed diisopropylamine, 84 mmol of trimethylsilylacetylene was added to the above reaction solution, and stirred for 24 h. After the reaction was complete, quenched by adding 200 mL of water, extracted with dichloromethane (3 x 70 mL), combined organic phase, Mg 2 SO 4 Dry, spin to dry the solvent, and purify by column chromatography (n-hexane) to give a pale yellow solid (yield: 33.2 mmol, 83%), 1 H NMR (400 MHz, CDCl 3 ): δ7.67(s, 2H), 0.27(s, 18H).

[0055] (2) Synthesis of raw material B, 1,4-bis(bis(trimethylphenylboron))-2,5-bis(...

Embodiment 3

[0064] A preparation method of a thiophene-containing conjugated organic boron polymer, comprising the following steps:

[0065] (1) Synthesis of raw material A, 1,4-bis(trimethylsilylacetylene)-2,5-dibromobenzene

[0066] Under anaerobic conditions, weigh 50 mmol of 1,4-dibromo-2,5-diiodobenzene, 2.5 mmol of bis(triphenylphosphine)palladium chloride, and 5 mmol of cuprous iodide in 250 In a mixed solution of degassed toluene and 125 mL of degassed diisopropylamine, 105 mmol of trimethylsilylacetylene was added to the above reaction solution, and stirred for 24 h. After the reaction was complete, quenched by adding 250 mL of water, extracted with dichloromethane (3 x 100 mL), combined organic phase, Mg 2 SO 4 Dry, spin to dry the solvent, and purify by column chromatography (n-hexane) to give a pale yellow solid (yield: 42.5 mmol, 85%), 1 H NMR (400 MHz, CDCl 3 ): δ7.67(s, 2H), 0.27(s, 18H).

[0067] (2) Synthesis of raw material B, 1,4-bis(bis(trimethylphenylboron))-2,5-...

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Abstract

The invention discloses a thiophene-containing conjugate organo-boron polymer and a preparation method therefor. The target compound is obtained through subjecting a 2,5-diboro-1,4-phenylacetylene unit and a 2,5-thiophene diiodide unit, which serve as raw materials, to Sonogashira coupling in the presence of tetra(triphenylphosphine)palladium and cuprous iodide in a manner of taking tetrahydrofuran as a solvent and taking diisopropylamine as alkali. The invention belongs to the technical field of functional organic semiconductor materials, particularly unique properties of the thiophene-containing conjugate organo-boron polymer are decided by electron deficiency of boron and empty p-orbit, a boron monomer has strong bluish green light emission in a solution, and strong yellow light emission is obtained in the solution through being coupled to thiophene. The thiophene-containing conjugate poly-boron organic compound synthesized by the method can be applied to luminescent materials, thereaction conditions are mild, the process is simple in operation, short in production cycle and low in cost and is environmentally friendly, and the product has relatively high stability in air.

Description

technical field [0001] The invention belongs to the technical field of functional organic semiconductor materials, and in particular relates to a thiophene-containing conjugated organic boron polymer and a preparation method thereof. Background technique [0002] Boron is a group IIIA element, and its outer electron structure is 2s 2 2p 1 . Empty P of three-coordinate organoboron compounds z -orbital leads to its electron-deficient nature, making it an excellent π-acceptor in conjugated organic chromophores, and the strength of the π-acceptor can be easily tuned by changing the organic substituents. As an important new class of materials, conjugated organoboron polymers have been widely used in the fields of nonlinear optics, two-photon excited emitters, organic light-emitting diodes, and fluorescent sensors. [0003] Three-coordinate organoboron units can also be incorporated into PAHs, like B-doped compounds with very interesting properties in terms of light emission. ...

Claims

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Application Information

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IPC IPC(8): C08G61/12
CPCC08G61/126C08G2261/12C08G2261/147C08G2261/18C08G2261/3223C08G2261/52
Inventor 秦冬冬张倩倩潘效波
Owner NORTHWEST NORMAL UNIVERSITY
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