Synthesis method of N-type conjugated polyelectrolyte based on electron deficiency heterocyclic ring main chain

A technology of conjugated polyelectrolyte and synthesis method, which is applied in the field of compound synthesis and can solve problems such as low efficiency

Inactive Publication Date: 2017-06-23
HANGZHOU DIANZI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this synthetic method is less efficient in preparing polymers containing electron-deficient building blocks
In addition, applicants have also found it challenging to quantitatively transform functional groups on precursor polymers based on benzothiadiazole and benzotriazole conjugated backbones, i.e. side chain terminal functional groups on such conjugated polymers. Complete conversion of the ionic side chains is not possible, and even during the conversion reaction, the polymer will precipitate and become insoluble in any solvent

Method used

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  • Synthesis method of N-type conjugated polyelectrolyte based on electron deficiency heterocyclic ring main chain
  • Synthesis method of N-type conjugated polyelectrolyte based on electron deficiency heterocyclic ring main chain
  • Synthesis method of N-type conjugated polyelectrolyte based on electron deficiency heterocyclic ring main chain

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Synthesis of cationic conjugated polyelectrolytes: PBTBTz-TMABr and PBTBTz-PyrBr using Suzuki coupling polymerization method.

[0030] The synthesis process of PBTBTz-TMABr and PBTBTz-PyrBr is as follows:

[0031]

[0032] reaction process:

[0033] (i) 4,7-dibromo-2H-benzotriazole, 1,4-dibromobutyl and potassium hydroxide were reacted at 60°C for 5h.

[0034] (ii) Tetrakis(triphenylphosphine)palladium, sodium carbonate, 4,7-dibromo-2-(6-bromo-hexyl)-2H-benzotriazole and 4,7-bis-(4,4, 5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[1,2,5]thiadiazole in THF / H 2 In O solvent, react at 90°C for 24h.

[0035] (iii) The side chain copolymer containing bromine at the end is placed in THF / H 2 O solvent, add trimethylamine or pyridine, react at 60°C for 24 hours.

[0036] The synthesis process of the conjugated polyelectrolyte is: under the nitrogen atmosphere of the glove box, add the component 2 (1.0 molar ratio), namely 4,7-bis-(4,4,5,5-tetramethyl -[1,3,...

Embodiment 2

[0037] Example 2: Synthesis of PBTBTz-SO using Suzuki coupling polymerization method 3 Na

[0038] PBTBTz-SO 3 The Na synthesis process is as follows:

[0039]

[0040]The synthesis process of the conjugated polyelectrolyte is: under the nitrogen atmosphere of the glove box, add component 3 (1.0 mole) respectively, namely 4,7-dibromo-2-(4-sodium sulfonate-butyl) in the microwave tube -2H-Benzotriazole, component 4 (1.0 mol), 4,7-bis-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane -2-yl)-benzo[1,2,5]thiadiazole, sodium carbonate (5.0 mol) and catalyst tetrakis(triphenylphosphine) palladium (2% mol) and a stirring bar, and then the microwave tube Seal and take out the glove box. The mixed solvent of dimethylformamide and water (volume ratio 4 / 1) was degassed and transferred directly into a microwave tube under a nitrogen atmosphere. The solution was placed in an oil bath, stirred at 80°C for 24 hours, and then poured into acetone to produce a red precipitate. The red precipit...

Embodiment 3

[0041] Example 3: Synthesis of PBTz-PyrBr, PBTz-TMABr and PBTz-SO using Yamamoto polymerization method 3 Na

[0042] In order to further improve the solubility of polyelectrolytes based on benzotriazole and benzothiadiazole backbones, homopolyelectrolytes with long side chains, that is, homopolybenzotriazoles with ionic side chains, are the most ideal choice. The synthesis process is as follows:

[0043]

[0044] Reaction conditions:

[0045] (i) 4,7-dibromo-2H-benzotriazole, 1,4-dibromobutane and potassium hydroxide were refluxed at 60°C for 5h.

[0046] (ii) Tetrakis(triphenylphosphine) palladium, sodium carbonate, 4,7-dibromo-2-(6-bromo-hexyl)-2H-benzotriazole in toluene / H 2 O solvent at 90°C for 24h.

[0047] (iii) The side chain homopolymer containing bromine at the end is placed in THF / H 2 O solvent, add trimethylamine or pyridine, react at 60°C for 24 hours.

[0048] (iv) 4,7-dibromo-2-(6-bromo-hexyl)-2H-benzotriazole 4,7-dibromo-2-(6-bromo-hexyl)-2H-benzotriaz...

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Abstract

The invention discloses a synthesis method of an N-type conjugated polyelectrolyte based on an electron deficiency heterocyclic ring main chain. The method provided by the invention solves the problem that the side chain functional groups (i.e., sulfonyl, quaternary ammonium groups and pyridine groups) of nonionic N-type conjugated polymers of electron main chain structures such as diazosulfide and benzotriazole cannot be completely converted into ion functional groups. The synthesis of the copolymerization conjugated polyelectrolytes based on the electron deficiency main chins such as diazosulfide and benzotriazole is realized. The conjugated polyelectrolyte prepared by the method is of an N type; the photoelectric performance is shown by the negative solvation color change effect.

Description

technical field [0001] The invention belongs to the technical field of compound synthesis, and relates to a method for synthesizing and realizing high molecular weight N-type conjugated polyelectrolytes based on electron-deficient heterocyclic main chains. Background technique [0002] The ionic side chains of conjugated polyelectrolytes can provide ion migration, dipole effect and solubility in polar solvents (such as water, methanol, etc.) and realize the preparation of multilayer electronic devices, so conjugated polyelectrolytes are widely used in various organic photovoltaic devices , such as organic polymer solar cells, field effect transistors, light emitting diodes and thermoelectric applications. In addition, ionic side chains can also be used as a design tool to induce aggregation of conjugated polyelectrolytes. [0003] There are many factors affecting the photoelectric properties of conjugated polyelectrolytes, including the main chain of conjugated polymers. F...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
CPCC08G61/124C08G61/123C08G2261/124C08G2261/143C08G2261/1452C08G2261/146C08G2261/18C08G2261/3241C08G2261/3246C08G2261/411C08G2261/412
Inventor 史月琴季振国刘照星孔亚广陆潇晓卿振军
Owner HANGZHOU DIANZI UNIV
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