Narrow-bandgap polypyrrylarylenemethine photoelectric functional polymer material and preparation method thereof

A polymer material, pyrromethene technology, applied in optics, nonlinear optics, instruments, etc., can solve problems such as difficult removal of solvents, difficult film formation, and influence on the practical application of polypyrromethene derivatives, and achieves a simple preparation method , good solubility and film-forming effect

Inactive Publication Date: 2011-04-27
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The polypyrromethene derivatives prepared at present can only be dissolved in high-boiling strong polar solvents such as dimethyl sulfoxide and N,N-dimethylformamide, and are not easy to form a film. After the film is formed, the solvent is difficult to remove, which greatly affects the Practical Application of Polypyrromethene Derivatives

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) Preparation of poly{(3-butyryl)pyrrole-[2,5-bis(p-tetradecyloxybenzenemethane)]}: massage 3-butyrylpyrrole with p-tetradecyloxybenzaldehyde Mole ratio 1:1 is dissolved in methylene chloride, is mixed with the solution that concentration is 0.5 mol / L, in this solution, drips 36% concentrated hydrochloric acid, and the control reaction system acidity is 1.5 mol / L; 2 Under gas protection, stir at room temperature for 10 h. After the reaction, the dichloromethane was distilled off. After the remaining solid was soaked in 2 mol / L ammonia water for 6 h, it was rinsed with deionized water until the water phase was neutral, and then rinsed with ethanol. Wash the remaining solid until the eluent is colorless, and dry in vacuo to obtain khaki poly{(3-butyryl)pyrrole-[2,5-bis(p-tetradecyloxybenzenemethane)]};

[0019] (2) Preparation of narrow-bandgap polypyrrolemethene photoelectric functional polymer material: Poly{(3-butyryl)pyrrole-[2,5-di(p-tetradecyloxybenzenemethane)]} ...

Embodiment 2

[0022] (1) Preparation of poly{(3-butyryl)pyrrole-[2,5-bis(p-tetradecyloxybenzenemethane)]}: massage 3-butyrylpyrrole with p-tetradecyloxybenzaldehyde Mole ratio 1:1.2 is dissolved in methylene chloride, is mixed with the solution that concentration is 0.4 mol / L, in this solution, drips 36% concentrated hydrochloric acid, and the control reaction system acidity is 1.4 mol / L; 2 Stir at room temperature for 8 h under the protection of air. After the reaction, the dichloromethane was distilled off. After the remaining solid was soaked in 2 mol / L ammonia water for 4 h, it was rinsed with deionized water until the water phase was neutral, and then rinsed with ethanol. Wash the remaining solid until the eluent is colorless, and dry in vacuo to obtain khaki poly{(3-butyryl)pyrrole-[2,5-bis(p-tetradecyloxybenzenemethane)]};

[0023](2) Preparation of poly{(3-butyryl)pyrrole-[2,5-di(p-tetradecyloxybenzene)]}: poly{(3-butyryl)pyrrole-[2,5 -bis(p-tetradecyloxybenzenemethane)]} was disso...

Embodiment 3

[0026] (1) Preparation of poly{(3-butyryl)pyrrole-[2,5-bis(p-tetradecyloxybenzenemethane)]}: massage 3-butyrylpyrrole with p-tetradecyloxybenzaldehyde Mole ratio 1:0.8 is dissolved in methylene chloride, is mixed with the solution that concentration is 0.6 mol / L, in this solution, drips 36% concentrated hydrochloric acid, and the control reaction system acidity is 1.8 mol / L; 2 Under gas protection, stir at room temperature for 10 h. After the reaction, the dichloromethane was distilled off. After the remaining solid was soaked in 2 mol / L ammonia water for 6 h, it was rinsed with deionized water until the water phase was neutral, and then rinsed with ethanol. Wash the remaining solid until the eluent is colorless, and dry in vacuo to obtain khaki poly{(3-butyryl)pyrrole-[2,5-bis(p-tetradecyloxybenzenemethane)]};

[0027] (2) Preparation of poly{(3-butyryl)pyrrole-[2,5-di(p-tetradecyloxybenzene)]}: poly{(3-butyryl)pyrrole-[2,5 -bis(p-tetradecyloxybenzenemethane)]} was dissolved...

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Abstract

The invention discloses a preparation method of a narrow-bandgap polypyrrylarylenemethine photoelectric functional polymer material, belonging to a synthesis technology of a conjugated polymer material. The preparation method comprises the following processes: reacting 3-butyrylpyrrole with para-tetradecyloxybenzaldehyde under an acidic condition to prepare poly-[(3-butyrylpyrrole)-2,5-di(para-tetradecyloxyphenylmethane)](PBPDTBA); and carrying out further quinonization on the PBPDTBA with tetrachlorobenzoquinone to obtain poly-[(3-butyrylpyrrole)-2,5-di(para-tetradecyloxyphenylmethylene)](PBPDTBE). The prepared polypyrrylarylenemethine can be dissolved in chloroform, benzene and other low-boiling solvents and has fine solubility and film-forming property, the optical bandgap and the electrochemical bandgap are respectively 1.84 eV and 1.60 eV, and the third-order nonlinear optical polarizability measured by the Z-scanning method can be up to 1.22*10<-8>esu.

Description

technical field [0001] The invention relates to a narrow band gap polypyrrole methylene photoelectric functional polymer material and a preparation method thereof, belonging to the synthesis technology of conjugated polymer materials. Background technique [0002] Narrow-bandgap π-conjugated polymers have attracted extensive research interest due to their unique electronic structures. Jenkhe S A. (Jenkhe S A. Nature, 1986, 322: 345), Zou Yingping (Zou Yingping, Gendron David, Badrou-A?ch Réda, et al. Macromolecules, 2009, 42 (8): 2891-2894) , Brabec C J (Brabec C J, Winder C, Sariciftci N S, et al. Advanced Functional Materials, 2002, 12 (10): 709-712), Yu Chao-Ying (Yu Chao-Ying, Chen Chih-Ping, Chan Shu- Hua, et al. Chemistry of Materials, 2009, 21 (14): 3262-3269), Qinghui Zhang, Qinghui Zhang, Jichang Feng, Kuan Liu, et al. Synthetic Metals, 2006, 156 (11-13): 804- 808) and Wen-Chang Chen (Wen-Chang Chen, Cheng-Liang Liu, Cheng-Tyng Yen, et al. Macromolecules, 2004, 37...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G12/40C08G12/26G02F1/361
Inventor 李宝铭涂兆王攀郑玉婴
Owner FUZHOU UNIV
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