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Polyimide containing porphyrin, preparation method and application thereof

A technology of polyimide and polyamic acid, which is applied in the field of porphyrin polymer compounds, can solve problems such as the application of backward materials, and the excellent photoelectric properties of porphyrin have not been effectively utilized, so as to achieve good thermal stability and avoid fluorescence quenching Extinguishment, good thermal stability and chemical stability

Inactive Publication Date: 2010-07-28
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthesis of porphyrin-containing polyimide and the research on the preparation of related materials have progressed, its application is still far behind the development of materials, especially the excellent photoelectric properties of porphyrin as a central molecule have not been effectively utilized.

Method used

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  • Polyimide containing porphyrin, preparation method and application thereof
  • Polyimide containing porphyrin, preparation method and application thereof
  • Polyimide containing porphyrin, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] (1) Synthesis of porphyrin-containing polyimide

[0054] Preparation of 5,15-diaminotetraphenylporphyrin (trans-DATPP) and 5,10-diaminotetraphenylporphyrin (cis-DATPP) monomers: in 0.326 mmol tetraphenylporphyrin (TPP) Add 10mL trifluoroacetic acid (TFA) and 2.65mmol sodium nitrite, stir magnetically at room temperature for 90s, add 100mL water, extract 6 times with dichloromethane, each time 25mL, the extracted dichloromethane organic layer with saturated After washing with aqueous sodium bicarbonate solution (100 mL), dry over anhydrous sodium sulfate for 24 h, and evaporate the solvent to obtain a solid. Then 3.55 mmol of stannous chloride and 50 mL of hydrochloric acid were added, heated to 65° C. for 1 h under magnetic stirring, and then the reaction was stopped. After the system was cooled, 100 mL of water was added, neutralized with ammonia water to pH=8, extracted 6 times with dichloromethane, each time 25 mL, and the extracted dichloromethane organic layer was...

Embodiment 2

[0063] (1) Synthesis of porphyrin-containing polyimide

[0064] The synthetic steps of 5,15-diaminotetraphenylcadmium porphyrin (trans-CdDATPP) monomer are the same as in Example 1, except that the metal salt Zn(OAc) 2 2H 2 Replace O with Cd(OAc) 2 2H 2 O makes trans-CdDATPP.

[0065] Under nitrogen protection, 5,15-diaminotetraphenylcadmium porphyrin and 4,4'-diaminodiphenyl ether (ODA) as diamine monomers were dissolved in N,N-dimethylethyl ether in an ice-water bath. In amide (DMAc), the molar ratio of trans-CdDATPP to ODA is 0.1:1, and electromagnetic stirring is used to dissolve it to obtain a homogeneous system, and then 4,4'- (Hexafluoroisopropyl) diphthalic acid dianhydride (6FDA) monomer was added to the reaction system twice, with half an hour between the two additions; 4,4'-(hexafluoroisopropyl) bis The ratio of the added amount of phthalic dianhydride (6FDA) to N,N-dimethylacetamide (DMAc) was 50 mg / mL. After continuing to react for 4 hours in an ice-water ba...

Embodiment 3

[0073] (1) Synthesis of porphyrin-containing polyimide

[0074] 5, the synthesis steps of 15-diaminotetraphenyl copper porphyrin (trans-CuDATPP) monomer are the same as in Example 1, except that the metal salt Zn(OAc) 2 2H 2 O is replaced by CuCl 2 The trans-CuDATPP was prepared.

[0075] Under nitrogen protection, 5,15-diaminotetraphenylcopper porphyrin and 4,4'-diaminodiphenyl ether (ODA) were dissolved in N,N-dimethylethyl ether as diamine monomers in an ice-water bath. In amide (DMAc), the molar ratio of trans-CuDATPP to ODA is 0.15:1, and electromagnetic stirring is used to dissolve it to obtain a homogeneous system, and then the molar amount of 4,4'- (2,2,2-trifluoro-1-phenylethylene)diphthalic anhydride (3FDA) monomer was added to the reaction system twice, wherein the interval between two additions was half an hour; 4,4'-(2 , The ratio of the added amount of 2,2-trifluoro-1-phenylethylene) diphthalic anhydride (3FDA) to N,N-dimethylacetamide (DMAc) was 50 mg / mL. A...

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Abstract

The invention discloses a polyimide containing porphyrin, and aromatic polyimide with better thermal stability is obtained by using aromatic dicarboxylic anhydride with better thermal stability and aromatic organic diamine as basic framework. The preparation method comprises the following step of carrying out condensation reaction on diamino tetraphenyl porphyrin, the aromatic organic diamine and the aromatic dicarboxylic anhydride to synthesize soluble polyimide containing porphyrin, having the characteristics of simple operation, strong controllability and recyclable use of products. The polyimide containing the porphyrin can be used for preparing a corresponding nano fiber film of the polyimide containing the porphyrin by using an electrostatic spinning method, and the nano fiber film is used for detecting explosive steam under an extreme environment, having advantages of high sensitivity and rapid response.

Description

technical field [0001] The invention relates to a porphyrin-type polymer compound, in particular to a porphyrin-containing polyimide and a preparation method and application thereof. Background technique [0002] In recent years, with the increasing demand for anti-terrorism, non-metal mine detection, and environmental quality monitoring, countries around the world have paid more and more attention to the research of various high-performance explosive sensors, and the detection technology for explosive vapor has gradually begun to be accepted by researchers. s concern. Optical sensors have attracted much attention in the detection of explosives due to their advantages of simple operation and portability. Such sensors generally use electron-rich fluorescent molecules as sensing elements, which undergo energy transfer after combining with explosives (mostly electron-deficient aromatic hydrocarbons), causing fluorescence quenching, so as to achieve the purpose of detection. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10D04H3/16G01N21/64
Inventor 吴健吕媛媛徐志康
Owner ZHEJIANG UNIV
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