Triarylboron conjugated polymer porous material as well as preparation method and application thereof

Abstract

The invention discloses a triarylboron conjugated polymer porous material as well as a preparation method and application thereof. The invention provides a novel preparation method of a triaryl conjugated polymer porous material, i.e., the novel triaryl conjugated polymer porous material is prepared by using a boron-tin exchange reaction as a polymerization means. The defects of high cost, difficulty in purification and the like in a preparation method of carbon-carbon coupling reaction catalyzed by noble metal are overcome, and the method is more economical and efficient. The triaryl conjugated polymer porous material disclosed by the invention can realize fluorescence detection on organic ammonia, the fluorescence quenching ratios of pyridine to P2-Th, P2-Th2 and P2-Th3 of the triaryl conjugated polymer porous material disclosed by the invention are 83.8%, 73.5% and 41.3% respectively, and the triaryl conjugated polymer porous material disclosed by the invention has a good application prospect in the field of fluorescence detection.

Description

technical field

[0001] The invention relates to a triaryl boron conjugated polymer porous material and its preparation method and application, belonging to the technical field of organic porous materials. Background technique

[0002] In the development history of nearly a hundred years, porous materials have gone through the process from natural porous materials to synthetic porous materials, from inorganic porous materials to inorganic-organic hybrid porous materials to organic porous materials. Porous organic polymers are a kind of polymer porous materials with large specific surface area composed of carbon, hydrogen, oxygen, nitrogen, phosphorus, sulfur and other elements. While having a high specific surface area, organic small molecules are covalently Bond connection construction endows porous organic polymers with the advantages of light weight, good thermochemical stability, strong structural design and various synthesis methods, making porous organic polymers a poro...

Examples

Embodiment 1

[0058] A kind of triaryl boron conjugated polymer porous material P 1 The synthetic route and steps of -Th are as follows:

[0059]

[0060] Join BBr first 3 (0.424g, 1.69mmol) in a 100-mL Schlenk tube, followed by 10mL of dichlorobenzene, the compound 2,5-bis(trimethyltin-based)thiophene (1.03g, 2.51mmol) was dissolved in dichloro Benzene was added dropwise slowly. At this time, a large number of yellow precipitates were formed, and the stirring was increased, and the total amount of solvent was added to 30 mL. The Schlenk tube was transferred to an oil bath, and the branch port was protected with nitrogen at 180 ° C for 3 days. After the reaction time is over, transfer the Schlenk tube to the glove box after cooling. The solid was repeatedly washed with dichloromethane in a glove box and filtered through a sand core funnel. Finally, the solid was transferred to a vial and extracted under vacuum for 4 hours to obtain 240.0 mg of a yellow solid. 11 B MAS SSNMR(400MHz)δ...

Embodiment 2

[0062] A kind of triaryl boron conjugated polymer porous material P 2 The synthetic route and steps of -Th are as follows:

[0063]

[0064] Compound P 2 The synthetic method of -Th is the same as that of compound P 1 -Th (Example 1). Feed: BBr 3 (0.371g, 1.48mmol), compound 2,5-bis(tri-n-butyltinyl)thiophene (1.47g, 2.22mmol), finally obtained 204.0mg of yellow solid. 11 B MAS SSNMR(400MHz)δ (iso) 46.1ppm; BET area: 648.7 m 2 / g; its infrared spectrum is as figure 2 shown.

Embodiment 3

[0066] A kind of triaryl boron conjugated polymer porous material P 1 -Th 2 The synthetic route and steps are as follows:

[0067]

[0068] Compound P 1 -Th 2 The synthetic method is with embodiment 1. Feed: BBr 3 (0.374g, 1.49mmol), the compound 5,5'-bis(trimethyltin-yl)-2,2'-bithiophene (1.01g, 2.05mmol), finally obtained 369.6 mg of orange-red solid. 11 BMAS SSNMR(400MHz)δ (iso) 43.6ppm; BET area: 164.6m 2 / g; its infrared spectrum is as follows image 3 shown.

technical field

[0001] The invention relates to a triaryl boron conjugated polymer porous material and its preparation method and application, belonging to the technical field of organic porous materials. Background technique

[0002] In the development history of nearly a hundred years, porous materials have gone through the process from natural porous materials to synthetic porous materials, from inorganic porous materials to inorganic-organic hybrid porous materials to organic porous materials. Porous organic polymers are a kind of polymer porous materials with large specific surface area composed of carbon, hydrogen, oxygen, nitrogen, phosphorus, sulfur and other elements. While having a high specific surface area, organic small molecules are covalently Bond connection construction endows porous organic polymers with the advantages of light weight, good thermochemical stability, strong structural design and various synthesis methods, making porous organic polymers a poro...

Examples

Embodiment 1

[0058] A kind of triaryl boron conjugated polymer porous material P 1 The synthetic route and steps of -Th are as follows:

[0059]

[0060] Join BBr first 3 (0.424g, 1.69mmol) in a 100-mL Schlenk tube, followed by 10mL of dichlorobenzene, the compound 2,5-bis(trimethyltin-based)thiophene (1.03g, 2.51mmol) was dissolved in dichloro Benzene was added dropwise slowly. At this time, a large number of yellow precipitates were formed, and the stirring was increased, and the total amount of solvent was added to 30 mL. The Schlenk tube was transferred to an oil bath, and the branch port was protected with nitrogen at 180 ° C for 3 days. After the reaction time is over, transfer the Schlenk tube to the glove box after cooling. The solid was repeatedly washed with dichloromethane in a glove box and filtered through a sand core funnel. Finally, the solid was transferred to a vial and extracted under vacuum for 4 hours to obtain 240.0 mg of a yellow solid. 11 B MAS SSNMR(400MHz)δ...

Embodiment 2

[0062] A kind of triaryl boron conjugated polymer porous material P 2 The synthetic route and steps of -Th are as follows:

[0063]

[0064] Compound P 2 The synthetic method of -Th is the same as that of compound P 1 -Th (Example 1). Feed: BBr 3 (0.371g, 1.48mmol), compound 2,5-bis(tri-n-butyltinyl)thiophene (1.47g, 2.22mmol), finally obtained 204.0mg of yellow solid. 11 B MAS SSNMR(400MHz)δ (iso) 46.1ppm; BET area: 648.7 m 2 / g; its infrared spectrum is as figure 2 shown.

Embodiment 3

[0066] A kind of triaryl boron conjugated polymer porous material P 1 -Th 2 The synthetic route and steps are as follows:

[0067]

[0068] Compound P 1 -Th 2 The synthetic method is with embodiment 1. Feed: BBr 3 (0.374g, 1.49mmol), the compound 5,5'-bis(trimethyltin-yl)-2,2'-bithiophene (1.01g, 2.05mmol), finally obtained 369.6 mg of orange-red solid. 11 BMAS SSNMR(400MHz)δ (iso) 43.6ppm; BET area: 164.6m 2 / g; its infrared spectrum is as follows image 3 shown.

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