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Benzo [5]helicene-based conjugated polymer, as well as preparation method and application thereof

A conjugated polymer and helicene technology, applied in the field of polymer materials, can solve the problems of sensitivity and selectivity to be improved, and achieve the effect of strengthening charge transfer and electrostatic interaction, enhancing sensitivity, and high sensitivity

Inactive Publication Date: 2017-06-27
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, although significant progress has been made in the detection of nitroaromatic explosives based on conjugated polymers, the sensitivity and selectivity still need to be improved

Method used

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  • Benzo [5]helicene-based conjugated polymer, as well as preparation method and application thereof
  • Benzo [5]helicene-based conjugated polymer, as well as preparation method and application thereof
  • Benzo [5]helicene-based conjugated polymer, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Embodiment 1: the synthesis of monomer

[0098] The reaction steps are as follows:

[0099]

[0100] Step A: Preparation of compound 2

[0101] Add 2,15-dimethoxybenzo[5]helicene (388mg, 1mmol) in a 100mL round bottom flask, add 30mL dry dichloromethane to dissolve 2,15-dimethoxybenzo[5] Helicene dissolved, measure BBr 3 (0.94mL, 10mmol) was dissolved in 10mL of dry dichloromethane and added dropwise to a round bottom flask under ice-cooling over 8h. After the reaction was completed, 30 mL of ice water was added to the round bottom flask to quench the reaction, and the organic phase was extracted with 50 mL of ethyl acetate, and the organic phase was washed with anhydrous MgSO 4 Dry, filter, and spin-dry to obtain a green crude product powder. The obtained product is dissolved in 15 mL of dry DMF, and 1-bromododecane (525 mg, 2.1 mmol) and K 2 CO 3 (552mg, 4mmol), heated to 100°C under the protection of argon, and stirred for 12h. After the reaction was complet...

Embodiment 2

[0121] Example 2: Synthesis of Conjugated Polymer P1 and Its Detection of Nitroaromatic Explosives

[0122] 1) The synthesis method of P1 is as follows:

[0123]

[0124] Under argon protection, weigh compound 3 (77mg, 0.09mmol), compound 4 (67mg, 0.09mmol), Pd(PPh 3 ) 4 (3.2mg, 0.006mmol) and CuI (0.86mg, 0.016mmol) were placed in a 25mL Schlenk bottle, 5mL of dry triethylamine was added as a solvent, and reacted at 90°C for 3 days in an argon atmosphere. After the reaction was completed, it was cooled to room temperature, and 50 mL each of chloroform and water were added to the reaction liquid. The organic phase was separated, and the organic phase was washed with anhydrous MgSO 4 After drying the solvent was removed to give the crude product. The crude product was redissolved in chloroform (3 mL), added methanol (60 mL) for precipitation, and suction filtered to obtain orange-red powder P1 (95 mg), with a yield of 72%.

[0125] The structure detection result of this...

Embodiment 3

[0140] Example 3: Synthesis of conjugated polymer P2 and its detection of nitroaromatic explosives

[0141] 1) The synthesis method of P2 is as follows:

[0142]

[0143] Under the protection of argon, compound 3 (200mg, 0.23mmol) was weighed in a 25mL Schlenk bottle, and dissolved in a mixed solution of 3.9mL dry toluene and 1.3mL DMF. After flowing argon for 20 minutes, add Ni(COD) 2 (191mg, 0.74mmol), COD (81mg, 0.74mmol) and 2,2'-bipyridine (108mg, 0.74mmol), stirred at 90°C for 5 days in an argon atmosphere. After the reaction, the reaction solution was cooled to room temperature, and 50 mL each of chloroform and water were added to the reaction solution. The organic phase was separated, and the organic phase was washed with anhydrous MgSO 4 After drying the solvent was removed to give the crude product. The crude product was re-dissolved in chloroform (3 mL), added methanol (60 mL) for precipitation, and filtered with suction to obtain pale yellow P2 (110 mg) with...

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Abstract

The invention relates to a benzo[5]helicene-based conjugated polymer as well as a preparation method and application thereof. The polymer has a structure as shown in a formula I, wherein R is independently selected from substituted or unsubstituted linear or branched alkyl having a carbon number of 1-20; Ar is independently selected from -aryl-, -heteroaryl-, -acetenyl-aryl-acetenyl- and -acetenyl-heteroaryl-acetenyl-, and the aryl and heteroaryl can be randomly substituted by a substituent group; n is the number of repetitive units of the polymer, and is more than or equal to 3. The polymer can be used for detecting nitro aromatic explosives, and optimally used for detecting the nitro aromatic explosives in a liquid phase or a gaseous phase.

Description

technical field [0001] The invention belongs to the field of polymer materials, and in particular relates to a class of conjugated polymers based on benzo[5]helicene, a preparation method thereof and an application in the detection of nitroaromatic explosives. Background technique [0002] Nitroaromatic compounds are an important class of explosives. However, due to the threat of terrorism and the toxicity of their residues in the environment, the detection of such explosives has received widespread attention. In recent years, a variety of technical means for the detection of nitroaromatic explosives have been developed, such as: mass spectrometry, surface-enhanced Raman spectroscopy, ion mobility spectrometry, electron capture analysis, electrochemical methods, fluorescence methods, chemiluminescence methods, etc. Compared with other methods, the fluorescence method is favored by researchers due to its high sensitivity, good selectivity, simple requirements for instruments,...

Claims

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Application Information

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IPC IPC(8): C08G61/02C08G61/10G01N21/64
CPCC08G61/02C08G61/10C08G2261/11C08G2261/12C08G2261/314C08G2261/342G01N21/64
Inventor 陈传峰周丽丽李猛吕海燕
Owner INST OF CHEM CHINESE ACAD OF SCI
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