Electro-polymeric organic fluorescent material and application of material in TNT detection

A fluorescent material and electropolymerization technology, applied in the field of fluorescent sensing, can solve problems such as material waste, and achieve the effect of clear structure, easy control, and stable mesh film

Inactive Publication Date: 2013-01-30
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Method used

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  • Electro-polymeric organic fluorescent material and application of material in TNT detection
  • Electro-polymeric organic fluorescent material and application of material in TNT detection
  • Electro-polymeric organic fluorescent material and application of material in TNT detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Embodiment 1: the synthesis of compound TCPC:

[0077]

[0078]

[0079] 2,7-Dibromofluorene

[0080] 6g (36mmol) of fluorene, 92mg (1.6mmol) of ferric chloride, and 4ml of liquid bromine were reacted in dichloromethane solvent for 12 hours in the dark. The resulting solid was filtered and recrystallized from ethanol to obtain a white solid product with a yield of 75%. 1 H NMR (500MHz, CDCl 3 ): δ7.66(s, 2H, Ar-H), δ7.60-7.59(d, 2H, Ar-H), δ7.51-7.49(d, 2H, Ar-H), δ3.87(s , 2H, Ar-H-Ar) Mass Spectrum (m / z) 323.9 Elemental Analysis: Calculated Value: C 13 h 8 Br 2 : C, 48.19; H, 2.49 Test value: C, 48.54; H, 2.51

[0081] 2,7-Dibromo-9-fluorenone

[0082] A methanol solution of 1.3g (4mmol) 2,7-dibromofluorene and 0.1ml tetrabutylhydroxylamine was vigorously stirred in a pyridine solvent, and oxygen was introduced at the same time. After a large amount of solid was produced, a large amount of water was injected, and a yellow solid product was obtained by fil...

Embodiment 2

[0095] Embodiment 2: the synthesis of compound OCPC:

[0096]

[0097] 9, 9, 9", 9"-bis(N-carbazol-hexyl)-9', 9', 9", 9"-biphenyl dibromofluorene

[0098] Take 2.0 grams of borofat, 3.12 grams of dibromine, 9 milliliters of anhydrous toluene, 219 milligrams of tetraphenylphosphopalladium, and 6 milligrams of sodium carbonate aqueous solution, and react at 90 degrees for two days. Petroleum ether dichloride (1:1) developing solvent column chromatography separation. Obtain product 2.18 grams, yield 61%

[0099] 1 H NMR (500MHz, CDCl3, 25°C, TMS): δ=8.04(d, J=7.6Hz, 8H; Ar-H), 7.70(m, 3H; Ar-H), 7.57(m, 5H; Ar -H), 7.45(m, 1H; Ar-H), 7.37(m, 10H; Ar-H), 7.24(m, 10H; Ar-H), 7.17(t, J=7.6Hz, 8H; Ar- H), 4.10(m, 8H; CH 2 ), 1.90(m, 8H; CH2), 1.63(m, 8H; CH 2 ), 1.07(m, 16H; CH 2 ), 0.60ppm (m, 8H; CH 2 ); 13C NMR (125MHz, CDCl 3 , 25°C, TMS): mass spectrum: 1406[M+]; elemental analysis theoretical value: C 98 h 93 BrN 4 : C, 83.67; H, 6.66; N, 3.98; test value: C, 83....

Embodiment 3

[0106] Embodiment 3: the preparation of electropolymerization film

[0107] The electropolymerization film was prepared by cyclic voltammetry, using tetra-n-butylammonium hexafluorophosphate TPAPF6 as the electrolyte, the concentration of TCPC or OCPC was 0.5mg / ml, and the mixed solution of dichloroacetonitrile (volume ratio 2:3) Accompanied by the dedoping process of each layer of electrochemically polymerized film. We chose 0.89 V as the upper limit of the scan range for cyclic voltammetry settings. In order to improve the dedoping performance of the electrochemically polymerized film, we set the lower limit of the cyclic voltammetry scanning range to be -0.9V, and then set the cyclic voltammetry scanning range to be -0.9V~0.89V. Set the scanning speed to 200mV / s, and the number of scanning cycles to 8.

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Abstract

The invention belongs to the fluorescent sensing technical field and specifically relates to a high-efficiency organic fluorescent material and application of the material in TNT (trinitrotoluene) detection. The structural formula of the high-efficiency organic fluorescent material provided by the invention is Ar2-Ar1-Ar-Ar1-Ar2, wherein Ar1-Ar-Ar1 forms a light-emitting unit; the light-emitting center Ar can be spirofluorene, benzene, carbazole (alkyl chains different in length can be connected at No.9 site) or fluorene (alkyl chains different in length can be connected at No.9 site); Ar1 can be fluorene, biphenyl or difluorene; and electric-active unit Ar2 can be furan, pyrrole, thiophene, carbazole, diphenylamine or triphenylamine. An electro-polymeric thin film formed from the material through electrochemical polymerization is characterized in that intermolecular aggregation in the electrochemical polymerization process can be effectively reduced, the fluorescence efficiency of the electro-polymeric thin film is improved, and the electro-polymeric thin film is capable of effectively transferring charges with TNT molecules to quench fluorescent light, and therefore, effective detection on TNT is realized.

Description

technical field [0001] The invention belongs to the technical field of fluorescence sensing, and in particular relates to a class of high-efficiency electropolymerized organic fluorescent materials and the application of the materials in detecting TNT. Background technique [0002] How to detect explosives has become a global problem. TNT (2,4,6-trinitrotoluene) was found in 21 compounds associated with explosives, the study found. Therefore, the detection of explosives mainly focuses on the detection of TNT. The current detection methods mainly include infrared absorption spectrometry, gas chromatography, mass spectrometry, ion mobility spectrometry and so on. However, these methods have certain limitations, such as relatively low detection limit, high false detection rate, poor stability, and complicated operation. [0003] Compared with other methods, the sensor method has great advantages in detecting nitro explosives such as TNT. The principle is to convert the "che...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/86C08G61/02C08G61/12G01N21/64C25D9/02
Inventor 张明聂赫然姚亮马洪伟吉长印
Owner JILIN UNIV
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