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Organic Fluorescent Small Molecule Thin Film Materials and Their Applications in DNT and TNT Vapor Detection

A thin film material and small molecule technology, applied in the field of fluorescence sensing, can solve problems such as limited application, complicated operation, and long detection time, and achieve the effect of improving solubility

Active Publication Date: 2019-05-21
陕西金士盾防务技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, some technologies have begun to be applied to the trace detection of TNT and DNT: including surface-enhanced Raman detection technology, fluorescence detection technology, liquid chromatography detection technology, X-ray imaging detection technology, mass spectrometry detection technology, etc., but due to these The technology generally has shortcomings such as high cost, complicated operation, long detection time, and large-scale instruments, which limit its application in on-site detection

Method used

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  • Organic Fluorescent Small Molecule Thin Film Materials and Their Applications in DNT and TNT Vapor Detection
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  • Organic Fluorescent Small Molecule Thin Film Materials and Their Applications in DNT and TNT Vapor Detection

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the synthesis of compound TCA:

[0034]

[0035] Synthesis of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaboron)-9,9-dihexylfluorene

[0036] 4.77g of 2-bromo-9,9-dihexylfluorene, 4.40g of pinacol diboronate, and 3.4g of potassium acetate were dissolved in 50mL of 1,4-dioxane. Freeze with nitrogen for 8 minutes, then vacuumize for 5 minutes, add catalyst (1,1'-bis(diphenylphosphino)ferrocene)palladium dichloride) 282.4 mg, freeze and vacuum three times, remove oxygen, 80°C Under reflux for 24h. Transfer the solution to a separatory funnel and extract. Using a mixed solvent of dichloromethane and petroleum ether as an eluent, a white solid was obtained by column chromatography with a yield of 55%.

[0037] δ H (500MHz, CDCl 3 )7.83(1H,d,J=7.5),7.78-7.70(3H,m),7.38-7.31(3H,m),2.00(4H,pd,J=13.3,5.1),1.42(12H,s), 1.15-1.01 (12H, m), 0.78 (6H, t, J = 7.2), 0.60 (4H, dt, J = 18.5, 6.6).

[0038] Synthesis of 9,10-bis(9,9-dihexyl)fluorenylanthracene (TCA)

[003...

Embodiment 2

[0041] Embodiment 2: the preparation of spin coating film

[0042] Prepare a TCA solution with a concentration of 0.5mg / mL, the solvent is tetrahydrofuran, the speed of the homogenizer is 1500r / min, and the homogenization time is 30s. Finally, the film is vacuum-dried for 10min. The thickness of the film obtained on the substrate is 8nm. The substrate is ITO (Indium tin oxide) glass electrode, ITO needs to be ultrasonicated for 10 minutes with water, ethanol, acetone, toluene and other solvents before use, so as to remove surface impurities.

Embodiment 3

[0043] Embodiment 3: TCA film detects various explosive gases

[0044] Put the explosive powder in the cuvette respectively: 2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene (DNT), trimethyltrinitroamine (RDX), three Nitrobenzyl nitramine (Tetryl), cyclotetramethylene tetranitramine (HMX) and pentaerythritol tetranitrate (PETN), the powder covers the bottom of the cuvette, and after sealing for 60 minutes, quickly put it into Example 2 to prepare The obtained TCA thin film, fluorescence spectrometer records the fluorescence quenching rate (1-I / I) of thin film in different explosive vapors in 30 seconds 0 )(I 0 : the initial fluorescence intensity of the film; I: the intensity of the film after it is quenched by the vapor of the explosive) (such as figure 1 ).

[0045] We further prolong the exposure time of TCA film in TNT and DNT vapor. The TCA film is exposed to DNT vapor for 30 seconds, and the fluorescence quenching rate is nearly 90%, but the TCA film has only 13% quen...

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Abstract

The invention provides organic fluorescent micromolecule thin-film materials and application thereof in DNT and TNT vapor detection, and belongs to the technical field of fluorescence sensing. Central cores of organic fluorescent micromolecule thin-film material molecules have relatively high steric hindrance, so that accumulation among the molecules is reduced; furthermore, the central cores have relatively high luminous efficiency, and the high luminescence property of a thin film is ensured. The thin-film material molecules with a rigid main chain and relatively high conjugation degree are beneficial to formation of high-permeability thin-films, and are beneficial to diffusion of DNT and TNT vapor and charge transfer because of relatively high electron donating ability; the periphery of the main chain is connected with an alkyl chain (or an alkoxy chain and an oxygroup chain, so that such a structure is capable of improving the dissolubility of the molecules, and furthermore is beneficial to formation of the uniform thin film; the fluorescent thin-film materials have the advantages of low detection cost, high flexibility, good repeatability and short detection time.

Description

technical field [0001] The invention belongs to the technical field of fluorescent sensing, and specifically relates to a class of organic fluorescent small molecule film materials and their application in the detection of DNT and TNT nitro explosive vapors. The fluorescent film materials have the advantages of low detection cost, high sensitivity and repeatability It has the advantages of good performance and short detection time. Background technique [0002] 2,4,6-Trinitrotoluene (TNT) and 2,4-Dinitrotoluene (DNT) are currently the most widely used explosives in the world, and their environmental pollution and public safety hazards have brought human beings Huge harm, so TNT and DNT trace detection has been highly valued by people. At present, some technologies have begun to be applied to the trace detection of TNT and DNT: including surface-enhanced Raman detection technology, fluorescence detection technology, liquid chromatography detection technology, X-ray imaging d...

Claims

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Application Information

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IPC IPC(8): C07C1/32C07C13/567C09K9/02G01N21/64
CPCC07C1/321C07C13/567C09K9/02G01N21/643G01N2021/6432
Inventor 张明李峰马洪伟
Owner 陕西金士盾防务技术有限公司