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Aggregation-induced luminescent organic fluorescent small-molecule material and application thereof in DNT and TNT gas fluorescence detection

An aggregation-induced luminescence, small molecule technology, applied in the field of fluorescence sensing, can solve the problems of low fluorescence efficiency and poor photostability

Active Publication Date: 2018-11-23
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most organic fluorescent small molecule materials have problems such as poor photostability and low fluorescence efficiency caused by aggregation, which limits the further application of such materials.

Method used

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  • Aggregation-induced luminescent organic fluorescent small-molecule material and application thereof in DNT and TNT gas fluorescence detection
  • Aggregation-induced luminescent organic fluorescent small-molecule material and application thereof in DNT and TNT gas fluorescence detection
  • Aggregation-induced luminescent organic fluorescent small-molecule material and application thereof in DNT and TNT gas fluorescence detection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the synthesis of compound BTT

[0041]

[0042] Synthesis of 4-N,N-diphenylamine-3,5-bis-(4-bromophenyl)-4H-1,2,4-triazole

[0043] Under the protection of argon, the monomer aminotriphenylamine (0.54g, 2mmol), 1,2-bis((4-bromophenyl)chloromethylene)hydrazine (0.87g , 2mmol) and 15mL of N,N-dimethylaniline, reacted at 135°C for 12h, then added 2M HCl (30mL) solution. After reacting again for 30 minutes, a large amount of precipitates were generated. After vacuum filtration, washing and drying, the crude reaction product was purified and separated by column chromatography with a mixed solvent of dichloromethane:ethyl acetate / 5:1 (volume ratio) as a developer. , a white solid 5 was obtained with a reaction yield of 67%.

[0044] 1 H NMR (500MHz, CDCl 3 ): δ8.20(d, 1H), 7.75(d, 1H), 7.57(d, 2H), 7.51(t, 1H), 7.43(d, 4H), 7.38(t, 1H). MALDI-TOF MS(mass m / z):620.00[M] + .

[0045] Synthesis of BTT

[0046] 622.45mg 4-N,N-diphenylamine-3,5-bis-(4-brom...

Embodiment 2

[0048] Embodiment 2: the synthesis of compound BPT:

[0049]

[0050] 9-9H-carbazole-3,5-bis-(4-bromophenyl)-4H-1,2,4-triazole

[0051] Under argon protection, the monomer 4-(9H-carbazole)aniline (0.52g, 2mmol), 1,2-bis((4-bromophenyl)chloromethylene ) hydrazine (0.87g, 2mmol) and 15mL N,N-dimethylaniline were reacted at 135°C for 12h, and then 2M HCl (30mL) solution was added. After reacting again for 30 minutes, a large amount of precipitates were generated. After vacuum filtration, washing and drying, the crude reaction product was purified and separated by column chromatography with a mixed solvent of dichloromethane:ethyl acetate / 5:1 (volume ratio) as a developer. , a white solid 5 was obtained with a reaction yield of 67%.

[0052] 1 H NMR (500MHz, CDCl 3 ; 25°C, TMS) δ=8.20(d, J=7.7Hz, 2H; Ar H), 7.75(d, J=8.5Hz, 2H; Ar H), 7.57(d, J=8.5Hz, 4H; Ar H), 7.51(t, J=7.7Hz, 2H; Ar H), 7.43(d, J=8.4Hz, 8H; Ar H), 7.38(t, J=7.4Hz, 2H; Ar H).MALDI- TOFMS(mass m / z):620.0...

Embodiment 3

[0056] Embodiment 3: the fluorescence emission spectrum of the BTT solution of normalized different water and tetrahydrofuran volume ratio

[0057] Prepare ten 50mL volumetric flasks, add 0.5mg BTT to them respectively, and then add water and tetrahydrofuran mixed solvent with the volume percentage of water increasing from 0 to 90% to 50mL. Take 3mL and add it to a quartz cuvette, and use a fluorescence spectrometer to record the fluorescence emission spectrum of the solution when the volume percentage of the configured water increases from 0 to 90%. We can see from the figure that as the proportion of water increases, the fluorescence intensity increases and the brightness increases. This phenomenon also demonstrates the AIE property of our material.

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Abstract

The invention provides an aggregation-induced luminescent organic fluorescent small-molecule material and application thereof in DNT and TNT gas fluorescence detection and belongs to the technical field of fluorescent sensing. The invention particularly relates to an AIE type fluorescent sensing material which takes 3,4,5-triphenyl-4H-1,2,4-triazole as a structural center and is connected with tetraphenyl ethylene, triphenylamine or carbazole. The material shows weak fluorescence in a dilute solution and shows strong fluorescence in an aggregation process or a solid state. As a core construction unit of the fluorescent molecule, the tetraphenyl ethylene enables the material to have AIE properties, and a benzene ring capable of freely rotating has a promoting effect on constructing a film with a porous structure. The fluorescent material can not only form the film with the porous structure and but also form Pi-Pi stacking with NACS explosives, thereby ensuring that the fluorescent material not only has extremely high selectivity and sensitivity for DNT and TNT detection but also has fast response.

Description

technical field [0001] The invention belongs to the technical field of fluorescent sensing, in particular to an aggregation-induced emission (AIE) organic fluorescent small molecule material and its reaction in 2,4-dinitrotoluene (DNT) and 2,4,6-trinitrotoluene ( TNT) in the application of gas fluorescence detection, so as to be used in the detection of explosives. Background technique [0002] People pay attention to nitroaromatic compounds (NACs) not only because of the grim situation of anti-terrorism at home and abroad, but also because of the increasing threat of NACs to the environment and human health. Therefore, the development of new and efficient NACs explosion sensing materials has become an important topic. [0003] At present, the common NACs detection techniques mainly include surface-enhanced Raman spectroscopy (SERS), plasma desorption mass spectrometry (PDMS), ion mobility spectrometry (IMS), electrochemical voltammetry, gas chromatography-mass spectrometry...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D249/08C07D403/10G01N21/64
CPCC07D249/08C07D403/10C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1059G01N21/643G01N2021/6432
Inventor 张明张曌霞李峰
Owner JILIN UNIV
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