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Biimidazole derivatives modified modified by triphenylethylene and preparation and application of biimidazole derivatives

A technology of triphenylethylene and biimidazole, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of weak light emission and unfavorable application of fluorescent sensing materials, and achieve low preparation cost, low cost, The effect of convenience

Active Publication Date: 2019-06-14
NANJING UNIV OF INFORMATION SCI & TECH
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Problems solved by technology

At present, organic fluorescent materials emit weak light in the solid state or aggregated state, which is not conducive to the application of fluorescent sensing materials. The technical solution to this problem is to use aggregation-induced luminescence materials instead of the original traditional aggregation-causing quenching materials, but how to quickly and effectively The construction of low-cost fluorescent materials for quantitative testing of nitro-type explosives needs to be improved urgently. This technology has distinctive features and application prospects

Method used

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  • Biimidazole derivatives modified modified by triphenylethylene and preparation and application of biimidazole derivatives
  • Biimidazole derivatives modified modified by triphenylethylene and preparation and application of biimidazole derivatives
  • Biimidazole derivatives modified modified by triphenylethylene and preparation and application of biimidazole derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Weigh 0.10g (0.26mmol) of 5,5'-dibromo-1,1'-di-n-propyl-1H,1'H-2,2'-biimidazole, mix it with 10ml 1,4-di Put oxyhexane and 2ml of water into a 50mL flask for dissolution, then add 0.22g (0.58mmol) of 4,4,5,5-tetramethyl-2-(1,2- 2-triphenylethenyl)-1,3-dioxaborane, 0.22 g (0.66 mmol) of cesium carbonate and 30.7 mg (0.026 mmol) of catalyst tetrakis (triphenylphosphine) palladium, at 95° C. The reaction was stirred slowly under gas protection for 24 hours. 5,5'-dibromo-1,1'-di-n-propyl-1H,1'H-2,2'-biimidazole The molar ratio of 2-(1,2-2-triphenylethenyl)-1,3-dioxaborane to cesium carbonate was 10:20:25. When the reaction is over, 1 / 2 of the 1,4-dioxane in the flask is removed by a rotary evaporator, solids are precipitated, and a filter cake is obtained after filtration, using ethyl acetate / petroleum at a volume ratio of 10:1 Purified by ether column chromatography and further purified by recrystallization to obtain a yellow solid, namely 1,1'-di-n-propyl-5'5'-bis(1,2,2...

Embodiment 2

[0039] The preparation method is similar to Example 1, except that the alkyl chains are different. Weigh 0.16g (0.26mmol) of 5,5'-dibromo-1,1'-di-n-dodecyl-1H,1'H-2,2'-biimidazole, and 10ml 1,4-di Oxyhexane and 2ml of water were loaded into a 50mL flask, and 0.22g (0.58mmol) of 4,4,5,5-tetramethyl-2-(1,2-2-triphenyl Vinyl)-1,3-dioxaborane, 0.22g (0.66mmol) of cesium carbonate and 30.7mg (0.026mmol) of catalyst tetrakis (triphenylphosphine) palladium, under the protection of argon at 95°C, slowly stirred the reaction 24 hours, 5,5'-dibromo-1,1'-di-n-dodecyl-1H,1'H-2,2'-biimidazole, 4,4,5,5-tetramethyl-2- The molar ratio of (1,2-2-triphenylvinyl)-1,3-dioxaborane to cesium carbonate was 10:20:25. After the reaction is over, remove 1 / 2 of the organic solvent in the reaction system, filter, take the filter cake, use ethyl acetate / petroleum ether=10:1 column chromatography to purify and further recrystallize and purify to obtain a yellow solid, namely 1,1'-Di-n-dodecyl-5'5'-bis(1...

Embodiment 3

[0046] An application example of triphenylethylene-modified biimidazole derivatives as fluorescent probes for the detection of nitro explosives.

[0047] Step 1: Configure the density as 10 respectively -4 mol / L nitrobenzene THF solution, o-nitrotoluene THF solution, p-nitrotoluene THF solution, m-nitrotoluene THF solution, 2,6-dinitrotoluene THF solution and 2,4,6-trinitrotoluene THF solution 100 mL of phenol THF solution.

[0048] Step 2: Combine 1,1'-di-n-propyl-5'5'-bis(1,2,2-triphenylethenyl)-1H,1'H-2,2'-linked Imidazole was dissolved in anhydrous tetrahydrofuran to make 10 -4 mol / L solution (mother liquor), pipette 1.00mL mother liquor, and add 9.00mL distilled water to obtain a water content of 90% 1,1'-di-n-propyl-5'5'-bis(1,2 , 2-triphenylvinyl)-1H,1'H-2,2'-biimidazole in tetrahydrofuran. Similarly, the 1,1'-di-n-dodecyl-5'5'-bis(1,2,2-triphenylethenyl)-1H,1'H-2,2' in Example 2 - Biimidazole can also be made into 90% water content 1,1'-di-n-dodecyl-5'5'-bis(1,2,2...

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Abstract

The invention discloses a biimidazole derivatives modified modified by triphenylethylene and preparation and application of the biimidazole derivatives. The biimidazole derivatives is 1,1'-di-normal propyl-5,5'-double (1,2,2-triphenylethylene)-1H, 1'H-2,2'-biimidazole or 1,1'-bi-normal dodecyl-5,5'-double (1,2,2-triphenylethylene)-1H,1'H-2,2'-biimidazole. The biimidazole derivatives modified modified by the triphenylethylene is used as a fluorescent probe, and obvious fluorescence emission is achieved in a green-yellow light area (450-600 nm). A THF solution of the biimidazole derivatives modified modified by the triphenylethylene is transferred into a water solution, then, nitro class explosive is added, with the concentration increasing of the nitro class explosive, the fluorescent weakening degree of the fluorescent probe is enhanced, and the fluorescent strength is inversely proportional to the concentration of the nitro class explosive. A detection range of the biimidazole derivatives modified modified by the triphenylethylene for 2,4,6-trinitrophenol is from 0 to 10<-4>M, the detection range is wide, and the accuracy degree deviation is lower than + / -0.8%.

Description

technical field [0001] The invention relates to the technical field of biimidazole derivatives, in particular to a triphenylethylene-modified biimidazole derivative and its preparation and application. Background technique [0002] Monitoring and identification of nitro-type explosives has great scientific significance and engineering practice value, which is not only beneficial to anti-terrorism and explosion prevention, but also beneficial to the safety of land and water resources. In addition, nitroaromatic compounds are extremely harmful to human health and the natural environment, so it is particularly important to detect such toxic explosives accurately and quickly. Most of the traditional detection methods for nitro explosives rely on expensive and complex large-scale instruments, such as gas chromatography-mass spectrometry (GC-MS) or liquid chromatography-mass spectrometry (LC-MS). Although the effect is ideal, the detection process is expensive and complicated , c...

Claims

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Application Information

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IPC IPC(8): C07D233/58C09K11/06G01N21/64
Inventor 陶涛许家澍方昊
Owner NANJING UNIV OF INFORMATION SCI & TECH
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