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S-triazine derivative, and preparation method and application thereof

A technology of s-triazine and its derivatives, which is applied in the direction of chemical instruments and methods, instruments, analytical materials, etc., and can solve the problems such as the decrease of fluorescence intensity

Inactive Publication Date: 2014-07-16
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in this comb-like monolayer, the fluorophores are all located at the ends of the flexible graft chains, and the fluorophores are easy to stack up from side to side π-π, resulting in fluorescence self-quenching and a decrease in fluorescence intensity.

Method used

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  • S-triazine derivative, and preparation method and application thereof
  • S-triazine derivative, and preparation method and application thereof
  • S-triazine derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation method of s-triazine derivative (compound II):

[0029] (1) Synthesis of 4-(N-ethyl-N-hydroxyethyl)aminobenzaldehyde (I)

[0030] In a round bottom flask, weigh 0.5 g p-fluorobenzaldehyde and 0.72 g 2-(ethylamino)ethanol, 0.005 g CTAB, 5 g K 2 CO 3 , dissolved in 50ml DMSO, and magnetically stirred in an oil bath at 95°C for 24h. The mixture was then poured into 100ml of distilled water, extracted twice with 50ml of dichloromethane, the organic layers were combined and dried over anhydrous magnesium sulfate, the solvent was removed with a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (ethyl acetate Esters: Petroleum ether = 1:10) to obtain compound (I) in the form of yellow oil.

[0031] 1 H NMR (CDCl3, 400MHz): δ(ppm) 1.18(t, 3H, J=6.8Hz), 3.54(t, 2H, J=5.6Hz), 3.51-3.46(m, 2H, J=7.2Hz), 3.81(t,2H,J=5.6Hz),4.28(t,1H),6.71(d,2H,J=8.4Hz),7.62(d,2H,J=8.4Hz),9.60(s,1H). Calcd for C 11 h 15 NO 2 :C,68....

Embodiment 2

[0036] (1) Synthesis of 4-(N-ethyl-N-hydroxyethyl)aminobenzaldehyde (I)

[0037] In a round bottom flask, weigh 0.2g of p-fluorobenzaldehyde and 0.6g of 2-(ethylamino)ethanol, CTAB0.01g, K 2 CO 3 3g, dissolved in 30ml DMSO, stirred magnetically in an oil bath at 80°C for 30h. Then the mixture was poured into 90ml of distilled water, extracted three times with 60ml of dichloromethane, the organic layers were combined and dried over anhydrous magnesium sulfate, the solvent was removed with a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (ethyl acetate : Petroleum ether=1:5) to obtain yellow oily compound (I).

[0038] (2) Synthesis of 2,4,6-tris[4-(N-ethyl-N-2-hydroxyethyl)styryl]-s-triazine (II)

[0039] In a round bottom flask, 0.1 g of 2,4,6-trimethyl-s-triazine and 0.1 g of KOH were added to 10 ml of ethanol. After stirring at 80° C. for 30 min, 5 ml of ethanol solution of Compound I with a concentration of 0.05 g / ml was sl...

Embodiment 3

[0041] (1) Synthesis of 4-(N-ethyl-N-hydroxyethyl)aminobenzaldehyde (I)

[0042] In a round bottom flask, weigh 1 g of p-fluorobenzaldehyde and 2 g of 2-(ethylamino)ethanol, CTAB 0.02 g, K 2 CO 3 10g, dissolved in 100ml DMSO, and magnetically stirred in an oil bath at 110°C for 30h. Then the mixture was poured into 100ml of distilled water, extracted twice with 100ml of dichloromethane, the organic layers were combined and dried over anhydrous magnesium sulfate, the solvent was removed with a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (ethyl acetate Esters: Petroleum ether = 1:8) to obtain compound (I) in the form of yellow oil.

[0043] (2) Synthesis of 2,4,6-tris[4-(N-ethyl-N-2-hydroxyethyl)styryl]-s-triazine (II)

[0044] In a round bottom flask, 0.5 g of 2,4,6-trimethyl-s-triazine and 1.0 g of KOH were added to 40 ml of ethanol. After stirring at 110° C. for 30 minutes, slowly add 60 ml of an ethanol solution of Compou...

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Abstract

The invention relates to an s-triazine derivative, and a preparation method and application thereof. The structural formula of the derivative is as shown in the specification. The preparation method comprises the following steps: weighing p-fluorobenzaldehyde, 2-(ethylamino)ethanol, cetyl trimethyl ammonium bromide (CTAB) and K2CO3, dissolving in dimethylsulfoxide (DMSO), stirring for 15-30 hours at 80-120 DEG C, and separating to obtain a compound I; and adding 2,4,6-trimethyl s-triazine and KOH into a solvent, stirring for 30 minutes at 60-110 DEG C, dripping an ethanol solution of the compound I, continuously reacting for 15-30 hours at 60-110 DEG C, and separating to obtain the s-triazine derivative. The s-triazine derivative can be grafted on the surface of a glass sheet in a flat-lying manner to form a monomolecular film fluorescence sensor for DNT (dinitrotoluene) detection. Due to the flat-lying grafting manner, the probability of pi-pi stacking formed between fluorescent molecules can be greatly reduced, and the optical property and response sensitivity of fluorescent molecules can be improved.

Description

technical field [0001] The invention relates to a s-triazine derivative, in particular to a s-triazine derivative and a preparation method and application thereof, and belongs to the technical field of compound synthesis and fluorescent sensing materials. Background technique [0002] Nitroaromatic compounds (NACs), such as 2,4,6-trinitrotoluene (TNT), 2,4-dinitrotoluene (DNT), etc., are the main components of various explosives. Realizing the rapid and sensitive detection of p-nitroaromatics is of great significance to the safety inspection of public places, industrial process control, environmental monitoring and so on. At present, X-ray diffractometers and ion mobility spectrometers are mostly used in railway stations and airports. However, these detectors are expensive and bulky, and it is not convenient to prepare portable detectors for on-site real-time detection. [0003] In recent years, fluorescence sensors have shown the advantages of high sensitivity, simple ope...

Claims

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Application Information

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IPC IPC(8): C07D251/24C09K11/06G01N21/64
CPCC07D251/24C09K11/06C09K2211/1059G01N21/643G01N2021/6432
Inventor 崔月芝王栋号王爱清石强李俊英陶芙蓉李天铎
Owner QILU UNIV OF TECH
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