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Derivative fluorescent probe based on diketopyrrolopyrrole and application thereof

A technology of diketopyrrolopyrrole and fluorescent probe, which is applied in the field of derivatives and its application in the detection of TNP, can solve the problems of long time required for the detection process, high dependence on analytical instruments, complicated preparation work, etc. Achieve the effect of wide detection linear range, sensitive detection effect and good selectivity

Active Publication Date: 2021-11-16
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these methods can realize the detection of TNP, there are generally some disadvantages: the instrument is bulky and highly dependent on the analytical instrument; the preparation work is complicated and time-consuming; It takes a long time, etc., which is not suitable for large-scale promotion and application
At present, researchers have developed some fluorescent probes for TNP detection, but these fluorescent probes are mostly polymers, which generally have low solubility in common solvents, poor photostability and complex synthetic routes In recent years, fluorescent probes have gradually developed into organic small molecule compounds.

Method used

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  • Derivative fluorescent probe based on diketopyrrolopyrrole and application thereof
  • Derivative fluorescent probe based on diketopyrrolopyrrole and application thereof
  • Derivative fluorescent probe based on diketopyrrolopyrrole and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] Add p-cyanobenzaldehyde (10 g, 76.5 mmol), ethylene glycol (5 mL, 90.5 mmol), p-toluenesulfonic acid (1.25 g, 6.5 mmol) to a round bottom flask containing 25 mL of toluene, and connect The water separator and the condenser tube are reacted at a temperature of 150°C for 2 to 3 hours, and water is removed in time during the reaction. After the reaction was completed, the reaction solution was cooled to room temperature, and 150 mL of saturated aqueous sodium bicarbonate solution was added to the reaction solution for extraction to remove p-toluenesulfonic acid. The organic phase was collected and dried over anhydrous sodium sulfate. Compound A was further refined by silica gel column chromatography, and the eluent was dichloromethane to obtain 11.02 g of compound A with a yield of 82.3%. 1 H-NMR (400MHz, CDCl3) δ: 7.71(d, 2H), 7.65(d, 2H), 5.82(s, 1H), 3.98-4.11(m, 4H). 13 CNMR (100MHz, CDCl3) δ: 142.7, 133.6, 127.3, 118.5, 112.3, 103.6, 65.6.

[0033]

...

Embodiment 2

[0042]

[0043] The synthesis steps of compound C-2 are similar to the synthesis steps of compound C-1 in Example 1, except that the n-bromobutane used in the synthesis of compound C-1 in Example 1 is replaced by bromoethane (2.778mmol ), the synthetic steps of the remaining compounds are the same as in Example 1, and the amount of each compound is also the same as that in Example 1. The NMR data of compound C-2 are as follows: 1 HNMR (400MHz, CDCl 3 )δ: 7.49(d,4H), 7.32(d,4H), 5.80(s,2H), 4.09-3.95(m,8H), 3.75(q,4H), 1.21(t,6H); 13 CNMR (100MHz, CDCl 3 )δ: 163.1, 143.8, 136.7, 135.9, 128.8, 127.5, 106.1, 104.7, 65.7, 38.6, 14.5.

[0044]

[0045] The preparation of compound D-2 was carried out with reference to Example 1, and the NMR data of compound D-2 are as follows: 1 HNMR (400MHz, CDCl 3 )δ: 9.76(s,2H), 7.84(d,4H), 7.58(d,4H), 3.68(q,4H), 1.21(t,6H); 13 CNMR (100MHz, CDCl 3 )δ: 191.4, 166.0, 144.7, 142.4, 135.6, 129.1, 127.6, 106.5, 39.1, 14.5.

[0046] ...

Embodiment 3

[0049]

[0050] The synthesis steps of compound C-3 are similar to the synthesis steps of compound C-1 in Example 1, except that the n-bromobutane used in the synthesis of compound C-1 in Example 1 is replaced by n-bromopropane (2.778mmol ), the synthetic steps of the remaining compounds are the same as in Example 1, and the amount of each compound is also the same as that in Example 1. The NMR data of compound C-3 are as follows: 1 HNMR (400MHz, CDCl 3)δ: 7.38(d,4H), 7.29(d,4H), 5.04(s,2H), 4.21-3.92(m,8H), 3.42(t,4H), 1.50(m,4H), 0.87(t ,6H); 13 CNMR (100MHz, CDCl 3 )δ: 163.1, 140.1, 139.5, 137.4, 129.7, 127.2, 108.1, 104.6, 66.1, 46.1, 21.5, 11.9.

[0051]

[0052] The preparation of compound D-3 was carried out with reference to Example 1, and the NMR data of compound D-3 are as follows: 1 HNMR (400MHz, CDCl 3 )δ: 9.61(s,2H), 7.66(d,4H), 7.41(d,4H), 3.39(t,4H), 1.51(m,4H), 0.77(t,6H); 13 CNMR (100MHz, CDCl 3 )δ: 191.2, 165.5, 144.0, 141.9, 135.7, 129.6, 125.9...

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Abstract

The invention discloses a derivative based on diketopyrrolopyrrole; and the structural formula of the derivative is as shown in formula I in the specification, wherein R is selected from -CH3, -(CH2)nCH3, -(CH2)mCH2X, -CH(CH3)2 and -CH2CH(CH3)2, n is an integer of 1-6, m is an integer of 1-6, and X is selected from F, Cl and Br. The derivative based on diketopyrrolopyrrole provided by the invention, as a TNP fluorescent probe, has relatively strong fluorescence intensity, good selectivity and wide detection linear range, and can realize identification and detection of TNP (2, 4, 6-trinitrophenol).

Description

technical field [0001] The invention belongs to the technical field of preparation of fluorescent detection functional materials, in particular to a diketopyrrolopyrrole-based derivative and its application in TNP (2,4,6-trinitrophenol) detection. Background technique [0002] Explosives are a class of extremely dangerous substances, especially explosive chemicals. In recent years, frequent terrorist attacks at home and abroad have seriously threatened the lives of the people. How to effectively identify and detect explosives has brought enormous pressure to public security agencies, border defense agencies, customs ports and other departments. [0003] TNP (2,4,6-trinitrophenol), also known as picric acid, is a common explosive dangerous chemical, often used as a high explosive, and its power is stronger than the common TNT explosive. In addition to being used as explosives, TNP is also widely used in pesticides, dyes, leather, rocket fuel and other fields. However, in th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D519/00C09K11/06G01N21/64
CPCC07D487/04C07D519/00C09K11/06G01N21/643C09K2211/1029C09K2211/1044C09K2211/1007G01N2021/6432G01N2021/6443
Inventor 王利民杜磊钱辉杨森何玉龙尹鑫鹏侯盈颖周雯琪孙昕瑜田禾韩建伟
Owner EAST CHINA UNIV OF SCI & TECH