Benzene Derivative Metal Ion Fluorescent Probe and Its Application

A technology of metal ions and fluorescent probes, applied in the field of biochemistry, can solve problems such as changes in spectral performance, complex synthesis, and difficulty in ensuring the accuracy of detection results, and achieve good application prospects, good selectivity, and high sensitivity.

Inactive Publication Date: 2011-12-21
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of fluorescent molecular probes to detect metal ions such as zinc, copper, iron, and mercury has been reported in the literature. There are many types of fluorescent molecular probes, but many organic fluorescent molecular probe compounds are often affected by protons, resulting in a change in the spectral performance of the response. changes, it is difficult to ensure the accuracy of test results
The synthesis of existing metal ion fluorescent probes is relatively complicated, and the synthesis yield of some probe molecules is low

Method used

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  • Benzene Derivative Metal Ion Fluorescent Probe and Its Application
  • Benzene Derivative Metal Ion Fluorescent Probe and Its Application
  • Benzene Derivative Metal Ion Fluorescent Probe and Its Application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In the general formula, R 3 is pyridyl, R 1 , R 2 , R 4 , R 5 Fluorescent probes for phenyl groups A

[0030] Its synthesis steps: Dissolve 630.8 mg of 1,3-diphenylacetone in 6 mL of ethanol, and then add 634.9 mg of diphenyl ketone. After all dissolved, 187.7 mg of KOH solid was added, refluxed for 5 min, cooled and placed in the refrigerator for 5 h, filtered with suction, washed with ethanol to obtain 987.5 mg of black purple solid with a yield of 86.18%, and dried.

[0031] Reaction intermediates are characterized as follows:

[0032] Yield 86%. 1 H-NMR: δ H (400 MHz; CDCl 3 ; ppm) 7.27 (m, 4H), 7.19 (m, 8H), 6.94 (m, 8H). 13 C-NMR: δ C (100 MHz, CDCl 3 ): 200.35, 154.48, 133.06, 130.75, 129.34, 128.51, 128.04, 127.99, 127.47, 125.31.

[0033]Under the protection of argon, 768.9 mg of the above product was dissolved in 6 mL of o-xylene, pumped three times, added 0.24 mL of 2-alkynylpyridine, heated to 150 °C, and refluxed for 15 h. Natural cooling, r...

Embodiment 2

[0037] In the general formula, R 3 is the anilino group, R 1 , R 2 , R 4 , R 5 Fluorescent probes for phenyl groups B

[0038] Using 2-alkynylaniline instead of 2-alkynylpyridine, the synthesis steps and conditions are the same as in Example 1.

[0039] Final Product Fluorescent Probes B :

[0040] Yield 71.31%. 1 H NMR (400 MHz, CDCl 3 , ppm): 3.72 (s, 2H), 6.50 (d, 2H), 6.52 (q, 2H), 6.77-7.18 (m, 20H), 7.57 (s, 1H). 13 C NMR (400 MHz, CDCl 3 , ppm): 114.44(2C), 125.23, 125.43, 125.50, 126.17, 126.57(2C), 126.88(2C), 126.95(2C), 127.56(2C), 129.98(2C), 130.513(2C), 203.1 (2C), 131.59(4C), 131.96, 138.06, 139.09, 140.11, 140.33, 140.53, 140.64, 140.70, 141.68, 141.87, 144.67. ESI-MS: m / z = 474.2218. [M + H] + .

Embodiment 3

[0041] Embodiment 3 Application of derivative fluorescent probe of the present invention

[0042] fluorescent probe A Shows high sensitivity for iron and copper ions, such as figure 1 , 2 shown; B Respectively show high selectivity for iron ion and copper ion, such as Figure 9 , 10 shown. The above experiments also investigated the effects of complex anions, interfering ions and other factors. Figure 7 , 8 and 12 and 13, it can be seen that anion and interference ion are to the fluorescent probe of the present invention A , B It has no effect on the identification of iron ions and copper ions, and has good selectivity and sensitivity. It will be applied to the identification and detection of metal ions in biological tissues and environmental sewage, and has a good application prospect.

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Abstract

The invention discloses a novel compound for metal ion fluorescent identification, particularly relates to a benzene derivative metal ion fluorescent probe and use thereof, and belongs to the field of biochemistry. The general structural formula of the fluorescent molecular probe is shown in the specification, wherein R1, R2, R3, R4 and R5 in the general formula represent aromatic groups such as phenyl, pyridyl, quinolyl, naphthyridine, pyrryl, phenylamino and the like; and R1, R2, R3, R4 and R5 cannot all be phenyl. The fluorescent ion probe can identify metal ions such as copper ions and iron ions with high sensitivity; the selectivity and sensitivity of the probe are high; and when used in identification and detection of metal ions in a biological sample or environments, the probe has a bright prospect.

Description

technical field [0001] The invention relates to a class of novel compounds that can be used for metal ion fluorescence recognition, in particular to a benzene derivative metal ion fluorescence probe and its application, belonging to the field of biochemistry. Background technique [0002] Metal ions are closely related to medicine, life science and environmental science, and are of great significance to the identification, detection and qualitative analysis of metal ions. Especially for individual transition metal and heavy metal ions, it is difficult to obtain satisfactory results with conventional analysis methods. The use of fluorescent molecular probes to detect metal ions has the characteristics of real-time detection, low detection threshold, high sensitivity and easy operation, and is a very effective method. Transition metals and heavy metals widely exist in various living organisms and play an important role in life activities. Some transition metals in the living ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D213/16C07D213/127C07C211/45C07C209/68G01N21/64
Inventor 于明明李占先魏柳荷张利锋赵万莹王丽娜
Owner ZHENGZHOU UNIV
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