Fluorescent molecular probe and use for inspecting transient metal and heavy metal ion

A fluorescent molecular probe and molecular structure technology, applied in the application field of the fluorescent molecular probe in the identification and detection of transition metal and heavy metal ions, to achieve the effect of good selective fluorescence enhanced recognition and good selectivity

Inactive Publication Date: 2007-01-17
QIQIHAR UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Designing and synthesizing fluorescent molecular probes that are selective in aqueous s

Method used

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  • Fluorescent molecular probe and use for inspecting transient metal and heavy metal ion
  • Fluorescent molecular probe and use for inspecting transient metal and heavy metal ion
  • Fluorescent molecular probe and use for inspecting transient metal and heavy metal ion

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0028] Example 1

[0029]

[0030] 180 mg (0.385 mmol) of N-butyl-4-(2-(2-hydroxyethylamino)ethylamino)-1,8-naphthalimide, 70 mg (0.40 mmol) of 2,6-dichloromethylpyridine Dissolve in 50ml of acetonitrile and reflux for about 8h. The solvent was evaporated. The intermediate (P-1-1) was isolated as a dark yellow viscous liquid by silica gel column chromatography, and the yield was 69% (130 mg).

[0031] The above intermediate P-1-1130mg (0.262mmol), monoethanolamine 8mg (0.13mmol) was added to 50ml acetonitrile solvent, N 2 protection, heated to reflux for about 7h, and cooled to room temperature. After the reaction solution was spin-dried, it was separated by silica gel column chromatography to obtain a dark yellow viscous liquid (P-1), yield: 55% (70 mg). 1 H-NMR (400MHz, CDCl 3 )δ: 8.46(d, J=7.2Hz, 2H), 8.27(d, J=8.4Hz, 2H), 8.15(d, J=8.2Hz, 2H), 7.44(m, 4H), 6.95(m, 4H), 6.53 (br, 2H), 4.16 (t, J=7.6Hz, 4H), 3.6-3.8 (m, 14H), 3.20 (br, ...

Example Embodiment

[0032] Example 2

[0033]

[0034] N-hydroxyethoxyethyl-4-piperazinyl-1,8-naphthalimide 401 mg (1.09 mmol) and 229 mg (1.30 mmol) of 2,6-dichloromethylpyridine were added to 50 ml of acetonitrile solvent , N 2 protection, heated to reflux for about 6h, and cooled to room temperature. The reaction solution was spin-dried and separated by silica gel column chromatography to obtain a pale yellow solid (P-2-1). Melting point: 119.3-120.1°C, Yield: 53% (290 mg).

[0035] P-2-1203 mg (0.398 mmol) and 11 mg (0.18 mmol) of monoethanolamine were added to 30 ml of acetonitrile solvent, N 2 protection, heated to reflux for about 6h, and cooled to room temperature. After the reaction solution was spin-dried, it was separated by silica gel column chromatography to obtain a yellow solid (P-2). Melting point: 89.0-90.1°C, yield: 45% (80 mg).

[0036] 1 H-NMR (400MHz, CDCl 3 )δ: 8.57(d, J=7.2Hz, 2H), 8.50(d, J=8.4Hz, 2H), 8.40(d, J=8.4Hz, 2H), 7.66(m, ...

Example Embodiment

[0037] Example 3

[0038]

[0039] N-butyl-4-piperazinyl-1,8-naphthalimide 380mg (1.126mmol) and 2,6-dichloromethylpyridine 200mg (1.136mmol) were added to 50ml of acetonitrile solvent, N 2 protection, heated to reflux for about 7h, and cooled to room temperature. After the reaction solution was spin-dried, it was separated by silica gel column chromatography to obtain the intermediate as a yellow-green solid (P-3-1). Melting point: 147.0-147.8°C, yield: 58% (290 mg).

[0040] Take the above-mentioned intermediate P-3-1172 mg (0.360 mmol) and 10 mg (0.164 mmol) of monoethanolamine into 30 ml of acetonitrile solvent, N 2 protection, heated to reflux for about 6h, and cooled to room temperature. After the reaction solution was spin-dried, it was separated by silica gel column chromatography to obtain a golden yellow solid (P-3). Melting point: 85.8-86.9°C, yield: 60% (92 mg). 1 H-NMR (400MHz, CDCl 3 )δ: 8.57(d, J=7.2Hz, 2H), 8.50(d, J=8.0Hz...

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PUM

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Abstract

A fluorescent molecular probe and its use for inspecting transition metal and heavy metal ion are disclosed. It has better quenching and selective performances and can be used to inspect cobalt ion in cell, biological tissue, sewage water, water solution, emulsion and suspending system.

Description

technical field [0001] The invention relates to a fluorescent molecular probe, including its design and synthesis, and also relates to an application of the fluorescent molecular probe in the identification and detection of transition metal and heavy metal ions. Background technique [0002] Fluorescent molecular probe technology is applied to the detection of transition metals and heavy metal ions, which can realize in situ detection in microenvironment. However, usually the transition metal and heavy metal ions can quench the fluorescence of the fluorophore through spin-orbit coupling and electron or energy transfer, resulting in a decrease in detection sensitivity. In addition, the solvation tendency of the recognition groups of metal ions and fluorescent molecular probes in aqueous solution is stronger than that of organic solvents, which reduces the binding performance of fluorescent molecular probes and detected species. Therefore, many probe molecules can only be dete...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D403/14C07D413/14C07D213/36C07D221/06G01N21/64C09K11/00
Inventor 郭祥峰贾丽华李树亮王金玲
Owner QIQIHAR UNIVERSITY
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