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

A technology of fluorescent molecular probe and molecular structure, which is applied in the field of application of the fluorescent molecular probe in the identification and detection of transition metal and heavy metal ions, and achieves the effects of good selective fluorescence enhanced recognition and good selectivity

Inactive Publication Date: 2009-05-13
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 solution and can achieve fluorescence-enhanced recognition is still a challenging research work.

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

Embodiment 1

[0029]

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

[0031] The above-mentioned intermediate P-1-1130mg (0.262mmol), monoethanolamine 8mg (0.13mmol) was added to 50ml of acetonitrile solvent, N 2 Protection, heated to reflux for about 7h, 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% (70mg). 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, 4H), 2.98(br, 6H), 2.75(br, 4H ), 1.70(m, 4H), 1.44(m, 4H), 0.97(t, J=6...

Embodiment 2

[0033]

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

[0035] Add P-2-1203mg (0.398mmol) and monoethanolamine 11mg (0.18mmol) to 30ml of acetonitrile solvent, N 2 Protection, heated to reflux for about 6h, 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, 4H), 7.38(d, J=7.2Hz, 2H), 7.30(d, J=10.8Hz, 2H), 7.20(d, J=8.4Hz, 2H), 4.4...

Embodiment 3

[0038]

[0039] Add 380 mg (1.126 mmol) of N-butyl-4-piperazinyl-1,8-naphthalimide and 200 mg (1.136 mmol) of 2,6-dichloromethylpyridine into 50 ml of acetonitrile solvent, N 2 Protection, heated to reflux for about 7h, 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% (290mg).

[0040] Take the above-mentioned intermediate P-3-1172mg (0.360mmol), monoethanolamine 10mg (0.164mmol) and add it to 30ml of acetonitrile solvent, N 2 Protection, heated to reflux for about 6h, 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, 2H), 8.40(d, J=8.4Hz, 2H), 7.68(t, J=8.0, 2H), 7.63(...

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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 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 detected...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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