Carbazole-contained benzimidazole-substituted quinoline derivative, preparation method and application thereof
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A technology of benzimidazole and derivatives, applied in the field of analytical chemistry, can solve the problems of low detection limit, probe selectivity interference, etc., and achieve the effect of fast detection process, strong complexation and accurate results
Active Publication Date: 2016-09-28
CHINA THREE GORGES UNIV
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However, many fluorescent probes have deficiencies, such as most of the probes are limited by Cd in terms of selectivity. 2+ interference
Therefore, the development of Zn with low cost, easy operation, good selectivity, high sensitivity, fast response and low detection limit 2+ The detection method is still a challenging task
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Embodiment 1
[0038] 3-(2-(8-(1H-Benzo[d]imidazol-2-yl)quinolin-2-yl)vinyl)-9-benzyl-9H-carbazole (zinc ion fluorescent probe)
[0039] Add 0.1g 2-methyl-8-(2-benzimidazolyl)quinoline, 0.17g 9-benzyl-9H-carbazole-3-carbaldehyde, 8mL n-butanol, 1.0mL piperpene Pyridine, 0.5mL glacial acetic acid, refluxed for 5h, cooled, a yellow solid precipitated out, and the solid filtered by suction was recrystallized with ethanol aqueous solution to obtain 0.61g of the product, yield: 75.1%. 1H NMR (400MHz, CDCl3): δ: 13.87(s, 1H), 9.10(d, J=7.1Hz, 1H), 8.41(s, 1H), 8.23-8.14(m, 2H), 7.90(s, 1H ),7.87-7.75(m,3H),7.72(d,J=8.6Hz,1H),7.62(t,J=7.7Hz,1H),7.51-7.38(m,4H),7.37-7.26(m, 6H), 7.16(d, J=6.6Hz, 2H), 5.52(s, 2H); ESI-MS, m / z(%): 527.2633(100)[M+H+].
Embodiment 2
[0041] (1) Preparation of test solution:
[0042] In a 10mL sample bottle, add 1.0mL HEPES buffer solution (pH=7.40), then add 0.1mol / L Zn 2+ Standard solution (20μL, 20eq), then add 9.0mL acetonitrile, mix well; finally add 100μL 1×10 -3 Probe L in ethanol, mix again. After standing for 30 minutes, the ultraviolet absorption and fluorescence emission were measured at 390nm as the excitation wavelength. The above operation, without adding metal ion solution, is the preparation of blank test solution. Measure UV absorption and fluorescence emission.
[0043] (2) Ultraviolet spectrum and fluorescence spectrum test:
[0044] The blank test solution of probe L has a weaker fluorescence intensity at 490nm, and no fluorescence emission at 570nm; when zinc ions exist, the fluorescence intensity at 490nm is significantly weakened, and the fluorescence intensity at 570nm is significantly enhanced, see Figure 8 .
[0045] (3) Ion selectivity experiment:
[0046] When various met...
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Abstract
The invention belongs to the technical field of analytical chemistry, and in particular relates to a carbazole-contained benzimidazole-substituted quinoline derivative, a preparation method and an application thereof. The carbazole-contained benzimidazole-substituted quinoline derivative is 3-(2-(8-(1H-benzo[d] imidazole-2-yl) quinoline-2-yl) ethenyl)-9-benzyl-9H-carbazole. The preparation method includes the steps of placing 2-methyl-8-(1H-benzimidazole) quinoline and 9-benzyl-9H-carbazole-3-formaldehyde into polar solvents, adding catalysts, stirring and performing backflow reaction; performing purification after the backflow reaction to obtain a target compound carbazole and benzimidazole-substituted quinoline derivative L. A benzimidazole quinoline derivative zinc ion fluorescent probe is excellent in complexing action with zinc ions and rapid in response, the response time of the Zn<2+>fluorescent probe for Zn<2+> is 50s, the lowest detection limit is 6.69*10-8mol / L, and the fluorescent probe can be used for quantitative trace detection of the zinc ions by fluorescence spectrophotometry.
Description
technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a quinoline derivative substituted with carbazole and benzimidazole, a preparation method and application thereof. Background technique [0002] As one of the most important transition metal ions in the human body, zinc ions not only participate in physiological processes such as nerve signal transmission, gene transcription, signal transduction and immune response, but also are associated with some neurodegenerative diseases (such as Parkinson's, Alzheimer's, etc. Mercury) and the occurrence of Zn in nerve tissue 2+ related to metabolic disorders. On the other hand, zinc batteries and alloys also have a broad market in new energy materials; in recent years, environmental pollution caused by excessive discharge of zinc-containing pollutants has gradually attracted people's attention. [0003] Currently established methods for the determination of metal ...
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