Fluorescent probe compounds, preparation method and use thereof

一种荧光探针、化合物的技术，应用在荧光探针化合物及其制备领域，能够解决平衡时间长、不能用于检测零价钯等问题，达到荧光强度增强、反应条件温和、紫外吸收增强的效果

Inactive Publication Date: 2010-06-16
DALIAN CHROMAS BIOSCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still deficiencies in their respective performances: the first case of thiaether-based maleonitrile palladium ion fluorescent probes produces spectral changes through the complexation of sulfur heteroatoms to palladium ions, and the excitation light is not in the visible light region, and cannot be used for Detection of zero valent palladium
Although the third allyl-complexed palladium ion probe solved the problems of the first two probes, it also had the shortcoming that the equilibrium time was too long (Honglin Li, Jiangli Fan, Jianjun Du, Kexin Guo, Shiguo Sun, Xiaojian Liu and Xiaojun Peng, Chem.Commun., 2010, DOI: 10.1039 / b916915f)

Method used

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  • Fluorescent probe compounds, preparation method and use thereof
  • Fluorescent probe compounds, preparation method and use thereof
  • Fluorescent probe compounds, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Example 1 Synthesis of fluorescent probe compound RPd1:

[0076]

[0077] (1) Synthesis of intermediate 1

[0078] Rhodamine 6G (1.2 g, 2.5 mmol) was added into a 100 ml single-necked flask filled with 30 ml of ethanol. Stir vigorously at room temperature, and then measure 3 ml of 85% hydrazine hydrate (excess). After the dropwise addition was completed, the mixture was refluxed in air for 2 hours. The solution color first changed from dark purple to light brown and finally almost clear. After cooling to room temperature, the ethanol was distilled off under reduced pressure. Then 50ml of hydrochloric acid (1M) was added to obtain a red solution; while stirring, 70ml of sodium hydroxide (1M) was added until the pH reached between 9-10, and a large amount of precipitation appeared. Filter and wash the filter cake 3 times with 15 ml of water. After vacuum drying, 0.64 g of the target product was obtained by column separation, with a yield of 60.0%. 1 H NMR (400MHz...

Embodiment 2

[0081] Example 2 Fluorescent probe compound RPd1 selectivity to palladium ion:

[0082] The selectivity to palladium ion was evaluated using the compound RPd1 synthesized above. Add 10 μM compound RPd1 to the ethanol solution of the same amount of various metal ions, the excitation wavelength of the probe is 505nm, and the emission wavelength of the probe is 552nm. The test results are shown in figure 1 middle. It can be seen from the figure that the fluorescent probe compound RPd1 has a high selectivity to palladium ions, and the addition of palladium ions produces a large fluorescence and ultraviolet enhancement. In addition, metal ions such as sodium, potassium, calcium, magnesium, and copper are highly selective Detection without interference. The abscissa is the wavelength (nm), and the ordinate is the fluorescence intensity. The instrument used is a fluorescence spectrophotometer, model: LS 55.

Embodiment 3

[0083] Example 3 The selectivity of fluorescent probe compound RPd1 to common platinum group metal ions:

[0084] The selectivity to palladium ion was evaluated using the compound RPd1 synthesized above. Add 10 μM compound RPd1 to the ethanol solution of the same amount of various common platinum group metal ions. The excitation wavelength of the probe is 505nm, and the emission wavelength of the probe is 552nm. The test results are shown in figure 2 middle. It can be seen from the figure that the fluorescent probe compound RPd1 has a high selectivity for palladium ions, and the addition of palladium ions produces a large fluorescence and ultraviolet enhancement. In addition, metal ions such as platinum, rhodium, and ruthenium do not interfere with the detection. The abscissa is the wavelength (nm), and the ordinate is the fluorescence intensity. The instrument used is a fluorescence spectrophotometer, model: LS 55.

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Abstract

The invention provides fluorescent probe compounds, a preparation method and use thereof, belonging to the detection of palladium ions in the field of fine chemical industry. The fluorescent probe compounds designed on the basis of the 'opening-closing' property of the spiral ring in the molecule of a rhodamine luminescent dye well solve the difficult problem that the palladium ions quench fluorescence. The excitation wavelength and the emission wavelength of the probe compounds are both in a visible light region. The compounds have excellent selectivity to the palladium ions in the practical detection range of nearly neutral pH and have excellent sensitivity. The fluorescence is obviously enhanced in the process of detecting the palladium ion concentration of 0-10ppb, an excellent linear relationship between the palladium ion concentration and the fluorescence enhancement is formed, and the palladium ions of 5nm can be detected at lowest. The probe compounds have extremely quick response for distinguishing the palladium ions and are the reported palladium ion probes with the shortest response time so far. The probe compounds can be used for realizing the detection of the palladium ions in the two manners of fluorescent light and color comparison, and has potential application value in the detection of palladium pollution and residual level in medicines, water samples, soils and catalytic reactors.

Description

technical field [0001] The invention relates to a class of fluorescent probe compound and its preparation method and application. The compound is suitable for the detection of palladium ions in the field of fine chemical industry. Background technique [0002] Palladium is widely used in social production activities. For example, dental crowns, catalysts, fuel cells and jewelry. Palladium is used to design catalytic converters to effectively control vehicle exhaust pollution, but at the same time, palladium is also deposited in large quantities in the soil (<0.3ppm) and plants near the road. Rainwater will bring the palladium deposited in the soil into rivers, lakes and oceans, further causing pollution of the water system. In addition, palladium is often used as a catalyst to synthesize compounds with complex structures, and has extremely important applications in the pharmaceutical industry. Although widely used in catalytic reactions, a large amount of palladium wil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6561C09K11/06G01N21/64
CPCG01N2021/7786C09K2211/1007C09K2211/1029G01N21/643C09K11/06C07F9/6561G01N2021/6439C09K2211/1088G01N21/75
Inventor 彭孝军樊江莉李宏林王静云孙世国
Owner DALIAN CHROMAS BIOSCI
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