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Palladium ion fluorescent probe, and preparation method and applications thereof

A fluorescent probe and palladium ion technology, applied in the field of dye chemistry, can solve problems such as low detection wavelength, difficulty in eliminating environmental interference, and easy damage to cells and tissues, and achieve high yield, good structural stability of dyes, and easy The effect of separation and purification

Inactive Publication Date: 2015-10-07
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the fluorescent probes used to detect palladium ions have the following two limitations: (1) it is only a simple off-on system, and it is difficult to eliminate environmental interference; (2) the detection wavelength is low, and it is easy to damage cells and tissues

Method used

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  • Palladium ion fluorescent probe, and preparation method and applications thereof
  • Palladium ion fluorescent probe, and preparation method and applications thereof
  • Palladium ion fluorescent probe, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Synthesis of compound III

[0027] Dissolve isophorone I (5.0g, 36.2mmol) and malononitrile II (2.87g, 43.4mmol) in 50ml of ethanol, and then add piperidine (0.5g, 4.8mmol), at 120°C under nitrogen protection Heat to reflux for 12 hours. After the reaction, the solvent is evaporated to dryness, dissolved in dichloromethane, washed with water, dried over anhydrous sodium sulfate, filtered with suction, and rotary evaporated under reduced pressure to obtain the crude product of formula III; after separation and purification on a silica gel column, compound III 4.72 g, the productive rate is 70%. The eluent is: petroleum ether:ethyl acetate=5:1

[0028]

[0029] (2) Synthesis of Compound V

[0030] Dissolve (3,5,5-trimethylcyclohex-2-enylidene)malononitrile (compound III) (300mg, 1.6mmol) and p-acetamidobenzaldehyde (compound IV) (263mg, 1.6mmol) In 20 milliliters of toluene, 0.3 milliliters of piperidine and acetic acid were respectively added as catalysts, and ...

Embodiment 2

[0038] Embodiment 2, probe compound VII to Pd (PPh 3 ) 4 response time experiment

[0039] Using the compound VII synthesized in Example 1, use DMSO to make 1×10 -4 mol / L of the probe mother solution, and then add 0.3 ml of the mother solution to a mixed solution of 1.5 ml of PBS buffer (20 mM) and 1.2 ml of DMSO. Add 50 μM Pd(PPh 3 ) 4 Detect the change of its fluorescence intensity and ultraviolet absorbance within 0-30min. The slit during the fluorescence spectrum test was set to 5 / 5. Test results such as figure 1 and figure 2 It can be seen that with the increase of adding time, the ultraviolet absorbance at 420nm decreases continuously, while the fluorescence intensity at 472nm increases continuously, while the fluorescence intensity at 570nm decreases continuously, and the fluorescence intensity at 643 increases continuously. Both groups of experiments could achieve response saturation within 30 minutes.

Embodiment 3

[0040] Embodiment 3, probe compound VII to Pd (PPh 3 ) 4 concentration titration experiment.

[0041] Compound VII synthesized in Example 1 was prepared as a solution according to Example 2 and diluted into a mixed solution of 1.5 ml of PBS buffer (20 mM) and 1.2 ml of DMSO. Add 0, 2, 5, 7, 10, 15, 20 μM Pd(PPh 3 ) 4 , Wait for 30 minutes for each addition and then detect the changes of its UV absorbance and fluorescence intensity. The slit during the fluorescence spectrum test was set to 5 / 5. From image 3 and Figure 4 It can be seen that with Pd(PPh 3 ) 4 As the concentration increases, the UV absorbance at 420nm decreases continuously, while the UV absorbance at 472nm increases continuously. At the same time, the fluorescence intensity at 570nm decreases continuously, and the fluorescence intensity at 643 increases continuously. The ultraviolet red shift of two groups of experiments reached 52nm, and the fluorescence red shift reached 73nm.

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Abstract

The invention discloses a palladium ion fluorescent probe, and a preparation method and applications thereof. According to the palladium ion fluorescent probe, allyl formate is taken as a response group, and bathochromic shift in an absorption spectrum and bathochromic shift in a fluorescence excitation spectrum are both caused after adding of palladium ions. The palladium ion fluorescent probe is capable of detecting palladium ions with high sensitivity and selectivity, and quantitative determination on palladium ions can be realized via ratio method. The palladium ion ratio fluorescent probe can be used for rapid high-sensitivity specificity detection on low concentration palladium ions; the synthetic method is simple; and industrialized batch production can be realized.

Description

technical field [0001] The invention relates to a ratio-type fluorescent probe which can be used for quantitatively detecting palladium ions, and belongs to the field of dye chemistry. Background technique [0002] It is of great significance to use fluorescent probes for the detection of heavy metals and transition metals in the environment and in vivo. In particular, metal palladium, as a rare transition metal, is often used in catalytic reactions, dye batteries, jewelry and other fields. Although metal palladium plays a very important role in these applications, palladium ions in the environment can cause damage to organisms when they enter the organism. It can bind to DNA, proteins and other biomolecules and biological processes, thereby interfering with normal physiology. progress of the process. [0003] Therefore, it is very necessary to invent some analytical methods with high selectivity and high sensitivity for the detection of palladium ions. Some classical ana...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C271/28C07C269/04G01N21/64
Inventor 田宝柱相开强张金龙陈日升常顺周李长江刘允昌
Owner EAST CHINA UNIV OF SCI & TECH
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