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Photochromic fluorescent probe for detecting copper ions, preparation method and application thereof

A fluorescent probe, photochromic technology, applied in the direction of color-changing fluorescent materials, fluorescence/phosphorescence, chemical instruments and methods, etc., to achieve the effects of simple preparation process, good response speed, fatigue resistance, and fast response speed

Active Publication Date: 2022-07-29
CHINA UNIV OF MINING & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the paramagnetism of copper ions, when combined with organic molecules, it often leads to a response of fluorescence quenching, which is easily affected by other factors in the surrounding environment.

Method used

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  • Photochromic fluorescent probe for detecting copper ions, preparation method and application thereof
  • Photochromic fluorescent probe for detecting copper ions, preparation method and application thereof
  • Photochromic fluorescent probe for detecting copper ions, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1: Synthesis of probe compound TPE-Rh-Sal

[0061] (1) TPE-Rh-NH 2 Synthesis

[0062] Dissolve 0.1882 g (0.5 mmol) of 1-(4-carboxylic acid phenyl)-1,2,2-triphenylene into 20 mL of dichloromethane, weigh 0.068 g (0.5 mmol) of HoBt, 0.096 g (0.5 mmol) of EDCI mmol) was added to the reaction solution, and reacted at room temperature for 2 h; 0.23 g (0.5 mmol) of rhodamine compound B was weighed into the reaction solution, and reacted at room temperature for 8-12 h. After the reaction is completed, pour into 20 mL of deionized water, extract three times with dichloromethane, combine the organic phases, and evaporate the solvent under reduced pressure to obtain a crude product, which is purified by passing through a silica gel column with a dichloromethane:methanol solution with a volume ratio of 20:1. , get 0.25g pure TPE-Rh-NH 2 , Yield: 60%, Melting point: 199-202°C. hydrogen spectrum as figure 1 As shown, the mass spectrum is as figure 2 shown, 1 H NMR (6...

Embodiment 2

[0065] Example 2: AIE properties of probe TPE-Rh-Sal

[0066] like Figure 5 and Image 6As shown, the AIE property of TPE-Rh-Sal (2 μM) is the change in fluorescence emission of the test solution in tetrahydrofuran-water solution at an excitation wavelength of 365 nm. The probe TPE-Rh-Sal is in a dissolved state when the water content of the solution is 0-60%, and there is no obvious fluorescence emission. When the water content of the solution reaches 70%, the TPE-Rh-Sal appears in an aggregated state (average particle size: 458.7nm). ), the unique AIE characteristics of tetraphenylethylene show that an obvious fluorescence emission peak appears at the wavelength of 485nm, which is a typical fluorescence emission peak of tetraphenylethylene, which emits yellow-green fluorescence; with the increase of water content, the fluorescence intensity increases, When the water content of the solution reaches 90%, the average particle size reaches 190.1 nm, and the fluorescence inten...

Embodiment 3

[0067] Example 3: Piezo-induced fluorescence enhancement properties of the probe TPE-Rh-Sal

[0068] like Figure 7 As shown in the figure, the probe TPE-Rh-Sal showed no fluorescence emission peak when the probe TPE-Rh-Sal was excited by ultraviolet light at 365 nm; after grinding, the probe TPE-Rh-Sal emitted strong yellow-green fluorescence, which was in the same The fluorescence properties are the same in the aggregated state. like Figure 8 As shown, the XRD data pattern of the probe TPE-Rh-Sal in the original state has sharp crystal diffraction peaks; after grinding, the original sharp crystal diffraction peaks of its XRD become smaller, forming an amorphous powder; this is due to The probe TPE-Rh-Sal is in a crystalline state in its original state, and the molecules are packed regularly and tightly, causing the phenomenon of fluorescence weakening or quenching; In addition, the dislocation and sliding between the molecules make the molecules become loose, causing the...

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Abstract

A photochromic fluorescent probe for detecting copper ions and a preparation method and application thereof, the fluorescent probe is named TPE-Rh-Sal, and the chemical structural formula is shown in formula I; )-1,2,2-triphenylene and rhodamine compound B are synthesized under catalyst action to obtain TPE-Rh-NH 2 , and then reacted with salicylaldehyde to synthesize and purify. In the present invention, the probe shows a good response to Cu in tetrahydrofuran solution. 2+ and UV dual stimuli-responsive properties to Cu 2+ The identification shows high selectivity and high sensitivity; the probe has photochromic properties, and the probe and the composite material using paraffin to support the probe have fast response speed and good anti-fatigue performance. The probe is prepared The process is simple and the synthesis route is short. The probe is applied to the detection of copper ions, and the composite material is applied to optical information storage, ultraviolet rapid detection, and anti-counterfeiting materials, thus broadening the application range of the probe.

Description

technical field [0001] The invention belongs to the field of organic fluorescent molecular probes, and in particular relates to a photochromic fluorescent probe for detecting copper ions and a preparation method and application thereof. Background technique [0002] Since the concept of smart materials was proposed, many researchers have been searching for new multi-functional materials with excellent properties such as multi-stimulus response, responsiveness, and self-recovery. Among many multifunctional materials, photochromic materials started early. After decades of rapid development, they have been widely used in high-tech fields such as optical switches, information storage, anti-counterfeiting technology, light-controlled drug release, and photoresist. Common organic photochromic materials include azobenzenes, spiropyrans, and dithienylethylenes. Although photochromic materials have developed rapidly and achieved great progress and fruitful results, there are still s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09D5/29C09K9/02G01N21/64
CPCC09K9/02C07D491/107G01N21/6428C09D5/29C09K2211/1033C09K2211/1044C09K2211/1007G01N2021/6439
Inventor 张然赵鑫榆苗保喜倪中海
Owner CHINA UNIV OF MINING & TECH
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