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Water-soluble phosphorescent polymer for detecting pH as well as preparation method and application thereof

A polymer, water-soluble technology, applied in the direction of fluorescence/phosphorescence, indium organic compounds, compounds containing elements of Group 8/9/10/18 of the periodic table, etc., can solve the problems of biocompatibility, poor water solubility and high toxicity , Luminescence is easily affected by a variety of factors in the organism, etc., to achieve the effects of less damage, less toxicity, good water solubility and biocompatibility

Inactive Publication Date: 2018-06-29
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the pH probes in the prior art are single small molecules, which have poor biocompatibility and water solubility, high toxicity, and luminescence is easily affected by various factors in the body, which is not conducive to accurate detection of pH

Method used

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  • Water-soluble phosphorescent polymer for detecting pH as well as preparation method and application thereof
  • Water-soluble phosphorescent polymer for detecting pH as well as preparation method and application thereof
  • Water-soluble phosphorescent polymer for detecting pH as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: Preparation of complex Ir2 sensitive to pH

[0031]

[0032] The specific operation steps are:

[0033] (1) Preparation of Compound 2: Combine 1 (2.2mmol) and IrCl 3 ·3H 2 O (1.2mmol) in a mixed solution of ethylene glycol ether and water (12mL) at 110°C and N 2 Reacted for 24 hours under protection to obtain iridium dichloro bridge 2 with a yield of 80%;

[0034] The preparation of compound 4: the iridium dichloro bridge 2 (1.0mmol) and N^N ligand 3 (0.5mmol) at 50 ℃ and N 2 Reaction under protection for 5h. The reaction solution was cooled to room temperature, and KPF was added thereto 6 (1.4mmol) and continued to stir for 4 hours. After the reaction, the organic solvent was spun off, and the obtained solid was separated and purified by column chromatography to obtain a yellow-brown powder 4 with a yield of 80%;

[0035] 1 H NMR (400MHz, DMSO) δ (ppm): 8.96 (d, J = 8.8Hz, 1H), 8.61-8.52 (m, 4H), 8.46 (d, J = 4.8Hz, 1H), 8.31 (dd, J =10.0Hz,8.8...

Embodiment 2

[0038] Example 2: Preparation of pH-sensitive complex water-soluble polymer probe P

[0039]

[0040] a+b+c=1, different values ​​of a, b, and c correspond to iridium complexes with different contents.

[0041] The specific operation steps are: add Ir1 (0.15mmol), Ir2 (0.05mmol), AIBN (0.5mmol), pyrrolidone (100mmol) and 3mL tetrahydrofuran into the polymerization tube, react overnight under nitrogen atmosphere, and settle with ether for post-treatment, and filter with suction An orange-yellow solid was obtained

Embodiment 3

[0042] Embodiment 3: complexes Ir1, Ir2 are tested to pH responsive emission spectrum

[0043] The spectrum test concentration of iridium complex Ir1 and Ir2 used in the present invention is 10 μM, the test solvent is PBS solution mixed with 1% DMSO, and when the emission spectrum is measured, the excitation wavelength is 405 nm.

[0044] The emission spectra of complex Ir1 in neutral (pH=7.34) and acidic (pH=3.01) solutions are as follows figure 1 shown. Its luminescence is very weakly affected by pH, and the luminescence hardly changes with the increase of pH, indicating that the iridium complex Ir1 can be used as a reference in pH detection, and a ratio method can be constructed with Ir2, which reduces unnecessary interference in the environment and increases the detection accuracy.

[0045] The emission spectra of the complex Ir2 in neutral (pH=7.34) and acidic (pH=3.01) solutions are as follows figure 2 shown. Its luminescence is very sensitive to pH, and the lumines...

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Abstract

The invention discloses a water-soluble phosphorescent polymer for detecting pH by a ratio method as well as a preparation method and application thereof. The polymer consists of two iridium complexes(Ir1, Ir2) and polyvinylpyrrolidone, wherein the Ir1 is a reference complex and does not respond to pH; the Ir2 can specifically respond to pH, and the luminous intensity of the Ir2 is weakened alongwith reduction of pH; and the polyvinylpyrrolidone gives high water solubility and biocompatibility to the polymer. The luminous intensity and the emitting life of the water-soluble phosphorescent polymer P disclosed by the invention are reduced along with reduction of pH, so that the pH of a cell is detected through confocal imaging; and the water-soluble phosphorescent polymer is a phosphorescent probe integrating excellent water solubility and biocompatibility and has important application prospect in aspects of biological imaging and sensing.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and in particular relates to a water-soluble phosphorescent polymer used for measuring pH by a ratio method, a preparation method and application thereof. Background technique [0002] The pH value is a measure of the acidity and alkalinity of a solution in the usual sense. The pH value includes intracellular (pHi) and extracellular (pHe). The pH value is widely used in medicine, chemistry, and agriculture. As an important physiological parameter, pH value plays a vital role in some physiological processes. For example, in eukaryotic cells, membrane transport, receptor recycling, lysosomal degradation and other processes are all affected by intracellular pH ( Such as the control and direct influence of phagocytic vesicles); at the same time, the pH value has also been described as a significant sign of cancer. According to research, cancer cells show a "reversed...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06G01N21/64
CPCC07F15/0033C09K11/06C09K2211/185G01N21/6486
Inventor 赵强刘淑娟孟祥春陈泽晶石玉祥黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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