A spiropyran-bipyridine derivative and its naked-eye detection of copper(ii)

A derivative, spiropyran technology, applied in the preparation of biological probe materials and its application field, can solve the problems of poor water solubility, light sensitivity of spiropyran, complicated operation, etc., achieve rapid response, realize naked eye detection, dissolve good effect

Active Publication Date: 2021-02-02
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention provides a spiropyran-bipyridine derivative and a spiropyran-bipyridine derivative in order to solve the problems of poor water solubility of the current spiropyran derivatives, spiropyran being sensitive to light, making it have high requirements on the environment and complicated operation. For the naked-eye detection of copper (II), the derivative is based on the spiropyran structure with two pyridine groups added. The highly polar structure greatly improves the solubility of the probe in the water system

Method used

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  • A spiropyran-bipyridine derivative and its naked-eye detection of copper(ii)
  • A spiropyran-bipyridine derivative and its naked-eye detection of copper(ii)
  • A spiropyran-bipyridine derivative and its naked-eye detection of copper(ii)

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Effect test

Embodiment 1

[0020] Embodiment 1: a kind of spiropyran-bipyridine derivative, the structural formula of the probe compound is:

[0021] , abbreviated as SP-DP.

[0022] The method for preparing the spiropyran-bispyridine derivatives, heat reflux of semicyanine and ethyl bromide in acetonitrile solvent to generate semicyanine derivatives, which generate yellow oily liquid under the action of alkali , the oily liquid and 5-nitrosalicylaldehyde are heated under reflux in ethanol to form a ring-forming reaction to generate spiropyranyl nitro derivatives, and the spiropyranyl nitro derivatives are reduced to spiropyranyl under the action of stannous chloride and acetic acid Nylamino derivatives, spiropyranyl amino derivatives and twice the amount of chloromethylpyridine under the action of potassium carbonate and potassium iodide, the two hydrogens on the amino group are replaced by pyridine rings to generate spiropyridine with two pyridine rings Fyran-bipyridine derivative SP-DP.

[0023] ...

Embodiment 2

[0028] Embodiment 2: spiropyran-bipyridine probe detects Cu 2+ :

[0029] Preparation of spiropyran-bipyridine probe mother solution: DMSO was used as a solvent to prepare a spiropyran-bipyridine probe molecule mother solution with a final concentration of 2 mM.

[0030] Take 20µL of the mother solution of the probe molecule SP-DP and 1980µL of PB (pH=7.4, 50 mM) in the cuvette, so that the final concentration is 20 µM, and measure the UV-Vis absorption spectrum. It can be seen that there is a The absorption peak of the spiropyran ring. After adding 1 equivalent of Cu 2+ , a new peak appears at 517 nm in the UV absorption, which indicates that the Cu 2+ Combined with spiropyran probe molecules in a certain way to generate new substances.

[0031] In the detection with Cu 2+ Under exactly the same conditions, for other common metal ions (Fe 3+ , Zn 2+ , Mn 2+ 、Co 2+ , Hg 2+ 、Cd 2+ , Sn 2+ 、Ni 2+ 、Cr 2+ 、Ag + , Fe 2+ ) were detected. Take 20 µL of the mother sol...

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Abstract

The invention belongs to the technical field of preparation and application of biological probe materials. In order to solve the problems of poor water solubility of current spiropyran derivatives, spiropyran is sensitive to light, which makes it have high requirements on the environment and complicated operation. A spiropyran derivative and its naked-eye detection of copper (II) are provided. The derivative is based on the spiropyran structure with two pyridine groups added. The structural formula of the probe is; Before and after the addition of copper ions, the color of the solution changes from colorless to pink in 60 seconds, and the response is rapid, but there is no change when other cations are added. Therefore, the copper ions can be detected under the interference of other ions. Selective detection. The highly polar structure greatly improves the solubility of the probe in water systems. Response was quick and remarkable. with Cu 2+ After complexation, the probe molecules absorb in the visible light region, thereby realizing naked-eye detection.

Description

technical field [0001] The invention belongs to the technical field of preparation and application of biological probe materials, and specifically relates to a spiropyran-bipyridine derivative and its naked-eye detection of copper (II). The derivative combines the photochromic molecule spiropyran with Pyridine-bound probe for naked-eye detection of copper ions. Background technique [0002] Copper, the third most abundant transition metal in the human body, is a cofactor for proteins and enzymes and plays a vital role in many fundamental biological processes. However, high concentrations of Cu 2+ Can cause severe liver and kidney damage. However, the existing methods for detecting copper ions have slow reaction speed and low measurement accuracy, and cannot realize reversible and real-time detection of metal ions. Photochromic sensors overcome these shortcomings well. [0003] As a pair of photoisomers, Spiropyran (SP) and Merocyanine (MC) have been extensively studied. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052C09K11/06G01N21/64
CPCC07D491/052C09K11/06C09K2211/1029C09K2211/1088G01N21/643G01N21/6447
Inventor 赵宏伟韩辉
Owner SHANXI UNIV
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