Photochromic perfluorocyclopentene molecular fluorescent probe compound and its preparation method and application

A perfluorocyclopentene, fluorescent probe technology, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., to achieve high selectivity and sensitivity

Inactive Publication Date: 2017-08-25
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] So far, although there are examples of Schiff bases introduced into traditional perfluorocyclopentene molecules, a new type of molecular fluorescent probe can be constructed from the reaction of benzohydrazide and diarylene salicylaldehyde to generate Schiff bases, and it can be used in incompatible The perfluorocyclopentene photochromic compound system for the highly selective detection of two different metal ions in a solvent system has not been reported in any literature or patents

Method used

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  • Photochromic perfluorocyclopentene molecular fluorescent probe compound and its preparation method and application
  • Photochromic perfluorocyclopentene molecular fluorescent probe compound and its preparation method and application
  • Photochromic perfluorocyclopentene molecular fluorescent probe compound and its preparation method and application

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Embodiment 1

[0024] In the molecular structural formula, the final compound of the present invention is named as: {1-(3,5-dimethyl-4-isoxazolyl), 2-{2-methyl-5-[3-(methylene -Benzohydrazide)-4-hydroxyphenyl]-3-thienyl}} perfluorocyclopentene (1o), the synthetic scheme of this novel perfluorocyclopentene diarylethene photochromic compound is as follows Scheme 1 shows:

[0025] Scheme 1:

[0026]

[0027] Concrete synthetic steps are as follows:

[0028] 1. 1-[3,5-Dimethyl-4-isoxazole] perfluorocyclopentene (2)

[0029] Under the protection of argon and a liquid nitrogen acetone bath, 4-iodo-3,5-dimethylisoxazole (1) (1.12 g, 5 mmol) was dissolved in 50 mL of refined tetrahydrofuran. Inject n-butyllithium (5mmol, 2.3mL) under rapid stirring, continue the low-temperature reaction for 0.5 hours; inject perfluorocyclopentene (5mmol, 0.7mL) rapidly under high-speed stirring, continue the low-temperature reaction for 1.0 hour and then naturally rise to room temperature, and then add an app...

Embodiment 2

[0049] Example 2: The functional experiments of the compounds of the present invention are mainly reflected in two aspects: detection of metal ions as fluorescent probes and dual regulation of fluorescent molecular switches.

[0050] 1. Compound 1 detects metal ions in different solvent systems

[0051] Such as Figure 5 As shown in (A), in the acetonitrile solution of compound 1 (2.0×10 -5 mol L -1 ), after various metal ions were added in 3-fold equivalent, the fluorescence spectrum under 438nm light excitation changed significantly. in Pb 2+ ,Cu 2+ ,Al 3+ ,Cr 3+ ,Hg 2+ , Ni 2+ ,Mg 2+ ,Cd 2+ ,Co 3+ ,Mn 2+ , Ba 2+ ,Sr 2+ ,K + and Ca 2+ The fluorescence of the solution did not change significantly after the addition of the plasma. And only after adding Zn 2+ Afterwards, the solution had an obvious fluorescence emission peak at 560 nm, and the fluorescence intensity was enhanced by 200 times compared with the initial value. Due to Zn 2+ and Cd 2+ Most of t...

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Abstract

The invention belongs to the field of chemical synthesis and discloses a photochromic perfluorocyclopentene molecular fluorescent probe compound and a preparation method thereof. The uses of the photochromic perfluorocyclopentene molecular fluorescent probe compound of the present invention include: realizing molecular recognition through specific receptor binding targets; having high selectivity and sensitivity, and being able to realize in-situ real-time detection at the single-molecule level , can use optical fiber to carry out long-distance detection and realize the visualization of detection results through changes in output signals such as ultraviolet absorption and fluorescence; use its fluorescent switch properties to prepare multiple control light-controlled switch elements; use to prepare photochromic light-emitting devices; use Its fluorescence multiple regulation characteristics can be used to design new logic gates and so on.

Description

technical field [0001] The invention belongs to the field of organic photochromic materials, in particular to a synthesis method and application of a novel photochromic perfluorocyclopentene molecular fluorescent probe compound containing salicylaldehyde Schiff base. Background technique [0002] With the rapid development of social economy, more and more problems have been highlighted, especially environmental pollution, food safety, etc. Among them, metal ions, especially toxic metal ions, have attracted widespread attention and concern because of their toxicity. Therefore, rapid and accurate detection of metal ions is particularly important. Developing efficient sensors is one of the important strategies to solve such problems. The various analytical methods currently used to detect heavy metal ions are expensive, usually require a relatively large sample size and cannot be continuously detected. Fluorescent molecular probes are a new method emerging in the field of mol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/06C09K11/06G01N21/64H01L51/54
CPCG01N21/64C09K11/06C07D413/06C09K2211/1014C09K2211/1092C09K2211/1033H10K85/649
Inventor 蒲守智刘刚马乐乐范从斌崔士强
Owner JIANGXI SCI & TECH NORMAL UNIV
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