Electropolymerizable fluorescent sensing material and application on fluorescent or electropolymerizable detection of metal ions

A fluorescent sensing and metal ion technology, applied in the field of fluorescent sensing materials, can solve the problems of hindering the rapid diffusion of metal ions to be measured, weakening the fluorescence quantum efficiency of thin films, and unstable film materials, and achieves controllable aggregate structure and guarantees The effect of permeability and stability, enhancing responsiveness

Inactive Publication Date: 2013-01-30
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far, there are few reports on efficient thin-film fluorescence detection of metal ions. This is mainly because the use of fluorescent detection substances in the form of thin films, dense thin films hinder the rapid diffusion of metal ions to be detected, and the fluorescence quantum efficiency of thin films is weakened. , the membrane material is unstable, easy to swell, dissolve, decay quickly, poor stability, poor selectivity and other problems when used

Method used

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  • Electropolymerizable fluorescent sensing material and application on fluorescent or electropolymerizable detection of metal ions
  • Electropolymerizable fluorescent sensing material and application on fluorescent or electropolymerizable detection of metal ions
  • Electropolymerizable fluorescent sensing material and application on fluorescent or electropolymerizable detection of metal ions

Examples

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Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Electropolymerizable compound M1 with 2,2'-bipyridine as the metal ion recognition center

[0038] We only take the synthesis of compound M1 as an example (the preparation method of other compounds is similar to the synthesis of compound M1, synthesized by the reaction of Suzuki et al.), to illustrate the present invention, rather than limit the present invention. All polyfluorene, polyphenylene, polystyrene, polyphenylene and trapezoidal polyphenylene with electropolymerization active groups (carbazole, diphenylamine, triphenylamine, thiophene or ethylenedioxythiophene, etc.) on the side chain emit light The idea or route of synthesis of the material, and its use in the sensing of metal ions by fluorescent electrochemical polymer film are all within the scope of the design idea of ​​the present invention.

[0039] synthetic route:

[0040]

[0041] 1. Synthesis of N-(6-bromo-hexane)-carbazole

[0042] Dissolve 5g (30mmol) of carbazole and 5ml (31mmol) o...

Embodiment 2

[0049] Example 2: Synthesis of 5,5'-bis(9,9-bis(6-(9H-carbazol-9 base)hexyl-9H-fluoren-2 base)-1,10-phenanthroline (M2)

[0050] The first three parts of the synthesis of compound M2 are the same as those of compound M1, so details will not be repeated. Take 30mg of 3,8-dibromo-1,10-phenanthroline in a round bottom flask, add 3mL of purified toluene and 2mL of 2mol / L Na 2 C0 3 Aqueous solution, degassed by freezing, quickly added 17.5mg Pd (PPh 3 ) 4 and 150mg of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborin)-9,9-(N-carbazole-hexyl)fluorene, freeze degassed 3 times, in The reaction was stirred at 90°C for 3 days. After cooling, it was washed with water, extracted three times with dichloromethane, and dried over anhydrous magnesium sulfate. After concentration, using a mixed solvent of dichloromethane and petroleum ether as a developing solvent, a yellow solid (60 mg) was obtained by thin chromatography with a yield of 50%. 1H NMR (500MHz, DMSO): δ9.55(d, 2H), 8.84(d, 2H), 8.11...

Embodiment 3

[0051] Embodiment 3: Preparation of electrochemically polymerized film

[0052] The electrochemical polymerization was completed on a CHI660C electrochemical workstation produced by Shanghai Chenhua Company. The electrolytic cell is a three-electrode system: the working electrode is an ITO electrode, which is ultrasonically cleaned with semiconductor cleaning solution, water, toluene, acetone, and ethanol in sequence. The electrode is a metal titanium plate, and the reference electrode is Ag / Ag + . Electrolyte is TBAPF 6 , whose concentration is 0.1molL -1 . Put the pretreated indium tin oxide (ITO) working electrode into the solution containing 1mg / mL compound M1 and supporting electrolyte TBAPF 6 In the electrochemical workstation system, the organic solvent is a mixed solution of dichloromethane (2mL) and acetonitrile (3mL), the electropolymerization start potential is -0.9V, the end potential is 0.85V, and the number of scan cycles is 12. The CV method is used to ini...

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Abstract

The invention belongs to the field of a metal ion sensing technology, in particular to an electropolymerizable fluorescent sensing material and application of the electropolymerizable fluorescent sensing material on fluorescent or electropolymerizable detection of metal ions. According to the electropolymerizable fluorescent sensing material, 2, 7-fluorene and 2, 2'-dipyridyl (or 1, 10-phenanthroline) are served as a main chain, and a side chain is connected with a carbazole group through an alkyl group. A rigid main chain structure of a compound provided by the invention guarantees the fluorescent sensing material to have high fluorescent efficiency, but a side chain of strong metal identification unit guarantees selectivity of a detection material. In addition, a micropore structure of a film prepared by electropolymerization can effectively guarantee the metal ions to quickly diffuse in the film and improve flexibility of film detection. According to the fluorescent sensing material provided by the invention, raw materials with cheap prices are easily obtained, and a synthesis process is relatively simple, so that the electropolymerizable fluorescent sensing material is a metal ion fluorescent/ electrochemical sensing film material with high potential.

Description

technical field [0001] The invention belongs to the technical field of metal ion sensing, and specifically relates to a class of 2,7-fluorene and 2,2'-bipyridine (or 1,10-phenanthroline) as the main chain, and the side chain is connected to a carbazolyl group through an alkyl group. A group of electropolymerizable fluorescent sensing materials and the application of such materials in the fluorescence or electrochemical detection of metal ions. Background technique [0002] The detection of metal ions is closely related to human life. On the one hand, with the rapid development of industrialization, environmental pollution is becoming more and more serious. Especially heavy metal ions, because they cannot be decomposed by microorganisms and easily deposited in the soil, have become a class of substances that seriously threaten human health. For example, the Minamata disease and bone pain disease that appeared in Japan in the 1950s were caused by mercury pollution and cadmiu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D401/14C07D471/04C08G61/12G01N21/64C25D9/02
Inventor 张明李鹏赵阳吉长印马洪伟
Owner JILIN UNIV
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