A disc-shaped fluorine ion fluorescence probe and a preparing method thereof

A technology of fluorescent probes and fluorine ions, applied in the field of fluorescent probes, can solve problems such as complex synthesis, poor selectivity, and long response time, and achieve high quantum yield, excellent luminescent performance, and rapid effect

Active Publication Date: 2017-12-19
HENAN INST OF ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there is a lot of research work in this field, the existing fluoride ion fluoresce

Method used

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  • A disc-shaped fluorine ion fluorescence probe and a preparing method thereof
  • A disc-shaped fluorine ion fluorescence probe and a preparing method thereof
  • A disc-shaped fluorine ion fluorescence probe and a preparing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The steps of the preparation method of the discoid fluoride ion fluorescent probe of the present embodiment are as follows:

[0040] (1) put R 2 The compound I that is chlorine atom drops in the solvent toluene, heats reflux and makes compound (I) dissolve completely, forms the compound (I) toluene solution that molar concentration is 1mol / L; Compound (I) structural formula is as follows:

[0041]

[0042] (2) Under the condition of heating to reflux (110°C), the R with a molar concentration of 0.8mol / L 1 -NH 2 The toluene solution was slowly added dropwise to the compound (I) toluene solution, and the compound (I) and R 1 -NH 2 The feeding molar ratio is 1:0.95, the dropping rate is 10 drops / min, R 1 -NH 2 After the toluene solution has been added dropwise, continue heating to reflux (110° C.) for 3 hours, R 1 for where R 3 is isopropyl;

[0043] (3) Cool to room temperature after stopping heating, remove toluene by rotary evaporation, use sherwood oil: me...

Embodiment 2

[0050] The steps of the preparation method of the discoid fluoride ion fluorescent probe of the present embodiment are as follows:

[0051] (1) put R 2 The compound (I) that is a hydrogen atom is dropped in solvent toluene, and heating reflux makes compound (I) dissolve completely, and the formation molar concentration is the compound (I) toluene solution of 0.5mol / L; The structural formula of compound (I) is as follows:

[0052]

[0053] (2) Under the condition of heating to reflux (110°C), the R with a molar concentration of 0.8mol / L 1 -NH 2 The toluene solution was slowly added dropwise to the compound (I) toluene solution, and the compound (I) and R 1 -NH 2 The feeding molar ratio is 1:0.90, the dropping rate is 30 drops / min, R 1 -NH 2 After the toluene solution was added dropwise, continue to reflux (110° C.) for 6 hours, R 1 for where R 3 is cyclohexyl;

[0054] (3) After stopping heating, cool to room temperature, remove toluene by rotary evaporation, use p...

Embodiment 3

[0060] The steps of the preparation method of the discoid fluoride ion fluorescent probe of the present embodiment are as follows:

[0061] (1) put R 2 Be that the compound (I) of bromine atom drops in the solvent toluene, heat reflux and make compound (I) dissolve completely, form the compound (I) toluene solution that molar concentration is 0.8mol / L; The structural formula of compound (I) is as follows:

[0062]

[0063] (2) Under the condition of heating to reflux (110°C), add R with a molar concentration of 0.3mol / L 1 -NH 2 The toluene solution was slowly added dropwise to the compound (I) toluene solution, and the compound (I) and R 1 -NH 2 The feeding molar ratio is 1:0.85, the dropping rate is 20 drops / min, R 1 -NH 2 After the toluene solution has been added dropwise, continue to reflux (110° C.) for 4 hours, R 1 for where R 3 is n-octyl;

[0064] (3) Cool to room temperature after stopping heating, remove toluene by rotary evaporation, use petroleum ether:...

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Abstract

A disc-shaped fluorine ion fluorescence probe and a preparing method thereof are disclosed. The structure of the probe is shown as a formula (III), wherein R1 is separately independently selected from a structure shown in the specification or another structure shown in the specification, R2 is separately independently selected from hydrogen, chlorine or bromine, and R3 is separately independently selected from C3-C8 direct-chain alkyl chains, branched alkyl chains or naphthenic chains. The probe has two detection mechanisms, namely an electron transfer function between perylene diimide units and fluorine ions and a function between the fluorine ions and Si-O bonds, and therefore the probe can detect fluorine ions more rapidly and more sensitively, can exclude interferences of other ions and can selectively detect the fluorine ions. The probe is provided with the three perylene diimide units, and introduced hexahedral silsesquioxane units can effectively increase a distance among the perylene diimide units, and therefore a higher quantum yield in an aqueous solution can be achieved, the probe has excellent luminescence properties and fluorine ion detection is more sensitive.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and in particular relates to a disc-shaped fluoride ion fluorescent probe compound and a preparation method thereof. Background technique [0002] Fluorine is a widely distributed non-metallic element, and its content in the earth’s crust ranks 13th. Fluorine in nature is mainly composed of fluorite (CaF 2 ), cryolite (Na 3 AlF 6 ) form exists. More importantly, fluorine is an important trace element in the human body, and its content is relatively high in teeth and bones. Intake of low levels of fluorine is beneficial to the human body, can protect teeth, treat osteoporosis and other symptoms. However, excessive fluorine intake can cause poisoning, damage human health, induce various diseases, and cause environmental pollution. At present, there are three main types of fluorosis: (1) drinking water type fluorosis, long-term drinking of water with excessive fluorine content; (2) c...

Claims

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Application Information

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IPC IPC(8): C07F7/21C09K11/06G01N21/64
CPCC07F7/21C09K11/06C09K2211/1096G01N21/6428
Inventor 于翔王娜李玥王延伟辛长征
Owner HENAN INST OF ENG
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