Isoquinoline-based ratio-dependent detecting probe for fluoride ions and preparation method and application of isoquinoline-based ratio-dependent detecting probe

A technology for detecting probes and fluoride ions, applied in the field of chemical analysis and detection, can solve the problems affecting the accuracy of detection results, single wavelength, etc., and achieve the effects of low detection limit, sensitive identification and strong specificity

Pending Publication Date: 2019-11-01
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the traditional fluorescent sensors rely on the change of fluorescence intensity to identify and detect fluorine ions, and most of the fluorescent probes are of a single wavelength, which are easily interfered by the outside world and background signals, thus affecting the accuracy of the detection results

Method used

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  • Isoquinoline-based ratio-dependent detecting probe for fluoride ions and preparation method and application of isoquinoline-based ratio-dependent detecting probe
  • Isoquinoline-based ratio-dependent detecting probe for fluoride ions and preparation method and application of isoquinoline-based ratio-dependent detecting probe
  • Isoquinoline-based ratio-dependent detecting probe for fluoride ions and preparation method and application of isoquinoline-based ratio-dependent detecting probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of fluorescent probes of the present invention

[0042] The preparation route of fluorescent probe of the present invention is as follows:

[0043]

[0044] Dissolve compound 1a and o-alkynyl aldehyde compound 2a in 1,2-dichloroethane, the ratio of the amount of compound 1a and 2a is 1:1, add silver nitrate, stir at 80 degrees for 12 After the reaction was completed, saturated saline was added, then extracted with chloroform, dried over anhydrous sodium sulfate for 1 hour, filtered to remove the sodium sulfate solid, the solution was rotary evaporated under reduced pressure, and the crude product was obtained by column chromatography as a yellow solid fluorescent probe compound Ia. That is, the fluoride ion detection probe represented by the formula (I), the yield is 66%.

[0045] Ia, yellow solid, IR(KBr)cm -1 3441, 2927, 2853, 2048, 2025, 1704, 1635, 1506, 1383, 1256, 1179, 1110, 1028, 916, 826, 703, 572. 1 H NMR (500MHz, CDCl 3)δ10.675(s, 1H), 8.580(...

Embodiment 2

[0047]

[0048] Compound 1b and o-alkynyl aldehyde compound 2b are dissolved in a solvent, the ratio of the amount of the compound 1b and 2b is 1:1, and silver trifluoromethanesulfonate is added, stirred at 70 degrees for 10 hours, and the reaction After completion, add saturated saline, then extract with chloroform, dry over anhydrous sodium sulfate for 1 hour, filter and remove the sodium sulfate solid, and the solution is rotary evaporated under reduced pressure, and the crude product is obtained by column chromatography as a yellow solid fluorescent probe compound Ib, i.e. the formula ( The fluoride ion detection probe shown in I) has a yield of 50%.

Embodiment 3

[0050]

[0051] Dissolve compound 1c and o-alkynyl aldehyde compound 2b in a solvent, the ratio of the amount of compounds 1c and 2b is 1:1, add cuprous iodide, stir at 70 degrees for 10 hours, after the reaction is completed Add saturated saline, then extract with chloroform, dry over anhydrous sodium sulfate for 1 hour, filter to remove the sodium sulfate solid, and rotate the solution under reduced pressure, and the crude product is column chromatographed to obtain yellow solid fluorescent probe compound Ic, i.e. formula (I) The fluoride ion detection probe shown has a yield of 50%.

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Abstract

The invention discloses an isoquinoline-based ratio-dependent detecting probe for fluoride ions and a preparation method and application of the isoquinoline-based ratio-dependent detecting probe. Thefluorescent probe has a structure as shown in a formula I, o-alkynyl aldehyde is adopted as a raw material of the probe, and a reaction is performed between the raw material and a benzylamine derivative so as to obtain the probe. The probe has stable optical performance, high detection sensitivity to fluoride ions, a lower limit of detection, a detection limit of 3.79 nM and a response range of 0.2-10 [mu]M; good selectivity is achieved, no responses to chloride ions, bromide ions, iodate ions, periodate ions, nitrate ions, nitrite ions, acetate ions, carbonate ions, sulfate ions, sulfite ionsand other negative ions are generated; and synthesis is simple, the conditions are mild, and the yield is high. The fluorescent molecular probe has practical application values in biochemistry and environmental chemistry and other fields, especially detection of fluoride ions in water.

Description

technical field [0001] The invention relates to the technical field of chemical analysis and detection, in particular to a ratiometric fluoride ion detection probe based on isoquinoline and its preparation method and application. Background technique [0002] Anions are important elements to maintain biological life activities, and the design and synthesis of new anion fluorescent detection probes is an important research field in the discipline of chemical analysis. Fluoride ion is considered as a trace element necessary for the growth of teeth and human body, it can protect teeth and prevent osteoporosis. Both excess and deficiency may lead to certain diseases. Excessive intake of fluorine-containing compounds can cause serious diseases, such as fluorosis, urinary stones, tumors, organ lesions, and skeletal fluorosis. The United States Environmental Protection Agency requires that the maximum fluoride ion concentration in healthy drinking water is 4ppm (211μM). Therefore,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F7/18G01N21/64
CPCC07F7/1804C07F7/1892C09K11/06C09K2211/1007C09K2211/1029G01N21/643
Inventor 赵云辉周智华唐子龙刘立华刘俪喆
Owner HUNAN UNIV OF SCI & TECH
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