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Preparation method of BOPYIN fluorescent dye responding to trifluoroacetic acid

A fluorescent dye and trifluoroacetic acid technology, applied in the field of BOPYIN fluorescent dye preparation, can solve the problems of long reaction time, low sensitivity, and long time consumption, and achieve the effects of easy control of reaction conditions, simple product purification, and mild reaction conditions

Active Publication Date: 2021-07-09
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Irritating to human tissue and skin, only mildly toxic, but accumulation in stagnant surface waters can affect agricultural and aquatic systems
Trifluoroacetic acid decomposes into fluoroform and carbon dioxide in the presence of aniline. Carbon dioxide has a great impact on the greenhouse effect. At present, the determination methods and data of trace THA concentrations in the environment in my country are relatively blank.
Headspace sampling can be used to enrich MTFA vapor for analysis, but the method of enriching MTFA by headspace sampling is more complicated and time-consuming.
[0004] Most of the existing domestic and foreign methods of using different fluorescent probes to detect TFA have defects such as complex operation methods, long reaction time, and low sensitivity.

Method used

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  • Preparation method of BOPYIN fluorescent dye responding to trifluoroacetic acid
  • Preparation method of BOPYIN fluorescent dye responding to trifluoroacetic acid
  • Preparation method of BOPYIN fluorescent dye responding to trifluoroacetic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Weigh compound 1 (298mg, 1mmol), take 30.00mL toluene, mix and dissolve, then add p-dimethylaminobenzaldehyde (149mg, 1mmol), piperidine (0.09ml, 1mmol), acetic acid (0.06ml, 1mmol), After heating and stirring at 100°C for 12 hours, the reaction was complete. The reactant was rotary evaporated and purified by column chromatography to obtain a dark green solid I (134.6 mg), with a yield of 31.3%.

[0028]

Embodiment 2

[0030] Weigh compound 1 (298mg, 1mmol), take 30.00mL toluene, mix and dissolve, then add p-dimethylaminobenzaldehyde (298mg, 2mmol), piperidine (0.09ml, 1mmol), acetic acid (0.06ml, 1mmol), After heating and stirring at 100°C for 10 hours, the reaction was complete. The reactant was rotary evaporated and purified by column chromatography to obtain a dark green solid I (157.4 mg), with a yield of 36.6%. When the amount of p-dimethylaminobenzaldehyde increased by 2 times equivalent to that of Example 1, the yield increased by 5.3%, and the reaction time was shortened by 2 hours.

Embodiment 3

[0032] Weigh compound 1 (298mg, 1mmol), take 30.00mL toluene, mix and dissolve, then add p-dimethylaminobenzaldehyde (298mg, 2mmol), piperidine (0.18ml, 2mmol), acetic acid (0.12ml, 2mmol), After heating and stirring at 100°C for 10 hours, the reaction was complete. The reactant was rotary evaporated and purified by column chromatography to obtain a dark green solid I (160.4 mg), with a yield of 37.3%. When piperidine, the amount of acetic acid is equivalent to example 2 when increasing 2 times, productive rate has no obvious change.

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Abstract

The invention discloses a preparation method of a BOPYIN fluorescent dye responsive to trifluoroacetic acid. The dye is prepared by one-step condensation of p-dimethylaminobenzaldehyde and a seven-membered fluorine boron fluorescent dye serving as raw materials under the catalytic action of piperidine and acetic acid; and the method is simple in synthesis, convenient for separation and purification and high in yield. The fluorescent dye can distinguish the molar amounts of trifluoroacetic acid according to different fluorescence intensities in a dichloromethane liquid environment. According to the invention, a seven-membered fluorine boron compound is taken as a center, and a carbon-carbon double bond is added on a methyl group of the seven-membered ring double bond for conjugation with an aromatic ring, so absorption and emission spectrums undergo red shift; the fluorescent dye is substituted by a dimethylamino group and has fluorescent emission wavelength of 717 nm in a DMSO solvent; and a substituted compound has obvious response to trifluoroacetic acid and is relatively stable in neutral and alkaline solutions, so the compound has application prospects as an acid pH probe.

Description

technical field [0001] The invention discloses a preparation method of BOPYIN fluorescent dye responsive to trifluoroacetic acid. Background technique [0002] Trifluoroacetic acid is harmful if inhaled, taken orally, or absorbed through the skin. Irritating to human tissue and skin, only mildly toxic, but accumulation in stagnant surface waters can affect agricultural and aquatic systems. Trifluoroacetic acid decomposes into fluoroform and carbon dioxide in the presence of aniline. Carbon dioxide has a great impact on the greenhouse effect. At present, the determination methods and data of trace THA concentrations in the environment in my country are relatively blank. [0003] Chromatography is commonly used to detect concentration, but TFA cannot be directly analyzed and determined by chromatography. In strong acid medium, CF 3 COO - It can undergo nucleophilic substitution reaction with dimethyl sulfate (DMS). TFA can be fully dissociated in sulfuric acid reaction me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09B23/12C09K11/06G01N21/64G01N21/33
CPCC07F5/022C09B23/12C09K11/06G01N21/6428G01N21/33G01N2021/6443
Inventor 张诺诺袁晓慧粟鹏晏佳莹文柳
Owner CHINA THREE GORGES UNIV
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