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A kind of preparation method of bopyin fluorescent dye responsive to trifluoroacetic acid
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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: 2022-08-09
CHINA THREE GORGES UNIV
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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.
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Embodiment 1
[0027] Compound 1 (298 mg, 1 mmol) was weighed, 30.00 mL of toluene was mixed and dissolved, p-dimethylaminobenzaldehyde (149 mg, 1 mmol), piperidine (0.09 ml, 1 mmol), acetic acid (0.06 ml, 1 mmol) were added in sequence, The reaction was completed by heating and stirring at 100° C. for 12 hours, 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] Compound 1 (298mg, 1mmol) was weighed, 30.00mL of toluene was mixed and dissolved, and p-dimethylaminobenzaldehyde (298mg, 2mmol), piperidine (0.09ml, 1mmol), acetic acid (0.06ml, 1mmol) were added in sequence, The reaction was completed by heating and stirring at 100° C. for 10 hours, 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 was increased by a factor of 2, the yield was increased by 5.3%, and the reaction time was shortened by 2 hours.
Embodiment 3
[0032] Compound 1 (298mg, 1mmol) was weighed, 30.00mL of toluene was mixed and dissolved, p-dimethylaminobenzaldehyde (298mg, 2mmol), piperidine (0.18ml, 2mmol), acetic acid (0.12ml, 2mmol) were added successively, The reaction was completed by heating and stirring at 100° C. for 10 hours, 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 the amount of piperidine, acetic acid was increased by a factor of 2 corresponding to Example 2, the yield did not change significantly.
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Abstract
The invention discloses a preparation method of p-trifluoroacetic acid-responsive BOPYIN fluorescent dye. The dye uses p-dimethylaminobenzaldehyde and heptafluoroboron fluorescent dye as raw materials, and is condensed in one step under the catalytic action of piperidine and acetic acid. The synthesis method is simple, the separation and purification are convenient, and the yield is high. Fluorescent dyes that can distinguish the amount of trifluoroacetic acid species by different fluorescence intensities in a dichloromethane liquid environment. The synthesis of the invention takes the seven-membered fluoroboron compound as the center, adds a carbon-carbon double bond to the methyl group of the seven-membered ring double bond and is conjugated with the aromatic ring, so that the absorption and emission spectra are red-shifted. Substituted with dimethylamino, the fluorescence emission wavelength reaches 717 nm in DMSO solvent, and the substituted compound has obvious response to trifluoroacetic acid, and the compound is relatively stable in neutral and alkaline solutions, indicating that the compound has application as an acid pH probe Prospects.
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 by inhalation, oral administration, or absorption through the skin. Able to irritate human tissue and skin, with only mild toxicity, but enrichment in stagnant surface water can affect agricultural and aquatic systems. Trifluoroacetic acid is decomposed into fluoroform and carbon dioxide in the presence of aniline. Carbon dioxide has a great impact on the greenhouse effect. At present, the measurement method and measurement data of trace THA concentration in the environment in my country are relatively blank. [0003] The commonly used method for detecting concentration is chromatography, while TFA cannot be directly analyzed and determined by chromatography. In strong acid medium, CF 3 COO - Nucleophilic substitution reaction with dimethyl sulfate (DMS) can occur. TFA can be fully...
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