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Fluorescent probe capable of simultaneously recognizing H2S and HSO3 <-> through near-infrared emission and application thereof

An HSO3-, fluorescent probe technology, applied in luminescent materials, fluorescence/phosphorescence, material excitation analysis, etc., can solve the problems of few fluorescent probes, complex synthesis, short emission wavelength, etc., to achieve easy separation and purification, and simple synthesis process , the effect of good sensitivity

Active Publication Date: 2021-01-01
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it is currently possible to simultaneously identify H 2 S and HSO 3 - Relatively few fluorescent probes have been reported
Analyst (2014), 139, 3373 and Sensors & Actuators: B. Chemical (2018), 277, 647-653 although the two documents can be used for HSO 3 - Double recognition with HS-, but the synthesis is complicated, it cannot emit near-infrared, and it cannot be recognized in food samples
Dyes and Pigments (2019), 160, 757-764, although HSO can be detected in food samples 3 - , but the synthesis is complicated, the emission wavelength is short, and the interference of background fluorescence cannot be ruled out
RSC Advances (2016), 6, 85529-85537, although it can emit near-infrared, but the synthesis is complicated, and HSO cannot be detected in food samples 3 - and H 2 S
It can be seen that the existing reported fluorescent probes have certain limitations, so the development and synthesis are simple, can emit near infrared, and can detect HSO in water samples, cells and food samples 3 - and H 2 The fluorescent probe of S is of great significance

Method used

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  • Fluorescent probe capable of simultaneously recognizing H2S and HSO3 &lt;-&gt; through near-infrared emission and application thereof
  • Fluorescent probe capable of simultaneously recognizing H2S and HSO3 &lt;-&gt; through near-infrared emission and application thereof
  • Fluorescent probe capable of simultaneously recognizing H2S and HSO3 &lt;-&gt; through near-infrared emission and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The specific synthesis steps of fluorescent probe L are as follows:

[0038]

[0039] Compound 1 (374.4 mg, 1.0 mmol), triethylamine (101.0 mg, 1.0 mmol) was dissolved in dry CH 2 Cl 2 2,4-Dinitrobenzenesulfonyl chloride (266.6 mg, 1.0 mmol) was slowly added dropwise under stirring in an ice bath, and then stirred at room temperature for 8 hours. After the reaction was completed, the obtained crude product was purified by thin-layer column chromatography, using EA:PE=1:10~1:3 (v / v) as gradient elution to obtain 302.07 mg of probe L, with a yield of 50%.

[0040] 1 H NMR (400MHz, DMSO-d 6 )δ9.15(d, J=2.2Hz, 1H), 8.70(dd, J=8.6, 2.0Hz, 1H), 8.42(d, J=8.7Hz, 1H), 8.05(d, J=9.3Hz, 1H), 7.93(d, J=15.9Hz, 1H), 6.95(d, J=15.9Hz, 1H), 6.87(d, J=7.4Hz, 1H), 6.31(d, J=2.1Hz, 1H) ,3.39(dd,J=14.0,7.0Hz,4H),1.69(s,6H),1.03(t,J=7.0Hz,6H).

[0041] 13 C NMR (101MHz, DMSO-d 6 )δ177.87, 140.51, 134.07, 131.12, 129.09, 128.14, 112.38, 44.99, 40.56, 40.35, 40.14, 39.93, 39.72, ...

Embodiment 2

[0044] The specific synthesis steps of fluorescent probe L are as follows:

[0045] Compound 1 (374.4 mg, 1.0 mmol), triethylamine (202.0 mg, 2 mmol) was dissolved in dry CH 2 Cl 2 2,4-Dinitrobenzenesulfonyl chloride (399.9 mg, 1.5 mmol) was slowly added dropwise under stirring in an ice bath, followed by stirring at room temperature for 16 hours. After the end, the crude product was spin-dried to obtain the crude product. The crude product was purified by thin-layer column chromatography, and 392.67 mg of probe L was obtained with a yield of 65% using EA:PE=1:10~1:3 (v / v) for gradient elution. . The fluorescent probe L of this embodiment 1 H NMR spectrum as figure 1 , 13 C NMR spectrum as figure 2 , high-resolution mass spectrometry such as image 3 shown.

Embodiment 3

[0047] The specific synthesis steps of fluorescent probe L are as follows:

[0048] Compound 1 (374.4 mg, 1.0 mmol), triethylamine (303.0 mg, 3 mmol), dissolved in dry CH 2 Cl 2 2,4-Dinitrobenzenesulfonyl chloride (533.2mg, 2mmol) was slowly added dropwise under stirring in an ice bath, and then stirred at room temperature for 24 hours. After the reaction was completed, the solvent was spin-dried, and the obtained crude product was purified by thin-layer column chromatography, and EA:PE=1:0~1:3 (v / v) was used as gradient elution to obtain 362.48mg of probe L, with a yield of 60% . The fluorescent probe L of this embodiment 1 H NMR spectrum as figure 1 , 13 C NMR spectrum as figure 2 , high-resolution mass spectrometry such as image 3 shown.

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Abstract

The invention discloses a fluorescent probe capable of simultaneously recognizing H2S and HSO3<-> through near-infrared emission and application of the fluorescent probe. The structural formula of thefluorescent probe L is shown in the specification; the fluorescent probe L with a D-pi-A structure and capable of simultaneously recognizing H2S and HSO3<-> can be prepared through simple and mild reaction; the fluorescent probe L is simple in synthesis method, can simultaneously recognize H2S and HSO3<-> in a buffer solution with the EtOH: HEPES ratio of 2: 8 (v / v, pH=7.4), has high selectivityand good sensitivity, and can be applied to detection of H2S in actual water samples, cells and red wine and detection of HSO3<-> in white sugar samples.

Description

technical field [0001] The invention relates to a kind of donor-π-acceptor (D-π-A) structure, near-infrared emission recognition H 2 S, HSO 3 - Fluorescent probes and their synthesis methods and applications. Background technique [0002] Hydrogen sulfide (H 2 S) has a very strong smell of rotten eggs and is considered to be the third gaseous signal molecule besides carbon monoxide (CO) and nitric oxide (NO). Several studies have shown that H 2 S, as a bioregulator and gaseous signal transduction factor, plays an important pathological role in ischemic heart disease, atherosclerosis, hypertension, Down's syndrome and various other cardiovascular diseases. h 2 S is also a common component of wine fermentation, which has a negative impact on the quality of wine, leading to a decline in the quality of wine, which may bring huge economic losses, and may also face food safety issues. due to H 2 The decomposition rate of S is fast, which will lead to fluctuations in the co...

Claims

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Application Information

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IPC IPC(8): C07D307/68C09K11/06G01N21/64
CPCC07D307/68C09K11/06G01N21/643G01N21/6428G01N2021/6432C09K2211/1088C09K2211/1007C09K2211/1014Y02A50/30
Inventor 曲秀莉赵洪雷李秋莹陈琳杨雅馨钟克利高雪刘秀英汤立军
Owner BOHAI UNIV
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