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A benzamide derivative fluorescent probe for identifying and detecting ferric ions and mercury ions and its preparation method and application

A technology of fluorescent probe and benzamide, applied in the field of fluorescent probe, can solve the problems of poor water solubility and low sensitivity, and achieve the effects of simple method, low cost and good selectivity

Inactive Publication Date: 2018-12-11
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the problems of low sensitivity or poor water solubility of existing fluorescent probes, the object of the present invention is to provide a fluorescent probe for benzamide derivatives that recognize and detect ferric ions and mercury ions. The benzamide derivatives The fluorescent probes have different responses to Fe(Ⅲ) and Hg(Ⅱ), which are caused by the reaction of benzoic acid derivatives with 3,6-dithia-1,8-octanediamine under the action of EDCI and HOBt. acquired

Method used

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  • A benzamide derivative fluorescent probe for identifying and detecting ferric ions and mercury ions and its preparation method and application
  • A benzamide derivative fluorescent probe for identifying and detecting ferric ions and mercury ions and its preparation method and application
  • A benzamide derivative fluorescent probe for identifying and detecting ferric ions and mercury ions and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Preparation of 3,6-dithia-1,8-octanediamine

[0045] Dissolve 43mmol sodium ethoxide in 40mL absolute ethanol, cool to 10°C, add 24mmol cysteamine hydrochloride to the above solution under nitrogen protection, react for 1 hour, add 10mmol 1,2-dibromoethane, and react overnight at room temperature. After the reaction was completed, filter, spin evaporate, add diluted NaOH solution, and refrigerate overnight. Next, CH 2 Cl 2 Extracted, washed with water three times, dried over anhydrous sodium sulfate, rotary evaporated, and vacuum dried to obtain 3,6-dithia-1,8-octanediamine, weighing 1.2623g, yield 70.02%, the product structural formula is 1 H NMR, 13 Confirmed by CNMR and HRMS.

[0046] 1 H NMR (600MHz, CDCl 3 ):2.89(t, J=6.3Hz, 2H), 2.74(s, 2H), 2.66(t, J=6.3Hz, 2H); 13 C NMR (147MHz, CD 3 OD): 41.53, 35.45, 32.71; HRMS (ESI) m / z calcd for C 6 h 16 N 2 S 2 ,[M+H] + 181.08, found 181.0810.

Embodiment 2

[0047] Synthesis and identification data of embodiment 2 benzamide derivative fluorescent probe 1a

[0048] Dissolve 5.16mmol of benzoic acid in 50mL of dichloromethane, add EDCI (5mmol) and HOBt (5mmol) under stirring and cooling with ice water, stir and activate for 0.5-1h. Then 2 mmol of 3,6-dithia-1,8-octanediamine (obtained from Example 1) was added, and stirred overnight at room temperature. rotary steaming, CH 2 Cl 2 Extraction, successively with saturated NaHCO 3 , saturated NaCl, the organic phase was washed with water, and dried over anhydrous sodium sulfate. Rotary evaporation, the thick product is purified by silica column chromatography, and vacuum-dried to obtain fluorescent probe 1a, weighing 0.4913g, yield 63.3%, and the product structural formula is 1 H NMR, 13 Confirmed by C NMR and HRMS.

[0049] 1 H NMR (600MHz, DMSO-d 6 ):12.48(s, J=6.24Hz, 2H), 2.73(s, 4H), 2.66(t, J=6.24Hz, 4H); 13 C NMR (150MHz, CDCl 3 ):167.54,134.08,131.38,128.37,126.79,39.1...

Embodiment 3

[0052] Example 3 Synthesis and identification data of benzamide derivative fluorescent probe 1b

[0053] Dissolve 2.8mmol salicylic acid in 50mL dichloromethane, add EDCI (4mmol) and HOBt (4mmol) under stirring and cooling with ice water, stir and activate for 0.5-1h. Then 1 mmol of 3,6-dithia-1,8-octanediamine (obtained from Example 1) was added, and stirred overnight at room temperature. rotary steaming, CH 2 Cl 2 Extraction, successively with saturated NaHCO 3 , saturated NaCl, the organic phase was washed with water, and dried over anhydrous sodium sulfate. Rotary evaporation, the crude product is purified by silica column chromatography, and vacuum-dried to obtain fluorescent probe 1b with a yield of 46.9%, and the product structural formula is as follows: 1 H NMR, 13 Confirmed by C NMR and HRMS.

[0054] 1 H NMR (600MHz, DMSO-d 6 ):12.48(s,2H),8.95(t,J=5.6Hz,2H),7.82(d,J=7.9Hz,2H),7.39(t,J=8.1Hz,2H),6.93–6.85(m ,4H),3.48(q,J=6.6Hz,4H),2.78(s,4H),2.74(t,J=7.1Hz,4...

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Abstract

The invention discloses seven benzoyl amide derivative fluorescence probes, a preparation method and an application thereof. The benzoyl amide derivative fluorescence probes provided by the invention are prepared according to the following steps: taking benzoyl amide derivatives as a fluorophore and taking 3,6-dithio-1,8-diaminooctane as a main identifying part for metal ion, thereby compounding the benzoyl amide derivative fluorescence probes for detecting Fe3+ and Hg2+. The method is simple and the cost is low. The fluorescence probes 1b and 1c respectively have excellent selectivity to Fe3+ and Hg2+ and high determining sensitivity to Fe3+ and Hg2+, can qualitatively and quantitatively detect Fe3+ and Hg2+, can be used for identifying and detecting Fe (III) and Hg (II) in water and have excellent application prospect.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes for detecting metal ions, in particular, it relates to a method for identifying and detecting Fe 3+ and Hg 2+ The benzamide derivative fluorescent probe and its preparation method and application. Background technique [0002] Metal ions widely present in nature play important roles in environmental, medical, biological, and chemical sciences. Among them, heavy metals and transition metal ions play a very important role in life activities and are closely related to human health. Low levels of certain transition metal ions in the living body can cause various diseases. On the contrary, excessive concentrations not only cause environmental damage Destruction, but also a great threat to human health. [0003] Mercury ions have long been regarded as one of the most toxic metal ions. Due to its enrichment and highly toxic characteristics, mercury can cause serious health problems such as...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/42C07C319/20C07C319/28C09K11/06G01N21/64
CPCC07C319/20C07C319/28C07C323/42C09K11/06C09K2211/1007G01N21/6486
Inventor 何汉平吕贺红常钢张修华王升富
Owner HUBEI UNIV