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A kind of fluorescent probe for detecting ethylene and its preparation method and application

A fluorescent probe and reaction technology, applied in the field of fluorescent probes, can solve the problems of poor biocompatibility and low sensitivity, and achieve the effects of good selectivity, high sensitivity, and easy availability of raw materials

Active Publication Date: 2022-05-13
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problems of low sensitivity and poor biocompatibility of existing ethylene probes, the present invention provides a fluorescent probe with high sensitivity, low detection limit and good specificity that can be used to detect ethylene in plants and environmental samples

Method used

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  • A kind of fluorescent probe for detecting ethylene and its preparation method and application
  • A kind of fluorescent probe for detecting ethylene and its preparation method and application
  • A kind of fluorescent probe for detecting ethylene and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Synthesis of embodiment 1 fluorescent probe CEP-1

[0030] N-coumarinoxyamide (21.9 mg, 0.1 mmol), dichloro(pentamethylcyclopentadienyl) rhodium (III) dimer (34.0 mg, 0.055 mmol) and potassium carbonate (13.8 mg , 0.1 mmol) was added to 2 mL of acetonitrile solvent. Under the protection of nitrogen, the mixture was stirred and reacted for 8 h at 25°C at room temperature, then filtered and washed with ether to obtain the target probe compound CEP-1 with a yield of 95%. 1 H NMR (500MHz, methanol-d 4 )δ7.83(d, J=9.3Hz, 1H), 7.20(d, J=8.2Hz, 1H), 6.90-6.69(m, 1H), 6.15(d, J=9.4Hz, 1H), 2.22( s, 3H), 1.66 (s, 15H); 13C NMR (125MHz, methanol-d 4 )δ170.5, 165.2, 164.2, 159.2, 145.7, 125.8, 113.8, 110.0, 105.1, 96.7, 21.42, 8.3; ESI-HRMS m / z: 456.0696 ([M+H] + ).

Embodiment 2

[0031] Fluorescence intensity of fluorescent probe CEP-1 under different volumes of ethylene in embodiment 2

[0032] 10, 20, 50, 100, 150, 200 and 250 μL volumes of ethylene were added to the CEP-1 probe solution (100 μM) through a gas syringe, and the fluorescence detection (λ ex =365nm,λ em =460nm), detect the fluorescence intensity in each system, and make a curve with the volume of relative fluorescence intensity-ethylene, such as figure 1 As shown, the minimum detection limit of the probe to ethylene was finally obtained as 52ppb.

Embodiment 3

[0033] The selectivity of embodiment 3 ethylene probes

[0034] Olefins in plants or the environment may interfere with the detection of ethylene, so it is necessary to determine whether the synthetic ethylene fluorescent probe has good selectivity in recognizing ethylene.

[0035] Take 9 sample vials, add 100 μM CEP-1 fluorescent probe solution, 1 sample vial is used as blank control, and add 1 mL of ethylene (concentration is about 2 mM), 6 mM farnesol, 6 mM citronellol respectively to 9 sample vials , 6mM dipentene, 6mM myrcene, 6mMα-pinene and 6mM terpinolene, after reacting for 1min, record the fluorescence intensity of different reaction systems, the results are as follows figure 2 shown. Depend on figure 2 It can be seen that the probe solution only responds to ethylene, and the fluorescence intensity increases nearly 50 times, while the fluorescence intensity of other reaction systems does not change significantly, which shows that the fluorescent probe is highly s...

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Abstract

The present invention provides a fluorescent probe compound and its preparation and application, which has the following structural formula: In the formula, R 1 , R 2 , R 3 and R 4 each independently selected from hydrogen, halogen, hydroxyl, nitro, difluoromethyl, trifluoromethyl, C 1‑6 Alkyl, C 1‑6 Alkoxy, and C substituted by 1-3 halogen 1‑6 Alkyl and C substituted by 1-3 halogen 1‑6 of alkoxy. The fluorescent probe provided by the invention can be used to detect ethylene, has the advantages of high sensitivity, strong selectivity, etc., and has good biocompatibility, can detect ethylene in plants and environmental samples, and has high application value.

Description

technical field [0001] The invention relates to the synthesis of an ethylene fluorescent probe compound and its application as a molecular probe in plants and environmental samples, belonging to the technical field of fluorescent probes. Background technique [0002] Ethylene is an important gaseous plant hormone, which is involved in the control of various growth and development processes such as seed germination, cell elongation, fruit ripening, and seed dispersal. In addition, ethylene plays an important role in the defense against pathogens and in the immune response to external stressors. In the field of fruit and vegetable storage, the ethylene concentration needs to be controlled within different ranges according to different storage types. Usually in the ripening room, the ethylene concentration is required to be maintained between 10 and 200ppm; in the storage room, the ethylene concentration is required to be less than 1ppm. Therefore, detection and monitoring of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06G01N21/64
CPCC07F15/0073C09K11/06G01N21/6428C09K2211/185C09K2211/1088
Inventor 叶永浩陈议亮严威
Owner NANJING AGRICULTURAL UNIVERSITY
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