Preparation and application of optical switch fluorescence molecules with hydrogen sulfide recognition function

A technology of fluorescent molecules and optical switches is applied in the field of preparation of fluorescent molecules of optical switches to achieve the effects of good selectivity and strong anti-interference ability of other molecules.

Active Publication Date: 2017-12-22
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although a large number of Cys/Hcy, GSH and H 2 S fluorescent probe

Method used

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  • Preparation and application of optical switch fluorescence molecules with hydrogen sulfide recognition function
  • Preparation and application of optical switch fluorescence molecules with hydrogen sulfide recognition function
  • Preparation and application of optical switch fluorescence molecules with hydrogen sulfide recognition function

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] A preparation of an optical switch molecule with a hydrogen sulfide recognition function, comprising the following steps:

[0043](1) Preparation of the compound of formula II: under the protection of an inert gas, add 2-methylquinoline and 2-bromoethanol into the reaction flask, react at 140°C for 1~3h, cool down to room temperature after the reaction, dissolve with methanol, and Precipitate with ethyl acetate and filter with suction to obtain the compound of formula II; wherein the molar ratio of 2-methylquinoline to 2-bromoethanol is 1:1-1:2.

[0044] (2) Preparation of the compound of formula III: under the protection of inert gas, add the compound of formula II and malononitrile into the reaction flask, use ethanol as the solvent, add sodium ethylate dropwise under ice bath, react for 1~3h, and react at room temperature for 4~ After 18 hours, after the reaction was completed, suction filtered to obtain a yellow filter cake, which was washed with ethanol to obtain t...

Embodiment 2

[0049] Embodiment 2: detection experiment of hydrogen sulfide.

[0050] Take 15 5 mL sample vials, add 3 mL of the solution prepared by the molecule of formula I obtained in Example 1 (the concentration of the molecule is 10 μM, V tetrahydrofuran: V water = 90: 10), and then respectively add the concentration of [ HS - ] = 0(a), 1.0×10 -3 mol / L(b), 2.0×10 -3 mol / L(c), 5.0×10 -3 mol / L(d), 1×10 -2 mol / L(e), 2.0×10 - 2 mol / L(f), 3.0×10 -2 mol / L (g), 4×10 -2 mol / L(h), 5×10 -2 mol / L(i), 6×10 -2 mol / L(j), 7×10 -2 mol / L (k), 8×10 -2 mol / L(l), 9×10 -2 mol / L(m), 1.0×10 -1 mol / L l(n), 1.1×10 -1 mol / L (o) 3 µL hydrogen sulfide solution was added to 15 sample bottles, stirred at room temperature for 90 minutes, and the fluorescence intensity of these samples was measured with 450 nm as the excitation wavelength, and the fluorescence emission spectrum changes of the 15 samples were obtained. ,See image 3 . The measurement results show that the fluorescence in...

Embodiment 3

[0051] Example 3: Comparative detection experiments of other ions and molecules.

[0052] Take 19 5 mL sample vials, add 3 mL of the solution prepared by the molecule of formula I obtained in Example 1 (the concentration of the molecule is 10 μM, V tetrahydrofuran: V water = 90: 10), and then respectively add the concentration of 5.0 ×10 -1 mol / L Cl - (1), F - (2), CO 3 2- (3), H 2 PO 4 - (4), HCO 3 - (5), HSO 4 - (6), NO 3 - (7), OAc - (8), PO 4 3- (9), SO 4 2- (10), ClO - (11), H 2 o 2 (12), NO 2 - (13), SO 3 2- (14), GSH(15), Cys(16), Hcy(17), and HS - (18) Take 3 µL each and add to the other first 18 sample vials, and sample No. 19 is the blank sample. Then measure the fluorescence emission intensity at 450 nm wavelength excitation and 592 nm wavelength emission of 19 samples respectively, the results are shown in Figure 5 . The measurement results show that, except hydrogen sulfide, other above-mentioned various ions and molecules have no obvi...

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Abstract

The invention discloses preparation and application of optical switch fluorescence molecules with a hydrogen sulfide recognition function. According to obtained target molecules, properties of a group with hydrogen sulfide response and a spiropyran group with photoresponse are combined successfully, and the molecules in a water-based solvent not only can perform high-selectivity and high-sensitivity detection for hydrogen sulfide molecules, but also have good optical switch performance and can show rapid and reversible fluorescence switch performance under irradiation of ultraviolet light and green light. The optical switch fluorescence molecules with the hydrogen sulfide recognition function have great application prospect in the technical fields of hydrogen sulfide detection, environmental protection, super-resolution imaging, life science and the like.

Description

technical field [0001] The present invention relates to the preparation and application of an optical switch fluorescent molecule with hydrogen sulfide recognition function, specifically, to the preparation of a molecule with H2S recognition function and reversible fluorescent switch characteristics under the irradiation of ultraviolet light and visible light The invention and its application belong to the field of chemical material preparation and analysis and detection. Background technique [0002] Hydrogen sulfide (H 2 S) has always been considered to be just a poisonous gas with the smell of rotten eggs, but in recent years, it has been found that it is the third gas signal molecule that can play a physiological role in the living body after carbon monoxide and nitric oxide. A gaseous transmitter, it can quickly and freely pass through the cell membrane without any special carrier, affect a series of biological targets, and participate in the regulation of various func...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1022C09K2211/1029C09K2211/1088G01N21/64
Inventor 陈建洪永想张培盛王宏余茂林张媛邹朝
Owner HUNAN UNIV OF SCI & TECH
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