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Novel indole hemicyanine-based SO3<2-> ratiometric fluorescent probe and applications thereof

A ratiometric fluorescent probe, SO32- technology, applied in fluorescence/phosphorescence, luminescent materials, material analysis by optical means, etc.

Inactive Publication Date: 2019-04-30
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ratiometric fluorescent probes can greatly reduce the influence of external factors, and there are few ratiometric fluorescent probes currently used to detect sulfite.

Method used

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  • Novel indole hemicyanine-based SO3&lt;2-&gt; ratiometric fluorescent probe and applications thereof
  • Novel indole hemicyanine-based SO3&lt;2-&gt; ratiometric fluorescent probe and applications thereof
  • Novel indole hemicyanine-based SO3&lt;2-&gt; ratiometric fluorescent probe and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: The synthesis scheme of the compound of formula (1) is shown in the following formula:

[0019]

[0020] Concrete synthetic steps are as follows:

[0021] In a 25 mL round bottom flask, add successively) 0.29 g (1.0 mmol) of 4-phenyl-pyrido[1,2-a]benzimidazole-3-carboxylic acid, 0.56 g (1.2 mmol) of 3,3-di Methyl-1-ethyl-2-(4-(piperazinyl)-styryl) indole iodide, 0.18g (1.5mmol) DMAP, 0.29g (1.5mmol) EDC, 20ml dichloromethane, room temperature React for 24 hours. After the reaction was detected by TLC, the heating was stopped, and about 1 g of silica gel was added after cooling to room temperature, concentrated and dried on a vacuum rotator, sampled by dry method, separated by column chromatography, and concentrated to obtain 0.64 g of a purple solid with a yield of 86.5%.

[0022] H NMR spectrum determination: 1 H NMR (400 MHz, CDCl 3 ): δ 8.57 (d, 1H), 8.20 (d, 2H), 8.0 (m, 3H), 7.87 (d, 2H), 7.65 (d, 1H), 7.50 (ddd, 9H), 6.95 (d, 1H ), 6.82 (d,2H...

Embodiment 2

[0024] To the compound of formula (1) (5×10 -5 M) were added to the neutral solution of 10 equivalents of SO 3 2- , AcO - , Br - , H 2 PO 4 - , Cl - , CO 3 - , HCO 3 - , F - , HPO 4 2- , HS - , I - , NO 2 - , NO 3 - , S 2 o 3 2- , SO 4 2- , Fe 3+ , Ca 2+ , Cu 2+ , K + , Na + , Zn 2+, GSH, Hcy and Cys, measured the changes in the ratio of fluorescence emission intensity at 470nm and 578nm and found that: the compound of formula (1) has 3 2- Has a unique fluorescence selectivity, adding 10 equivalents of SO 3 2- Afterwards, the fluorescence intensity of compound 1 at 578nm was significantly reduced, and at the same time, the fluorescence intensity at 470nm was significantly enhanced, I 470 / I 578 = 7.19, such as figure 2 shown.

Embodiment 3

[0026] Formula (1) compound (5 × 10 -5 M) Add 10 equivalents of SO to the neutral aqueous solution 3 2- , AcO - , Br - , H 2 PO 4 - , Cl - , CO 3 - , HCO 3 - , F - , HPO 4 2- , HS - , I - , NO 2 - , NO 3 - , S 2 o 3 2- , SO 4 2- , Fe 3+ , Ca 2+ , Cu 2+ , K + , Na + , Zn 2+ , GSH, Hcy and Cys, measured the changes in the fluorescence emission curves at 470nm and 578nm and found that the compound of formula (1) has strong anti-interference ability to other ions, such as image 3 shown.

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Abstract

The present invention discloses a novel pyrido[1,2-a]benzimidazole substituted indole hemicyanine-based sulfite ratiometric fluorescent probe, which is a 3,3-dimethyl-1-ethyl-2-(N-(4-phenyl-3-pyrido[1,2-a]benzimidazoleformyl)-4-(piperazinyl)-styryl)indole iodide, wherein the chemical structural formula is represented by a formula (1). According to the present invention, the fluorescent probe has unique selectivity and high sensitivity to SO3<2-> in aqueous solutions, can accurately and quickly distinguish sulfite ions from various anions, and has broad application prospects.

Description

technical field [0001] The invention relates to the field of organic small molecule fluorescent probes, in particular to a pyrido[1,2-a]benzimidazole substituted indole hemicyanine SO 3 2- Ratiometric fluorescent probes and their applications. Background technique [0002] Sulfites are widely used in food and industry as preservatives, antioxidants, bacteriostats, etc., and have been used in the past few decades for preservation and storage of fruits and vegetables. In addition, sulfite plays a role in maintaining drug stability in drug manufacturing. Even so, sulfites can cause many problems during use. For example, high concentrations of sulfites can cause asthma and allergy symptoms, and large amounts of sulfites can lead to a decrease in the concentration of dissolved oxygen in water, leading to serious environmental problems. Therefore, it is very important to invent a highly sensitive, convenient and quick method to detect sulfite content for food safety and enviro...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D471/04G01N21/64
CPCC09K11/06C07D471/04C09K2211/1007C09K2211/1029C09K2211/1044G01N21/643
Inventor 葛燕青刘爱坤吉瑞雪曹晓群
Owner TAISHAN MEDICAL UNIV
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