Imidazopyridine rhodamine salicylaldehyde copper ion ratiometric fluorescent probe and its application

A technology of ratio fluorescent probe and salicylaldehyde, which is applied in the direction of fluorescence/phosphorescence, luminescent materials, and material analysis through optical means, can solve the problem of fewer ratio fluorescent probes, and achieve strong anti-interference ability of other ions , huge application prospects, high sensitivity effect

Inactive Publication Date: 2019-02-22
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, almost all copper ion probes are single signal enhancement or weakening probes, and there are few ratiometric fluorescent probes with two or more signal response changes.

Method used

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  • Imidazopyridine rhodamine salicylaldehyde copper ion ratiometric fluorescent probe and its application
  • Imidazopyridine rhodamine salicylaldehyde copper ion ratiometric fluorescent probe and its application
  • Imidazopyridine rhodamine salicylaldehyde copper ion ratiometric fluorescent probe and its application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: The synthesis scheme of the compound of formula (1) is shown in the following formula:

[0015]

[0016] Concrete synthetic steps are as follows:

[0017] Add 0.704g (1.0 mmol) imidazo[1,5-a]pyridine rhodamine hydrazide, 0.122g (1.0 mmol) salicylaldehyde, and 20 mL absolute ethanol in sequence in a 50 mL round bottom flask, reflux at 80°C React for 3-6 hours. After the completion of the reaction as detected by TLC, it was concentrated under reduced pressure and 0.707 g of off-white solid was obtained by column chromatography, with a yield of 89.0%.

[0018] H NMR spectrum determination: 1 H NMR (400 MHz, CDCl 3 ): δ11.03(s, 1H), 8.43(s, 1H), 7.95(m, 1H), 7.72 (dd, J = 4.0 Hz, 8.0 Hz, 1H), 7.55-7.41 (m, 5H), 7.10-7.01 (m,3H), 6.70-6.67 (m, 2H), 6.56 (m, 2H), 6.46 (d, J = 12.0 Hz, 1H), 6.42 (d, J =4.0 Hz, 1H), 6.31 (dd, J = 2.8 Hz, 8.0 Hz, 1H), 3.82 (s, 4H), 3.34 (q, J =8.0 Hz, 4H), 3.28 (s, 4H), 2.96 (d, J = 4.0 Hz, 4H), 1.82 (m, 2H), 1.62...

Embodiment 2

[0020] To formula (1) compound (10 -5 M) was added to the ethanol solution of 2 equivalents of Mg 2+ , Ca 2+ , Al 3+ ,Sn 2+ , Pb 2+ ,Cr 3+ , Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ ,Zn 2+ ,Cd 2+ ,Pd 2+ ,Hg 2+ and Ag + After measuring the change in the ratio of fluorescence emission intensity at 465nm and 585nm, it was found that: the compound of formula (1) has 2+ Has a unique fluorescence selectivity, adding 1 equivalent of Cu 2+ After that, the fluorescence intensity of compound 1 at 465nm was significantly reduced, and at the same time, the fluorescence intensity at 585nm was significantly enhanced, I 585 / I 465 = 3.35, such as figure 2 shown.

Embodiment 3

[0022] In formula (1) compound (10 -5 M) and 1 equivalent of Cu 2+ 2 equivalents of Mg were added to the ethanol solution 2+ , Ca 2+ , Al 3+ ,Sn 2+ , Pb 2+ ,Cr 3+ , Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ ,Zn 2+ ,Cd 2+ ,Pd 2+ ,Hg 2+ and Ag + After measuring the change in the ratio of fluorescence emission intensity at 465nm and 585nm, it was 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 invention discloses an imidazo[1,5-a]pyridine-rhodamine salicylaldehyde copper ion ratio fluorescent probe and its application. The probe is substituted by imidazo[1,5-a]pyridine Rhodamine salicylaldehyde, its chemical structure is shown in formula (1). Fluorescence probe of the present invention is to Cu in ethanol solution 2+ It has unique fluorescence selectivity, high sensitivity and strong anti-interference ability of other ions, and has great application prospects.

Description

technical field [0001] The invention relates to the field of organic small molecule fluorescent probes, in particular to a Cu 2+ Ratiometric fluorescent probe imidazo[1,5-a]pyridine substituted rhodamine salicylaldehyde and its application. Background technique [0002] Due to its emission and absorption in the visible region, large molar extinction coefficient, high photostability, high fluorescence quantum yield, and easy synthesis, rhodamine fluorescent dyes are widely used as fluorescent probes or fluorescent probes for detecting metal ions after structural modification. Research on chemical sensors. [0003] Cu 2+ It is the third most abundant transition metal element in the human body after iron and zinc. It plays a very important role in many physiological processes, and the reduction of copper content may lead to anemia diseases. Cu 2+ It can participate in the enzyme reaction, enzyme transcription and some oxidation-reduction processes in the body, and is also ...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07D519/00C09K11/06G01N21/64
CPCC07D519/00C09K11/06C09K2211/1044C09K2211/1088G01N21/643
Inventor曹晓群葛燕青段桂运董建
OwnerTAISHAN MEDICAL UNIV