Imidazopyridine rhodamine salicylaldehyde copper ion ratio fluorescence probe and application thereof

A ratiometric fluorescent probe, clear salicylaldehyde technology, applied in fluorescence/phosphorescence, luminescent materials, material analysis by optical means, etc., can solve the problem of less ratiometric fluorescent probes, and achieve strong resistance to other ions interference , Unique fluorescence selectivity, high sensitivity effect

Inactive Publication Date: 2016-11-09
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 ratio fluorescence probe and application thereof
  • Imidazopyridine rhodamine salicylaldehyde copper ion ratio fluorescence probe and application thereof
  • Imidazopyridine rhodamine salicylaldehyde copper ion ratio fluorescence probe and application thereof

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Experimental program
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Embodiment 1

[0015]

[0016] The specific synthesis steps are as follows:

[0017] Add 0.704g (1.0 mmol) imidazo[1,5-a]pyridine rhodamine hydrazide, 0.122g (1.0 mmol) salicylaldehyde, 20 mL absolute ethanol in sequence to a 50 mL round-bottomed flask, reflux at 80 degrees React for 3-6 hours. After TLC detected the reaction, 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 spectrometry: 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 (s, 2H), 1.44 (m, 2H), 1.17 (t, J = 8.0 Hz, 6H), 0.97 (t, J = 8.0 Hz, 3H).

Embodiment 2

[0020] To the compound of formula (1) (10 -5 M) were added 2 equivalents of Mg 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 the fluorescence emission intensity at 465nm and 585nm, it was found that the compound of formula (1) has a strong effect on Cu 2+ Unique fluorescence selectivity, adding 1 equivalent of Cu 2+ After , the fluorescence intensity of compound 1 at 465 nm was significantly reduced, and at the same time, the fluorescence intensity at 585 nm was significantly enhanced. 585 / I 465 = 3.35, as figure 2 shown.

Embodiment 3

[0022] Compounds of formula (1) (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 of the ratio of fluorescence emission intensity at 465nm and 585nm, it is 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 in imidazo[1,5-a]pyridine-rhodamine salicylaldehyde copper ion ratio fluorescence probe and an application thereof. The probe is imidazo[1,5-a]pyridine substituted rhodamine salicylaldehyde, and the chemical structural formula of the probe is represented by formula (1). The fluorescence probe has unique fluorescence selectivity and high sensitivity on Cu<2+> in an ethanol solution, has strong resistance to interference of other ions, and has great application prospect.

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 applications. Background technique [0002] Rhodamine fluorescent dyes are widely used as fluorescent probes or fluorescent probes for the detection of metal ions after structural modification due to their emission and absorption in the visible light region, large molar extinction coefficient, high photostability, high fluorescence quantum yield, and simple synthesis. 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 enzymatic reactions, enzymatic transcription and some redox processes in vivo, and is als...

Claims

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Application Information

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Patent Type & Authority Applications(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
Owner TAISHAN MEDICAL UNIV
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