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Schiff base type fluorescent probe compound and preparation method thereof

A technology of fluorescent compounds and Schiff bases, applied in the field of fluorescent probes, can solve the problems of lack of detection of intracellular metal ions, poor two-photon performance, general fluorescence performance, etc., and achieves high yield, strong fluorescence, good repeatability

Inactive Publication Date: 2015-02-25
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In recent years, many fluorescent probes of Schiff bases have been reported, but the Schiff bases are mainly synthesized with coumarin, p-phenylenediamine, salicylaldehyde, triphenylamine, etc., and their fluorescence properties are average. The excitation wavelength is short, the two-photon performance is not good, and the ability to detect intracellular metal ions is not yet available, and the synthesis of Schiff base probes using rhodamine B hydrazide and carbazolyl aldehyde compounds is rarely reported.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Weigh 1.2g of rhodamine B and 1.5ml of (85%) hydrazine hydrate, add them to 30ml of ethanol, stir evenly, raise the temperature to 75°C, and react for 2 hours. After spin-drying ethanol, add 50ml of 1mol / L dilute hydrochloric acid, configure NaOH solution with the same molar concentration as hydrochloric acid, adjust the pH to 7, filter, wash with water, and dry to obtain white powdery solid rhodamine hydrazide; 1 H-NMR (400MHz, CDCl 3 ), δ=1.14 (t, 12H, CH3, J=7.0Hz), 3.39 (q, 8H, CH2, J=7.0Hz), 3.60 (s, 2H, NH2), 6.37 (dd, 2H, Xanthene-H , J 1 =9.0Hz,J 2 =2.4Hz), 6.42 (s, 2H, Xanthene-H), 6.50 (d, 2H, Xanthene-H, J=9.0Hz), 7.14 (dd, 1H, Ar-H. J 1 =5.4Hz,J 2 =3.3Hz), 7.49 (m, 2H, Ar-H), 7.94 (dd, 1H, Ar-H, J 1 =5.4Hz,J 2 =3.3Hz).

[0031] (2) Weigh 5g of carbazole, 0.96g of tetrabutylammonium bromide, 25ml of 1,2-dibromoethane into a 250ml three-neck flask, stir magnetically at room temperature for 2 hours, weigh 16g of KOH solid, distilled water 16ml was c...

Embodiment 2

[0035] (1) Weigh 4.79g of rhodamine B and 12mL of (85%) hydrazine hydrate, add them to 100mL of ethanol, stir evenly, raise the temperature to 90°C, and react for 6 hours. After spin-drying ethanol, add 200ml of 3mol / L dilute hydrochloric acid, configure NaOH solution with the same molar concentration as hydrochloric acid, adjust the pH to 9, filter, wash with water, and dry to obtain rhodamine hydrazide as a powdery white powder solid; 1 H-NMR (400MHz, CDCl 3 ), δ=1.17 (t, 12H, CH3, J=7.0Hz), 3.38 (q, 8H, CH2, J=7.0Hz), 3.61 (s, 2H, NH2), 6.32 (dd, 2H, Xanthene-H , J 1 =9.0Hz,J 2 =2.4Hz), 6.44 (s, 2H, Xanthene-H), 6.49 (d, 2H, Xanthene-H, J=9.0Hz), 7.13 (dd, 1H, Ar-H. J 1 =5.4Hz,J 2 =3.3Hz), 7.47 (m, 2H, Ar-H), 7.96 (dd, 1H, Ar-H, J 1 =5.4Hz,J 2 =3.3Hz).

[0036] (2) Weigh 10g of carbazole, 2.11g of tetrabutylammonium bisulfate, 60ml of 1,2-dibromoethane into a 250ml three-necked flask, stir magnetically at room temperature for 2 hours, weigh 32g of KOH solid, distille...

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Abstract

The invention discloses a Schiff base type fluorescent probe compound and a preparation method thereof. The Schiff base type fluorescent probe compound has a structure as shown in formula (I) in the specification and is characterized by comprising the following steps: (1) preparing a Rhodamine B-hydrazide compound; (2) preparing 9-bromoethyl carbazole; (3) preparing 3-formyl-9 ethyl carbazole; (4) synthesizing a Schiff base type fluorescent compound, wherein the synthesized Schiff base type fluorescent compound has ''C=N'' bonds, and the prepared compound has a large ''Pi'' conjugate plane aromatic ring structure and is good in fluorescence property; structurally, lone pair electrons and heterocyclic atoms such as O and N exist on the C=N, so the compound has a potential application in detection of metal ions in cells.

Description

technical field [0001] The invention relates to a Schiff base fluorescent probe compound and its preparation, belonging to the technical field of fluorescent probes. technical background [0002] Fluorescent molecular probes are the result of the combination of molecular recognition and fluorescence technology. They bind to targets through specific receptors, and convert molecular binding information into easily detectable fluorescent signals, thereby realizing in situ real-time detection at the single-molecule level. [0003] In biochemistry, medicine, environmental science, and molecular biology, the analysis of fluorescent probes for the detection of metal ions is the most widely and thoroughly studied aspect. Because some metal ions will cause serious harm to human health and the environment, the design and synthesis of fluorescent probes that can accurately analyze and detect metal ions has attracted a lot of attention. Compared with traditional analysis methods such a...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1022C09K2211/1033G01N21/64
Inventor 张献刘叔尧孙明明
Owner QILU UNIV OF TECH
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