Rhodamine B-based multifunctional fluorescent probe for recognizing Fe<3+>, Al<3+> and Cr<3+> ions and preparation method and application of rhodamine B-based multifunctional fluorescent probe for recognizing Fe<3+>, Al<3+> and Cr<3+> ions

A fluorescent probe, multi-functional technology, applied in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of increasing detection costs, and achieve the effect of saving detection costs and saving detection time

Inactive Publication Date: 2016-06-01
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

while detection of Fe 3+ 、Cr 3+ and Al 3+ Need to use different fluorescent probes, which increases the detection cost

Method used

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  • Rhodamine B-based multifunctional fluorescent probe for recognizing Fe&lt;3+&gt;, Al&lt;3+&gt; and Cr&lt;3+&gt; ions and preparation method and application of rhodamine B-based multifunctional fluorescent probe for recognizing Fe&lt;3+&gt;, Al&lt;3+&gt; and Cr&lt;3+&gt; ions
  • Rhodamine B-based multifunctional fluorescent probe for recognizing Fe&lt;3+&gt;, Al&lt;3+&gt; and Cr&lt;3+&gt; ions and preparation method and application of rhodamine B-based multifunctional fluorescent probe for recognizing Fe&lt;3+&gt;, Al&lt;3+&gt; and Cr&lt;3+&gt; ions
  • Rhodamine B-based multifunctional fluorescent probe for recognizing Fe&lt;3+&gt;, Al&lt;3+&gt; and Cr&lt;3+&gt; ions and preparation method and application of rhodamine B-based multifunctional fluorescent probe for recognizing Fe&lt;3+&gt;, Al&lt;3+&gt; and Cr&lt;3+&gt; ions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Synthetic compound 2 The reaction formula is as follows:

[0052]

[0053] (1) Synthesis of compound 1

[0054] Put (3.0g, 6.8mmol) Rhodamine B in a round bottom flask, add 100mL of absolute ethanol to make it fully dissolved, then add 7.5mL of hydrazine hydrate, reflux and stir for 4h, after the reaction is over, the solvent ethanol is distilled off under reduced pressure. The remaining solid was acidified with an excess of 1mol / L HCl, and 0.5mol / L NaOH was adjusted to pH 7. At this time, a large amount of precipitate was precipitated, filtered with suction, washed the filter cake with deionized water, and dried in vacuum to obtain a yellowish solid compound 1.

[0055] (2) Synthesis of compound 2

[0056] Compound 1 (0.5g, 1mmol) was placed in a 100mL flask, and 30mL of dichloromethane was added to make it completely dissolved. Then 0.1 mL of chloroacetyl chloride was dissolved in a small amount of dichloromethane (5 mL). Under an ice bath, the mixed solution of chloroac...

Embodiment 2

[0058] Synthesize fluorescent probe L1, the reaction formula is as follows:

[0059]

[0060] The specific steps are:

[0061] Take compound 2 (0.15g, 28mmol) dissolved in 20mL of acetonitrile, add morpholine (0.031g, 0.35mmol), KI (0.03g, 0.18mmol) and diisopropylethylamine (0.5mL, 2.9mmol), under nitrogen protection The reaction was stirred and refluxed at 70°C for 10 hours; after the reaction was completed, it was cooled to room temperature, the solvent was distilled off under reduced pressure, and column chromatography was used to separate the white solid fluorescent probe L1 with a yield of 85%.

[0062] Basic data of this rhodamine multifunctional fluorescent probe:

[0063] 1 HNMR(400MHz, CDCl 3 )δ8.25(s,1H),7.98(d,J=8.0Hz,1H),7.51-7.49(m,2H),7.33(t,J=7.5Hz,1H),7.15(d,J=6.7 Hz, 1H), 6.65 (d, J = 8.8 Hz, 2H), 6.32 (m, 4H), 3.48 (br, 4H), 4.53 (s, 2H), 3.38-3.28 (m, 8H), 2.96 (s ,2H),2.32(br,4H),1.17(t,J=7.0Hz,12H)(such as figure 1 ).

[0064] 13 CNMR(100.6MHz, CDCl 3 ) 167.3, ...

Embodiment 3

[0072] Example 3 Synthesis of Compound 3 And compound 6

[0073] The reaction formula is as follows:

[0074]

[0075] (1) Compound 3 Synthesis

[0076] Rhodamine B (444mg, 1.0mmol) and propargylamine (82.5mg, 1.5mmol), dissolved in dry dichloromethane, add benzotriazole-N,N,N',N'-tetramethylurea Hexafluorophosphate (HBTU) (568mg, 1.5mmol)) and triethylamine (152mg, 1.5mmol), react at room temperature for 15h, spin dry under reduced pressure, silica gel column chromatography to obtain a white solid 359mg, the yield was 75%.

[0077] (2) Compound 4 Synthesis

[0078] 2-Aminobenzothiazole (1g, 6.8mmol) and (0.65g, 8.2mmol) pyridine were dissolved in dry dichloromethane. Under ice bath conditions, bromoacetyl bromide (1.7g, 8.2mmol) was added dropwise. Methyl chloride solution. TLC tracking, silica gel column chromatography to obtain yellow solid compound 4 The yield was 85%.

[0079] (3) Compound 6 Synthesis

[0080] Compound 4 (270 mg, 1 mmol) and sodium azide (650 mg, 10 mmol) w...

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Abstract

The invention discloses a rhodamine B-based multifunctional fluorescent probe for recognizing Fe<3+>, Al<3+> and Cr<3+> ions and a preparation method and application of the rhodamine B-based multifunctional fluorescent probe for recognizing the Fe<3+>, Al<3+> and Cr<3+> ions. The rhodamine B-based multifunctional fluorescent probe is shown as the specific structural formula below, wherein R refers to the description below. The rhodamine B-based multifunctional fluorescent probe recognizes the trivalent metal ions including Fe<3+>, Al<3+> and Cr<3+> in methanol. The rhodamine B-based multifunctional fluorescent probe for recognizing the Fe<3+>, Al<3+> and Cr<3+> ions, the preparation method and application have the advantages that the rhodamine B-based multifunctional fluorescent probe can be used for recognizing the trivalent metal ions including Fe<3+>, Al<3+> and Cr<3+>, thereby being multifunctional; the rhodamine B-based multifunctional fluorescent probe is excellent in selectivity when recognizing the Fe<3+>, Al<3+> and Cr<3+>, is high in anti-interference capability and is unaffected by other divalent metal ions; the rhodamine B-based multifunctional fluorescent probe which is a fluorescence-enhanced fluorescent probe is high in detection sensitivity.

Description

Technical field [0001] The invention belongs to the field of fluorescent molecular probes, and particularly relates to a kind of Rhodamine B-based recognition Fe 3+ , Al 3+ And Cr 3+ Ion multifunctional fluorescent probe and its preparation method and application. Background technique [0002] Trivalent metal ions especially Fe 3+ , Cr 3+ And Al 3+ It plays a very important role in life activities. Fe 3+ It is the basic element that constitutes protein, cytochrome and various enzymes, and participates in cell metabolism. Fe in human body 3+ Imbalance can cause metabolic disorders and lead to diseases such as anemia, liver damage, and kidney failure. Cr 3+ The lack of chromium can cause many diseases such as diabetes and arteriosclerosis, but when Cr 3+ When the content is too high, it will destroy the cell structure and composition, causing harm to the human body. Al 3+ It is not a trace element necessary for the human body. Usually excessive intake of Al 3+ It can cause Alzhe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1059C09K2211/1088G01N21/6428
Inventor 侯淑华任冬梅赵岩刘玉静钟克利汤立军边延江
Owner BOHAI UNIV
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