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Symmetrical double-rhodamine fluorescent probe for detecting trivalent bismuth ions as well as preparation method and use thereof

A fluorescent probe, bismuth ion technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effect of high sensitivity

Inactive Publication Date: 2014-08-27
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Regrettably, no rhodamine-based fluorescent probes for recognizing trivalent bismuth ions have been reported yet.

Method used

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  • Symmetrical double-rhodamine fluorescent probe for detecting trivalent bismuth ions as well as preparation method and use thereof
  • Symmetrical double-rhodamine fluorescent probe for detecting trivalent bismuth ions as well as preparation method and use thereof
  • Symmetrical double-rhodamine fluorescent probe for detecting trivalent bismuth ions as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036](1) Add 2.0g (4.18mmoL) of rhodamine B and 15mL of absolute ethanol into a 100mL three-neck round bottom flask, stir until rhodamine B is completely dissolved, then slowly add 1.4mL (20.9mmoL) of ethylenediamine dropwise Into the ethanol solution of rhodamine B mentioned above, after the dropwise addition, keep the reaction at 50° C. for 6 hours. The reaction solution was left to stand, cooled to room temperature, and filtered with suction to obtain a light pink precipitate. Wash with distilled water until the washing liquid is colorless and close to neutral to obtain 1.55 g of rhodamine ethylenediamine intermediate with a yield of 76.5%. m.p. 216°C-217°C (literature value 216°C-218°C).

[0037] (2) Add 0.60g (1.2mmoL) of rhodamine ethylenediamine intermediate and 0.83mL (6mmoL) of triethylamine into a 100mL three-neck round bottom flask, dissolve them in 10mL of dry dichloromethane, and dissolve 0.36g (1.2mmoL) 10mL dry dichloromethane solution of bis(trichloromethyl)...

Embodiment 2

[0039] (1) Add 2.0g (4.18mmoL) of Rhodamine B and 15mL of absolute ethanol into a 100mL three-neck round bottom flask, stir until Rhodamine B is completely dissolved, then add 3.5mL (41.8mmL) of 1,3-propanedi The amine was slowly added dropwise into the flask, and after the dropwise addition was completed, the reaction was kept at 50°C for 7h. The reaction solution was left to stand, cooled to room temperature, and filtered with suction to obtain a light pink precipitate. Wash with distilled water until the washing liquid is colorless and close to neutral to obtain 1.50 g of rhodamine propylenediamine intermediate, with a yield of 72.0%. m.p. 189°C-191°C (literature value 188°C-191°C).

[0040] (2) Add 0.5g (1.0mmoL) of rhodamine propylenediamine intermediate and 0.48mL (6mmoL) pyridine into a 100mL three-neck round bottom flask, dissolve them in 10mL dry acetonitrile, and dissolve 0.3g (1.0mmoL) of ) The dry acetonitrile of bis(trichloromethyl)carbonate was slowly added...

Embodiment 3

[0042] (1): Add 4.0g (8.36mmoL) of Rhodamine B and 20mL of absolute ethanol into a 100mL three-neck round bottom flask, stir until Rhodamine B is completely dissolved, and then add 6.7mL (66.88mmoL) of 1,4-butyl Diamine was slowly added dropwise into the flask, and after the dropwise addition was completed, the temperature was kept at 50°C for 8 hours. The reaction solution was left to stand, cooled to room temperature, and filtered with suction to obtain a light pink precipitate. Wash with distilled water until the washing liquid is colorless and close to neutral to obtain 2.36 g of rhodamine butylenediamine intermediate with a yield of 56.0%.

[0043] (2) Add 0.6g (1.2mmoL) of rhodamine butylenediamine intermediate and 0.83mL (6mmoL) triethylamine into a 100mL three-neck round bottom flask, dissolve them in 10mL of dried dichloromethane, and dissolve the dissolved 0.36g (1.2mmoL) of bis (trichloromethyl) carbonate in 10mL of dry dichloromethane solution was slowly added dro...

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Abstract

The invention discloses a symmetrical double-rhodamine fluorescent probe for detecting trivalent bismuth ions as well as a preparation method and use thereof. The fluorescent probe comprises a structural general formula as shown in the specification, wherein R1, R2, R3 and R4 simultaneously adopt hydrogen, or R1, R2, R3 or R4 is selected from one of hydrogen, alkyl with 2-6 carbon atoms or naphthenic base with 4-8 carbon atoms; n is a natural number between 2 and 9. The symmetrical double-rhodamine fluorescent probe is applied to detection of trivalent bismuth ions in a solution system, analysis detection and fluorescence imaging detection of the trivalent bismuth ions in biological living cells and living tissues, or medical detection of the trivalent bismuth ions.

Description

technical field [0001] The invention belongs to the field of fluorescent probes and their preparation, in particular to a symmetrical bisrhodamine fluorescent probe for detecting trivalent bismuth ions, its preparation method and application. Background technique [0002] Bismuth is located in group VA of the sixth cycle of the periodic table of elements, at the junction of metals and non-metals. It is a non-toxic element with a large atomic number and is considered to be the safest green metal. Bismuth in nature mainly exists in trivalent and pentavalent forms. Many trivalent bismuth ion compounds are biologically active and are used as antibacterial and anticancer drugs. For example, bismuth ranitidine citrate is a new compound approved by many countries for the treatment of peptic ulcer and eradication of Helicobacter pylori (Metal Ions In Biological Systems, 41, 333-378). 212 Bi and 213 Bi compounds can be used as drugs against radiotherapy to treat cancer with less s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D519/00C07D491/107G01N21/64
Inventor 高勇申川川陈庆华余喜娣张晓伟付妹
Owner FUJIAN NORMAL UNIV
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