Rhodamine derivative and preparation method and application thereof

The technology of a derivative, rhodamine hydrazide, is applied in the field of rhodamine derivatives, achieving the effects of mild reaction conditions and short structural synthesis routes

Inactive Publication Date: 2013-05-22
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A large number of rhodamine-based spectral probes and sensors have been reported, but there are few rhodamine-based spectr

Method used

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  • Rhodamine derivative and preparation method and application thereof
  • Rhodamine derivative and preparation method and application thereof
  • Rhodamine derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Preparation of intermediate rhodamine hydrazide (RBH)

[0036] The intermediate rhodamine hydrazide (RBH) was synthesized according to literature.

[0037] Dujols V, Ford F, Czarnik AW. A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water. Am Chem Soc 1997;119:7386-7.

[0038] Yang X-F, Guo X-Q, Zhao Y-B. Development of a novel rhodamine-type fluorescent probe to determine peroxynitrite. Talanta 2002;57:883-90.

[0039] Wu C-M, Chen Y-H, Dayananda K, Shiue T-W, Hung C-H, Liaw W-F, Chen P-Y,Wang Y-M. Sensitivity evaluation of rhodamine B hydrazide towards nitric oxide and its application for macrophage cells imaging. Anal Chim Acta 2011;708:141- 8.

[0040] The specific operation is: in a 100 mL three-neck flask, dissolve 2 g rhodamine B (RB) in 25 mL ethanol, stir for 10 min, slowly add 6 mL of hydrazine hydrate with a dropping funnel, stir for another 10 min, and then heat to The reaction was refluxed for 6 h, and the reaction wa...

Embodiment 2

[0041] Example 2: Preparation of spectral probe RNBD

[0042] in dark and N 2 Under protective conditions, with acetonitrile as solvent, with anhydrous K 2 CO 3 is the acid-binding agent, the molar ratio n (RBH ) : n (acid-binding agent) : n (NBD-Cl) = 1:1:1. Dissolve RBH in acetonitrile in a 100 mL three-neck flask, stir for 10 min, then add anhydrous K 2 CO 3and NBD-Cl were dispersed in acetonitrile and slowly added to the RBH solution, stirred and reacted at 25 °C for 36 h, and the reaction solution was rotatably evaporated to remove acetonitrile, and the residue was first dispersed in deionized water, and then extracted with dichloromethane. The organic phase was taken, dried with anhydrous sodium sulfate, filtered to remove sodium sulfate, and the filtrate was rotary evaporated to remove the solvent to obtain a crude product. The crude product was subjected to silica gel column chromatography (the eluent was ethyl acetate / petroleum ether, volume ratio 1:5), and wash...

Embodiment 3

[0044] Example 3: Preparation of spectral probe RNBD

[0045] in dark and N 2 Under protective conditions, with acetonitrile as solvent, with anhydrous K 2 CO 3 is the acid-binding agent, the molar ratio n (RBH ) : n (acid-binding agent) : n (NBD-Cl) = 1.0:1.0:1.5. Dissolve RBH in acetonitrile in a 100 mL three-neck flask, stir for 10 min, then add anhydrous K 2 CO 3 and NBD-Cl were dispersed in acetonitrile and slowly added to the RBH solution, stirred and reacted at 25 °C for 36 h, and the reaction solution was rotatably evaporated to remove acetonitrile, and the residue was first dispersed in deionized water, and then extracted with dichloromethane. The organic phase was taken, dried with anhydrous sodium sulfate, filtered to remove sodium sulfate, and the filtrate was rotary evaporated to remove the solvent to obtain a crude product. The crude product was subjected to silica gel column chromatography (the eluent was ethyl acetate / petroleum ether, volume ratio 1:5), a...

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Abstract

The invention discloses a rhodamine derivative and a preparation method and application thereof. The rhodamine derivative is prepared by reacting rhodamine hydrazide and 4-chloro-7-nitro-2,1,3-benzoxaoxadiazole in the presence of an acid binding agent. The Cu<2+> and Fe<3+> can be respectively detected at high selectivity and high sensitivity. The designed and synthesized structure is short in synthetic route and mild in reaction conditions, the obtained derivative can be used for an aqueous phase system, and the ultraviolet-visible absorption spectrum and fluorescence spectrum are insensitive to the acid-base property of the system.

Description

technical field [0001] The invention relates to a rhodamine derivative and the application of the rhodamine derivative as a spectral probe. Background technique [0002] The structure of rhodamine derivatives contains parts that can be opened and closed. The opening and closing of the ring will cause obvious changes in the ultraviolet-visible absorption spectrum and fluorescence spectrum of rhodamine derivatives. When the ring is closed, it is generally colorless, non-fluorescent, or light-colored , Weak fluorescence, colored and strong fluorescence when the ring is opened, and rhodamine derivatives have high fluorescence quantum yield, adjustable fluorescence properties, low sensitivity to acidity and alkalinity, and excitation and emission wavelengths in the visible light region. One of the most widely used reporter groups in spectroscopic probes and sensors. A large number of rhodamine-based spectral probes and sensors have been reported, but there are few rhodamine-base...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64G01N21/33
Inventor 徐冬梅刘爱风
Owner SUZHOU UNIV
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