Rhodamine-oxadiazole derivative and preparation method and application thereof

A technology of oxadiazole and derivatives, which is applied in the field of organic synthesis, can solve the problems of low total yield of rhodamine derivatives and cumbersome reaction process, and achieve the effects of avoiding fluorescence resonance energy transfer, high reaction efficiency and high sensitivity

Inactive Publication Date: 2014-02-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The above method can synthesize rhodamine derivatives; however, the intermediates need to be separated and purified before subsequent reactions, resulting in a cumbersome reaction process; and the total yield of rhodamine derivatives (probes) is low

Method used

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

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Experimental program
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Effect test

Embodiment 1

[0032] Embodiment one: H + Preparation of probe rhodamine-oxadiazole derivatives (RPBD)

[0033] N-aminoethylpiperazine (AEP), rhodamine B (RB), DIPEA, 4-chloro-7-nitro-2,1,3-benzoxadiazole (NBD-Cl), K 2 CO 3 The molar ratio is: 1:1:1:1:1. in N 2 Under protection, AEP and DIPEA were dissolved in acetonitrile in a 100 mL three-neck flask, RB was dissolved in acetonitrile and added dropwise to the above solution, stirred at room temperature for 30 min, then heated to reflux for 12 h, then cooled, and rotary evaporated Acetonitrile was removed, the residue was washed with water and dissolved in acetonitrile, and K 2 CO 3 , then NBD-Cl dissolved in the same solvent was added dropwise to the above solution, reacted at room temperature for 30 min, the solvent was removed by rotary evaporation, and the residue was separated by silica gel column chromatography, developing solvent: ethyl acetate / petroleum ether (vol. Ratio 2 / 1), the orange-red solid target product RPBD was obtain...

Embodiment 2

[0035] Embodiment two: H + Preparation of probe RPBD

[0036] N-aminoethylpiperazine (AEP), rhodamine B (RB), DIPEA, 4-chloro-7-nitro-2,1,3-benzoxadiazole (NBD-Cl), K 2 CO 3 The molar ratio is: 7:1:12:1:1. in N 2 Under protection, AEP and DIPEA were dissolved in acetonitrile in a 100 mL three-neck flask, RB was dissolved in acetonitrile and added dropwise to the above solution, stirred at room temperature for 30 min, then heated to reflux for 12 h, then cooled, and rotary evaporated Acetonitrile was removed, the residue was washed with water and dissolved in acetonitrile, and K 2 CO 3 , then NBD-Cl dissolved in the same solvent was added dropwise to the above solution, reacted at room temperature for 30 min, the solvent was removed by rotary evaporation, and the residue was separated by silica gel column chromatography, developer: ethyl acetate / petroleum ether (vol. Ratio 2 / 1), the orange-red solid target product RPBD was obtained with a yield of 82.5%.

Embodiment 3

[0037] Embodiment three: H + Preparation of probe RPBD

[0038] N-aminoethylpiperazine (AEP), rhodamine B (RB), DIPEA, 4-chloro-7-nitro-2,1,3-benzoxadiazole (NBD-Cl), K 2 CO 3 The molar ratio is: 10:1:20:1:1. in N 2 Under protection, AEP and DIPEA were dissolved in acetonitrile in a 100 mL three-neck flask, RB was dissolved in acetonitrile and added dropwise to the above solution, stirred at room temperature for 30 min, then heated to reflux for 12 h, then cooled, and rotary evaporated Acetonitrile was removed, the residue was washed with water and dissolved in acetonitrile, and K 2 CO 3 , then NBD-Cl dissolved in the same solvent was added dropwise to the above solution, reacted at room temperature for 30 min, the solvent was removed by rotary evaporation, and the residue was separated by silica gel column chromatography, developer: ethyl acetate / petroleum ether (vol. Ratio 2 / 1), the orange-red solid target product RPBD was obtained with a yield of 78.3%.

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Abstract

The invention discloses a rhodamine-oxadiazole derivative and a preparation method and an application thereof. The specific preparation method comprises the following step: with N-aminoethylpiperazine, rhodamine B, DIPEA (Diisopropyl Ethyl Amine), 4-chloro-7-nitro-2, 1, 3-benzoxepin oxadiazole and K2CO3 with a mol ratio of (1-10): 1: (1-20): (1-1.5): 1 as reactants, preparing a product by a two-step-one-pot method, wherein the product can be used for H<+> ion colorimetry and used as a fluorescent probe. The structure designed and synthesized by the invention is short in synthesis route and mild in reaction conditions, an intermediate is unnecessary to be separated to obtain a target probe with a high yield, and no obvious FRET (fluorescence resonance energy transfer) exists between the oxadiazole and rhodamine fluorophores with matched spectrums in the structure, so that the H<+> can be detected through three channels, and the rhodamine-oxadiazole derivative has high selectivity, high sensitivity and large application potential.

Description

technical field [0001] The invention relates to a fluorescent material, in particular to a rhodamine-oxadiazole derivative and its preparation method and application, belonging to the field of organic synthesis. Background technique [0002] Hydrogen ions are the most widely distributed cations in nature. They exist in almost all aqueous solutions and affect the properties of aqueous solutions. The conduct or completion of chemical reactions, and many important physiological processes of cells and organelles are closely related to pH. Fluorescent probes for hydrogen ions can be used for pH monitoring in the field of environment and industrial and agricultural production, pH measurement inside and outside cells and pH in blood, providing important information for studying the impact of changes in hydrogen ion concentration on the environment and life activities. [0003] Rhodamine has become the most widely used fluorescent probe and sensor due to its high fluorescence quant...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1033C09K2211/1044C09K2211/1088G01N21/64G01N21/78
Inventor 徐冬梅刘爱风
Owner SUZHOU UNIV
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