Rhodamine B derivative, preparation method and application of rhodamine B derivative serving as fluorescent probe

Abstract

The invention provides a rhodamine B derivative, a preparation method and application of the rhodamine B derivative serving as a fluorescent probe. The rhodamine B derivative adopts a chemical structural formula shown in the specification. The rhodamine B derivative can selectively react with bivalent copper ions, becomes red from colorless, has colorimetric fluorescence enhancement effect, can realize naked-eye discrimination and detection, and particularly realize the application to convenient detection of cupper ions in cells by serving as the fluorescent probe.

Description

technical field

[0001] The invention belongs to the field of organic synthesis, and specifically relates to rhodamine B derivatives and their preparation methods and applications. Background technique

[0002] Copper is an important trace element in the human body. It plays a very important role in different physiological processes such as mitochondrial respiration, iron absorption, and enzyme redox. However, if the metabolic balance of copper ions in the body is destroyed, it may cause metabolic disorders and many diseases, such as elevated cholesterol, decreased arterial elasticity, and elevated blood pressure. In addition, copper has also become an important metal pollutant due to the large amount of copper ions mined and widely used. In view of its importance to life and the environment, scientists have been working on the detection of copper ions in biological and environmental systems using selective colorimetric and fluorescent sensing probes.

[0003] In recent yea...

Examples

Embodiment 1

[0028] Synthesis of Rhodamine B Derivatives

[0029]

[0030] Dissolve 0.167g of 3,5-dimethyl-pyrrole-2-carbaldehyde in 10mL of absolute ethanol, then add 0.46g of Rhodamine B hydrazide, and stir under reflux for 24 hours under normal pressure. After cooling to room temperature, a large amount of solids are precipitated. After filtering, the filter residue was washed with absolute ethanol to obtain a white solid, which was the target product, and the yield of the target product was 76%.

[0031] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the rhodamine B derivative that makes, calculation result is as follows:

[0032] 1HNMR (400MHz, CDCl 3 ), δ (ppm): 9.03 (s, 1H, NH), 8.08 (s, 1H, CH=N), 7.93-7.96 (m, 1H, Aryl-H), 7.41-7.42 (m, 2H, Aryl- H), 7.04-7.05 (m, 1H, Aryl-H), 6.47-6.50 (d, 2H, Aryl-H), 6.38 (s, 2H, Aryl-H), 6.21-6.23 (m, 2H, Aryl-H), H), 5.09-5.60 (d, 1H, pyrrole-CH), 3.24-3.35 (q, 8H, 4CH 2 ), 2.14 (s, 3H, ...

Embodiment 2

[0035] Dissolve 12.32g of 3,5-dimethyl-pyrrole-2-carbaldehyde in 0.5L of absolute ethanol, then add 45.5g of rhodamine B hydrazide, and stir under reflux for 12 hours under normal pressure. After cooling to room temperature, a large amount of solids are precipitated. After pressure filtration, the filter residue was washed with 75% ethanol solution to obtain a white solid, which was the target product, and the yield of the target product was 72.5%.

Embodiment 3

[0037] Dissolve 9.823g of 3,5-dimethyl-pyrrole-2-carbaldehyde in 0.4L of absolute ethanol, then add 36.21g of rhodamine B hydrazide, and stir under reflux for 12 hours under normal pressure. After cooling to room temperature, a large amount of solids are precipitated. After pressure filtration, the filter residue was washed with 75% ethanol solution to obtain a white solid, which was the target product, and the yield of the target product was 75.3%.

technical field

[0001] The invention belongs to the field of organic synthesis, and specifically relates to rhodamine B derivatives and their preparation methods and applications. Background technique

[0002] Copper is an important trace element in the human body. It plays a very important role in different physiological processes such as mitochondrial respiration, iron absorption, and enzyme redox. However, if the metabolic balance of copper ions in the body is destroyed, it may cause metabolic disorders and many diseases, such as elevated cholesterol, decreased arterial elasticity, and elevated blood pressure. In addition, copper has also become an important metal pollutant due to the large amount of copper ions mined and widely used. In view of its importance to life and the environment, scientists have been working on the detection of copper ions in biological and environmental systems using selective colorimetric and fluorescent sensing probes.

[0003] In recent yea...

Examples

Embodiment 1

[0028] Synthesis of Rhodamine B Derivatives

[0029]

[0030] Dissolve 0.167g of 3,5-dimethyl-pyrrole-2-carbaldehyde in 10mL of absolute ethanol, then add 0.46g of Rhodamine B hydrazide, and stir under reflux for 24 hours under normal pressure. After cooling to room temperature, a large amount of solids are precipitated. After filtering, the filter residue was washed with absolute ethanol to obtain a white solid, which was the target product, and the yield of the target product was 76%.

[0031] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the rhodamine B derivative that makes, calculation result is as follows:

[0032] 1HNMR (400MHz, CDCl 3 ), δ (ppm): 9.03 (s, 1H, NH), 8.08 (s, 1H, CH=N), 7.93-7.96 (m, 1H, Aryl-H), 7.41-7.42 (m, 2H, Aryl- H), 7.04-7.05 (m, 1H, Aryl-H), 6.47-6.50 (d, 2H, Aryl-H), 6.38 (s, 2H, Aryl-H), 6.21-6.23 (m, 2H, Aryl-H), H), 5.09-5.60 (d, 1H, pyrrole-CH), 3.24-3.35 (q, 8H, 4CH 2 ), 2.14 (s, 3H, ...

Embodiment 2

[0035] Dissolve 12.32g of 3,5-dimethyl-pyrrole-2-carbaldehyde in 0.5L of absolute ethanol, then add 45.5g of rhodamine B hydrazide, and stir under reflux for 12 hours under normal pressure. After cooling to room temperature, a large amount of solids are precipitated. After pressure filtration, the filter residue was washed with 75% ethanol solution to obtain a white solid, which was the target product, and the yield of the target product was 72.5%.

Embodiment 3

[0037] Dissolve 9.823g of 3,5-dimethyl-pyrrole-2-carbaldehyde in 0.4L of absolute ethanol, then add 36.21g of rhodamine B hydrazide, and stir under reflux for 12 hours under normal pressure. After cooling to room temperature, a large amount of solids are precipitated. After pressure filtration, the filter residue was washed with 75% ethanol solution to obtain a white solid, which was the target product, and the yield of the target product was 75.3%.

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