Preparation and application of aminoacylmethyl-(2-methylaminofuran)rhodamine amide derivative

A technology of methylaminofuran and aminoacylmethyl, which is applied in the field of simple preparation of rhodamine derivative optical sensing materials, and can solve the problems of low sensitivity and selectivity of optical sensing, harsh reaction conditions, and expensive raw materials for preparation , to achieve the effect of good naked-eye recognition, high selectivity, and strong cell penetration ability

Active Publication Date: 2019-07-19
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the disadvantages of the existing copper ion colorimetric and fluorescent molecular probes, such as expensive raw materials, complex synthesis process, harsh reaction conditions, difficult purification and separation, low optical sensing sensitivity and selectivity, etc., through a simple reaction , relatively mild reaction conditions, higher yield and purity to prepare and isolate rhodamine derivative molecular probes containing conjugated double bonds and more active chromogenic groups in the molecular structure, and use copper ions to the rhodamine derivatives in the molecular probes Chelation-induced ring-opening of spironolactam produces fluorescence and UV spectra and color changes, allowing naked-eye, high-sensitivity, single-selectivity recognition and detection of copper ions

Method used

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  • Preparation and application of aminoacylmethyl-(2-methylaminofuran)rhodamine amide derivative
  • Preparation and application of aminoacylmethyl-(2-methylaminofuran)rhodamine amide derivative
  • Preparation and application of aminoacylmethyl-(2-methylaminofuran)rhodamine amide derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Weigh 2.40g (5.00mmol) of Rhodamine B and place it in a flask, add 65mL of ethanol to dissolve it, then slowly add 5.0mL of hydrazine hydrate (98% by mass) dropwise, after reflux for 3 hours, evaporate the solvent, The residual solvent was dissolved in water, and the pH was adjusted to about 7.0. A large amount of precipitate was precipitated, and the precipitate was filtered and dried to obtain rhodamine B hydrazide.

[0029] (2) Weigh 1.438g (3.12mmol) of rhodamine B hydrazide and dissolve it in 60mL of dichloromethane, add 2.0mL (12.50mmol) of chloroacetyl chloride, and add 3.0mL of triethylamine as an acid-binding agent , reacted rapidly under ice-salt bath for 10 h, and evaporated the solvent to obtain a lavender solid crude product, and then passed through a neutral alumina column to obtain a yellow-white solid.

[0030] The molar ratio of rhodamine B hydrazide to chloroacetyl chloride is 1:4.

[0031] When neutral alumina passes through the column, the volum...

Embodiment 2

[0035] (1) Weigh 2.40g (5.00mmol) Rhodamine B and place it in a flask and add 70mL of ethanol to dissolve it, then slowly add 6.0mL of hydrazine hydrate (98% by mass) dropwise, after the reaction is refluxed for 3h, after evaporating the solvent, The residual solvent was dissolved in water, and the pH was adjusted to about 7.0. A large amount of precipitate was precipitated, and the precipitate was filtered and dried to obtain rhodamine B hydrazide.

[0036] (2) Weigh 1.438g (3.12mmol) of rhodamine B hydrazide and dissolve it in 65mL of dichloromethane, add 2.25mL (14.06mmol) of chloroacetyl chloride, and add 3.5mL of triethylamine as the acid-binding reagent, reacted rapidly under ice-salt bath for 11 h, and evaporated the solvent to obtain a lavender solid crude product, and then passed through a column of neutral alumina to obtain a yellow-white solid.

[0037] The molar ratio of rhodamine B hydrazide to chloroacetyl chloride is 1:4.5.

[0038] When neutral alumina passes th...

Embodiment 3

[0042] (1) Weigh 2.40g (5.00mmol) Rhodamine B and place it in a flask and add 60mL of ethanol to dissolve it, then slowly add 6.0mL of hydrazine hydrate (98% by mass) dropwise, after the reaction is refluxed for 4h, after evaporating the solvent, The residual solvent was dissolved in water, and the pH was adjusted to about 7.0. A large amount of precipitate was precipitated, and the precipitate was filtered and dried to obtain rhodamine B hydrazide.

[0043] (2) Weigh 1.438g (3.12mmol) of rhodamine B hydrazide and dissolve it in 60mL of dichloromethane, add 2.0mL (12.50mmol) of chloroacetyl chloride, and add 4.0mL of triethylamine as an acid-binding agent , reacted rapidly under ice-salt bath for 12h, and evaporated the solvent to obtain a lavender solid crude product, and then passed through a neutral alumina column to obtain a yellow-white solid.

[0044] The molar ratio of rhodamine B hydrazide to chloroacetyl chloride is 1:4.

[0045] When neutral alumina passes through t...

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Abstract

The invention discloses preparation and application of an aminoacylmethyl-(2-methylaminofuran)rhodamine amide derivative, and belongs to the technical field of synthesis and application of inorganic materials. The aminoacylmethyl-(2-methylaminofuran) rhodamine amide derivative is prepared by performing a reaction between rhodamine B and hydrazine hydrate to produce rhodamine B hydrazide first andthen respectively performing a condensation reaction with chloroacetyl chloride and 2-furanmethylamine. A aminoacylmethyl-(2-methylaminofuran)rhodamine amide compound synthesized according to a preparation method provided by the invention is a rhodamine derivative containing a lactone ring structure, and has the characteristics of excitation and emission wavelengths in a visible region, high fluorescence quantum yield, a molar extinction coefficient, good biocompatibility and the like; the preparation method thereof is simple, a reaction condition is mild, and the yield is relatively high; after combination with copper ions, the naked-eye recognition effect is good, the response is rapid, and the specific selectivity is high; even, the aminoacylmethyl-(2-methylaminofuran)rhodamine amide derivative can be applied to real-time online microdetection of the copper ions and can be developed into an optical sensing material with an important research significance.

Description

technical field [0001] The invention belongs to the technical field of synthesis and application of inorganic materials, and in particular relates to a preparation method for easily preparing rhodamine derivative optical sensing materials and its application. Background technique [0002] As one of the soft transition metals that plays a key role in various physiological processes and is closely related to human health, the content of copper ions is lower than that of iron and zinc ions in the body, however, excessive accumulation of copper ions may cause severe as a result of. For example, short-term exposure of the human body to an environment with high concentrations of copper ions can cause gastrointestinal discomfort, while long-term exposure can lead to liver and kidney damage. Studies have shown that the abnormal accumulation of copper ions in the human body can also cause many neurodegenerative diseases, such as Wilson's disease and Alzheimer's disease. Therefore, ...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64G01N21/78G01N21/33
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/33G01N21/643G01N21/6447G01N21/78
Inventor 吴芳辉罗祥瑞杨俊卿魏先文余爱民
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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