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Synthesis method of dihydroxy rhodamine derivative or trihydroxy rhodamine derivative

A synthesis method and trihydroxyl technology, which are applied in chemical instruments and methods, organic chemistry, color-changing fluorescent materials, etc., can solve the problems of difficulty in introducing polymer chains, few external functional groups of rhodamine chromophore, etc., and achieve a simple and efficient synthesis route. The effect of simple and easy-to-obtain reaction substrates and broad application prospects

Inactive Publication Date: 2019-02-12
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few reports on the introduction of rhodamine derivatives into polymer systems to prepare force-responsive materials. The main reason is that the rhodamine chromophore has few external functional groups and is difficult to introduce into the polymer chain.

Method used

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  • Synthesis method of dihydroxy rhodamine derivative or trihydroxy rhodamine derivative
  • Synthesis method of dihydroxy rhodamine derivative or trihydroxy rhodamine derivative
  • Synthesis method of dihydroxy rhodamine derivative or trihydroxy rhodamine derivative

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0030] Take a 150mL round-bottomed flask, add Rh6G-OH (1.00g, 2.1mmol) and ethylene oxide (0.96g, 21.0mmol) into 70mL of glacial acetic acid in THF (1 / 1, v In / v), after stirring at room temperature for 48h, the solvent was removed by rotary evaporation to obtain a crude product. The crude product was separated by column chromatography (dichloromethane:ethanol=35:1, v / v) to obtain Rh6G-2OH (white solid) and Rh6G-3OH (pink solid). Overall yield: 72% (dihydroxy product: 0.40 g, 36%, trihydroxy product: 0.43 g, 36%).

example 2

[0032] Take a 150mL round-bottomed flask, add Rh6G-OH (1.00g, 2.1mmol) and ethylene oxide (0.96g, 21.0mmol) into 70mL of glacial acetic acid in THF (1 / 1, v In / v), after stirring at room temperature for 60 h, the solvent was removed by rotary evaporation to obtain a crude product. The crude product was separated by column chromatography (dichloromethane:ethanol=35:1, v / v) to obtain Rh6G-2OH (white solid) and Rh6G-3OH (pink solid). Overall yield: 75% (dihydroxy product: 0.17 g, 15%, trihydroxy product: 0.72 g, 60%).

example 3

[0034] Take a 150mL round-bottomed flask, add Rh6G-OH (1.00g, 2.1mmol) and ethylene oxide (0.96g, 21.0mmol) into 70mL of glacial acetic acid in THF (1 / 1, v In / v), after stirring at room temperature for 72h, the solvent was removed by rotary evaporation to obtain a crude product. The crude product was separated by column chromatography (dichloromethane:ethanol=35:1, v / v) to obtain Rh6G-3OH (pink solid). All trihydroxy product: 0.95 g, 80%.

[0035] Rh6G-2OH

[0036] H NMR 1 H NMR (400MHz, CDCl 3 )δ / ppm: 8.07–7.83(m,1H), 7.57–7.40(m,2H),7.13–6.99(m,1H),6.91(s,2H),6.48(d,J=10.4 Hz,2H) ,3.62(t,J=5.3Hz,4H),3.41(d,J=25.5Hz,2H),3.28(dd,J=9.4,4.7Hz,2H),3.25–3.14(m,4H),3.08– 2.96(m,4H),2.09(d,J=9.1Hz,6H),1.03(t,J=7.1Hz,6H).

[0037] C NMR 13 C NMR (101MHz, CDCl 3 )δ / ppm:170.14,153.52, 151.46,150.56,150.44,147.74,132.92,130.25,130.00,129.49,128.44, 128.01,123.82,123.13,118.51,113.83,110.44,104.85,96.49,65.70, 62.40,59.07,53.76 ,48.32,44.81,38.35,17.85,16.75,14.69,11.66.

[00...

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Abstract

The invention discloses a synthesis method of a dihydroxy rhodamine derivative or trihydroxy rhodamine derivative, and belongs to the field of organic synthesis methods. Rh6G-OH and ethylene oxide areadded into a tetrahydrofuran solution of glacial acetic acid under an ice-salt bath condition, wherein a molar ratio of the Rh6G-OH to the ethylene oxide is 1 to (5 to 20), and a molar ratio of the Rh6G-OH to the glacial acetic acid is 1 to 300; after normal-temperature stirring reaction is carried out for more than 48 h, rotary evaporateion is conducted to remove a solvent and obtain a crude product; after column chromatography is used for separating the crude product, white solid is obtained. According to the synthesis method of the dihydroxy rhodamine derivative or trihydroxy rhodamine derivative, a synthesis route is simple and efficient, the reaction substrates are simple and easy to get, reaction conditions are very mild (normal temperature and normal pressure), and the obtained product can be controlled by changing reaction time. The dihydroxy rhodamine derivative or trihydroxy rhodamine derivative can be easily introduced into a polyurethane (or polyurea) chain, can also be easily connected with a double bond or an initiator to be connected with polyolefin chains of more types, and has very wide application prospects.

Description

technical field [0001] The invention belongs to the field of organic synthesis methods, and the content of the invention is a synthesis method and application of dihydroxy and trihydroxy rhodamine derivatives. Background technique [0002] Intelligent responsive fluorescent color-changing materials have gradually become a research hotspot in recent years. This kind of materials can reversibly change their fluorescent properties (such as the color and intensity of light emission) under the action of external stimuli. Rhodamine is a common fluorescent chromophore. Rhodamine has good photophysical properties, such as high extinction coefficient, high quantum yield, photostability and long emission wavelength. In addition, rhodamine molecules can be synthesized through structural design to obtain derivatives with different functional groups, which is beneficial to adjust their luminescent properties. Our previous studies have shown that rhodamine lactams are a class of force-se...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K9/02
CPCC07D491/107C09K9/02C09K2211/1029C09K2211/1088C09K2211/1466
Inventor 马志勇杨扬胡欢
Owner BEIJING UNIV OF CHEM TECH
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