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An acid-resistant light-controlled fluorescent molecular switch in an organic solution and its synthesis method

A technology of organic solutions and fluorescent molecules, applied in the fields of organic chemistry, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve problems such as interference with the authenticity of fluorescent signals and failure of photoactivation performance of dyes

Active Publication Date: 2021-06-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If the traditional rhodamine spiroamide dye is used to detect heavy metal ions in these acidic waste liquids, the fluorescence generated by its acid activation will seriously interfere with the authenticity of the fluorescence signal, and even lead to the complete failure of the photoactivation performance of the dye. When dyes are used for ion detection in acidic environments, they have great limitations

Method used

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  • An acid-resistant light-controlled fluorescent molecular switch in an organic solution and its synthesis method
  • An acid-resistant light-controlled fluorescent molecular switch in an organic solution and its synthesis method
  • An acid-resistant light-controlled fluorescent molecular switch in an organic solution and its synthesis method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Molecule (P1) synthetic route and product structure are as follows:

[0032]

[0033] Synthesis steps and characterization: 3-Nitrorhodamine (5mmol, 2.4g) and n-butylamine (20mmol, 1.4g) were dissolved in absolute ethanol (50mL). The temperature was raised to 78°C for reflux, and after stirring for 8 hours, the solvent was evaporated under reduced pressure, and the product was separated and purified by silica gel chromatography (petroleum ether / ethyl acetate, 8:1v / v), and the obtained light yellow powder (2.6g, 95% ). Then all the powder was dissolved in methanol / dichloromethane (50mL, 3:1v / v) mixed solvent, under hydrogen atmosphere, by palladium carbon (0.21g, 10%wt) catalytic reduction, the filtrate was taken by suction filtration, and the The final product (2 g, 98%) was obtained as a white powder after removal of the solvent by autoclaving.

[0034] The product was characterized by NMR and mass spectrometry: 1 H NMR (400MHz, CDCl 3 )δ7.14(t, J=7.6Hz, 1H), 6....

Embodiment 2

[0038] Molecular (P2) synthetic route and product structure are as follows:

[0039]

[0040] Synthesis steps and characterization: P1 (0.25g, 0.5mmol), iodomethane (0.28g, 2mmol) and potassium carbonate (0.34g, 2.5mmol) were mixed in acetonitrile (8mL), stirred at reflux for 10 hours, cooled to room temperature and filtered The filtrate was obtained, and the solvent was evaporated under reduced pressure. The crude product was separated and purified by column chromatography (silica gel, petroleum ether / ethyl acetate, 10:1 v / v) to obtain white powder P2 (0.17 g, 65%).

[0041] The product was characterized by NMR and mass spectrometry: 1 H NMR (400MHz, CDCl 3 )δ7.23(t, J=7.9Hz, 1H), 6.75(d, J=4.9Hz, 1H), 6.57(t, J=9.3Hz, 2H), 6.49(d, J=8.1Hz, 1H) ,6.41–6.22(m,5H),3.33(q,J=7.0Hz,8H),3.04(s,2H),2.97(d,J=4.9Hz,3H),1.16(t,J=6.9Hz, 12H), 1.07(s, 4H), 0.67(t, J=6.5Hz, 3H). 13 C NMR (101MHz, CDCl 3 )δ 170.15, 154.93, 153.09, 148.60, 147.23, 133.78, 129.01, 113.08, 110.19, 108....

Embodiment 3

[0045] Molecular (P3) synthetic route and product structure are as follows:

[0046]

[0047] Synthesis steps and characterization: P1 (0.25g, 0.5mmol) and acetyl chloride (58mg, 0.75mmol) were mixed in dichloromethane (5mL), stirred for 2 hours, and the solvent was evaporated under reduced pressure, and the crude product was passed through column chromatography (silica gel, Petroleum ether / ethyl acetate, 8:1 v / v) was separated and purified to obtain white powder P3 (0.26 g, 95%).

[0048] The product was characterized by NMR and mass spectrometry: 1 H NMR (400MHz, CDCl 3 )δ10.60(s,1H),8.43(d,J=8.2Hz,1H),7.39(t,J=7.9Hz,1H),6.74(d,J=7.6Hz,1H),6.46(d, J=8.8Hz, 2H), 6.38(d, J=2.6Hz, 2H), 6.28(dd, J=8.9, 2.6Hz, 2H), 3.34(q, J=7.0Hz, 8H), 3.06(t, J=7.0Hz, 2H), 2.29(s, 3H), 1.17(t, J=7.0Hz, 12H), 1.12–1.02(m, 4H), 0.69(t, J=6.7Hz, 3H). 13 CNMR (101MHz, CDCl 3 )δ169.30,168.85,158.27,153.50,153.27,148.83,136.75,133.81,128.78,117.95,117.52,116.43,108.07,105.32,101.26,99.97,97.7...

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Abstract

The invention provides an acid-resistant light-controlled fluorescent molecular switch in an organic solution and a synthesis method thereof. The specific molecular structure of the molecular switch uses 3-primary amines or secondary amines to replace rhodamine spiramide dyes as basic structural units, and its structural formula is as follows: 1) as shown. The invention develops an acid-resistant light-controlled fluorescent molecular switch in an organic solution, which has acid-resistant properties and retains light-activated properties. Therefore, such acid-resistant photoactivated dyes can be applied to sensing and detection in organic solvents, avoiding the interference of fluorescent background caused by acidic environments. In addition, the acid-resistant light-controlled fluorescent molecular switch in the organic solution of the present invention can also be used as a molecular fluorescent probe in the field of sensing and detection.

Description

technical field [0001] The invention belongs to the field of molecular switches, in particular to an acid-resistant light-controlled fluorescent molecular switch in an organic solution and a synthesis method thereof. Background technique [0002] Rhodamine is a kind of dye with xanthene as the parent material, which has the interconverting molecular structure of spiro ring and ring opening. Compared with other fluorescent dyes, rhodamine has the advantages of good photostability, large molar extinction coefficient, and high fluorescence quantum yield, so it has received extensive attention. The fluorescent "light-dark" state of rhodamine dyes is based on the amide spiro switch. In addition to good optical properties, rhodamine dyes also have a great advantage in that their structures are easy to modify. Usually, simple structural modifications or The introduction of some recognition groups can be used for detection. Before the probe is combined with the target molecule, th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/643G01N2021/6439
Inventor 徐兆超祁清凯陈婕
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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