Acid-resistant photo-controlled fluorescent molecular switch in organic solution, and synthesis method thereof

A technology of organic solutions and fluorescent molecules, applied in the fields of organic chemistry, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problems of interference with the authenticity of fluorescent signals and the failure of photoactivation performance of dyes, so as to reduce background fluorescence interference and avoid fluorescence The effect of background distraction

Active Publication Date: 2019-09-24
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • 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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  • Acid-resistant photo-controlled fluorescent molecular switch in organic solution, and synthesis method thereof
  • Acid-resistant photo-controlled fluorescent molecular switch in organic solution, and synthesis method thereof
  • Acid-resistant photo-controlled fluorescent molecular switch in organic solution, and synthesis method thereof

Examples

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 photo-controlled fluorescent molecular switch in an organic solution, and a synthesis method thereof. The specific molecular structure of the molecular switch adopts a 3-primary amine or secondary amine substituted rhodamine spiroamide as a basic structural unit, and the structural formula of the molecular switch is represented by formula (1). The acid-resistant photo-controlled fluorescent molecular switch in the organic solution retains the photoactivation performance, so like acid-resistant photoactivated dyes can be applied to sensing detection in an organic solvent to avoid the inference of an acidic environment to the fluorescence background. In addition, the acid-resistant photo-controlled fluorescent molecular switch in the organic solution can also be used in the fields of sensing and detection as a molecular fluorescent probe.

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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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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