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Phenylhydrazone fluorescent probe, preparation and applications thereof

A technology of fluorescent probes and phenylhydrazones, which is applied in the field of fluorescent chemical sensing, can solve the problems of less fluorescence performance and less fluorine-boron-fluorescence complexation of the phenylhydrazone structure.

Active Publication Date: 2019-12-13
HANGZHOU VOCATIONAL & TECHN COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many reports on the phenylhydrazone structure and its complexes of transition metals, but there are not many reports on the fluoroboron-fluorine complex of the phenylhydrazone structure, and there are even fewer studies on the fluorescence properties.

Method used

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  • Phenylhydrazone fluorescent probe, preparation and applications thereof
  • Phenylhydrazone fluorescent probe, preparation and applications thereof
  • Phenylhydrazone fluorescent probe, preparation and applications thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Into a 250 mL three-neck round bottom flask, put 80% hydrazine hydrate (31.25 g, 0.37 mol) and dimethyl carbonate (54 g, 0.6 mol). Heat up to 80°C and reflux for 7 hours. After the reaction was completed, methanol and excess dimethyl carbonate were distilled off under reduced pressure until the end of the distillation was reached. After a large amount of foam was generated, the distillation was stopped. After cooling to room temperature, a white solid was precipitated, and the product was recrystallized with ethanol to obtain 25.5 g of white crystal IV-1. Yield 74.91%, m.p. 72-73°C.

Embodiment 2

[0042] In a 50mL three-necked round-bottom flask, add 2,4-dihydroxyacetophenone (1.52g, 10mmol), methyl carbazate (0.92g, 10mmol), ethanol (25mL), and heat to reflux. TLC tracking detection (developer toluene: ethyl acetate = 9:1), after the reaction, cooled to room temperature, put into the refrigerator, precipitated a large amount of white solid, filtered with suction, rinsed with a small amount of ethanol, and recrystallized from ethanol to obtain a white powder IV-2a 1.95g, yield 87.1%, m.p.208.8°C-212.3°C. 1H NMR (500MHz, DMSO) δ: 13.04(s, 1H), 10.59(s, 1H), 9.72(s, 1H), 7.33(d, J=8.7Hz, 1H), 6.29(dd, J=8.7, 2.4Hz, 1H), 6.23(d, J=2.4Hz, 1H), 3.74(s, 3H), 2.23(s, 3H); HRMS(ESI) m / z calcd for: C 10 h 13 N 2 o 4 + (M+H) + 225.0869, found 225.0869.

Embodiment 3

[0044] In a 50 mL three-neck round bottom flask, add 2,4-dihydroxybenzaldehyde (1.38 g, 10 mmol), methyl carbazate (0.92 g, 10 mmol), methanol (20 mL), and heat up to reflux. TLC tracking detection (developer toluene: ethyl acetate = 8:2), after the reaction, after cooling to room temperature, put it in the refrigerator, a large amount of white solid precipitated, filtered with suction, rinsed with a small amount of methanol, and recrystallized with ethanol to obtain a white solid. Crystal IV-2b 1.77g, yield 84.3%, m.p.109°C-113°C. 1 HNMR (500MHz, DMSO) δ: 11.07 (d, J = 42.9Hz, 2H), 9.81 (s, 1H), 8.10 (s, 1H), 7.20 (dd, J = 8.3, 2.8Hz, 1H), 6.44- 6.20(m,2H),3.69(s,3H);HRMS(ESI)m / z calcd for C 9 h 11 N 2 o 4 + (M+H) + 211.0713, found 211.0713.

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Abstract

The invention discloses a phenylhydrazone fluorescent probe, a preparation and applications thereof. According to the present invention, the fluorescence of the phenylhydrazone fluorescent probe can be enhanced in Al<3+>, Ba<2+>, Cu<2+>, Hg<2+>, Mg<2+>, Ag<+>, Ni<2+> and Zn<2+>, can be even enhanced by more than 20 times in Mg<2+> and Ni<2+>, and is almost completely quenched in Fe<3+>, such thatthe results show that the complexed phenylhydrazone has good selectivity on iron metal ions, and can be used for the naked eye qualitative identification of iron ions.

Description

technical field [0001] The invention belongs to the technical field of fluorescent chemical sensing, and the compound is a fluorescent probe for fluorescence quenching detection with high selectivity to iron ions. Background technique [0002] The phenylhydrazone structure and its complexes have a unique structure and catalytic activity, and have become a hot spot in coordination chemistry research. In 2010, Ni Xufeng from Zhejiang University prepared a series of 3,5 -Phenylhydrazone complexes with di-tert-butyl salicylaldehyde aniline as the main molecule, and found that this series of complexes can catalyze the ring-opening polymerization of ε-caprolactone with a single component, and the conversion rate of the monomer can reach up to 100 %, in 2010, Shinya Handa of Japan reported on J.A.C.S that the bimetallic phenylhydrazone complex containing transition metal Li and rare earth metal La has good asymmetric catalytic activity in the nitro-Mannich reaction. A series of 1,...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07C281/04C09K11/06G01N21/64
CPCC07C281/04C07F5/022C09K11/06C09K2211/1007C09K2211/104G01N21/643G01N2021/6432
Inventor 吕路平唐平
Owner HANGZHOU VOCATIONAL & TECHN COLLEGE
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