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N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine)hydrazone and application

A naphthalimide and butyl technology, which is applied in the fields of organic synthesis and iron ion detection, can solve the problems of complex operation, low selectivity, low detection sensitivity, etc., and achieves simple operation method, good selectivity, and detection sensitivity. high effect

Active Publication Date: 2019-04-09
TAIYUAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The present invention is to solve existing Fe 3+ Due to the technical problems of complex detection method operation or low selectivity and low detection sensitivity, a new compound, N-butyl-4-hydroxy-1,8-naphthalimide-3-carbaldehyde- (2-pyridine) hydrazone and its preparation method and application, using N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine) hydrazone as a fluorescent probe for Fe 3+ The detection can avoid the interference of various metal ions, detect iron ions in aqueous solution with high sensitivity, and the operation is simple, convenient and fast, and the result is clear and easy to distinguish

Method used

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  • N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine)hydrazone and application
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  • N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine)hydrazone and application

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Experimental program
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Effect test

Embodiment 1

[0033] Synthesis and characterization of N-butyl-4-hydroxy-1,8-naphthalimide-3-formaldehyde-(2-pyridine)hydrazone (L):

[0034]Dissolve 0.045g (0.15mmol) of N-butyl-4-hydroxyl-1,8-naphthalimide-3-carbaldehyde and 0.02g (0.18mmol) of 2-hydrazine pyridine in 8mL of methanol and heat to 65 After reflux at ℃ for 1 h, solids precipitated out after cooling to room temperature, filtered with suction, and washed with a small amount of methanol to obtain a yellow solid L (0.054 g, yield 92.7%), L is N-butyl-4-hydroxyl-1,8- Naphthalimide-3-carbaldehyde-(2-pyridine)hydrazone. 1 H NMR (DMSO-d 6 )δ: 11.48(s,1H), 8.68(d,1H), 8.63(s,1H), 8.55(s,1H), 8.49(d,1H), 8.23(d,1H), 7.83(t,1H ),7.75(t,1H),6.99(d,1H),6.89(t,1H),4.05(t,2H),1.61(m,2H),1.35(m,2H),0.93(t,3H) .HRMS(ESI):calcd.for C 22 h 21 N 4 o 3 389.1614 (L+H), found: 389.1615.

Embodiment 2

[0036] Determination of Spectral Properties of N-Butyl-4-Hydroxy-1,8-Naphthalimide-3-Formaldehyde-(2-Pyridine) Hydrazone (L)

[0037] The L prepared in Example 1 was dissolved in methanol to obtain 1 × 10 -3 M's stock solution, dispensing 10 -2 The metal ion stock solution of M was used for the metal ion selectivity determination. The stock solution was further diluted to an appropriate concentration for fluorescence detection. The pH of the detection system was adjusted with 0.05mol / L Tris-hydrochloric acid buffer solution, and the pH of the buffer solution was adjusted to 7.4 with hydrochloric acid. The detection system is DMSO:H 2 O=7:3 (v / v, pH=7.4). The fluorescence titration experiment process is as follows: take 25 μL of the L stock solution in a colorimetric tube, add a corresponding volume of 1×10 -3 Fe of M 3+ For the stock solution, add 1 mL of buffer and secondary water to make the total volume of water 1500 μL, then dilute to 5 mL with DMSO, shake well and u...

Embodiment 3

[0043] The N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine) hydrazone (L) prepared in embodiment 1 is to Fe 3+ Determination of selectivity experiments

[0044] In DMSO:H containing 5 μM of probe L prepared in Example 1 2 O=7:3 (v / v, pH=7.4) solution is added with an equal amount of K + , Ca 2+ , Na + ,Mg 2+ ,Al 3+ ,Zn 2+ , Ag + ,Hg 2+ ,Pb 2+ ,Cu 2+ , Fe 3+ , Fe 2+ ,Cd 2+ , Ni 2+ ,Cr 3+ ,Co 2+ ions, Fe only 3+ The fluorescence of the system is significantly enhanced, indicating that the probe L has an effect on Fe 3+ are very selective, such as Figure 4 shown. Interference experiments of coexisting ions showed that common metal ions on Fe 3+ The detection interference of L is very small, indicating that L detects Fe 3+ Has strong anti-interference ability, such as Figure 5 shown.

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Abstract

The invention belongs to the technical fields of organic synthesis and iron-ion detection and particularly relates to N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine)hydrazone and an application. The preparation method comprises the following steps of: dissolving N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde and 2-hydrazinopyridine into methanol, heating and refluxing, cooling till the reaction is ended, carrying out suction filtration, and washing with the methanol to obtain the N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine)hydrazone. The invention alsoprovides a qualitative and quantitative detection method of Fe3+ by the N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine)hydrazone and an application in realizing fluorescence imagingof Fe3+ in cells. The N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine)hydrazone and the application have the beneficial effects that the synthesis method of the N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine)hydrazone is simple; the N-butyl-4-hydroxyl-1,8-naphthalimide-3-formaldehyde-(2-pyridine)hydrazone is used for detection of Fe3+ as a fluorescence probe, the selection for Fe3+ is good, the interference of other coexisting positive ions can be avoided, the detection sensitivity is high, simultaneously the color is changed into light yellow from pink, the naked-eye recognition can be realized, the operation method is simple, the cost is low, and the fast and convenient effects are achieved; fluorescence imaging of Fe3+ can be realized in the cells, so that the potential application value is achieved in the aspect of sensor development.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and iron ion detection, and specifically relates to N-butyl-4-hydroxy-1,8-naphthalimide-3-formaldehyde-(2-pyridine) hydrazone and its application. Background technique [0002] Iron is one of the essential elements for the human body and is very important for the transport of oxygen in hemoglobin and myoglobin in the human body. However, iron deficiency or excessive intake in the human body is closely related to heart and liver diseases, cancer, etc., and can also lead to some neurobehavioral disorders, such as Parkinson's and Alzheimer's diseases. Therefore, it is necessary to establish a reliable, highly selective, and highly sensitive analytical method for the determination and detection of Fe content in biological and environmental samples. Many analytical methods have been used to determine iron in environmental and biological samples, including ion pair chromatography, electrother...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C09K11/06G01N21/64
CPCC07D401/12C09K11/06C09K2211/1029G01N21/6428G01N21/643G01N21/6447
Inventor 侯玲杰王煜刘涛
Owner TAIYUAN NORMAL UNIV
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