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Naphthoyl hydrazide-functionalized organic small-molecule gelatin factor DNS and synthesis and application thereof

A kind of technology of small molecule gel and naphthoyl hydrazone, applied in the field of ion detection and chemical synthesis

Inactive Publication Date: 2019-07-09
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although many methods for ion recognition have been reported, the development of supramolecular materials for the simultaneous detection of target guests remains an interesting challenge

Method used

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  • Naphthoyl hydrazide-functionalized organic small-molecule gelatin factor DNS and synthesis and application thereof
  • Naphthoyl hydrazide-functionalized organic small-molecule gelatin factor DNS and synthesis and application thereof
  • Naphthoyl hydrazide-functionalized organic small-molecule gelatin factor DNS and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1, the synthesis of supramolecular gelling factor DNS

[0045] (1) Synthesis of Compound D: See literature: Y. M. Zhang, J. X. Su, Q. Li, W. J. Qu, X. Zhu, Y. L. Leng, S. F. Xin, H. Yao, Q. Lin & T. B. Wei, Supramolecular Chemistry, 2017, 29:6, 411-416;

[0046] (2) Synthesis of compound DN: Take 1.72 g (5 mmol) of compound D, 1.14 g (7.5 mmol) of methyl p-hydroxybenzoate, K 2 CO 3 8.29 g (60 mmol), KI 0.42 g (2.5 mmol), (compound D and methylparaben 1:1.5, with K 2 CO 3 1 : 12, molar ratio to KI 1 : 0.5), was added to 200mL acetone, and reacted at 60°C for 84 h; Precipitate a white solid, collect the white solid by suction filtration under reduced pressure, and recrystallize with acetone and water after drying to obtain DN, and the productive rate is 89%;

[0047] (3) Synthesis of compound DNH: take 2.07g (5mmol) of compound DN, 4.25g (100mmol) of 85% hydrazine hydrate (the molar ratio of compound DN and 85% hydrazine hydrate is 1:20), add to 80 mL of...

Embodiment 2

[0050] Embodiment 2, the preparation of supramolecular organogel

[0051] Take a certain amount of gelling factor DNS, heat and dissolve in H 2 O-DMSO system (H 2 The volume ratio of O to DMSO is 1:3), so that the concentration of the gelling factor DNS is 30 mg / mL, and the supramolecular gel GDNS is formed after standing and cooling. The gel emits strong yellow-green aggregation-induced fluorescence under ultraviolet light with an excitation wavelength of 365 nm.

Embodiment 3

[0052] Example 3, Organogel GDNS Synchronous Fluorescence Recognition of Fe 3+ , Hg 2+ and Cu 2+

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Abstract

The invention designs and synthesizes a naphthoyl hydrazide-functionalized organic small-molecule gelatin factor DNS. The gelatin factor can form supramolecule organogel GDNS through intermolecular hydrogen bonds, Van der Waals' force and pi-pi interaction in a DMSO / H2O solution, and the GDNS can produce yellow-green aggregation induced fluorescence. Fe<3+>, Hg<2+>, Ag<+>, Ca<2+>, Cu<2+>, Co<2+>,Ni<2+>, Cd<2+>, Pb<2+>, Zn<2+>, Cr<3+>, Mg<2+> and other ions are dded separately to the GDNS, the fluorescence of the GDNS can be quenched by only Fe<3+>, Hg<2+> and Cu<2+>, and stable metal gel is formed; and in addition, the lowest limits of detection for the three metal ions by using GDNS are 1.00x10<-10> M, 9.29x10<-11> M and 1.26x10<-9> M, so that synchronous ultra-sensitive detection of thethree metal ions is achieved.

Description

technical field [0001] The invention relates to a naphthoylhydrazone functionalized organic small molecule gelling factor and a synthesis method thereof. The present invention also relates to a supramolecular organogel based on the gelling factor in synchronous ultrasensitive detection of Fe 3+ , Hg 2+ and Cu 2+ The application of the supramolecule belongs to the field of chemical synthesis and the field of ion detection. Background technique [0002] Fe 3+ Plays a key role in many biochemical processes at the cellular level, Fe deficiency in humans 3+ Can cause diseases such as anemia, liver damage, Parkinson's disease and cancer, meanwhile, Fe 3+ Due to its paramagnetic nature, it acts as a fluorescence quencher, which makes it difficult to develop a continuously off and on fluorescent sensor to detect Fe 3+ . In addition, heavy metal ions are widely used in industry, however, due to high toxicity and bioaccumulation, heavy metal ions released into the environment ca...

Claims

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Application Information

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IPC IPC(8): C07C241/04C07C243/38C09K11/06G01N21/64
CPCC07C67/31C07C241/04C07C243/38C09K11/06C09K2211/1007C09K2211/1011G01N21/643G01N2021/6432C07C69/92
Inventor 林奇陈燕燕樊彦青巩冠斐关晓文魏太保张有明姚虹
Owner NORTHWEST NORMAL UNIVERSITY