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A kind of organic small molecule gelling factor functionalized by naphthoylhydrazone and its synthesis and application

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

Inactive Publication Date: 2021-09-28
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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  • A kind of organic small molecule gelling factor functionalized by naphthoylhydrazone and its synthesis and application
  • A kind of organic small molecule gelling factor functionalized by naphthoylhydrazone and its synthesis and application
  • A kind of organic small molecule gelling factor functionalized by naphthoylhydrazone and its synthesis and application

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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 present invention designs and synthesizes a naphthoyl hydrazone functionalized organic small molecule gel factor DNS, the gel factor is in DMSO / H 2 Supramolecular organogel GDNS can be formed in O solution through intermolecular hydrogen bonding, van der Waals force and π-π interaction, and GDNS can produce yellow-green aggregation-induced fluorescence. Add Fe to GDNS separately 3+ , Hg 2+ , Ag + , Ca 2+ , Cu 2+ , Co 2+ , Ni 2+ , Cd 2+ , Pb 2+ , Zn 2+ , Cr 3+ , Mg 2+ Plasma, Fe only 3+ , Hg 2+ and Cu 2+ It can quench the fluorescence of GDNS and form a stable metal gel. In addition, the lowest detection line of GDNS for the detection of three metal ions is 1.00×10 ‑10 M, 9.29×10 ‑11 M, 1.26×10 ‑9 M, achieves simultaneous ultrasensitive detection of three metal ions.

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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Patent Type & Authority Patents(China)
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