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Synthesis and application of a benzimidazole-based supramolecular gelling factor based on hydroxynaphthaldehyde functionalization
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A technology of hydroxynaphthaldehyde and supramolecular gel, which is applied in the field of ion detection, can solve rare problems and achieve the effect of enhancing water solubility and good aggregation fluorescence performance
Inactive Publication Date: 2020-01-21
NORTHWEST NORMAL UNIVERSITY
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However, there are few reports on continuous relay recognition of iron ions and cysteine using the same sensor molecule
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Embodiment 1
[0040] Embodiment 1, the preparation of gel factor S
[0041] In 30ml absolute ethanol, add 1.36g (4×10 -3 mol) 2-undecyl-1H-benzimidazolyl-1-acetylhydrazide, 0.68g 2-hydroxy-1-naphthaldehyde (4×10 -3 mol), 2ml of glacial acetic acid, reacted at a temperature of 80°C for 8h, cooled to room temperature after the reaction was completed, filtered off the solvent, and recrystallized with DMF-EtOH to obtain a yellow solid product which was gel factor S; the yield was 78.2%. Its mass spectrum see figure 1 .
Embodiment 2
[0042] Embodiment 2, the preparation of organogel OG
[0043] Take 0.005 g of the gelling factor S prepared in Example 1, add it to 1.00 ml of glycerol, heat to dissolve it fully, let it stand, and form an organogel OG with a mass-volume ratio of 5 mg / ml after cooling to room temperature.
Embodiment 3
[0044] Example 3. Colorimetric / fluorescent recognition of iron ions and L-cysteine by organogel OG
[0045] Pipette organogel OG into a series of drip plates, add Mg 2+ , Ca 2+ 、Cr 3+ , Fe 3+ 、Co 2+ 、Ni 2+ 、Cu 2+ , Zn 2+ 、Ag + 、Cd 2+ , Hg 2+ , Pb 2+ 、Ba 2+ , Tb 3+ 、Al 3+ , La 3+ and Eu 3+ Cationic aqueous solution (concentration is 0.1M), if the fluorescence of the organic gel OG is quenched, and the color of the gel changes from yellow to black, it means that Fe is added dropwise. 3+ , if the fluorescence of the organogel is not quenched, it means that the dropwise addition is not Fe 3+ .
[0046] Fe 3+ The metal gel FeG formed by the organogel was added to a series of drip plates, and L-Leu, L-Pro, L-Ary, L-Ser, L-Thr, L-Phe, L-Gln, L Aqueous solutions of -IIe, -Glu, L-Ala, L-Met, L-Val, L-Tyr, DL-Asp, L-His, L-Gly, L-Cys (concentration: 0.1 M), if the metal organic condensation The fluorescence of the gel FeG recovers, and the color of the gel returns ...
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Abstract
The invention designs and synthesizes a benzimidazole-based super-molecular gel factor based on hydroxynaphthaldehyde functionalization. According to the benzimidazole-based super-molecular gel factorbased on the hydroxynaphthaldehyde functionalization, which is designed and synthesized by the invention, benzimidazole in a molecule of the gel factor is used as a system with a stable rigid structure so that a main body molecule emits strong fluorescent light; a naphthalene ring is used as a signal reporting group, so that the main body molecule has a good aggregation-state fluorescent propertyand the water solubility of a sensor molecule is enhanced. Organic gel formed by the gel factor in an organic solvent has a single-selectivity fluorescence identification property on Fe<3+>, Al<3+> and CN<->. After the organic gel and iron ions are combined, formed metal organic gel also can be used for continually identifying L-cysteine to cause fluorescence recovery of the gel factor and OFF-ONsignal expression of the sensor molecule is realized. The synthesis of an ON-OFF-ON type sensor molecule realizes multifunctional application of a sensor.
Description
technical field [0001] The invention relates to a benzimidazole-based supramolecular gel factor, in particular to a benzimidazole-based supramolecular gel factor based on hydroxynaphthaldehyde functionalization and a synthesis method thereof; the present invention also relates to the supramolecular gel The application of the factor in colorimetric-fluorescence identification of iron ions, L-cysteine, aluminum ions and cyanide belongs to the field of ion detection. Background technique [0002] Iron is one of the essential trace elements for the human body. Iron participates in the synthesis of myoglobin, cytochrome, hemoglobin, cytochrome oxidase and catalyst, while iron affects protein and hematopoietic vitamin metabolism and DNA synthesis. Because iron participates in hematopoietic function and the relationship between iron and enzymes, it is determined that iron deficiency can reduce the bactericidal ability of white blood cells, increase the body's infectivity, and dama...
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