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A class of chiral Schiff base polymers and their preparation methods and applications
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A technology of Schiff bases and polymers, applied in the fields of polymer chemistry and materials science, can solve the problems of difficult to obtain stable conformation and less chiral properties, achieve dual reversible fluorescence response and chiral response, preparation method Simple, achieve the effect of fluorescence response and chiral response
Active Publication Date: 2021-02-19
SOUTH CHINA UNIV OF TECH
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The currently reported salen ligand compounds are generally based on small molecules. Since most polymer structures do not contain large steric hindrance groups, it is not easy to obtain a stable conformation. There are very few reports on polymers. Moreover, in terms of chiral properties, there are currently study less
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Embodiment 1
[0044] A pair of chirally symmetrical Schiff base polymers, the structural formulas of which are shown in RR-P1 and SS-P1:
[0045]
[0046] The chiral Schiff base polymer is prepared by the direct reaction of salicylaldehyde and amine, and the reaction equation is as follows:
[0047]
[0048]Among them, the monomer (1R, 2R) / (1S, 2S)-(+)-1,2-diphenylethylenediamine can be purchased from the market, and this example was purchased from Anaiji Pharmaceutical Company. The monomer 4 is 4,4'-(9,9-dihexyl-9H-fluorene-2,7-diyl)bis(2-hydroxybenzaldehyde), which can be prepared from reference (Tetrahedron:Asymmetry 2012,23,570-576). The solvent N,N-dimethylformamide used can be purchased from the market, and in this example was purchased from Sigma Company.
[0049] The preparation steps of the described pair of chirally symmetrical Schiff base polymers are as follows:
[0052] A pair of chirally symmetrical Schiff base model compounds, the structural formulas of which are shown in RR-1 and SS-1:
[0053]
[0054] The chiral Schiff base model compound is prepared by the direct reaction of salicylaldehyde and amine, and the reaction equation is as follows:
[0055]
[0056] Among them, monomer 3 is 4-bromo-2-hydroxybenzaldehyde, which can be purchased from the market, and in this example, it was purchased from Anaiji Pharmaceutical Company.
[0057] The preparation steps of the pair of chirally symmetrical Schiff base model compounds are as follows: (1R,2R) / (1S,2S)-(+)-1,2-diphenylethylenediamine (1.06g, 5 mmol), 4-bromo-2-hydroxybenzaldehyde (monomer 3) (1.0 g, 5 mmol) and 30 mL of DMF were added to a 100 mL two necked round bottom flask. The mixture was reacted at 80°C for 1 h, cooled to room temperature, left standing, and the yellow suspension was filtered and washed three times with absolute ethanol to obtain RR-1 (2.52 g) and SS-1 ...
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Abstract
The invention belongs to the field of macromolecular chemistry and material science, and discloses a chiral Schiff basepolymer with dual reversible responses of fluorescence and chirality, a preparation method and application thereof. The structural formula of this chiral Schiff basepolymer is one of the following structures, and its preparation method comprises the following steps: by adding a chiral diamine compound and a 2-hydroxybenzaldehyde compound and an organic solvent under air conditions Mix, stir and react at 30-100°C for 10-30min, stop the reaction when the reaction solution gradually turns from turbid to a transparent yellow solution, and then purify the obtained reaction product to obtain a chiral Schiff basepolymer. The obtained chiral Schiff base polymer has high selectivity for the detection of zinc ions, and the double reversible response of fluorescence and chirality can be realized by gradually adding zinc ions and EDTA, so it can be applied to the detection of zinc ions and EDTA.
Description
technical field [0001] The invention belongs to the field of macromolecular chemistry and material science, and in particular relates to a chiral Schiff base polymer with dual reversible responses of fluorescence and chirality, a preparation method and application thereof. Background technique [0002] Chirality occurs widely in nature and is common in the most abundant forms of matter. In recent years, supramolecular chirality has attracted extensive attention due to its applications in chiral recognition, sensing, and catalysis. Schiff base structures (salen) containing C=N groups can form complexes with most different metal ions. Ligands (salen) and their metal complexes have a wide range of applications in molecular catalysis, biological activity, drug molecule design and functional materials. Since the selective coordination and binding of certain metal ions to polymeric chromophores can greatly affect the optical properties and chiral strength of materials, they are ...
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