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A kind of chiral chromatography packing of substituted polyalkyne grafted divinylbenzene microspheres and preparation method thereof

A technology of divinylbenzene and chiral chromatography, which is applied in the field of chiral chromatography packing and its preparation, can solve problems such as poor stability, and achieve the effect of improving stability and avoiding damage to the helical structure

Active Publication Date: 2022-07-12
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to overcome the defect of poor stability of helical polymer-based composite materials, the present invention grafts and copolymerizes substituted polyyne containing double bonds with highly cross-linked rigid PDVB to prepare a helical polymer-based core-shell structure compound with stable performance, which can be reused The complex in Cu 2+ A Novel Chiral Chromatography Packing Material Under Complexation Through the Transformation from Random Coil to Helical Conformation

Method used

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  • A kind of chiral chromatography packing of substituted polyalkyne grafted divinylbenzene microspheres and preparation method thereof
  • A kind of chiral chromatography packing of substituted polyalkyne grafted divinylbenzene microspheres and preparation method thereof
  • A kind of chiral chromatography packing of substituted polyalkyne grafted divinylbenzene microspheres and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0057] The first step was to prepare M1 as follows: 1.90 g of N-Boc-alanine ((N-tert-butoxycarbonyl-alanine; CAS: 15761-38-3) was dissolved in 40 mL of THF, followed by the addition of 1.3 mL of Isobutyl chloroformate and 1.1 mL of N-methylmorpholine were reacted at 30 °C for 15 min, then 0.7 mL of propargylamine was added to the flask, reacted in a water bath at 30 °C for 4 h, and the resulting precipitate was removed by filtration; the filtrate was washed with ethyl acetate Ester extraction, washed three times with 30 mL of hydrochloric acid solution (2M), twice with 30 mL of saturated sodium bicarbonate solution, and once with 80 mL of deionized water, then dried with anhydrous magnesium sulfate, distilled under reduced pressure, in THF / n-hexane Purify by cooling and crystallization in a system with a volume ratio of 1 / 6. After 5 hours, filter and dry at 30°C for 24h-48h to obtain M1 solid product with a yield of 80%.

[0058] The second step to prepare M2 is as follows: di...

Embodiment 2

[0075] The first step is to prepare the substituted alkyne monomer M1, and the specific method is as in Example 1.

[0076] The second step is to prepare the substituted alkyne monomer M2, and the specific method is as in Example 1.

[0077] The third step is to prepare the substituted polyalkyne P-M1-co-M2-Boc, as follows: add 0.113g of M1, 0.055g of M2, 0.005g of (nbd)Rh to the test tube + B - (C 6 H 5 ) 4 catalyst, and then the test tube was repeatedly vacuumed and argon treated for a total of three times. Then 5ml of THF was added under argon protection, the test tube was sonicated until the solid was dissolved, then the test tube was heated in a water bath at 30°C, and a pale red solution was obtained after polymerization for 6 hours. The obtained solution was added dropwise to n-hexane for precipitation and filtered. After drying, precipitation, filtration and drying were performed twice in a system with a volume ratio of THF / n-hexane of 1 / 6 to obtain yellow P-M1-co...

Embodiment 3

[0084] The first step is to prepare the substituted alkyne monomer M1, and the specific method is as in Example 1.

[0085] The second step is to prepare the substituted alkyne monomer M2, and the specific method is as in Example 1.

[0086] The third step is to prepare the substituted polyalkyne P-M1-co-M2-Boc, as follows: add 0.136g of M1, 0.044g of M2, 0.005g of (nbd)Rh to the test tube + B - (C 6 H 5 ) 4 catalyst, and then the test tube was repeatedly vacuumed and argon treated for a total of three times. Then 5ml of THF was added under argon protection, the test tube was sonicated until the solid was dissolved, then the test tube was heated in a water bath at 30°C, and a pale red solution was obtained after polymerization for 6 hours. The obtained solution was added dropwise to n-hexane for precipitation and filtered. After drying, precipitation, filtration and drying were carried out twice in a system with a volume ratio of THF / n-hexane of 1 / 6 to obtain yellow P-M1-...

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Abstract

The invention relates to the field of functional polymer materials, and discloses a chiral chromatographic filler of substituted polyalkyne-grafted divinylbenzene microspheres and a preparation method thereof, comprising the steps of: (1) using N-tert-butoxycarbonyl-alanine M1 is synthesized by amidation reaction with propargylamine; (2) M2 is synthesized by amidation reaction of acryloyl chloride and propargylamine; (3) M1 and M2 are initiated and copolymerized to obtain a copolymer; (4) Divinylbenzene is added to the initiator (5) Graft copolymerization of copolymer and PDVB microspheres under the action of initiator and cross-linking agent to obtain core-shell structure, and the core-shell structure is dispersed in Cu 2+ The chiral chromatographic packing is obtained by helical conformation induction in aqueous solution. To overcome the defect of poor stability of helical polymer-based composites, the graft copolymerization of substituted polyalkynes containing double bonds and highly cross-linked rigid PDVB greatly improves the stability of helical polymer-based composites.

Description

technical field [0001] The invention relates to the field of functional polymer materials, in particular to a chiral chromatographic filler of substituted polyalkyne-grafted divinylbenzene microspheres and a preparation method thereof. Background technique [0002] Chirality and helical structures exist widely in nature, and helical structures have attracted the interest of researchers since their discovery. In more than half a century of exploration, researchers have synthesized a series of helical polymers with exquisite structures. Due to its special secondary structure and chirality, helical polymers are widely used in enantiomeric recognition and resolution [Macromolecules, 2008, 41(1):3–12.], asymmetric catalysis [Chem.Eur.J., 2011, 17(31), 8514–8523.], controlled release of chiral drugs [Macromolecules, 2017, 50(11): 4114–4125.], circularly polarized luminescence [ACS Nano, 2020, 14(3): 3208– 3218.] and many other fields have shown great application potential. Howe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F281/00C08F257/00C08F212/36C08F8/00B01J20/29
CPCC08F281/00C08F257/00C08F8/00B01J20/29C08F212/36
Inventor 戚栋明殷丽杰段慧敏黄骅隽陈涛朱晨洁
Owner ZHEJIANG SCI-TECH UNIV
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