Substituted polyacetylene grafted divinyl benzene microspherechiral chromatographic packing 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: 2021-08-31
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 he...

Method used

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  • Substituted polyacetylene grafted divinyl benzene microspherechiral chromatographic packing and preparation method thereof
  • Substituted polyacetylene grafted divinyl benzene microspherechiral chromatographic packing and preparation method thereof
  • Substituted polyacetylene grafted divinyl benzene microspherechiral chromatographic packing and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The first step to prepare M1 is as follows: Dissolve 1.90 g of N-Boc-alanine ((N-tert-butoxycarbonyl-alanine; CAS: 15761-38-3) in 40 mL of THF, then add 1.3 mL After reacting isobutyl chloroformate and 1.1mL N-methylmorpholine at 30°C for 15min, add 0.7mL propargylamine to the flask, react in a water bath at 30°C for 4h, and remove the formed precipitate by filtration; the filtrate was washed with ethyl acetate Ester was extracted, and washed three times with 30mL hydrochloric acid solution (2M), washed twice with 30mL saturated sodium bicarbonate solution, and once with 80mL deionized water, then dried with anhydrous magnesium sulfate, after vacuum distillation, in THF / n-hexane Purification by cooling and crystallization in a system with a volume ratio of 1 / 6. After 5 hours, filter and dry at 30° C. for 24 hours to 48 hours to obtain M1 as a solid product with a yield of 80%.

[0058] The second step to prepare M2 is as follows: dissolve 1.4ml of propargylamine and 4.2...

Embodiment 2

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

[0076] The second step is to prepare the substituted alkyne monomer M2, the specific method is as 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 (nbd) Rh + B - (C 6 h 5 ) 4 Catalyst, and then the test tube was repeatedly evacuated and argon treated, a total of three times. Then add 5ml THF under the protection of argon, sonicate the test tube until the solid dissolves, then heat the test tube in a 30°C water bath, obtain a light red solution after polymerization for 6 hours, add the obtained solution dropwise to n-hexane to precipitate, filter After drying, precipitate twice in a THF / n-hexane volume ratio system of 1 / 6, filter, and dry to obtain yellow P-M1-co-M2-Boc with a yield of 76%.

[0078] The fourth step is to prepare the substituted polyalkyne P-M1-co-M2-NH...

Embodiment 3

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

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

[0086] The third step is to prepare the substituted polyalkyne P-M1-co-M2-Boc as follows: add 0.136 g of M1, 0.044 g of M2, 0.005 g (nbd) Rh + B - (C 6 h 5 ) 4 Catalyst, and then the test tube was repeatedly evacuated and argon treated, a total of three times. Then add 5ml THF under the protection of argon, sonicate the test tube until the solid dissolves, then heat the test tube in a 30°C water bath, obtain a light red solution after polymerization for 6 hours, add the obtained solution dropwise to n-hexane to precipitate, filter After drying, precipitate twice in a THF / n-hexane volume ratio system of 1 / 6, filter, and dry to obtain yellow P-M1-co-M2-Boc with a yield of 78.2%.

[0087] The fourth step is to prepare the substituted polyalkyne P-M1-co-M...

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Abstract

The present invention relates to the field of functional polymer materials, and discloses a substituted polyacetylene grafted divinyl benzene microsphere chiral chromatographic packing and a preparation method thereof. The preparation method comprises the following steps: (1) carrying out amidation reaction on N-t-butyloxycarboryl-alanine and propargylamine to synthesize M1; (2) carrying out amidation reaction on acryloyl chloride and propargylamine to synthesize M2; (3) initiating copolymerization of M1 and M2 to obtain a copolymer; (4) carrying out copolymerization on divinyl benzene in the presence of an initiator to obtain PDVB microspheres; and (5) carrying out graft copolymerization on the copolymer and the PDVB microspheres under the action of an initiator and a cross-linking agent to obtain a core-shell structure, and dispersing the core-shell structure in a Cu<2+> aqueous solution for helical conformation induction to obtain the chiral chromatographic packing. The defect of poor stability of the spiral polymer-based composite material is overcome, and the stability of the spiral polymer-based composite material is greatly improved by graft copolymerization of double-bond-containing substituted polyacetylene and highly-crosslinked rigid PDVB.

Description

technical field [0001] The invention relates to the field of functional macromolecular materials, in particular to a chiral chromatographic filler for substituted polyacetylene grafted divinylbenzene microspheres and a preparation method thereof. Background technique [0002] Chiral and helical structures widely exist 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 useful 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 show great application potential. However, due to...

Claims

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Application Information

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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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