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Method for constructing porous polymer on the basis of pure chiral molecules of 1, 1 '-bi-2-naphthol

A technology of porous polymers and chiral molecules, applied in the field of organic chemistry, can solve problems such as cumbersome methods and poor universal applicability of different ligands

Active Publication Date: 2017-07-11
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the methods reported for the preparation of heterogeneous chiral catalysts are generally cumbersome, and the general applicability of various preparation meth

Method used

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  • Method for constructing porous polymer on the basis of pure chiral molecules of 1, 1 '-bi-2-naphthol
  • Method for constructing porous polymer on the basis of pure chiral molecules of 1, 1 '-bi-2-naphthol
  • Method for constructing porous polymer on the basis of pure chiral molecules of 1, 1 '-bi-2-naphthol

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preparation example Construction

[0038] Preparation of Basic Framework Materials

[0039] The basic skeleton material is a chiral ligand of vinyl-functionalized BINOL group, which is a chiral phosphoramidite ligand or chiral phosphite ligand obtained by reacting vinyl-functionalized BINOL with amine, alcohol or phenolic compound. body. Preparation routes such as figure 1 with figure 2 shown.

[0040] The synthesis steps of 6,6'-dibromo-[1,1'-binaphthyl]-2,2'-diol (compound 1) are as follows, 5.0 g of BINOL was dissolved in 100 mL of CH 2 Cl 2 , after the system temperature drops to -10°C, 2.4mL Br 2 with 20mL CH 2 Cl 2 Diluted and slowly added dropwise to the above solution. Add NaHSO 3 aqueous solution is quenched. CH for aqueous phase 2 Cl 2 Extracted with MgSO 4 Dry, rotary evaporate CH 2 Cl 2 The obtained white solid is compound 1.

[0041] The synthesis steps of 6,6'-dibromo-[1,1'-binaphthalene]-2,2'-diyldioxybis(triisopropylsilane) (compound 2) are as follows, 17.4mL of triisopropyl Ch...

Embodiment 1

[0050] 1 g of compound 7, 20 g of ethyl acetate, and 0.001 g of azobisisobutyronitrile were mixed and stirred, heated to 120° C. under stirring, reacted for 6 h, and the solvent was distilled to obtain a white polymer. of the sample 13 C MAS NMR and 31 P MAS NMR image as shown Image 6 with Figure 7 As shown, it can be seen that there is also a strong peak at 41.2ppm on the solid carbon NMR of the polymer, which indicates that the vinyl polymerization has successfully occurred. 31 The P MAS NMR chart shows that the chemical shift of the P NMR of the polymer is almost the same as that of the monomer, indicating that the valence state of P has not changed during the polymerization process. N 2 The adsorption results showed that the specific surface area of ​​the obtained polymer was 490m 2 / g or so ( Figure 8 ), the pore size distribution is 0.5-150nm ( Figure 9 ).

Embodiment 2

[0052] 1 g of compound (8-20), 2 g of tetrahydrofuran, and 0.01 g of azobisisobutyronitrile were mixed and stirred, heated to 60° C. under stirring, reacted for 24 hours, and the solvent was distilled to obtain a white polymer. N 2 The adsorption results show that the specific surface area of ​​the obtained polymer is 400-780g / m 2 About, between 1 ~ 100nm.

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Abstract

The present invention relates to preparation of polymers, and aims to provide a method for constructing a porous polymer on the basis of pure chiral molecules of 1, 1 '-bi-2-naphthol. The method is as follows: dissolving a basic skeleton material in a pore-foaming solvent, and adding a polymerization initiator; stirring for polymerization for 6-48h at 60-240 DEG C, and distilling for removal of the solvent to obtain a porous polymer material constructed by the pure chiral molecules; the porous chiral polymer is obtained by a free radical polymerization one step synthesis method, due to no additional addition of a monomer in the synthesis process, the obtained porous chiral polymer has better chiral induction environment, a series of chiral ligands can be obtained by design of a vinyl functionalized BINOL molecule as a basic skeleton, the aperture of obtained resin is between 0.5-200nm, and the specific surface area is up to 1000m<2> / g.

Description

technical field [0001] The invention belongs to the fields of organic chemistry, chemical engineering, physical chemistry, and material chemistry, and relates to the preparation technology of polymers, in particular to a porous structure based on a homochiral molecule of 1,1'-bi-2-naphthol (BINOL). Polymer Synthesis Methods. Background technique [0002] Chirality is a fundamental feature of nature. The development of chiral catalysts is driven by the increasing demand for chiral compounds. [a) Peng, Y.; Gong, T.; Zhang, K.; Lin, X.; Liu, Y.; Jiang, J.; Cui, Y. Nat. Commun.2014, 5, 4406; , D.; Claridge, J.B.; Cussen, E.J.; Prior, T.J.; Rosseinsky, M.J. Acc. Chem. Res. 2005, 38, 273-282; c) Collins, A.N.; in the Commercial Manufacture and Applications of Optically Active Compounds. John Wiley&Sons: Chichester, 1992; d) Fernández-Pérez, H.; Etayo, P.; Panossian, A.; 2119-2176; e) Yang, H.; Zhang, L.; Zhong, L.; Yang, Q.; Li, C.Angew.Chem.Int.Ed.2007,46,6861-6865]. Catalys...

Claims

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Application Information

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IPC IPC(8): C08F130/02C08J9/28C08L43/02C07F9/6571
CPCC07F9/6571C08F130/02C08J9/28C08J2201/0502C08J2343/02
Inventor 孟祥举孙琦肖丰收
Owner ZHEJIANG UNIV
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