Synthesis of novel chiral polyester containing binaphthyl and application thereof to molecular recognition

A molecular recognition and binaphthyl technology, which can be used in the preparation of ethers by ester reaction, chemical instruments and methods, preparation of organic compounds, etc.

Inactive Publication Date: 2012-09-19
QIQIHAR UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But precisely because of its six-membered imide ring structure (the existence of such a large rigid group), the melting and solubility of polynaphthaleneimide are greatly reduced, which greatly limits its application.

Method used

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  • Synthesis of novel chiral polyester containing binaphthyl and application thereof to molecular recognition
  • Synthesis of novel chiral polyester containing binaphthyl and application thereof to molecular recognition
  • Synthesis of novel chiral polyester containing binaphthyl and application thereof to molecular recognition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] 2-Naphthol is reacted under ferric chloride to produce binaphthol, and then resolved to obtain R / S binaphthol. The resolved binaphthol is reacted with a halogenated alcohol to prepare a chiral diol containing a binaphthyl group.

[0015] The prepared chiral diol containing binaphthyl group was reacted with diacid, and the chiral polyester was prepared through esterification and polycondensation reaction, and finally its structure was characterized by infrared and nuclear magnetic resonance. The reaction formula is as follows:

[0016]

[0017]

Embodiment 2

[0019] Using 2-naphthylamine as raw material, binaphthylamine is first synthesized, and then split to obtain chiral binaphthylamine. The resolved binaphthylamine is reacted with chloryl chloride, and then hydrolyzed to obtain binaphthyl-containing chiral diol.

[0020] The prepared chiral diol containing binaphthyl is reacted with diacid to prepare chiral polyester through esterification and polycondensation. Its structure was characterized by infrared and NMR. The detailed reaction formula is shown below.

[0021]

[0022]

Embodiment 3

[0024] Makes synthetic polyester into 1.0×10 -5 mol / L tetrahydrofuran solution, the chiral small molecule guest is also prepared as 0.1mol / L tetrahydrofuran solution, wherein mandelic acid is acetonitrile solution. For each measurement, the guest solution was pipetted with a pipette gun and added to the polymer solution to form a series of solutions, and the fluorescence intensity was measured after standing at room temperature for 3-4 hours.

[0025] The molecular recognition behavior of chiral polyesters for binaphthols was studied by UV-vis spectrometric titration. Chiral polyester host concentration 2×10 -6 mol / L, added binaphthol or binaphthylamine guest concentration 1×10 -6 mol / L, use phenol / tetrachloroethane (volume ratio 2:3) mixture as solvent, fix the concentration of chiral polyester, gradually increase the volume of the guest, and make the ultraviolet absorption spectrum.

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Abstract

The invention discloses synthesis for chiral polyester containing binaphthyl. A binaphthyl compound is a common atropisomer compound with a C3 chiral axis. The axis of a binaphthyl structure is in an asymmetrical, multifunctional and stable chiral form, so that molecules and copolymers constructed by binaphthyl have superior structures and properties and wide application prospects in the field of materials. The patent is developed mainly around the synthesis of novel chiral polyester containing binaphthyl. A method for preparing the chiral polyester comprises the following steps of: synthesizing binaphthol or dinaphthyline by taking 2-naphthol or 2-naphthylamine as a raw material, and splitting to obtain chiral binaphthol or dinaphthyline; making dinaphthyline react with halohydrinare to obtain diol containing dinaphthalene radial, and react with the diacid to obtain chiral polyester; and making naphthidine react with chloride acyl chloride, hydrolyzing to obtain diol containing binaphthyl, and reacting with diacid to obtain chiral polyester containing binaphthyl. In the preparation of the chiral polyester, diol or diacid containing binaphthyl is prepared firstly, and then the chiral polyester is prepared by reacting. At last, the prepared chiral polyester is applied to molecular recognition.

Description

technical field [0001] Due to the highly stable chiral configuration of binaphthyl compounds, 1,1′-binaphthyl substituted at the 2,2′-position is widely used to control many asymmetric processes, the rigid structure and C2 axis of chiral binaphthyl molecules Asymmetry plays an important role in chiral induction. The chiral binaphthyl group with twisted and non-coplanar special rigid structure is a better chiral source for preparing these optically active polymers. The introduction of binaphthyl groups into the polymer chain can also improve the thermal stability of the polymer. Therefore the present invention is a novel binaphthyl compound-chiral polyester. Background technique [0002] Along with the research on binaphthyl derivatives, many researchers also use chiral binaphthyl on conventional polymers, such as using binaphthyl-containing polyimides in stereoselective chromatography. These polymers can separate the enantiomers of certain racemic aromatic amides and aroma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/672C08G63/685C07C43/23C07C41/16C07C235/16C07C231/12G01N21/33
Inventor 萧斌
Owner QIQIHAR UNIVERSITY
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