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Optically-active helix chain poly(phenyl isocyanide) and polymerization method thereof

An optically active, polyphenylene isonitrile technology, applied in the field of optically active helical chain polyphenylene isonitrile and its polymerization, can solve problems such as complex chiral structures, and achieve the effects of simplified synthesis steps, simple synthesis and simple operation

Inactive Publication Date: 2016-09-07
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these polyphenylene isonitriles usually have relatively complex chiral structures, such as: helical main chain, chiral groups on side groups, and chiral end groups, etc.

Method used

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  • Optically-active helix chain poly(phenyl isocyanide) and polymerization method thereof
  • Optically-active helix chain poly(phenyl isocyanide) and polymerization method thereof
  • Optically-active helix chain poly(phenyl isocyanide) and polymerization method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A kind of polymerization method of optically active helical chain polyphenylisonitrile, operates according to the following steps:

[0033] 1. Chiral phosphine ligand (S-BINAP) and palladium catalyst are carried out under strict anhydrous and oxygen-free conditions, and chiral phosphine ligand (S-BINAP) and palladium catalyst are added in a 10mL polymerization bottle, S-BINAP and The molar ratio of the palladium catalyst was 12:1, vacuumed and filled with nitrogen three times, added 0.3 mL of dry tetrahydrofuran, and stirred at room temperature for 3 h to obtain a mixture of S-BINAP and palladium catalyst.

[0034] 2. Weigh 0.1mmol (34mg) achiral benzene isonitrile monomer into a 10mL polymerization bottle, then add 0.8mL dry CHCl 3 Dissolved, then weighed 0.9 μmol of the mixed solution of S-BINAP and palladium catalyst, put it into the polymerization bottle under nitrogen atmosphere, reflux reaction at 55 ° C for 20 h, added 10 mL of methanol to quench, and precipitate...

Embodiment 2

[0036] A kind of polymerization method of optically active helical chain polyphenylisonitrile, operates according to the following steps:

[0037] 1. Chiral phosphine ligand (R-BINAP) and palladium catalyst are carried out under strict anhydrous and oxygen-free conditions, add chiral phosphine ligand (R-BINAP) and palladium catalyst in 10mL polymerization bottle, R-BINAP and The molar ratio of the palladium catalyst was 12:1. Vacuumize and inflate with nitrogen three times, add 0.3 mL of dry tetrahydrofuran, and stir at room temperature for 3 h to obtain a mixture of R-BINAP and palladium catalyst.

[0038] 2. Weigh 0.1mmol (34mg) achiral benzene isonitrile monomer into a 10mL polymerization bottle, then add 0.8mL dry CHCl 3 Dissolved, then weighed 0.9 μmol of the mixed solution of R-BINAP and palladium catalyst, put it into the polymerization bottle under nitrogen atmosphere, refluxed at 55 ° C for 20 h, added 10 mL of methanol to quench, and precipitated the polymer, washed ...

Embodiment 3

[0040] A kind of polymerization method of optically active helical chain polyphenylisonitrile, operates according to the following steps:

[0041] 1. Chiral phosphine ligand (S-BINAP) and palladium catalyst are carried out under strict anhydrous and oxygen-free conditions, and chiral phosphine ligand (S-BINAP) and palladium catalyst are added in a 10mL polymerization bottle, S-BINAP and The molar ratio of the palladium catalyst was 3:1. Vacuumize and inflate with nitrogen four times, add 0.3 mL of dry tetrahydrofuran, and stir at room temperature for 3 h to obtain a mixture of the palladium catalyst and S-BINAP.

[0042] 2. Weigh 0.1mmol (34mg) achiral benzene isonitrile monomer into a 10mL polymerization bottle, then add 0.8mL dry CHCl 3Dissolved, then weighed 0.9 μmol of the mixed solution of S-BINAP and palladium catalyst, put it into the polymerization bottle under nitrogen atmosphere, reflux reaction at 55 ° C for 20 h, added 10 mL of methanol to quench, and precipitated ...

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Abstract

The invention discloses an optically-active helix chain poly(phenyl isocyanide) and a polymerization method thereof. The polymerization process is shown as the general formula in the description; in the formula, the structural formula of a chiral phosphine ligand is shown in the description. A palladium catalyst is adopted, the chiral phosphine ligand (S-or R-BINAP) is added to induce polymerization of achiral phenyl isocyanide, and the optically-active polymer with excessive one-handed helixes is obtained; obtained poly(phenyl isocyanide) has a high molecular weight and narrow molecular weight distribution.

Description

technical field [0001] The invention relates to the field of polymer reaction, in particular to an optically active helical chain polyphenylisonitrile and a polymerization method thereof. Background technique [0002] Chirality is a phenomenon that exists widely in nature, and the helical structure is also the core structural module of biomolecules, such as the most familiar double helix structure of DNA and the α-helix structure of proteins. Their chiral helical secondary structures and higher-order structures formed alone or together play a decisive role in the process of assembling to form organisms and performing biological functions. Inspired by biological helical polymers in nature, there has been continuous and widespread research interest in helical polymers. In the helical polymer, the main chain carbon of the helical poly(phenyl isocyanide) contains a π-conjugated C=N to twist the main chain of the polymer to form a helical structure with a stable helical conforma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
CPCC08G61/12C08G2261/11C08G2261/1432C08G2261/1624C08G2261/312C08G2261/352
Inventor 吴宗铨杨莉刘娜林亚兰王倩
Owner HEFEI UNIV OF TECH
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