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Chiral fluorescence self-sorting polymerization bifunctional initiator, and preparation method and application thereof

A technology of self-classification polymerization and bifunctional group, which is applied in the field of polymer catalytic synthesis, can solve the problems of difficult implementation of hybrid polymerization, and achieve the effect of narrow molecular weight distribution and uniform molecular weight

Inactive Publication Date: 2015-05-20
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the implementation of hybrid polymerization is also very difficult, and there are few reports on such

Method used

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  • Chiral fluorescence self-sorting polymerization bifunctional initiator, and preparation method and application thereof
  • Chiral fluorescence self-sorting polymerization bifunctional initiator, and preparation method and application thereof
  • Chiral fluorescence self-sorting polymerization bifunctional initiator, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Embodiment 1: the preparation of D-phenylglycine, ethylenediamine initiator

[0079] a. Reflux Rhodamine B and ethylenediamine (excess) in the ethanol solution at 80°C overnight until the fluorescence disappears, spin to dry the ethanol, dissolve the residue with 1M hydrochloric acid and keep stirring, then slowly add 1M NaOH aqueous solution, And continue to stir until a pink precipitate is produced, suction filtered, washed with water, and dried to obtain Intermediate I, the structural formula is as follows:

[0080]

[0081] b. Add D-phenylglycine, di-tert-butyl dicarbonate, and sodium hydroxide to a mixed solvent of tetrahydrofuran and water (2:1) in a molar ratio of 1:1.1:1.2, wherein sodium hydroxide is 10% Stir overnight at room temperature, spin off THF, add dichloromethane, then dropwise add 1M hydrochloric acid solution until the white precipitate in the upper aqueous phase disappears, separate the organic phase, wash twice with water, dry over anhydrous so...

Embodiment 2

[0093] Embodiment 2: Initiate hydrophobic benzene isonitrile polymerization reaction

[0094] The polymerization of benzyl isonitrile is carried out under anhydrous and oxygen-free conditions. In a 10mL polymerization bottle, 1.49 μmol (1.60 mg) of the initiator prepared in Example 1 and 0.10 mmol (28.0 mg) of the benzyl isonitrile monomer are added, and the vacuum and nitrogen gas are repeated. 3 times, add 1.0 mL of dry chloroform, reflux at 60°C for 20 hours, add 10 mL of methanol to quench, and precipitate the polymer, wash 5 times with methanol, centrifuge to obtain a yellow flocculent precipitate, vacuum dry until the quality remains unchanged . Obtain 26.3mg polyisocyanide, its number-average molecular weight is 1.93×10 4 , the molecular weight distribution index is 1.17,

[0095] The structural formula of the benzene isonitrile monomer in the present embodiment is:

[0096]

Embodiment 3

[0097] Embodiment 3: initiate chiral benzene isocyanide polymerization reaction

[0098]The polymerization of chiral benzene isonitrile is carried out under anhydrous and oxygen-free conditions. In a 10mL polymerization bottle, 1.82 μmol (1.96 mg) of the initiator prepared in Example 1 and 0.12 mmol (33.0 mg) of the chiral benzene isonitrile monomer are added. Vacuum nitrogen filling was repeated 3 times, add dry chloroform 1.0mL, reflux reaction at 60°C for 20h, add 10mL methanol to quench, make the polymer precipitate, wash 5 times with methanol, centrifuge to obtain yellow flocculent precipitate, vacuum dry until the quality remains unchanged. Obtain 28.5mg polyisocyanide, its number-average molecular weight is 1.89×10 4 , the molecular weight distribution index is 1.18,

[0099] The structural formula of the benzene isonitrile monomer in the present embodiment is:

[0100]

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Abstract

The invention discloses a chiral-acid / alkali-stimulation-responsive difunctional fluorescence molecular initiator, and a preparation method and application thereof. The structure of the initiator is disclosed as the following general formula. The chiral center and chromophore are introduced into the initiator; the initiator can perform hybrid polymerization on isonitrile and lactide or epsilon-caprolactone monomers by a one-pot process, has the advantages of favorable self-sorting polymerizing power and high stability, and can be used for active / controllable polymerization of isonitrile, lactide, epsilon-caprolactone and other monomers; and the obtained polyisonitrile, polylactide homopolymer and block copolymers thereof have controllable molecular weight and narrow molecular weight distribution.

Description

technical field [0001] The invention relates to the field of polymer catalytic synthesis, in particular to a chiral fluorescent self-classification polymerization bifunctional initiator and its preparation method and application, which can hybridize and polymerize isonitrile and lactide or ε-hexyl in a "one-pot method". lactone monomer. Background technique [0002] Rhodamine has long-wavelength absorption and emission, high absorption coefficient and quantum efficiency, and good photostability. It is widely used in industrial coloring, biomarker use, ion detection and so on. As a fluorophore and chromophore with excellent photophysical properties, rhodamine derivatives are non-fluorescent and colorless, while the ring-opened corresponding spironolactams produce strong fluorescent emission and pink color, generally , in acidic solution by activation of the carbonyl group in spironolactone, rhodamine derivatization shows a red color change and produces strong fluorescence. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/04C08G63/82C08G63/08C07F15/00C09K11/06A61K49/00
Inventor 殷俊史声宇何亚光吴宗铨陈宇
Owner HEFEI UNIV OF TECH
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