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Synthesis and application of bifunctional initiator with near-infrared absorption and self-sorting polymerization characteristics

A self-classifying polymerization, bifunctional technology, applied in palladium organic compounds, platinum group organic compounds, organic chemistry, etc., can solve the problems of difficult implementation of hybrid polymerization, and achieve narrow molecular weight distribution, good stability, and monomer conversion rate. high effect

Active Publication Date: 2016-10-05
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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  • Synthesis and application of bifunctional initiator with near-infrared absorption and self-sorting polymerization characteristics
  • Synthesis and application of bifunctional initiator with near-infrared absorption and self-sorting polymerization characteristics
  • Synthesis and application of bifunctional initiator with near-infrared absorption and self-sorting polymerization characteristics

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the preparation of IR780 initiator

[0050] The iodide of IR780 and excess p-mercaptoaniline (added at a molar ratio of 1:1.02) were reacted in DMF solution at room temperature for 24 hours, and after being spin-dried, silica gel column chromatography (methanol: dichloromethane = 1:20), Intermediate I was obtained after drying

[0051]

[0052] Add p-aminobenzoic acid, anhydrous potassium carbonate, and propyne bromide in a molar ratio of 1:(1-3):1.2 to dry acetonitrile, stir and react at room temperature for 24 hours in a nitrogen atmosphere, wash with water, and saturate NaHCO 3 washing, salt washing, separation of the organic phase, spin-drying, the crude product is purified by silica gel column chromatography (eluent by volume: petroleum ether: ethyl acetate=4:1), and after drying, intermediate II is obtained. The structural formula is as follows:

[0053]

[0054] Add the intermediate IV, potassium carbonate, and potassium iodide to dry acetonit...

Embodiment 2

[0065] Embodiment 2: Initiate the polymerization reaction of hydrophilic benzene isocyanide

[0066] The polymerization of benzyl isonitrile is carried out under anhydrous and oxygen-free conditions. Add 7.63 μmol (8.21 mg) of the initiator prepared in Example 1 and 0.55 mmol (160.0 mg) of benzyl isonitrile monomer to a 10 mL polymerization bottle, and repeat by vacuumizing and filling with nitrogen 3 times, add 2.0 mL of dry chloroform, reflux at 60°C for 20 hours, add 10 mL of n-hexane to quench, precipitate the polymer, wash 5 times with n-hexane, centrifuge to obtain a yellow flocculent precipitate, vacuum dry to mass constant. Obtain 150.1mg polyisocyanide, its number-average molecular weight is 2.12×10 4 , the molecular weight distribution index is 1.09.

[0067] The structural formula of the benzene isonitrile monomer in the present embodiment is:

[0068]

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Abstract

The invention discloses a bifunctional initiator with near-infrared absorption and self-sorting polymerization characteristics, and a preparation method and application thereof. The initiator can perform hybrid polymerization on isonitrile and epsilon-caprolactone monomers by a one-pot process, has the advantages of favorable self-sorting polymerization capacity and high stability, and can be used for active controllable polymerization of isonitrile, epsilon-caprolactone and other monomers. The obtained polyisonitrile and polycaprolactone homopolymer and block copolymer 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 bifunctional initiator with near-infrared absorption and self-classification polymerization characteristics, a preparation method and application thereof, which can hybridize and polymerize isonitrile and acrylic acid in a "one-pot method". Lactide or ε-caprolactone monomer. Background technique [0002] IR-780 has tumor-targeting near-infrared fluorescence imaging properties, which provides a new idea and approach for the research of tumor-targeted diagnosis and treatment drugs. Based on the previous innovative findings, this study proposes whether IR-780 can be used as a targeting carrier for tumor drugs, that is, through chemical linkage strategies, anti-tumor drugs are covalently linked to it, and the targeted transport of IR-780 Next, improve the specific effect of drugs on tumors. Since IR-780 has tumor-targeting near-infrared fluorescence imaging properties, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/82C08G63/08C08G63/685C08G61/04C07F15/00
CPCC07F15/006C08G61/04C08G63/08C08G63/6852C08G63/823C08G63/826C08G2261/11C08G2261/126C08G2261/143C08G2261/148C08G2261/332C08G2261/522C08G2261/59
Inventor 殷俊陈宇史声宇张志煌许俊松薛天浩唐新锋张鑫
Owner HEFEI UNIV OF TECH
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