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Acrylamide type monomer containing dicyclopentadienyl iron structure, as well as amphipathic polymer, preparation method and use thereof

A technology of amphiphilic polymers and acrylamide, which is applied in chemical instruments and methods, metallocenes, organic chemistry, etc., can solve the problems of complex synthesis steps, difficult synthesis, and lack of universality of amphiphilic block copolymers

Active Publication Date: 2013-04-17
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis steps of amphiphilic block copolymers are relatively complicated, the synthesis is difficult, and the lack of universality

Method used

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  • Acrylamide type monomer containing dicyclopentadienyl iron structure, as well as amphipathic polymer, preparation method and use thereof
  • Acrylamide type monomer containing dicyclopentadienyl iron structure, as well as amphipathic polymer, preparation method and use thereof
  • Acrylamide type monomer containing dicyclopentadienyl iron structure, as well as amphipathic polymer, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The synthesis of embodiment 1. compound 2a

[0046]

[0047] Add ferrocenecarboxylic acid (9.2g, 40mmol), N-hydroxysuccinimide (5.75g, 50mmol), 200mL tetrahydrofuran into a dry 500mL three-necked flask, stir at room temperature for 5 minutes, then add DCC (10.3 g, 50mmol), stirred at room temperature for 12 hours, filtered to remove insoluble matter, slowly added the filtrate to 200mL tetrahydrofuran solution dissolved with triethylamine (5.6mL, 40mmol), ethylenediamine (5.4mL, 80mmol), and stirred overnight at room temperature. The insoluble matter was removed by filtration, concentrated, added dichloromethane, washed twice with water and saturated brine, dried over anhydrous sodium sulfate, and column chromatographed to obtain 8.31g of 2a, with a yield of 76.4%.

[0048] FT-IR (film): v (cm -1 ):3290,3081,2930,2856,1734,1627,1544,1453,1376,1301,1185,821.

[0049] 1 H NMR: δ(ppm): 1.85, 3.75, 4.12, 4.36, 4.74, 5.75.

Embodiment 2

[0050] The synthesis of embodiment 2 compound 2b

[0051]

[0052] Add ferrocenecarboxylic acid (9.2g, 40mmol), N-hydroxysuccinimide (5.75g, 50mmol), and 200mL dichloromethane into a dry 500mL three-necked flask, stir at room temperature for 5 minutes, and then add DCC to the solution (10.3g, 50mmol), stirred at room temperature for 12 hours, filtered to remove insoluble matter, and slowly added the filtrate to 200mL dichloromethane solution in which triethylamine (5.6mL, 40mmol) and propylenediamine (6.6mL, 80mmol) were dissolved, Stir overnight at room temperature. The insoluble matter was removed by filtration, concentrated, added dichloromethane, washed twice with water and saturated brine, dried over anhydrous sodium sulfate, and column chromatographed to obtain 9.17g of 2b with a yield of 80.2%.

[0053] FT-IR (film): v (cm -1 ):3292,3083,2931,2856,1735,1628,1544,1454,1378,1301,1186,821.

[0054] 1 H NMR: δ(ppm): 1.43, 1.72, 2.71, 4.12, 4.36, 4.74, 5.75.

Embodiment 3

[0055] The synthesis of embodiment 3 compound 2c

[0056]

[0057] Add ferrocenecarboxylic acid (9.2g, 40mmol), N-hydroxysuccinimide (5.75g, 50mmol), and 200mL dichloromethane into a dry 500mL three-necked flask, stir at room temperature for 5 minutes, and then add DCC to the solution (10.3g, 50mmol), stirred at room temperature for 12 hours, filtered to remove the insoluble matter, and slowly added the filtrate to 200mL of dichloromethane solution in which triethylamine (5.6mL, 40mmol) and butylenediamine (8.0mL, 80mmol) were dissolved, Stir overnight at room temperature. The insoluble matter was removed by filtration, concentrated, added dichloromethane, washed twice with water and saturated brine, dried over anhydrous sodium sulfate, and column chromatographed to obtain 8.68g of 2c with a yield of 72.3%.

[0058] FT-IR (film): v (cm -1 ):3282,3081,2930,2856,1734,1627,1539,1455,1372,1180,828.

[0059] 1 H NMR: δ(ppm): 1.48, 1.60, 2.71, 3.36, 4.20, 4.33, 4.70, 5.75.

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Abstract

The invention provides an acrylamide type monomer containing a dicyclopentadienyl iron structure, as well as an amphipathic polymer, a preparation method and a use thereof. The preparation method of the monomer comprises three steps of reactions: firstly enabling ferrocenecarboxylic acid to react with aliphatic diamine to generate an amino-containing dicyclopentadienyl iron compound, then reacting with 4-bromo-1-butyric acid tert-butyl ester to introduce a carboxylic ester structure, and finally reacting with acryloyl chloride to get the acrylamide type monomer containing the dicyclopentadienyl iron structure. An acrylamide type polymer containing the dicyclopentadienyl iron structure is obtained by free radical polymerization or active free radical polymerization of the monomers, and the acrylamide type amphipathic polymer containing the dicyclopentadienyl iron structure is generated by performing selective hydrolysis on the obtained polymer under the action of trifluoroacetic acid. The amphipathic polymer can form a self-assembled aggregate with a microstructure in a selective solvent and can be further applied to chemical modification of an electrode, and thus has potential applications in the fields of catalysis, optoelectronics, molecular recognition, sensors and the like.

Description

technical field [0001] The invention relates to a class of acrylamide monomers containing a ferrocene structure and amphiphilic polymers, preparation methods and uses thereof. Background technique [0002] Ferrocene is an aromatic compound with a sandwich structure and a highly electron-rich system. It has high thermal stability, chemical stability and radiation resistance, and it also has low toxicity, lipophilicity, rich electricity, oxidation Restorability and many other features. The ferrocene group in ferrocene has aromaticity, and various functional groups can be introduced by means of acylation, alkylation, halogenation and sulfonation, which makes the ferrocene structure introduced into molecules of various structures to form ferrocene Derivatives become possible, and many derivatives such as single and polynuclear ferrocene complexes, ferrocene-based polymers, ferrocene molecular tree complexes, chiral ferrocene complexes, etc. have been synthesized one after anoth...

Claims

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Application Information

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IPC IPC(8): C07F17/02C08F130/04C08F8/12
Inventor 黄晓宇张森冯纯邓妍
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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