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A catalyst containing a bithiophene structure and its application in the ring-opening polymerization of cyclic esters under the control of light

A ring-opening polymerization and catalyst technology, which is applied in the application field of catalysts containing bithiophene structure and ring-opening polymerization of cyclic esters, can solve the problems of low overall activity and slow polymerization rate, and achieve wide practicability and controllable effects ideal effect

Active Publication Date: 2022-06-07
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the polymerization rate slows down after light exposure, and the overall activity is very low
Therefore, the maintenance and control of the polymerization rate under light regulation is also a problem.

Method used

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  • A catalyst containing a bithiophene structure and its application in the ring-opening polymerization of cyclic esters under the control of light
  • A catalyst containing a bithiophene structure and its application in the ring-opening polymerization of cyclic esters under the control of light
  • A catalyst containing a bithiophene structure and its application in the ring-opening polymerization of cyclic esters under the control of light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Synthesis of 1,1'-(cyclopenten-1,2-diacylbis(5-methylthiophene-4,2-diacyl)) bis (2,6-diisopropyl-4,1-benzene) bis (3-cyclohexylthiourea).

[0045]

[0046] 1, at -10 °C 0.33g of compound 1 50ml of tetrahydrofuran solution added 11ml n-butyl lithium (2.5M), reaction at room temperature for half an hour, and then add 0.69g tri-tert-butylboronic acid reaction for 2h; in 0.62g of 4-iodine-2,6-bis(1-methylethyl) aniline tetrahydrofuran solution added 1g tetra-tetrahydrofuran solution (triphenylphosphine) palladium reaction for 15 minutes, add the above treated 1, and then add 100ml sodium carbonate 70 °C reaction for 1 day, to obtain the product 2.

[0047] 2. Under the protection of nitrogen, compound 2 and 0.42g of cyclohexyl isothiocyanate reacted overnight at room temperature in dichloromethane to obtain the product. The product catalyst a is light yellow. 1 H NMR(400MHz,CDCl 3)δ7.64(d,2H),7.22(d,4H),6.99(dt,2H),5.05-5.03(t,2H),4.21-4.14(m,2H),3.08(m,4H),2.80(m,...

Embodiment 2

[0049] Example 2: 1,1'- ((cyclopentene-1,2-diacylbis (5-methylthiophene-4,2-diacyl)) bis (2,6-diisopropyl-4,1-benzene) bis (3-(3,5-bis(trifluoromethyl)phenyl) thiourea synthesis.

[0050] The preparation process is similar to Example 1, the difference is that the cyclohexyl isothiocyanate in Example 1 is changed to 0.81g3,5-bis (trifluoromethyl) phenyl isothiocyanate.

[0051]

[0052] 1 H NMR(400MHz,CDCl 3 )δ9.25(d,2H),7.88(d,4H),7.66(dt,2H),7.41(t,4H),7.11(m,4H),3.08(m,4H),2.80(m,4H),2.07(m,2H),2.02(m,6H),1.31(m,24H)。 19 F NMR(400MHz,CDCl3)δ62.98(s)。

Embodiment 3

[0053] Example 3: Synthesis of 1,1'- (cyclopenten-1,2-diacylbis (5-methylthiophene-4,2-diacyl)) bis (4,1-benzene) bis (3-cyclohexylthiourea).

[0054] The preparation process is similar to Example 1, the difference is that the 4-iodo-2,6-bis (1-methylethyl) aniline in Example 1 is changed to 0.44g of p-iodoaniline.

[0055]

[0056] 1 H NMR(400MHz,CDCl 3 )δ9.25(d,2H),7.88(d,4H),7.66(dt,2H),7.41(t,4H),7.11(m,4H),3.08(m,4H),2.80(m,4H),2.07(m,2H),2.02(m,6H),1.31(m,24H)。 13 C NMR(101MHz,CDCl3)δ178.76,138.45,136.89,135.10,134.69,126.69,125.16,124.42,53.93,38.54,32.63,25.45,24.78,23.04,14.52。

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PUM

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Abstract

The invention discloses a catalyst containing a dithiophene structure and its application in the ring-opening polymerization of cyclic esters under light regulation. The catalyst contains a structure of dithiophene-urea or dithiophene-thiourea. The present invention uses the catalyst as a catalyst for the ring-opening polymerization of lactide and valerolactone, which can realize the ring-opening polymerization under light control. Compared with the known light-control ring-opening polymerization catalyst, it has the advantages of simple synthesis and no resistance to air and water. It has the advantages of being sensitive, regulating the polymerization effect obviously, and speeding up the polymerization rate under light.

Description

Technical field [0001] The present invention belongs to the field of catalyst technology, specifically relates to a catalyst containing a bisthiophene structure and its application in the open-loop polymerization of cyclic esters under photomodulation. Background [0002] Modulated polymerization through external stimuli such as light, electrochemistry, supramolecular and mechanical forces creates new opportunities for the intelligence and functionalization of polymer synthesis. In particular, light has some special advantages over other stimuli, including low cost, ubiquity, and non-invasiveness, and unique control over both the space and time of aggregation. This makes light regulation an ideal type of control. [0003] Using different catalytic / initiating systems, the biodegradable polyester prepared by the open-loop polymerization of cyclic esters has the characteristics of recyclability and degradability, which can solve the problem of white pollution in plastic applications...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/08C08G63/87
CPCC08G63/08C08G63/87Y02P20/584
Inventor 谭忱李杰王福周
Owner ANHUI UNIVERSITY