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Squaramide and amine binary H-bond organocatalysis in polymerizations of cyclic carbonates, lactones, and lactides

Multiple combinations of six squaramides (Sq) and eight amines as the co-catalysts were tried in ring-opening polymerizations (ROPs) of cyclic carbonates, lactones, and lactides. Sq and sparteine co-catalysts enabled ROPs of trimethylene carbonate (TMC) to poly(trimethylene carbonates) (PTMCs) with... Full description

Journal Title: Polymer Chemistry 2017, Vol.8(45), pp.7054-7068
Main Author: Liu, Jingjing
Other Authors: Xu, Jiaxi , Li, Zhenjiang , Xu, Songquan , Wang, Xin , Wang, Haixin , Guo, Tianfo , Gao, Yu , Zhang, Lei , Guo, Kai
Format: Electronic Article Electronic Article
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ID: ISSN: 1759-9954 ; E-ISSN: 1759-9962 ; DOI: 10.1039/c7py01671a
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title: Squaramide and amine binary H-bond organocatalysis in polymerizations of cyclic carbonates, lactones, and lactides
format: Article
creator:
  • Liu, Jingjing
  • Xu, Jiaxi
  • Li, Zhenjiang
  • Xu, Songquan
  • Wang, Xin
  • Wang, Haixin
  • Guo, Tianfo
  • Gao, Yu
  • Zhang, Lei
  • Guo, Kai
subjects:
  • Decarboxylation
  • Carbonates
  • Dichloromethane
  • Polydispersity
  • Benzyl Alcohol
  • Polycarbonates
  • Initiators
  • Lactones
  • Polymerization
  • Polymerization
  • Amines
  • Catalysis
  • Alcohol
  • Furfuryl Alcohol
  • Block Copolymers
  • Addition Polymerization
  • Chemical Bonds
  • Titration
  • Reaction Kinetics
  • Propargyl Alcohol
  • Catalysts
  • Chemical Synthesis
  • Nuclear Magnetic Resonance–NMR
ispartof: Polymer Chemistry, 2017, Vol.8(45), pp.7054-7068
description: Multiple combinations of six squaramides (Sq) and eight amines as the co-catalysts were tried in ring-opening polymerizations (ROPs) of cyclic carbonates, lactones, and lactides. Sq and sparteine co-catalysts enabled ROPs of trimethylene carbonate (TMC) to poly(trimethylene carbonates) (PTMCs) with benzyl alcohol (BnOH) as the initiator. The polymerization proceeded in 3 to 16 h without decarboxylation to afford polycarbonates with precise molecular weights ( M n,NMR = 1.95 to 10.1 kg mol 1 ) and narrow polydispersity indices ( = 1.121.17). 1 H NMR, SEC and MALDI-ToF MS measurements of the obtained PTMCs clearly indicated the quantitative incorporation of the initiator at the chain end. Kinetics and chain extension experiments demonstrated the controlled/living nature for the ROP of TMC using Sq and sparteine. NMR titration experiments confirmed that the polymerization proceeded in a H-bonding dual activation mechanism. In addition, 1,3-propanediol, pentaerythritol, propargyl alcohol, furfuryl alcohol and N -(2-hydroxyethyl)maleimide were used as functional initiators leading to production of ,-dihydroxy telechelic, star-shaped, and clickable end-functionalized polycarbonates. Homopolymers of valerolactone (VL), caprolactone (CL), and lactide (LA) and diblock copolymers PVL- b -PTMC and PCL- b -PTMC were successfully synthesized by using Sq and 1,8-diazabicyclo[5.4.0]undec-7-ene binary co-catalysts with BnOH as the initiator in dichloromethane at room temperature. Block copolymers PTMC- b -PVL, PTMC- b -PCL, and PTMC- b -PLA were successfully obtained by using the binary catalysts. Squaramides combined with amine co-catalysts are a generally applicable polymerization tool.
language:
source:
identifier: ISSN: 1759-9954 ; E-ISSN: 1759-9962 ; DOI: 10.1039/c7py01671a
fulltext: fulltext
issn:
  • 1759-9954
  • 1759-9962
  • 17599962
  • 17599954
url: Link


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titleSquaramide and amine binary H-bond organocatalysis in polymerizations of cyclic carbonates, lactones, and lactides
creatorLiu, Jingjing ; Xu, Jiaxi ; Li, Zhenjiang ; Xu, Songquan ; Wang, Xin ; Wang, Haixin ; Guo, Tianfo ; Gao, Yu ; Zhang, Lei ; Guo, Kai
ispartofPolymer Chemistry, 2017, Vol.8(45), pp.7054-7068
identifier
descriptionMultiple combinations of six squaramides (Sq) and eight amines as the co-catalysts were tried in ring-opening polymerizations (ROPs) of cyclic carbonates, lactones, and lactides. Sq and sparteine co-catalysts enabled ROPs of trimethylene carbonate (TMC) to poly(trimethylene carbonates) (PTMCs) with benzyl alcohol (BnOH) as the initiator. The polymerization proceeded in 3 to 16 h without decarboxylation to afford polycarbonates with precise molecular weights ( M n,NMR = 1.95 to 10.1 kg mol 1 ) and narrow polydispersity indices ( = 1.121.17). 1 H NMR, SEC and MALDI-ToF MS measurements of the obtained PTMCs clearly indicated the quantitative incorporation of the initiator at the chain end. Kinetics and chain extension experiments demonstrated the controlled/living nature for the ROP of TMC using Sq and sparteine. NMR titration experiments confirmed that the polymerization proceeded in a H-bonding dual activation mechanism. In addition, 1,3-propanediol, pentaerythritol, propargyl alcohol, furfuryl alcohol and N -(2-hydroxyethyl)maleimide were used as functional initiators leading to production of ,-dihydroxy telechelic, star-shaped, and clickable end-functionalized polycarbonates. Homopolymers of valerolactone (VL), caprolactone (CL), and lactide (LA) and diblock copolymers PVL- b -PTMC and PCL- b -PTMC were successfully synthesized by using Sq and 1,8-diazabicyclo[5.4.0]undec-7-ene binary co-catalysts with BnOH as the initiator in dichloromethane at room temperature. Block copolymers PTMC- b -PVL, PTMC- b -PCL, and PTMC- b -PLA were successfully obtained by using the binary catalysts. Squaramides combined with amine co-catalysts are a generally applicable polymerization tool.
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subjectDecarboxylation ; Carbonates ; Dichloromethane ; Polydispersity ; Benzyl Alcohol ; Polycarbonates ; Initiators ; Lactones ; Polymerization ; Polymerization ; Amines ; Catalysis ; Alcohol ; Furfuryl Alcohol ; Block Copolymers ; Addition Polymerization ; Chemical Bonds ; Titration ; Reaction Kinetics ; Propargyl Alcohol ; Catalysts ; Chemical Synthesis ; Nuclear Magnetic Resonance–NMR;
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titleSquaramide and amine binary H-bond organocatalysis in polymerizations of cyclic carbonates, lactones, and lactides
descriptionMultiple combinations of six squaramides (Sq) and eight amines as the co-catalysts were tried in ring-opening polymerizations (ROPs) of cyclic carbonates, lactones, and lactides. Sq and sparteine co-catalysts enabled ROPs of trimethylene carbonate (TMC) to poly(trimethylene carbonates) (PTMCs) with benzyl alcohol (BnOH) as the initiator. The polymerization proceeded in 3 to 16 h without decarboxylation to afford polycarbonates with precise molecular weights ( M n,NMR = 1.95 to 10.1 kg mol 1 ) and narrow polydispersity indices ( = 1.121.17). 1 H NMR, SEC and MALDI-ToF MS measurements of the obtained PTMCs clearly indicated the quantitative incorporation of the initiator at the chain end. Kinetics and chain extension experiments demonstrated the controlled/living nature for the ROP of TMC using Sq and sparteine. NMR titration experiments confirmed that the polymerization proceeded in a H-bonding dual activation mechanism. In addition, 1,3-propanediol, pentaerythritol, propargyl alcohol, furfuryl alcohol and N -(2-hydroxyethyl)maleimide were used as functional initiators leading to production of ,-dihydroxy telechelic, star-shaped, and clickable end-functionalized polycarbonates. Homopolymers of valerolactone (VL), caprolactone (CL), and lactide (LA) and diblock copolymers PVL- b -PTMC and PCL- b -PTMC were successfully synthesized by using Sq and 1,8-diazabicyclo[5.4.0]undec-7-ene binary co-catalysts with BnOH as the initiator in dichloromethane at room temperature. Block copolymers PTMC- b -PVL, PTMC- b -PCL, and PTMC- b -PLA were successfully obtained by using the binary catalysts. Squaramides combined with amine co-catalysts are a generally applicable polymerization tool.
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titleSquaramide and amine binary H-bond organocatalysis in polymerizations of cyclic carbonates, lactones, and lactides
authorLiu, Jingjing ; Xu, Jiaxi ; Li, Zhenjiang ; Xu, Songquan ; Wang, Xin ; Wang, Haixin ; Guo, Tianfo ; Gao, Yu ; Zhang, Lei ; Guo, Kai
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abstractMultiple combinations of six squaramides (Sq) and eight amines as the co-catalysts were tried in ring-opening polymerizations (ROPs) of cyclic carbonates, lactones, and lactides. Sq and sparteine co-catalysts enabled ROPs of trimethylene carbonate (TMC) to poly(trimethylene carbonates) (PTMCs) with benzyl alcohol (BnOH) as the initiator. The polymerization proceeded in 3 to 16 h without decarboxylation to afford polycarbonates with precise molecular weights ( M n,NMR = 1.95 to 10.1 kg mol 1 ) and narrow polydispersity indices ( = 1.121.17). 1 H NMR, SEC and MALDI-ToF MS measurements of the obtained PTMCs clearly indicated the quantitative incorporation of the initiator at the chain end. Kinetics and chain extension experiments demonstrated the controlled/living nature for the ROP of TMC using Sq and sparteine. NMR titration experiments confirmed that the polymerization proceeded in a H-bonding dual activation mechanism. In addition, 1,3-propanediol, pentaerythritol, propargyl alcohol, furfuryl alcohol and N -(2-hydroxyethyl)maleimide were used as functional initiators leading to production of ,-dihydroxy telechelic, star-shaped, and clickable end-functionalized polycarbonates. Homopolymers of valerolactone (VL), caprolactone (CL), and lactide (LA) and diblock copolymers PVL- b -PTMC and PCL- b -PTMC were successfully synthesized by using Sq and 1,8-diazabicyclo[5.4.0]undec-7-ene binary co-catalysts with BnOH as the initiator in dichloromethane at room temperature. Block copolymers PTMC- b -PVL, PTMC- b -PCL, and PTMC- b -PLA were successfully obtained by using the binary catalysts. Squaramides combined with amine co-catalysts are a generally applicable polymerization tool.
doi10.1039/c7py01671a
pages7054-7068
date2017-11-21