Chiral 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-Catalyzed Stereoselective Ring-Opening Polymerization of rac -Lactide: High Reactivity for Isotactic Enriched Polylactides (PLAs)

Chiral 4,8-diphenyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (DiPh-TBD) was synthesized and applied to a ring-opening polymerization of -lactide ( -LA). The chiral DiPh-TBD promoted the synthesis of isotactic enriched polylactides (PLAs) with controlled molecular weight and narrow molecular weight distri...

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Published inPolymers Vol. 12; no. 10; p. 2365
Main Authors Mahmood, Qaiser, Xu, Guangqiang, Zhou, Li, Guo, Xuanhua, Wang, Qinggang
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 15.10.2020
MDPI
Subjects
Amino acids
chiral TBD
high reactivity
Isotacticity
Molecular weight
Molecular weight distribution
NMR
Nuclear magnetic resonance
organocatalyst
Polylactic acid
Polymerization
Polymers
Ring opening polymerization
Room temperature
Stereoselectivity
chiral TBD
organocatalyst
high reactivity
stereoselectivity
ring-opening polymerization
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Abstract Chiral 4,8-diphenyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (DiPh-TBD) was synthesized and applied to a ring-opening polymerization of -lactide ( -LA). The chiral DiPh-TBD promoted the synthesis of isotactic enriched polylactides (PLAs) with controlled molecular weight and narrow molecular weight distributions under mild, metal-free conditions. When the [ -LA]/[Cat.] ratio was 100/1, full monomer conversion was achieved within only 1 min and a moderate probability of 0.67 dyads ( ) was obtained at room temperature. A chain-end control mechanism (CEC) was found to be responsible for the isoselectivity based on the homodecoupled H NMR spectrum, the chiral HPLC measurement, and kinetic studies.
AbstractList Chiral 4,8-diphenyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (DiPh-TBD) was synthesized and applied to a ring-opening polymerization of rac-lactide (rac-LA). The chiral DiPh-TBD promoted the synthesis of isotactic enriched polylactides (PLAs) with controlled molecular weight and narrow molecular weight distributions under mild, metal-free conditions. When the [rac-LA]/[Cat.] ratio was 100/1, full monomer conversion was achieved within only 1 min and a moderate probability of 0.67 meso dyads (Pm) was obtained at room temperature. A chain-end control mechanism (CEC) was found to be responsible for the isoselectivity based on the homodecoupled 1H NMR spectrum, the chiral HPLC measurement, and kinetic studies.
Chiral 4,8-diphenyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (DiPh-TBD) was synthesized and applied to a ring-opening polymerization of rac -lactide ( rac -LA). The chiral DiPh-TBD promoted the synthesis of isotactic enriched polylactides (PLAs) with controlled molecular weight and narrow molecular weight distributions under mild, metal-free conditions. When the [ rac -LA]/[Cat.] ratio was 100/1, full monomer conversion was achieved within only 1 min and a moderate probability of 0.67 meso dyads ( P m ) was obtained at room temperature. A chain-end control mechanism (CEC) was found to be responsible for the isoselectivity based on the homodecoupled 1 H NMR spectrum, the chiral HPLC measurement, and kinetic studies.
Chiral 4,8-diphenyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (DiPh-TBD) was synthesized and applied to a ring-opening polymerization of -lactide ( -LA). The chiral DiPh-TBD promoted the synthesis of isotactic enriched polylactides (PLAs) with controlled molecular weight and narrow molecular weight distributions under mild, metal-free conditions. When the [ -LA]/[Cat.] ratio was 100/1, full monomer conversion was achieved within only 1 min and a moderate probability of 0.67 dyads ( ) was obtained at room temperature. A chain-end control mechanism (CEC) was found to be responsible for the isoselectivity based on the homodecoupled H NMR spectrum, the chiral HPLC measurement, and kinetic studies.
Author Xu, Guangqiang
Mahmood, Qaiser
Wang, Qinggang
Zhou, Li
Guo, Xuanhua
AuthorAffiliation 2 Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing 100049, China
1 Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China; qaiser@qibebt.ac.cn (Q.M.); zhouli@qibebt.ac.cn (L.Z.); guoxh@qibebt.ac.cn (X.G.)
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/33076378$$D View this record in MEDLINE/PubMed
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CitedBy_id crossref_primary_10_1016_j_eurpolymj_2022_111571
crossref_primary_10_1007_s10118_021_2535_x
crossref_primary_10_1039_D1RE00434D
crossref_primary_10_3390_polym14245359
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Keywords chiral TBD
organocatalyst
high reactivity
stereoselectivity
ring-opening polymerization
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Snippet Chiral 4,8-diphenyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (DiPh-TBD) was synthesized and applied to a ring-opening polymerization of -lactide ( -LA). The chiral...
Chiral 4,8-diphenyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (DiPh-TBD) was synthesized and applied to a ring-opening polymerization of rac-lactide (rac-LA). The...
Chiral 4,8-diphenyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (DiPh-TBD) was synthesized and applied to a ring-opening polymerization of rac -lactide ( rac -LA). The...
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StartPage 2365
SubjectTerms Amino acids
chiral TBD
high reactivity
Isotacticity
Molecular weight
Molecular weight distribution
NMR
Nuclear magnetic resonance
organocatalyst
Polylactic acid
Polymerization
Polymers
Ring opening polymerization
Room temperature
Stereoselectivity
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Title Chiral 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-Catalyzed Stereoselective Ring-Opening Polymerization of rac -Lactide: High Reactivity for Isotactic Enriched Polylactides (PLAs)
URI https://www.ncbi.nlm.nih.gov/pubmed/33076378
https://www.proquest.com/docview/2550253965
https://pubmed.ncbi.nlm.nih.gov/PMC7602607
https://doaj.org/article/c1eee2183885464386dba8cde11d33f3
Volume 12
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