Rhodanine-based Knoevenagel reaction and ring-opening polymerization for efficiently constructing multicyclic polymers

Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic polymers are very limited, and some multicyclic polymers are still not accessible now. Here, we found that the five˗membered cyclic structure...

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Published inNature communications Vol. 11; no. 1; pp. 3654 - 10
Main Authors Zhang, Ze, Nie, Xuan, Wang, Fei, Chen, Guang, Huang, Wei-Qiang, Xia, Lei, Zhang, Wen-Jian, Hao, Zong-Yao, Hong, Chun-Yan, Wang, Long-Hai, You, Ye-Zi
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 21.07.2020
Nature Publishing Group
Nature Portfolio
Subjects
639/638/455/941
639/638/455/958
639/638/549/933
Aldehydes
Backbone
Chain branching
Chemical synthesis
Humanities and Social Sciences
Initiators
multidisciplinary
Physical properties
Polymerization
Polymers
Ring opening polymerization
Science
Science (multidisciplinary)
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Abstract Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic polymers are very limited, and some multicyclic polymers are still not accessible now. Here, we found that the five˗membered cyclic structure and electron withdrawing groups make methylene in rhodanine highly active to aldehyde via highly efficient Knoevenagel reaction. Also, rhodanine can act as an initiator for anionic ring-opening polymerization of thiirane to produce cyclic polythioethers. Therefore, rhodanine can serve as both an initiator for ring-opening polymerization and a monomer in Knoevenagel polymerization. Via rhodanine-based Knoevenagel reaction, we can easily incorporate rhodanine moieties in the backbone, side chain, branched chain, etc, and correspondingly could produce cyclic structures in the backbone, side chain, branched chain, etc, via rhodanine˗based anionic ring-opening polymerization. This rhodanine chemistry would provide easy access to a wide variety of complex multicyclic polymers. Cyclic polymers have a number of unique physical properties compared to their linear counterparts but their synthesis is very limited. Here, the authors show a method to form a wide variety of multicyclic polymers by a rhodanine˗based Knoevenagel reaction and ring-opening polymerization.
AbstractList Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic polymers are very limited, and some multicyclic polymers are still not accessible now. Here, we found that the five˗membered cyclic structure and electron withdrawing groups make methylene in rhodanine highly active to aldehyde via highly efficient Knoevenagel reaction. Also, rhodanine can act as an initiator for anionic ring-opening polymerization of thiirane to produce cyclic polythioethers. Therefore, rhodanine can serve as both an initiator for ring-opening polymerization and a monomer in Knoevenagel polymerization. Via rhodanine-based Knoevenagel reaction, we can easily incorporate rhodanine moieties in the backbone, side chain, branched chain, etc, and correspondingly could produce cyclic structures in the backbone, side chain, branched chain, etc, via rhodanine˗based anionic ring-opening polymerization. This rhodanine chemistry would provide easy access to a wide variety of complex multicyclic polymers.Cyclic polymers have a number of unique physical properties compared to their linear counterparts but their synthesis is very limited. Here, the authors show a method to form a wide variety of multicyclic polymers by a rhodanine˗based Knoevenagel reaction and ring-opening polymerization.
Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic polymers are very limited, and some multicyclic polymers are still not accessible now. Here, we found that the five-membered cyclic structure and electron withdrawing groups make methylene in rhodanine highly active to aldehyde via highly efficient Knoevenagel reaction. Also, rhodanine can act as an initiator for anionic ring-opening polymerization of thiirane to produce cyclic polythioethers. Therefore, rhodanine can serve as both an initiator for ring-opening polymerization and a monomer in Knoevenagel polymerization. Via rhodanine-based Knoevenagel reaction, we can easily incorporate rhodanine moieties in the backbone, side chain, branched chain, etc, and correspondingly could produce cyclic structures in the backbone, side chain, branched chain, etc, via rhodanine-based anionic ring-opening polymerization. This rhodanine chemistry would provide easy access to a wide variety of complex multicyclic polymers.Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic polymers are very limited, and some multicyclic polymers are still not accessible now. Here, we found that the five-membered cyclic structure and electron withdrawing groups make methylene in rhodanine highly active to aldehyde via highly efficient Knoevenagel reaction. Also, rhodanine can act as an initiator for anionic ring-opening polymerization of thiirane to produce cyclic polythioethers. Therefore, rhodanine can serve as both an initiator for ring-opening polymerization and a monomer in Knoevenagel polymerization. Via rhodanine-based Knoevenagel reaction, we can easily incorporate rhodanine moieties in the backbone, side chain, branched chain, etc, and correspondingly could produce cyclic structures in the backbone, side chain, branched chain, etc, via rhodanine-based anionic ring-opening polymerization. This rhodanine chemistry would provide easy access to a wide variety of complex multicyclic polymers.
Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic polymers are very limited, and some multicyclic polymers are still not accessible now. Here, we found that the five-membered cyclic structure and electron withdrawing groups make methylene in rhodanine highly active to aldehyde via highly efficient Knoevenagel reaction. Also, rhodanine can act as an initiator for anionic ring-opening polymerization of thiirane to produce cyclic polythioethers. Therefore, rhodanine can serve as both an initiator for ring-opening polymerization and a monomer in Knoevenagel polymerization. Via rhodanine-based Knoevenagel reaction, we can easily incorporate rhodanine moieties in the backbone, side chain, branched chain, etc, and correspondingly could produce cyclic structures in the backbone, side chain, branched chain, etc, via rhodanine-based anionic ring-opening polymerization. This rhodanine chemistry would provide easy access to a wide variety of complex multicyclic polymers.
Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic polymers are very limited, and some multicyclic polymers are still not accessible now. Here, we found that the five˗membered cyclic structure and electron withdrawing groups make methylene in rhodanine highly active to aldehyde via highly efficient Knoevenagel reaction. Also, rhodanine can act as an initiator for anionic ring-opening polymerization of thiirane to produce cyclic polythioethers. Therefore, rhodanine can serve as both an initiator for ring-opening polymerization and a monomer in Knoevenagel polymerization. Via rhodanine-based Knoevenagel reaction, we can easily incorporate rhodanine moieties in the backbone, side chain, branched chain, etc, and correspondingly could produce cyclic structures in the backbone, side chain, branched chain, etc, via rhodanine˗based anionic ring-opening polymerization. This rhodanine chemistry would provide easy access to a wide variety of complex multicyclic polymers. Cyclic polymers have a number of unique physical properties compared to their linear counterparts but their synthesis is very limited. Here, the authors show a method to form a wide variety of multicyclic polymers by a rhodanine˗based Knoevenagel reaction and ring-opening polymerization.
Cyclic polymers have a number of unique physical properties compared to their linear counterparts but their synthesis is very limited. Here, the authors show a method to form a wide variety of multicyclic polymers by a rhodanine˗based Knoevenagel reaction and ring-opening polymerization.
Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic polymers are very limited, and some multicyclic polymers are still not accessible now. Here, we found that the five˗membered cyclic structure and electron withdrawing groups make methylene in rhodanine highly active to aldehyde via highly efficient Knoevenagel reaction. Also, rhodanine can act as an initiator for anionic ring-opening polymerization of thiirane to produce cyclic polythioethers. Therefore, rhodanine can serve as both an initiator for ring-opening polymerization and a monomer in Knoevenagel polymerization. Via rhodanine-based Knoevenagel reaction, we can easily incorporate rhodanine moieties in the backbone, side chain, branched chain, etc, and correspondingly could produce cyclic structures in the backbone, side chain, branched chain, etc, via rhodanine˗based anionic ring-opening polymerization. This rhodanine chemistry would provide easy access to a wide variety of complex multicyclic polymers.
ArticleNumber 3654
Author Zhang, Ze
Wang, Fei
Hong, Chun-Yan
Nie, Xuan
Chen, Guang
Hao, Zong-Yao
Wang, Long-Hai
Xia, Lei
Huang, Wei-Qiang
You, Ye-Zi
Zhang, Wen-Jian
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  organization: CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China
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  organization: The First Affiliated Hospital of University of Science and Technology of China
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  fullname: Chen, Guang
  organization: CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China
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  surname: You
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  email: yzyou@ustc.edu.cn
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/32694628$$D View this record in MEDLINE/PubMed
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Snippet Cyclic polymers have a number of unique physical properties compared with those of their linear counterparts. However, the methods for the synthesis of cyclic...
Cyclic polymers have a number of unique physical properties compared to their linear counterparts but their synthesis is very limited. Here, the authors show a...
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SubjectTerms 639/638/455/941
639/638/455/958
639/638/549/933
Aldehydes
Backbone
Chain branching
Chemical synthesis
Humanities and Social Sciences
Initiators
multidisciplinary
Physical properties
Polymerization
Polymers
Ring opening polymerization
Science
Science (multidisciplinary)
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Title Rhodanine-based Knoevenagel reaction and ring-opening polymerization for efficiently constructing multicyclic polymers
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https://www.ncbi.nlm.nih.gov/pubmed/32694628
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