Well‐Defined Poly(Ester Amide)‐Based Homo‐ and Block Copolymers by One‐Pot Organocatalytic Anionic Ring‐Opening Copolymerization of N‐Sulfonyl Aziridines and Cyclic Anhydrides
We report a new synthetic methodology for poly(ester amide)s by anionic ring‐opening copolymerization of N‐sulfonyl aziridines and cyclic anhydrides. Phosphazenes organocatalysts have been found to promote a highly‐active, controlled, and selective alternating copolymerization in the absence of any...
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| Published in | Angewandte Chemie International Edition Vol. 60; no. 13; pp. 6949 - 6954 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
Wiley Subscription Services, Inc
22.03.2021
John Wiley and Sons Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | We report a new synthetic methodology for poly(ester amide)s by anionic ring‐opening copolymerization of N‐sulfonyl aziridines and cyclic anhydrides. Phosphazenes organocatalysts have been found to promote a highly‐active, controlled, and selective alternating copolymerization in the absence of any competitive side reaction (zwitterionic mechanism and exchange transacylations). Mechanistic studies have shown first‐order dependence of the copolymerization rate in N‐sulfonyl aziridines and phosphazenes, and zero‐order in cyclic anhydrides. This one‐pot methodology leads not only to homopolymers but also to poly(ester amide)‐based block copolymers. Two catalytic cycles involving ring‐opening alternating copolymerization of N‐sulfonyl aziridines with cyclic anhydrides and ring‐opening polymerization of N‐sulfonyl aziridines have been proposed to explain the one pot synthesis of poly(ester amide)‐based homo‐ and block copolymers.
Phosphazene organocatalysts have been found to promote a highly‐active, controlled, and selective alternating ring‐opening copolymerization of N‐sulfonyl aziridines and cyclic anhydrides. This one‐pot methodology leads not only to homopolymers but also to poly(ester amide)‐based block copolymers. |
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| AbstractList | We report a new synthetic methodology for poly(ester amide)s by anionic ring-opening copolymerization of N-sulfonyl aziridines and cyclic anhydrides. Phosphazenes organocatalysts have been found to promote a highly-active, controlled, and selective alternating copolymerization in the absence of any competitive side reaction (zwitterionic mechanism and exchange transacylations). Mechanistic studies have shown first-order dependence of the copolymerization rate in N-sulfonyl aziridines and phosphazenes, and zero-order in cyclic anhydrides. This one-pot methodology leads not only to homopolymers but also to poly(ester amide)-based block copolymers. Two catalytic cycles involving ring-opening alternating copolymerization of N-sulfonyl aziridines with cyclic anhydrides and ring-opening polymerization of N-sulfonyl aziridines have been proposed to explain the one pot synthesis of poly(ester amide)-based homo- and block copolymers. We report a new synthetic methodology for poly(ester amide)s by anionic ring‐opening copolymerization of N ‐sulfonyl aziridines and cyclic anhydrides. Phosphazenes organocatalysts have been found to promote a highly‐active, controlled, and selective alternating copolymerization in the absence of any competitive side reaction (zwitterionic mechanism and exchange transacylations). Mechanistic studies have shown first‐order dependence of the copolymerization rate in N ‐sulfonyl aziridines and phosphazenes, and zero‐order in cyclic anhydrides. This one‐pot methodology leads not only to homopolymers but also to poly(ester amide)‐based block copolymers. Two catalytic cycles involving ring‐opening alternating copolymerization of N ‐sulfonyl aziridines with cyclic anhydrides and ring‐opening polymerization of N ‐sulfonyl aziridines have been proposed to explain the one pot synthesis of poly(ester amide)‐based homo‐ and block copolymers. Phosphazene organocatalysts have been found to promote a highly‐active, controlled, and selective alternating ring‐opening copolymerization of N ‐sulfonyl aziridines and cyclic anhydrides. This one‐pot methodology leads not only to homopolymers but also to poly(ester amide)‐based block copolymers. We report a new synthetic methodology for poly(ester amide)s by anionic ring‐opening copolymerization of N ‐sulfonyl aziridines and cyclic anhydrides. Phosphazenes organocatalysts have been found to promote a highly‐active, controlled, and selective alternating copolymerization in the absence of any competitive side reaction (zwitterionic mechanism and exchange transacylations). Mechanistic studies have shown first‐order dependence of the copolymerization rate in N ‐sulfonyl aziridines and phosphazenes, and zero‐order in cyclic anhydrides. This one‐pot methodology leads not only to homopolymers but also to poly(ester amide)‐based block copolymers. Two catalytic cycles involving ring‐opening alternating copolymerization of N ‐sulfonyl aziridines with cyclic anhydrides and ring‐opening polymerization of N ‐sulfonyl aziridines have been proposed to explain the one pot synthesis of poly(ester amide)‐based homo‐ and block copolymers. We report a new synthetic methodology for poly(ester amide)s by anionic ring‐opening copolymerization of N‐sulfonyl aziridines and cyclic anhydrides. Phosphazenes organocatalysts have been found to promote a highly‐active, controlled, and selective alternating copolymerization in the absence of any competitive side reaction (zwitterionic mechanism and exchange transacylations). Mechanistic studies have shown first‐order dependence of the copolymerization rate in N‐sulfonyl aziridines and phosphazenes, and zero‐order in cyclic anhydrides. This one‐pot methodology leads not only to homopolymers but also to poly(ester amide)‐based block copolymers. Two catalytic cycles involving ring‐opening alternating copolymerization of N‐sulfonyl aziridines with cyclic anhydrides and ring‐opening polymerization of N‐sulfonyl aziridines have been proposed to explain the one pot synthesis of poly(ester amide)‐based homo‐ and block copolymers. Phosphazene organocatalysts have been found to promote a highly‐active, controlled, and selective alternating ring‐opening copolymerization of N‐sulfonyl aziridines and cyclic anhydrides. This one‐pot methodology leads not only to homopolymers but also to poly(ester amide)‐based block copolymers. We report a new synthetic methodology for poly(ester amide)s by anionic ring-opening copolymerization of N-sulfonyl aziridines and cyclic anhydrides. Phosphazenes organocatalysts have been found to promote a highly-active, controlled, and selective alternating copolymerization in the absence of any competitive side reaction (zwitterionic mechanism and exchange transacylations). Mechanistic studies have shown first-order dependence of the copolymerization rate in N-sulfonyl aziridines and phosphazenes, and zero-order in cyclic anhydrides. This one-pot methodology leads not only to homopolymers but also to poly(ester amide)-based block copolymers. Two catalytic cycles involving ring-opening alternating copolymerization of N-sulfonyl aziridines with cyclic anhydrides and ring-opening polymerization of N-sulfonyl aziridines have been proposed to explain the one pot synthesis of poly(ester amide)-based homo- and block copolymers.We report a new synthetic methodology for poly(ester amide)s by anionic ring-opening copolymerization of N-sulfonyl aziridines and cyclic anhydrides. Phosphazenes organocatalysts have been found to promote a highly-active, controlled, and selective alternating copolymerization in the absence of any competitive side reaction (zwitterionic mechanism and exchange transacylations). Mechanistic studies have shown first-order dependence of the copolymerization rate in N-sulfonyl aziridines and phosphazenes, and zero-order in cyclic anhydrides. This one-pot methodology leads not only to homopolymers but also to poly(ester amide)-based block copolymers. Two catalytic cycles involving ring-opening alternating copolymerization of N-sulfonyl aziridines with cyclic anhydrides and ring-opening polymerization of N-sulfonyl aziridines have been proposed to explain the one pot synthesis of poly(ester amide)-based homo- and block copolymers. |
| Author | Xu, Jiaxi Hadjichristidis, Nikos |
| AuthorAffiliation | 1 King Abdullah University of Science and Technology (KAUST) Physical Sciences and Engineering Division KAUST Catalysis Center Polymer Synthesis Laboratory Thuwal 23955 Saudi Arabia |
| AuthorAffiliation_xml | – name: 1 King Abdullah University of Science and Technology (KAUST) Physical Sciences and Engineering Division KAUST Catalysis Center Polymer Synthesis Laboratory Thuwal 23955 Saudi Arabia |
| Author_xml | – sequence: 1 givenname: Jiaxi orcidid: 0000-0003-0366-020X surname: Xu fullname: Xu, Jiaxi organization: King Abdullah University of Science and Technology (KAUST) – sequence: 2 givenname: Nikos orcidid: 0000-0003-1442-1714 surname: Hadjichristidis fullname: Hadjichristidis, Nikos email: Nikolaos.Hadjichristidis@kaust.edu.sa organization: King Abdullah University of Science and Technology (KAUST) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/33351198$$D View this record in MEDLINE/PubMed |
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| Keywords | N-sulfonyl aziridines anhydrides poly(ester amide)s phosphazenes anionic copolymerization |
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| Snippet | We report a new synthetic methodology for poly(ester amide)s by anionic ring‐opening copolymerization of N‐sulfonyl aziridines and cyclic anhydrides.... We report a new synthetic methodology for poly(ester amide)s by anionic ring‐opening copolymerization of N ‐sulfonyl aziridines and cyclic anhydrides.... We report a new synthetic methodology for poly(ester amide)s by anionic ring-opening copolymerization of N-sulfonyl aziridines and cyclic anhydrides.... |
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| SubjectTerms | Active control Anhydrides anionic copolymerization Block copolymers Communication Communications Copolymerization Copolymers N-sulfonyl aziridines phosphazenes poly(ester amide)s Polyesteramides Ring opening polymerization |
| Title | Well‐Defined Poly(Ester Amide)‐Based Homo‐ and Block Copolymers by One‐Pot Organocatalytic Anionic Ring‐Opening Copolymerization of N‐Sulfonyl Aziridines and Cyclic Anhydrides |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202015339 https://www.ncbi.nlm.nih.gov/pubmed/33351198 https://www.proquest.com/docview/2501877896 https://www.proquest.com/docview/2472111772 https://pubmed.ncbi.nlm.nih.gov/PMC8048504 |
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