Living Ring-Opening Polymerization of Lactones by N-Heterocyclic Olefin/Al(C6F5)3 Lewis Pairs: Structures of Intermediates, Kinetics, and Mechanism
Abstract
The strong Lewis acid Al(C 6 F 5 ) 3, in combination with a strong Lewis base N -heterocyclic olefin (NHO), cooperatively promotes the living ring-opening (co)polymerization of lactones, represented by δ-valerolactone (δ-VL) and ε-caprolactone (ε-CL) in this study. Medium to high molecular weight linear (co)polyesters ( M w up to 855 kg/mol) are achieved, and most of them exhibit narrow molecular weight distributions ( Đ as low as 1.02). Detailed investigations into the structures of key reaction intermediates, kinetics, and polymer structures have led to a polymerization mechanism, in that initiation involves nucleophilic attack of the Al(C 6 F 5 ) 3 -activated monomer by NHO to form a structurally characterized zwitterionic, tetrahedral intermediate, followed by its ring-opening to generate active zwitterionic species. In the propagation cycle, this ring-opened zwitterionic species and its homologues attack the incoming monomer activated by Al(C 6 F 5 ) 3 to generate the tetrahedral intermediate, followed by the rate-determining ring-opening step to regenerate the zwitterionic species that re-enters into the next chain propagation cycles. Owning to the living features and lack of transesterification side reactions possessed uniquely by this Lewis pair polymerization system, well-defined di- and triblock copolymers with narrow molecular weight distributions ( Đ = 1.06–1.15) have been successfully synthesized using this method, regardless of the comonomer addition order.
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End-group analysis revealed an imidazolium enol-like chain end of the final polymers, indicative of an intramolecular proton transfer within the zwitterionic intermediates generated from the nucleophilic addition of NHOs to the monomer.
“End-group analysis revealed an imidazolium enol-like chain end of the final polymers, indicative of an intramolecular proton transfer within the zwitterionic intermediates generated from the nucleophilic addition of NHOs to the monomer (Scheme 11D).”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [335]
The living polymerizations of VL and CL mediated by NHO-1/Al(C6F5)3 generated linear polyesters with high molecular weights up to 855 kDa (DP = 3200) and narrow molecular weight distributions (Ð = 1.03-1.63).
“The living polymerizations of VL and CL mediated by NHO-1/Al(C6F5)3 generated linear polyesters with high molecular weights up to 855 kDa (DP = 3200) and narrow molecular weight distributions (Ð = 1.03 -1.63).”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [335]
N-heterocyclic olefins have emerged as a class of active and versatile catalysts for the ROP of cyclic esters and carbonates.
“Recently, N-heterocyclic olefins (NHOs) have emerged as a class of active and versatile catalysts for the ROP of cyclic esters and carbonates.334,335”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [335]
Chen recently combined NHOs with a Lewis acid Al(C6F5)3 to develop a highly efficient catalytic system.
“Chen recently combined NHOs with a Lewis acid Al(C6F5)3 to develop a highly efficient catalytic system.335”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [335]
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- Authors
- Wang, Q., Zhao, W., He, J., Zhang, Y., & Chen, E. Y.-X.
- Affiliations
- Jilin University (CN)
- Colorado State University (US)
- Corresponding author
- Zhang, Yuetao
- Venue
- Macromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2016-12-28
- Volume
- 50
- Issue
- 1
- Pages
- 123-136
- ISSN
- 0024-9297 (ISSN-L)
- 1520-5835
- OpenAlex
- W2562177069
- Cited by
- 127
- References
- 111
- Citations by year
- 2026: 7 · 2025: 4 · 2024: 10 · 2023: 11 · 2022: 16 · 2021: 13 · 2020: 18 · 2019: 15 · 2018: 24 · 2017: 9
- FWCI
- 6.54
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Macromolecules (publishedVersion)
- Funders
- Jilin University
- National Natural Science Foundation of China (21374040, 21422401)
- National Science Foundation (1507702)
- Central People's Government of the People's Republic of China
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Chemistry › Organic Chemistry › Organometallic Complex Synthesis and Catalysis
- Keywords
- living ring-opening polymerization, lactones, N-heterocyclic olefins, Lewis acid-base pairs, δ-valerolactone, ε-caprolactone, zwitterionic intermediate, tetrahedral intermediate, polymerization mechanism, polymerization kinetics, block copolymers, polyester synthesis, molecular weight distribution
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