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Cited by 43biodegradable polymer synthesis and propertiesCarbon dioxide utilization in catalysisAdvanced Polymer Synthesis and Characterization

Zwitterionic Ring-Opening Polymerization of N-Substituted Eight-Membered Cyclic Carbonates to Generate Cyclic Poly(carbonate)s

Chang, Young A., Rudenko, Andrey E., Waymouth, Robert M.·2016·ACS Macro Letters
DOI 10.1021/acsmacrolett.6b00591
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Abstract

The zwitterionic ring-opening polymerization of N-functionalized eight-membered cyclic carbonates with N-heterocyclic carbenes (NHC) in the absence of alcohol initiators generates cyclic polycarbonates of Mn ∼ 30–100 kDa. The polymerization behavior of these eight-membered cyclic azacarbonates depends sensitively on the nature of the nitrogen substituent. The N -benzyl-substituted eight-membered cyclic carbonate (8CC Bn ) polymerizes readily with 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene to generate cyclic polycarbonates with molecular weights of M n = 14 000 to 96 000 Da. In contrast, the N -phenyl-substituted cyclic carbonate (8CC Ph ) catalytically dimerizes in the presence of the NHC to afford the crystalline cyclic dimer. The zwitterionic ring-opening copolymerization of δ-valerolactone (VL) and the cyclic carbonates afford gradient cyclic copolymers. The cyclic topology of both the homopolymers and copolymers was supported by MALDI-TOF MS and intrinsic viscosity measurements. 13 C NMR and differential scanning calorimetry of the cyclic copolymers are indicative of a gradient sequence distribution as a consequence of the more rapid enchainment of the cyclic carbonates relative to valerolactone.

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Crossref · 10.1021/acsmacrolett.6b00591

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  • N-substitution not only enhances the ring strain but also provides a synthetic handle to introduce functionality to these polycarbonates.

    “The N-substitution not only enhances the ring strain but also provides a synthetic handle to introduce functionality to these polycarbonates.”

    From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [284]

  • A class of strained 8-membered cyclic carbonates derived from diethanolamine were prepared and polymerized to well-defined N-substituted polycarbonates.

    “Recently a class of strained 8-memebered cyclic carbonates derived from diethanolamine were prepared and polymerized to well-defined N-substituted polycarbonates.283,284”

    From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [284]

  • This has led to the development of zwitterionic ring-opening polymerization for the synthesis of high molecular weight polyesters and polycarbonates with cyclic topology.

    “This has led to the development of zwitterionic ring-opening polymerization for the synthesis of high molecular weight polyesters 327 and polycarbonates 284 with cyclic topology.”

    From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [284]

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Authors
Chang, Y. A., Rudenko, A. E., & Waymouth, R. M.
Affiliations
Stanford University (US)
Corresponding author
Waymouth, Robert M.
ORCID
Venue
ACS Macro Letters
Publisher
American Chemical Society (ACS)
Published
2016-09-30
Volume
5
Issue
10
Pages
1162-1166
ISSN
2161-1653 (ISSN-L)
DOI
10.1021/acsmacrolett.6b00591
OpenAlex
W2527063451
Cited by
43
References
39
Citations by year
2026: 3 · 2025: 2 · 2024: 5 · 2023: 3 · 2022: 8 · 2021: 3 · 2020: 3 · 2019: 4 · 2018: 8 · 2017: 4
FWCI
2.18
Type
journal article
Language
en
Open access
closed
Locations
  • ACS Macro Letters (publishedVersion)
  • PubMed (publishedVersion)
Funders
  • American Philosophical Society
  • Division of Materials Research (DMR 1407658)
Topics
  • Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
  • Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
  • Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
Keywords
cyclic carbonates, N-heterocyclic carbenes, δ-valerolactone, gradient copolymers, sequence distribution, cyclic topology

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