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Zwitterionic Ring-Opening Polymerization of N-Substituted Eight-Membered Cyclic Carbonates to Generate Cyclic Poly(carbonate)s
- Source :
- ACS macro letters. 5(10)
- Publication Year :
- 2022
-
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 (8CCBn) polymerizes readily with 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene to generate cyclic polycarbonates with molecular weights of Mn = 14 000 to 96 000 Da. In contrast, the N-phenyl-substituted cyclic carbonate (8CCPh) 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. 13C NMR and differential ...
- Subjects :
- Polymers and Plastics
Dimer
Intrinsic viscosity
Organic Chemistry
Substituent
02 engineering and technology
Carbon-13 NMR
010402 general chemistry
021001 nanoscience & nanotechnology
01 natural sciences
Ring-opening polymerization
0104 chemical sciences
Inorganic Chemistry
chemistry.chemical_compound
Polymerization
chemistry
Polymer chemistry
Materials Chemistry
Copolymer
Organic chemistry
Carbonate
0210 nano-technology
Subjects
Details
- ISSN :
- 21611653
- Volume :
- 5
- Issue :
- 10
- Database :
- OpenAIRE
- Journal :
- ACS macro letters
- Accession number :
- edsair.doi.dedup.....00d74e40a1c673248d282c34241254fd