The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
First Example of N-Heterocyclic Carbenes as Catalysts for Living Polymerization: Organocatalytic Ring-Opening Polymerization of Cyclic Esters
Abstract
A novel metal-free, organocatalytic approach to living polymerization is presented. N-heterocyclic carbenes were employed as nucleophilic catalysts for the ring-opening polymerization (ROP) of cyclic ester monomers. The catalysts is used in combination with an initiator, such as an alcohol, which generates an alpha-end group bearing the ester from the initiating alcohol upon ring-opening and a hydroxyl functional omega-chain end that propagates the chain. This class of catalyst proved to be more reactive than tertiary amine and phosphine nucleophiles, producing narrowly dispersed polymers of predictable molecular weights at room temperature in 1-2 h. Catalysis with respect to both initiating alcohol and monomer was observed. Control of the alpha and omega end-groups was demonstrated with a pyrene-labeled initiator, allowing the preparation of well-defined macromolecular architectures. Analogous to the ROP of cyclic esters using biocatalysts, the polymeriztion pathway using the N-heterocyclic carbenes is believed to ensue through a monomer-activated mechanism.
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Cites
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Cited by
Controlled Ring-Opening Polymerization of Lactide and Glycolide
Dechy-Cabaret, O., Martin-Vaca, B., & Bourissou, D. (2004) · Chemical Reviews · doi:10.1021/cr040002s · Cited by 2,257
Organocatalytic Ring-Opening Polymerization
Kamber, N. E., Jeong, W., Waymouth, R. M., Pratt, R. C., Lohmeijer, B. G. G., & Hedrick, J. L. (2007) · Chemical Reviews · doi:10.1021/cr068415b · Cited by 1,489
Self-citationOrganocatalysis: Opportunities and Challenges for Polymer Synthesis
Kiesewetter, M. K., Shin, E. J., Hedrick, J. L., & Waymouth, R. M. (2010) · Macromolecules · doi:10.1021/ma9025948 · Cited by 907
Self-citationWU, J., YU, T., CHEN, C., & LIN, C. (2006) · Coordination Chemistry Reviews · doi:10.1016/j.ccr.2005.07.010 · Cited by 779
Biocompatible Initiators for Lactide Polymerization
Platel, R., Hodgson, L., & Williams, C. (2008) · Polymer Reviews · doi:10.1080/15583720701834166 · Cited by 706
Metadata
- Authors
- Connor, E. F., Nyce, G. W., Myers, M., Möck, A., & Hedrick, J. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-01-19
- Volume
- 124
- Issue
- 6
- Pages
- 914-915
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2066146098
- Cited by
- 472
- References
- 1
- FWCI
- 8.72
- Type
- journal article
- Language
- en
- Open access
- closed
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