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Cited by 472

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

Connor, Eric F., Nyce, Gregory W., Myers, Matthew, Möck, Andreas, Hedrick, James L.·2002·Journal of the American Chemical Society
DOI 10.1021/ja0173324
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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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Research works printed but not linked: 16

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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
DOI
10.1021/ja0173324
OpenAlex
W2066146098
Cited by
472
References
1
FWCI
8.72
Type
journal article
Language
en
Open access
closed

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