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Thiourea-Based Bifunctional Organocatalysis: Supramolecular Recognition for Living Polymerization
Abstract
A versatile, metal-free, organocatalytic approach to the living ring-opening polymerization of lactide using a bifunctional thiourea-tertiary amine catalyst is described. Mild and highly selective polymerization conditions produced poly(lactides) with predictable molecular weights and extremely narrow polydispersities ( approximately 1.05), characteristic of a living polymerization. The extraordinary selectivity of this catalyst system for polymerization relative to transesterification is remarkably unusual. The low polydispersities and exceptional control observed are a consequence of selective transesterification of lactide relative to the open chain esters. Presumably, the ring strain of lactide provides both a driving force for the polymerization and a kinetic preference for polymerization relative to transesterification with catalyst. We postulate that the initiating/propagating alcohol is activated by acid-base interaction with the tertiary amine moiety and the carbonyl of the lactide monomer is simultaneously activated by hydrogen bonding to the thiourea moiety of the catalyst.
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Cites
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Metadata
- Authors
- Dove, A. P., Pratt, R. C., Lohmeijer, B. G. G., Waymouth, R. M., & Hedrick, J. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-09-21
- Volume
- 127
- Issue
- 40
- Pages
- 13798-13799
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2004986011
- Cited by
- 438
- References
- 1
- FWCI
- 7.18
- Type
- journal article
- Language
- en
- Open access
- closed
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