The DOI matches its Crossref record; 12 of the 12 references it cites were found in a registry or an index.
Thiocarbonylthio Compounds (SC(Z)S−R) in Free Radical Polymerization with Reversible Addition-Fragmentation Chain Transfer (RAFT Polymerization). Effect of the Activating Group Z
Abstract
Free-radical polymerization in the presence of suitable addition−fragmentation chain transfer agents [S C(Z)S−R] (RAFT agents) possess the characteristics of a living polymerization (i.e., polymer products can be reactivated for chain extension and/or block synthesis, molecular weights are predetermined by RAFT agent concentration and conversion, narrow polydispersities are possible). Styrene polymerizations (110 °C, thermal initiation) were performed for two series of RAFT agents [S C(Z)S−CH 2 Ph and S C(Z)S−C(Me) 2 CN]. The chain transfer coefficients decrease in the series where Z is Ph > SCH 2 Ph ∼ SMe ∼ Me ∼ N -pyrrolo ≫ OC 6 F 5 > N -lactam > OC 6 H 5 > O(alkyl) ≫ N(alkyl) 2 (only the first five in this series provide narrow polydispersity polystyrene (< 1.2) in batch polymerization). More generally, chain transfer coefficients decrease in the series dithiobenzoates > trithiocarbonates ∼ dithioalkanoates > dithiocarbonates (xanthates) > dithiocarbamates. However, electron-withdrawing substituents on Z can enhance the activity of RAFT agents to modify the above order. Thus, substituents that render the oxygen or nitrogen lone pair less available for delocalization with the C S can substantially enhance the effectiveness of xanthates or dithiocarbamates, respectively. The trend in relative effectiveness of the RAFT agents is rationalized in terms of interaction of Z with the C S double bond to activate or deactivate that group toward free radical addition. Molecular orbital calculations and the estimated LUMO energies of the RAFT agents can be used in a qualitative manner to predict the effect of the Z substituent on the activity of RAFT agents.
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Chiefari, J., Chong, Y. K. (., Ercole, F., Krstina, J., Jeffery, J., Le, T. P. T., Mayadunne, R. T. A., Meijs, G. F., Moad, C. L., Moad, G., et al. (1998) · Macromolecules · doi:10.1021/ma9804951 · Cited by 5,147
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Self-citationChong, ). Y. K., Krstina, J., Le, T. P. T., Moad, G., Postma, A., Rizzardo, E., & Thang, S. H. (2003) · Macromolecules · doi:10.1021/ma020882h · Cited by 793
Self-citationA novel synthesis of functional dithioesters, dithiocarbamates, xanthates and trithiocarbonates
Thang, S. H., Chong, (. K., Mayadunne, R. T. A., Moad, G., & Rizzardo, E. (1999) · Tetrahedron Letters · doi:10.1016/s0040-4039(99)00177-x · Cited by 459
Self-citationMayo, F. R. (1968) · Journal of the American Chemical Society · doi:10.1021/ja01007a032 · Cited by 365
Alkoxyamine-Initiated Living Radical Polymerization: Factors Affecting Alkoxyamine Homolysis Rates
Moad, G., & Rizzardo, E. (1995) · Macromolecules · doi:10.1021/ma00130a003 · Cited by 349
Self-citationGoto, A., Sato, K., Tsujii, Y., Fukuda, T., Moad, G., Rizzardo, E., & Thang, S. H. (2001) · Macromolecules · doi:10.1021/ma0009451 · Cited by 328
Self-citationBarner-Kowollik, C., Quinn, J. F., Nguyen, T. L. U., Heuts, J. P. A., & Davis, T. P. (2001) · Macromolecules · doi:10.1021/ma010349m · Cited by 318
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Self-citationControlled Radical Polymerization of Acrylic Acid in Protic Media
Ladavière, C., Dörr, N., & Claverie, J. P. (2001) · Macromolecules · doi:10.1021/ma010358v · Cited by 202
Otsu, T., Matsunaga, T., Doi, T., & Matsumoto, A. (1995) · European Polymer Journal · doi:10.1016/0014-3057(94)00122-7 · Cited by 143
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Cited by
Controlled/living radical polymerization: Features, developments, and perspectives
Braunecker, W. A., & Matyjaszewski, K. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.11.002 · Cited by 3,202
Radical addition–fragmentation chemistry in polymer synthesis
Moad, G., Rizzardo, E., & Thang, S. H. (2008) · Polymer · doi:10.1016/j.polymer.2007.11.020 · Cited by 1,397
Self-citationKinetics of living radical polymerization
Goto, A., & Fukuda, T. (2004) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2004.01.002 · Cited by 914
Gregory, A., & Stenzel, M. H. (2012) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2011.08.004 · Cited by 470
Universal (switchable) RAFT agents
Benaglia, M., Chiefari, J., Chong, Y. K., Moad, G., Rizzardo, E., & Thang, S. H. (2009) · Journal of the American Chemical Society · doi:10.1021/ja901955n · Cited by 302
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Metadata
- Authors
- Chiefari, J., Mayadunne, R. T. A., Moad, C. L., Moad, G., Rizzardo, E., Postma, A., Melissa A. Skidmore, A., & Thang, S. H.
- Venue
- Macromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-03-15
- Volume
- 36
- Issue
- 7
- Pages
- 2273-2283
- ISSN
- 0024-9297 (ISSN-L)
- 1520-5835
- OpenAlex
- W1998811418
- Cited by
- 608
- References
- 12
- FWCI
- 35.92
- Type
- journal article
- Language
- en
- Open access
- closed
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