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Dibromomaleimide end functional polymers by RAFT polymerization without the need of protecting groups

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Robin, Mathew P., Jones, Mathew W., Haddleton, David M. and O'Reilly, Rachel K.. (2012) Dibromomaleimide end functional polymers by RAFT polymerization without the need of protecting groups. ACS Macro Letters, Vol.1 . pp. 222-226. ISSN 2161-1653

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Abstract

Polymers bearing the dibromomaleimide (DBM) group as a functional chain end have been synthesized by RAFT polymerization. A DBM functional chain transfer agent (CTA) was utilized to afford well-defined PtBA, PMA, and PTEGA, without the requirement of protecting group chemistry. It was found that RAFT polymerization of NIPAM and styrene with this CTA was severely retarded/inhibited which is ascribed to their relatively low propagation rate constants compared to acrylates. This observation is accounted for by a reversible trapping of propagating radicals by the DBM group in RAFT polymerizations using a monomer with low kp. However, further attempts to synthesize DBM-terminated PtBA and PMA by ATRP using an analogous initiator were unsuccessful, and broad PDI were observed. Furthermore, highly efficient postpolymerization functionalization of DBM-terminated PMA produced by RAFT, with the model compound thiophenol was also demonstrated.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Polymerization, Polymers, Protective groups (Chemistry)
Journal or Publication Title: ACS Macro Letters
Publisher: American Chemical Society
ISSN: 2161-1653
Official Date: 2012
Volume: Vol.1
Page Range: pp. 222-226
Identification Number: 10.1021/mz200164x
Status: Peer Reviewed
Publication Status: Published
Funder: Engineering and Physical Sciences Research Council (EPSRC), University of Warwick
References:

(1) Hall, D. J.; Van Den Berghe, H. M.; Dove, A. P. Polym. Int. 2011,
60, 1149.
(2) Mansfeld, U.; Pietsch, C.; Hoogenboom, R.; Becer, C. R.;
Schubert, U. S. Polym. Chem. 2010, 1, 1560.
(3) Dag, A.; Durmaz, H.; Hizal, G.; Tunca, U. J. Polym. Sci., Part A:
Polym. Chem. 2008, 46, 302.
(4) Dag, A.; Durmaz, H.; Tunca, U.; Hizal, G. J. Polym. Sci., Part A:
Polym. Chem. 2009, 47, 178.
(5) Durmaz, H.; Dag, A.; Hizal, G.; Tunca, U. J. Polym. Sci., Part A:
Polym. Chem. 2010, 48, 5083.
(6) Durmaz, H.; Dag, A.; Onen, C.; Gok, O.; Sanyal, A.; Hizal, G.;
Tunca, U. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 4842.
(7) Gacal, B.; Durmaz, H.; Tasdelen, M. A.; Hizal, G.; Tunca, U.;
Yagci, Y.; Demirel, A. L. Macromolecules 2006, 39, 5330.
(8) Gok, O.; Durmaz, H.; Ozdes, E. S.; Hizal, G.; Tunca, U.; Sanyal,
A. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 2546.
(9) Xiong, X.; Xu, Y. Polym. Bull. 2010, 65, 455.
(10) Canadell, J.; Fischer, H.; De With, G.; van Benthem, R. A. T. M.
J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 3456.
(11) Gousse, C.; Gandini, A.; Hodge, P. Macromolecules 1998, 31,
314.
(12) Syrett, J. A.; Mantovani, G.; Barton, W. R. S.; Price, D.;
Haddleton, D. M. Polym. Chem. 2010, 1, 102.
(13) Heredia, K. L.; Grover, G. N.; Tao, L.; Maynard, H. D.
Macromolecules 2009, 42, 2360.
(14) Kosif, I.; Park, E.-J.; Sanyal, R.; Sanyal, A. Macromolecules 2010,
43, 4140.
(15) Li, M.; De, P.; Li, H.; Sumerlin, B. S. Polym. Chem. 2010, 1, 854.
(16) Mantovani, G.; Lecolley, F.; Tao, L.; Haddleton, D. M.; Clerx, J.;
Cornelissen, J. J. L. M.; Velonia, K. J. Am. Chem. Soc. 2005, 127, 2966.
(17) Tao, L.; Kaddis, C. S.; Ogorzalek Loo, R. R.; Grover, G. N.; Loo,
J. A.; Maynard, H. D. Chem. Commun. 2009, 2148.
(18) Geng, J.; Mantovani, G.; Tao, L.; Nicolas, J.; Chen, G.; Wallis,
R.; Mitchell, D. A.; Johnson, B. R. G.; Evans, S. D.; Haddleton, D. M. J.
Am. Chem. Soc. 2007, 129, 15156.
(19) Gramlich, W. M.; Robertson, M. L.; Hillmyer, M. A.
Macromolecules 2010, 43, 2313.
(20) Xu, N.; Du, F.-S.; Li, Z.-C. J. Polym. Sci., Part A: Polym. Chem.
2007, 45, 1889.
(21) Pounder, R. J.; Stanford, M. J.; Brooks, P.; Richards, S. P.; Dove,
A. P. Chem. Commun. 2008, 5158.
(22) Stanford, M. J.; Pflughaupt, R. L.; Dove, A. P. Macromolecules
2010, 43, 6538.
(23) Kuroda, S.; Hagiwara, T. Polymer 2011, 52, 1869.
(24) Chen, G. Q.; Wu, Z. Q.; Wu, J. R.; Li, Z. C.; Li, F. M.
Macromolecules 2000, 33, 232.
(25) Moad, G.; Rizzardo, E.; Thang, S. H. Acc. Chem. Res. 2008, 41,
1133.
(26) Bays, E.; Tao, L.; Chang, C. W.; Maynard, H. D.
Biomacromolecules 2009, 10, 1777.
(27) Tolstyka, Z. P.; Kopping, J. T.; Maynard, H. D. Macromolecules
2007, 41, 599.
(28) Li, M.; De, P.; Gondi, S. R.; Sumerlin, B. S. J. Polym. Sci., Part A:
Polym. Chem. 2008, 46, 5093.
(29) Tedaldi, L. M.; Smith, M. E. B.; Nathani, R. I.; Baker, J. R. Chem.
Commun. 2009, 6583.
(30) Smith, M. E. B.; Schumacher, F. F.; Ryan, C. P.; Tedaldi, L. M.;
Papaioannou, D.; Waksman, G.; Caddick, S.; Baker, J. R. J. Am. Chem.
Soc. 2010, 132, 1960.
(31) Schumacher, F. F.; Nobles, M.; Ryan, C. P.; Smith, M. E. B.;
Tinker, A.; Caddick, S.; Baker, J. R. Bioconjugate Chem. 2011, 22, 132.
(32) Petzetakis, N.; Dove, A. P.; O’Reilly, R. K. Chem. Sci. 2011, 2,
955.
(33) Joyce, R. P.; Gainor, J. A.; Weinreb, S. M. J. Org. Chem. 1987,
52, 1177.
(34) Ladavière, C.; Lacroix-Desmazes, P.; Delolme, F. Macromolecules
2009, 42, 70.
(35) Strube, O. I.; Nothdurft, L.; Drache, M.; Schmidt-Naake, G.
Macromol. Chem. Phys. 2011, 212, 574.
(36) Jones, M. W.; Strickland, R. A.; Schumacher, F. F.; Caddick, S.;
Baker, J. R.; Gibson, M. I.; Haddleton, D. M. J. Am. Chem. Soc. 2012,
DOI: 10.1021/ja210335f.
(37) Clark, S. C.; Hill, D. J. T.; Hoyle, C. E.; Jonsson, S.; Miller, C.
W.; Shao, L. Y. Polym. Int. 2003, 52, 1701.
(38) Shinoda, H.; Matyjaszewski, K. Macromolecules 2001, 34, 6243.
(39) Roos, S. G.; Müller, A. H. E.; Matyjaszewski, K. Macromolecules
1999, 32, 8331.
(40) Lad, J.; Harrisson, S.; Haddleton, D. M. Advances in Controlled/
Living Radical Polymerization; American Chemical Society: Washington,
DC, 2003; Vol. 854, p 148.
(41) Moad, G.; Rizzardo, E.; Thang, S. H. Polymer 2008, 49, 1079.
URI: http://wrap.warwick.ac.uk/id/eprint/40488

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