Evans, Amanda C., Skey, Jared, Wright, Megan, Qu, Wenjun, Ondeck, Courtney, Longbottom, Deborah A. and O'Reilly, Rachel K. (2009) Functional and tuneable amino acid polymers prepared by RAFT polymerization. Journal of Polymer Science Part A -Polymer Chemistry, Vol.47 (No.24). pp. 6814-6826. ISSN 0887-624X

Full text not available from this repository.

Abstract

We report the application of reversible addition-fragmentation chain transfer polymerization using a novel chain transfer agent toward the synthesis of a variety of copolymers containing proline-derived monomeric units. This methodology enables ready access to a number of polymeric species with narrow molecular weight distributions, reliable functional unit incorporations, and high conversions. The methodology is also a facile approach to novel copolymeric species incorporating amino, acids, which possess unique material properties and the potential for further organocatalytic application. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47:6814-6826, 2009

Item Type:	Journal Item
Subjects:	Q Science > QD Chemistry T Technology > TP Chemical technology
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Copolymers, Polystyrene, Catalysis, Polymerization
Journal or Publication Title:	Journal of Polymer Science Part A -Polymer Chemistry
Publisher:	John Wiley & Sons Ltd.
ISSN:	0887-624X
Date:	15 December 2009
Volume:	Vol.47
Number:	No.24
Number of Pages:	13
Page Range:	pp. 6814-6826
Identification Number:	10.1002/pola.23721
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Funder:	Royal Society (Great Britain), Engineering and Physical Sciences Research Council (EPSRC), Downing College (University of Cambridge), Murray Edwards College (University of Cambridge), Churchill College (University of Cambridge), Homerton College (University of Cambridge), University of Cambridge, European Regional Development Fund (ERDF), Advantage West Midlands (AWM)
References:	1. Halab, L.; Lubell, W. D. J Am Chem Soc 2002, 124, 2474–2484. 2. Jeannotte, G.; Lubell, W. D. J Am Chem Soc 2004, 126, 14334–14335. 3. McColl, I. H.; Blanch, E. W.; Hecht, L.; Barron, L. D. J Am Chem Soc 2004, 126, 8181–8188. 4. Kakinoki, S.; Hirano, Y.; Oka, M. Polym Bull 2005, 53, 109–115. 5. Holmgren, S. K.; Taylor, K. M.; Bretscher, L. E.; Raines, R. T. Nature 1998, 392, 666–667. 6. Jenkins, C. L.; Bretscher, L. E.; Guzei, I. A.; Raines, R. T. J Am Chem Soc 2003, 125, 6422– 6427. 7. Bretscher, L. E.; Jenkins, C. L.; Taylor, K. M.; DeRider, M. L.; Raines, R. T. J Am Chem Soc 2001, 123, 777–778. 8. Lim, Y. B.; Choi, Y. H.; Park, J. S. J Am Chem Soc 1999, 121, 5633–5639. 9. Lee, R. S.; Yang, J. M.; Huang, K. H. Polym J 1999, 31, 569–573. 10. Vakiparta, M.; Forsback, A. P.; Lassila, L. V.; Jokinen, M.; Yli-Urpo, A. U. O.; Vallittu, P. K. J Mater Sci: Mater Med 2005, 16, 873–879. 11. Puska, M. A.; Kokkari, A. K.; Narhi, T. O.; Vallittu, P. K. Biomaterials 2003, 24, 417–425. 12. Bentolila, A.; Vlodavsky, I.; Ishai-Michaeli, R.; Kovalchuk, O.; Haloun, C.; Domb, A. J. J Med Chem 2000, 43, 2591–2600. 13. Farrera-Sinfreu, J.; Zaccaro, L.; Vidal, D.; Salvatella, X.; Giralt, E.; Pons, M.; Albericio, F.; Royo, M. J Am Chem Soc 2004, 126, 6048–6057. 14. Hanessian, S.; Papeo, G.; Fettis, K.; Therrien, E.; Viet, M. T. P. J Org Chem 2004, 69, 4891– 4899. 15. Sanda, F.; Kamatani, J.; Handa, H.; Endo, T. Macromolecules 1999, 32, 2490–2494. 16. Serron, S. A.; Aldridge, W. S.; Fleming, C. N.; Danell, R. M.; Baik, M. H.; Sykora, M.; Dattelbaum, D. M.; Meyer, T. J. J Am Chem Soc 2004, 126, 14506–14514. 17. Tonelli, R. R.; Silber, A. M.; Almeida-de-Faria, M.; Hirata, I. Y.; Colli, W.; Alves, M. J. M. Cell Microbiol 2004, 6, 733–741. 18. Li, M.; De, P.; Gondi, S. R.; Sumerlin, B. S. J Polym Sci Part A: Polym Chem 2008, 46, 5093–5100. 19. Boschmann, D.; Manz, M.; Poppler, A. C.; Sorensen, N.; Vana, P. J Polym Sci Part A: Polym Chem 2008, 46, 7280. 20. 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.; Rizzardo, E.; Thang, S. H. Macromolecules 1998, 31, 5559–5562. 21. Barner-Kowollik, C.; Davis, T. P.; Heuts, J. P. A.; Stenzel, M. H.; Vana, P.; Whittaker, M. J Polym Sci Part A: Polym Chem 2003, 41, 365–375. 22. Moad, G.; Rizzardo, E.; Thang, S. H. Aust J Chem 2005, 58, 379–410. 23. McCormick, C. L.; Lowe, A. B. Acc Chem Res 2004, 37, 312–325. 24. Perrier, S.; Takolpuckdee, P. J Polym Sci Part A: Polym Chem 2005, 43, 5347–5393. 25. Favier, A.; Charreyre, M. T. Macromol Rapid Commun 2006, 27, 653–692. 26. Moad, G.; Rizzardo, E.; Thang, S. H. Aust J Chem 2006, 59, 669–692. 27. Lowe, A. B.; McCormick, C. L. Prog Polym Sci 2007, 32, 283–351. 28. Barner-Kowollik, C.; Buback, M.; Charleux, B.; Coote, M. L.; Drache, M.; Fukuda, T.; Goto, A.; Klumperman, B.; Lowe, A. B.; McLeary, J. B.; Moad, G.; Monteiro, M. J.; Sanderson, R. D.; Tonge, M. P.; Vana, P. J Polym Sci Part A: Polym Chem 2006, 44, 5809–5831. 29. Coote, M. L.; Krenske, E. H.; Izgorodina, E. I. Macromol Rapid Commun 2006, 27, 473–497. 30. Barner, L.; Davis, T. P.; Stenzel, M. H.; Barner- Kowollik, C. Macromol Rapid Commun 2007, 28, 539–559. 31. Goto, A.; Fukuda, T. Prog Polym Sci 2004, 29, 329– 385. 32. Moad, G.; Rizzardo, E.; Thang, S. H. Polymer 2008, 49, 1079–1131. 33. Barner-Kowollik, C.; Perrier, S. J Polym Sci Part A: Polym Chem 2008, 46, 5715–5723. 34. Pavlovic, D.; Linhardt, J. G.; Kunzler, J. F.; Shipp, D. A. J Polym Sci Part A: Polym Chem 2008, 46, 7033–7048. 35. Chai, L. T.; Wang, Q. R.; Tao, F. G. J Mol Cat A: Chem 2007, 276, 137–142. 36. Deng, Z. C.; Bouchekif, H.; Babooram, K.; Housni, A.; Choytun, N.; Narain, R. J Polym Sci Part A: Polym Chem 2008, 46, 4984–4996. 37. Yang, J.; Sun, W. L.; Lin, W. H.; Shen, Z. Q. J Polym Sci Part A: Polym Chem 2008, 46, 5123– 5132. 38. Nghiem, Q. D.; Nguyen, C. T.; Kim, D. P. J Polym Sci Part A: Polym Chem 2008, 46, 4594– 4601. 39. Theato, P. J Polym Sci Part A: Polym Chem 2008, 46, 6677–6687. 40. Mori, H.; Iwaya, H.; Nagai, A.; Endo, T. Chem Commun 2005, 4872–4874. 41. Mori, H.; Iwaya, H.; Endo, T. React Funct Polym 2007, 67, 916–927. 42. Mori, H.; Iwaya, H.; Endo, T. Macromol Chem Phys 2007, 208, 1908–1918. 43. Mori, H.; Kato, I.; Matsuyama, M.; Endo, T. Macromolecules 2008, 41, 5604–5615. 44. Mori, H.; Matsuyama, M.; Endo, T. Macromol Chem Phys 2009, 210, 217–229. 45. Gujraty, K. V.; Yanjarappa, M. J.; Saraph, A.; Joshi, A.; Mogridge, J.; Kane, R. S. J Polym Sci Part A: Polym Chem 2008, 46, 7249–7257. 46. Takizawa, K.; Nulwala, H.; Thibault, R. J.; Lowenhielm, P.; Yoshinaga, K.; Wooley, K. L.; Hawker, C. J. J Polym Sci Part A: Polym Chem 2008, 46, 2897–2912. 47. Vestberg, R.; Piekarski, A. M.; Pressly, E. D.; van Berkel, K. Y.; Malkoch, M.; Gerbac, J.; Ueno, N.; Hawker, C. J. J Polym Sci Part A: Polym Chem 2009, 47, 1237–1258. 48. Becer, C. R.; Hahn, S.; Fijten, M. W. M.; Thijs, H. M. L.; Hoogenboom, R.; Schubert, U. S. J Polym Sci Part A: Polym Chem 2008, 46, 7138– 7147. 49. Akimoto, J.; Nakayama, M.; Sakai, K.; Okano, T. J Polym Sci Part A: Polym Chem 2008, 46, 7127–7137. 50. Kamei, Y.; Sudo, A.; Nishida, H.; Kikukawa, K.; Endo, T. J Polym Sci Part A: Polym Chem 2008, 46, 2525–2535. 51. Becker, M. L.; Liu, J. Q.; Wooley, K. L. Chem Commun 2003, 180–181. 52. ten Cate, M. G. J.; Rettig, H.; Bernhardt, K.; Borner, H. G. Macromolecules 2005, 38, 10643– 10649. 53. Lokitz, B. S.; Stempka, J. E.; York, A. W.; Li, Y. T.; Goel, H. K.; Bishop, G. R.; McCormick, C. L. Aust J Chem 2006, 59, 749–754. 54. Lokitz, B. S.; Convertine, A. J.; Ezell, R. G.; Heidenreich, A.; Li, Y. T.; McCormick, C. L. Macromolecules 2006, 39, 8594–8602. 55. Nicolas, J.; Mantovani, G.; Haddleton, D. M. Macromol Rapid Commun 2007, 28, 1083–1111. 56. Mori, H.; Sutoh, K.; Endo, T. Macromolecules 2005, 38, 9055–9065. 57. Mori, H.; Matsuyama, M.; Sutoh, K.; Endo, T. Macromolecules 2006, 39, 4351–4360. 58. Storer, R. I.; MacMillan, D. W. C. Tetrahedron 2004, 60, 7705–7714. 59. Sobhani, S.; Fielenbach, D.; Marigo, M.; Wabnitz, T. C.; Jorgensen, K. A. Chem Eur J 2005, 11, 5689–5694. 60. Marigo, M.; Wabnitz, T. C.; Fielenbach, D.; Jorgensen, K. A. Angew Chem Int Ed 2005, 44, 794–797. 61. Halland, N.; Lie, M. A.; Kjaersgaard, A.; Marigo, M.; Schiott, B.; Jorgensen, K. A. Chem Eur J 2005, 11, 7083–7090. 62. Diner, P.; Nielsen, M.; Marigo, M.; Jorgensen, K. A. Angew Chem Int Ed 2007, 46, 1983–1987. 63. Diner, P.; Kjaersgaard, A.; Lie, M. A.; Jorgensen, K. A. Chem Eur J 2008, 14, 122–127. 64. Brandau, S.; Landa, A.; Franzen, J.; Marigo, M.; Jorgensen, K. A. Angew Chem Int Ed 2006, 45, 4305–4309. 65. Alemparte, C.; Blay, G.; Jorgensen, K. A. Org Lett 2005, 7, 4569–4572. 66. Zhou, J.; List, B. Synlett 2007, 2037–2040. 67. Yang, J. W.; Fonseca, M. T. H.; List, B. J Am Chem Soc 2005, 127, 15036–15037. 68. Wang, X.; List, B. Angew Chem Int Ed 2008, 47, 1119–1122. 69. Seayad, J.; List, B. Org Bio Chem 2005, 3, 719– 724. 70. Pojarliev, P.; Biller, W. T.; Martin, H. J.; List, B. Synlett 2003, 1903–1905. 71. Pan, S. C.; Zhou, J.; List, B. Angew Chem Int Ed 2007, 46, 612–614. 72. Martin, H. J.; List, B. Synlett 2003, 1901–1902. 73. List, B. Adv Syn Cat 2004, 346, 1021. 74. Fu, A. P.; List, B.; Thiel, W. J. Org Chem 2006, 71, 320–326. 75. Fonseca, M. T. H.; List, B. Angew Chem Int Ed 2004, 43, 3958–3960. 76. Benaglia, M.; Celentano, G.; Cozzi, F. Adv Syn Cat 2001, 343, 171–173. 77. Benaglia, M.; Cinquini, M.; Cozzi, F.; Puglisi, A.; Celentano, G. Adv Syn Cat 2002, 344, 533– 542. 78. Benaglia, M.; Cinquini, M.; Cozzi, F.; Puglisi, A.; Celentano, G. J. Mol Cat A: Chem 2003, 204, 157–163. 79. Font, D.; Jimeno, C.; Pericas, M. A. Org Lett 2006, 8, 4653–4655. 80. Font, D.; Bastero, A.; Sayalero, S.; Jimeno, C.; Pericas, M. A. Org Lett 2007, 9, 1943–1946. 81. Font, D.; Sayalero, S.; Bastero, A.; Jimeno, C.; Pericas, M. A. Org Lett 2008, 10, 337–340. 82. Giacalone, F.; Gruttadauria, M.; Marculescu, A. M.; Noto, R. Tetrahedron Lett 2007, 48, 255–259. 83. Gruttadauria, M.; Giacalone, F.; Marculescu, A. M.; Lo Meo, P.; Riela, S.; Noto, R. Eur J Org Chem 2007, 4688–4698. 84. Aprile, C.; Giacalone, F.; Gruttadauria, M.; Marculescu, A. M.; Noto, R.; Revell, J. D.; Wennemers, H. Green Chem 2007, 9, 1328–1334. 85. Boyer, C.; Liu, J.; Wong, L.; Tippett, M.; Bulmus, V.; Davis, T. P. J Polym Sci Part A: Polym Chem 2008, 46, 7207–7224. 86. Akagawa, K.; Sakamoto, S.; Kudo, K. Tet Lett 2005, 46, 8185–8187. 87. Revell, J. D.; Gantenbein, D.; Krattiger, P.; Wennemers, H. Biopolymers 2006, 84, 105–113. 88. Andreae, M. R. M.; Davis, A. P. Tetrahedron: Asymmetry 2005, 16, 2487–2492. 89. Miao, W. S.; Chan, T. H. Adv Syn Cat 2006, 348, 1711–1718. 90. Bellis, E.; Kokotos, G. J Mol Cat A: Chem 2005, 241, 166–174. 91. Kehat, T.; Portnoy, M. Chem Commun 2007, 2823–2825. 92. Maliakal, A.; Greenaway, H.; O’Shaughnessy, B.; Turro, N. J. Macromolecules 2003, 36, 6075– 6080. 93. Altakrity, E. T. B. E. Polym J 1995, 31, 383–385. 94. Erdogan, M.; Hepuzer, Y.; Cianga, I.; Yagci, Y.; Pekcan, O. J Phys Chem A 2003, 107, 8363– 8370. 95. Duan, Q.; Miura, Y.; Narumi, A.; Shen, X.; Sato, S.; Satoh, T.; Kakuchi, T. J Polym Sci Part A: Polym Chem 2006, 44, 1117–1124. 96. Ge, Z. S.; Luo, S. Z.; Liu, S. Y. J Polym Sci Part A: Polym Chem 2006, 44, 1357–1371. 97. Nakayama, M.; Okano, T. Biomacromolecules 2005, 6, 2320–2327. 98. Scales, C. W.; Convertine, A. J.; McCormick, C. L. Biomacromolecules 2006, 7, 1389–1392. 99. Zhou, N.; Lu, L.; Zhu, J.; Yang, X.; Wang, X.; Zhu, X.; Zhang, Z. Polymer 2007, 48, 1255–1260. 100. Wutz, P. G. M.; Greene, T. W. Protective Groups in Organic Synthesis; John Wiley & Sons, Inc.: Hoboken, NJ, 2007. 101. Sajiki, H. Tetrahedron Lett 1995, 36, 3465–3468. 102. Benishai, D.; Berger, A. J. Org Chem 1952, 17, 1564–1570. 103. Francavilla, C.; Low, E.; Nair, S.; Kim, B.; Shiau, T. P.; Debabov, D.; Celeri, C.; Alvarez, N.; Houchin, A.; Xu, P.; Najafi, R.; Jain, R. Bioorg Med Chem Lett 2009, 19, 2731–2734. 104. Szalecki, W. Bioconj Chem 1996, 7, 271–273.
URI:	http://wrap.warwick.ac.uk/id/eprint/16799

Data sourced from Thomson Reuters' Web of Knowledge

Request changes to a record

Actions (login required)

View Item