Ievins, Alexander D., Wang, Xiaofan, Moughton, Adam O., Skey, Jared and O’Reilly, Rachel K.. (2008) Synthesis of core functionalized polymer micelles and shell cross-linked nanoparticles. Macromolecules, Vol.41 (No.9). pp. 2998-3006. ISSN 0024-9297

Full text not available from this repository.

Abstract

We present the synthesis of novel core reactive spherical polymeric micelles and nanoparticles using nitroxide mediated polymerization (NMP) techniques. These nanostructures have terpyridine functionality selectively located within their hydrophobic core domain and have been further modified by metal complexation (with Fe, Ru, and Cu) within this domain to afford novel metal functionalized polymer nanostructures. The hydrodynamic diameters (Dh) of these micelles and hybrid nanoparticles were determined by dynamic light scattering (DLS), and the dimensions of the nanoparticles were characterized using transmission electron microscopy (TEM) and confirmation of the complexation was achieved using UV–vis analysis. The reactivity of the Cu-tethered metal complex within the nanostructures was investigated and was found to be an active catalyst for the 1,3-dipolar cycloaddition “click” reaction of azido and alkynyl functionalized small molecules. This strategy provides a versatile synthetic route toward the selective incorporation of active sites within the core domain of a polymer nanoparticle.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Micelles, Diblock copolymers, Nanoparticles, Polymerization, Crosslinking (Polymerization)
Journal or Publication Title:	Macromolecules
Publisher:	American Chemical Society
ISSN:	0024-9297
Date:	2008
Volume:	Vol.41
Number:	No.9
Page Range:	pp. 2998-3006
Identification Number:	10.1021/ma702702j
Status:	Peer Reviewed
Publication Status:	Published
Funder:	Royal Society (Great Britain), Engineering and Physical Sciences Research Council (EPSRC), Interdisciplinary Research Collaboration in Nanotechnology, Downing College (University of Cambridge), Nuffield Foundation
References:	(1) Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. ReV. 2001, 101, 3661– 3688. (2) Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. ReV. 2001, 101, 3689– 3745. (3) Matyjaszewski, K.; Xia, J. H. Chem. ReV. 2001, 101, 2921–2990. (4) Perrier, S.; Takolpuckdee, P. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 5347–5393. (5) 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. (6) Mayadunne, R. T. A.; Rizzardo, E.; Chiefari, J.; Chong, Y. K.; Moad, G.; Thang, S. H. Macromolecules 1999, 32, 6977–6980. (7) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987–2988. (8) Isrealachvilli, J. N.; Mitchell, D. J.; Ninham, B. W. J. Chem. Soc., Faraday Trans. 1976, 72, 1525–1569. (9) Klok, H. A.; Lecommandoux, S. AdV. Mater. 2001, 13, 1217–1229. (10) Lowik, D. W. P. M.; van Hest, J. C. M. Chem. Soc. ReV. 2004, 33, 234–245. (11) Cao, L.; Manners, I.; Winnik, M. A. Macromolecules 2001, 34, 3353– 3360. (12) Sanji, T.; Nakatsuka, Y.; Kitayama, F.; Sakurai, H. Chem. Commun. 1999, 2201–2202. (13) Huang, H. Y.; Remsen, E. E.; Wooley, K. L. Chem. Commun. 1998, 1415–1416. (14) Butun, V.; Billingham, N. C.; Armes, S. P. J. Am. Chem. Soc. 1998, 120, 12135–12136. (15) Thurmond, K. B.; Kowalewski, T.; Wooley, K. L. J. Am. Chem. Soc. 1997, 119, 6656–6665. (16) Ding, J. F.; Liu, G. J. Macromolecules 1998, 31, 6554–6558. (17) Chen, Z.; Cui, H.; Hales, K.; Li, Z.; Qi, K.; Pochan, D. J.; Wooley, K. L. J. Am. Chem. Soc. 2005, 127, 8592–8593. (18) Hamley, I. W.; Ansari, I. A.; Castelletto, V.; Nuhn, H.; Roesler, A.; Klok, H.-A. Biomacromolecules 2005, 6, 1310–1315. (19) Cornelissen, J. J. L. M.; Fischer, M.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. Science 1998, 280, 1427–1430. (20) Minich, E. A. Polymer 2004, 45, 1951–1957. (21) Hanley, K. J.; Lodge, T. P.; Huang, C. I. Macromolecules 2000, 33, 5918–5931. (22) Li, Z.; Chen, Z.; Cui, H.; Hales, K.; Wooley, K. L.; Pochan, D. J. Langmuir 2007, 23, 4689–4694. (23) Hou, S.; Man, K. Y. K.; Chan, W. K. Langmuir 2003, 19, 2485– 2490. (24) Guler, M. O.; Pokorski, J. K.; Appella, D. H.; Stupp, S. I. Bioconjugate Chem. 2005, 16, 501–503. (25) Liu, D.; De Feyter, S.; Cotlet, M.; Wiesler, U.-M.; Weil, T.; Herrmann, A.; Muellen, K.; De Schryver, F. C. Macromolecules 2003, 36, 8489– 8498. (26) Zhang, L. F.; Eisenberg, A. Science 1995, 268, 1728–1731. (27) Choucair, A.; Lavigueur, C.; Eisenberg, A. Langmuir 2004, 20, 3894– 3900. (28) Terreau, O.; Luo, L. B.; Eisenberg, A. Langmuir 2003, 19, 5601– 5607. (29) Reiss, G. Prog. Polym. Sci. 2003, 28, 1107–1170. (30) Raez, S.; Manners, I.; Winnik, M. A. J. Am. Chem. Soc. 2002, 124, 10381–10395. (31) Wooley, K. L. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1397– 1407. (32) Vriezema, D. M.; Aragones, M. C.; Elemans, J. A. A. W.; Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M. Chem. ReV. 2005, 105, 1445–1489. (33) Rosler, A.; Vandermeulen, G. W. M.; Klok, H. A. AdV. Drug DeliVery ReV. 2001, 53, 95–108. (34) Torchilin, V. P. Cell. Mol. Life Sci. 2004, 61, 2549–2559. (35) Pressly, E. D.; Rossin, R.; Hagooly, A.; Fukukawa, K.; Messmore, B. W.; Welch, M. J.; Wooley, K. L.; Lamm, M. S.; Hule, R. A.; Pochan, D. J.; Hawker, C. J. Biomacromolecules 2007, 8, 3126–3134. (36) Read, E. S.; Armes, S. P. Chem. Commun. 2007, 3021–3035. (37) O’Reilly, R. K.; Hawker, C. J.; Wooley, K. L. Chem. Soc. ReV. 2006, 35, 1068–1083. (38) Hawker, C. J.; Wooley, K. L. Science 2005, 309, 1200–1205. (39) Elemans, J. A. A. W.; Rowan, A. E.; Nolte, R. J. M. J. Mater. Chem. 2003, 13, 2661–2670. (40) Prochaska, K.; Baloch, M. K. Makromol. Chem. 1979, 180, 2521– 2523. (41) Guo, A.; Liu, G. J.; Tao, J. Macromolecules 1996, 29, 2487–2493. (42) Henselwood, F.; Liu, G. J. Macromolecules 1997, 30, 488–493. (43) Sumerlin, B. S.; Lowe, A. B.; Thomas, D. B.; Convertine, A. J.; Donovan, M. S.; McCormick, C. L. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 1724–1734. (44) Huang, H. Y.; Kowalewski, T.; Remsen, E. E.; Gertzmann, R.;Wooley, K. L. J. Am. Chem. Soc. 1997, 119, 11653–11659. (45) Thurmond, K. B.; Kowalewski, T.; Wooley, K. L. J. Am. Chem. Soc. 1996, 118, 7239–7240. (46) Liu, S.; Armes, S. P. J. Am. Chem. Soc. 2001, 123, 9910–9911. (47) Iijima, M.; Nagasaki, Y.; Okada, T.; Kato, M.; Kataoka, K. Macromolecules 1999, 32, 1140–1146. (48) Zhang, L.; Katapodi, K.; Davies, T. P.; Barner-Kowollik, C.; Stenzel, M. H. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 2177–2194. (49) Joralemon, M. J.; O’Reilly, R. K.; Hawker, C. J.; Wooley, K. L. J. Am. Chem. Soc. 2005, 127, 16892–16899. (50) Ma, Q.; Remsen, E. E.; Kowalewski, T.; Schaefer, J.; Wooley, K. L. Nano Lett. 2001, 1, 651–655. (51) Murthy, K. S.; Ma, Q.; Clark, C. G., Jr.; Remsen, E. E.; Wooley, K. L. Chem. Commun. 2001, 773–774. (52) O’Reilly, R. K.; Joralemon, M. J.; Hawker, C. J.; Wooley, K. L. Eur. J. Chem. 2006, 12, 6776–6786. (53) Butun, V.; Wang, X. S.; Banez, M. V. D.; Robinson, K. L.; Billingham, N. C.; Armes, S. P.; Tuzar, Z. Macromolecules 2000, 33, 1–3. (54) O’Reilly, R. K. Philos. Trans. R. Soc. London, A 2007, 365, 2863– 2878. (55) Dwars, T.; Paetzold, E.; Oehme, G. Angew. Chem., Int. Ed. 2005, 44, 7174–7199. (56) Kobayashi, S.; Akiyama, R. Chem. Commun. 2003, 449–460. (57) Mason, B. P.; Bogdan, A. R.; Goswami, A.; McQuade, D. T. Org. Lett. 2007, 9, 3449–3451. (58) Schubert, U. S.; Eschbaumer, C.; Hien, O.; Andres, P. R. Tetrahedron Lett. 2001, 42, 4705–4707. (59) Hofmeier, H.; Schubert, U. S. Chem. Soc. ReV. 2004, 33, 373–399. (60) Lohmeijer, B. G. G.; Schubert, U. S. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 4016–4027. (61) Schubert, U. S.; Hofmeier, H. Macromol. Chem. Phys. 2002, 203, 561–566. (62) Chiper, M.; Meier, M. A. R.; Kranenburg, J. M.; Schubert, U. S. Macromol. Chem. Phys. 2007, 208, 679–689. (63) Lohmeijer, B. G. G.; Schubert, U. S. Macromol. Chem. Phys. 2003, 204, 1072–1078. (64) Lohmeijer, B. G. G.; Schlaad, H.; Schubert, U. S. Macromol. Symp. 2003, 196, 125–135. (65) Lohmeijer, B. G. G.; Schubert, U. S. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1413–1427. (66) Gohy, J. F.; Hofmeier, H.; Alexeev, A.; Schubert, U. S. Macromol. Chem. Phys. 2003, 204, 1524–1530. (67) Andres, P. R.; Schubert, U. S. AdV. Mater. 2004, 16, 1043–1068. (68) Calzia, K. J.; Tew, G. N. Macromolecules 2002, 35, 6090–6093. (69) Tew, G. N.; Aamer, A. K.; Shunmuugam, R. Polymer 2005, 46, 8440– 8447. (70) Shunmuugam, R.; Tew, G. J. Am. Chem. Soc. 2005, 127, 13567– 13572. (71) Aamer, A. K.; Tew, G. N. Macromolecules 2007, 40, 2737–2744. (72) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596–2599. (73) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004–2021. (74) Binder, W. H.; Sachsenhofer, R. Macromol. Chem. Phys. 2007, 208, 15–54. (75) Benoit, D.; Chaplinski, V.; Braslau, R.; Hawker, C. J. J. Am. Chem. Soc. 1999, 121, 3904–3920. (76) Schubert, U. S.; Schmatloch, S.; Precup, A. A. Des. Monomers Polym. 2002, 5, 211–221. (77) Gujadhur, R.;Venkataraman, D.;Kintigh, J. T. Tetrahedron Lett. 2001, 42, 4971–4973. (78) Sivakumar, K.; Xie, F.; Cash, B. M.; Long, S.; Barnhill, H. N.; Wang, Q. Org. Lett. 2004, 6, 4603–4606. (79) Andres, P. R.; Hofmeier, H.; Lohmeijer, B. G. G.; Schubert, U. S. Synthesis 2003, 18, 2865–2871. (80) Ma, Q.; Wooley, K. L. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 4805–4820. (81) O’Reilly, R. K.; Joralemon, M. J.; Hawker, C. J.; Wooley, K. L. Chem. Mater. 2005, 17, 5976–5988. (82) Deleted in proof. (83) Hofmeier, H.; Schubert, U. S. Macromol. Chem. Phys. 2003, 204, 1391–1397. (84) Yoo, D.-W.; Yoo, S.-K.; Kim, C.; Lee, J.-K. Chem. Commun. 2002, 3931–3932. (85) Golas, P. L.; Tsarevsky, N. V.; Sumerlin, B. S.; Matyjaszewski, K. Macromolecules 2006, 39, 6451–6457.
URI:	http://wrap.warwick.ac.uk/id/eprint/40575

Request changes to a record

Actions (login required)

View Item