Embedding multiple site-specific functionalities into polymer chains via nitrone-mediated radical coupling reactions

Wong, E. H. H., Stenzel, M. H., Junkers, T., & Barner-Kowollik, C. (2011) Embedding multiple site-specific functionalities into polymer chains via nitrone-mediated radical coupling reactions. Journal of Polymer Science, Part A: Polymer Chemistry, 49(10).

View at publisher


A facile method to generate polymer materials with embedded functional groups at known and precise positions along the polymer backbone is described. In the presented approach, well-defined bifunctional poly(isobornyl acrylate)s preformed via atom transfer radical polymerization (ATRP) containing α,ω-bromo end groups are reactivated and subsequently coupled in a stepwise manner via the nitrone-mediated radical coupling (NMRC) technique. The generated polymers contain on average four nitrone moieties at evenly spaced locations. The number of embedded functionalities, and thus, the size of the polymer is limited by disproportionation reactions occurring during the nitroxide termination sequence. Using the nitrone as a functional carrier, secondary functionalities can be incorporated into the polymer with ease. To exemplify such an approach, an alkyne-functionalized nitrone is used to construct a multisegment structure via NMRC reactions followed by postmodification of the obtained polymers with 3-mercaptopropionic acid via UV-induced thiol-yne reactions. © 2011 Wiley Periodicals, Inc.

Impact and interest:

25 citations in Scopus
Search Google Scholar™
24 citations in Web of Science®

Citation counts are sourced monthly from Scopus and Web of Science® citation databases.

These databases contain citations from different subsets of available publications and different time periods and thus the citation count from each is usually different. Some works are not in either database and no count is displayed. Scopus includes citations from articles published in 1996 onwards, and Web of Science® generally from 1980 onwards.

Citations counts from the Google Scholar™ indexing service can be viewed at the linked Google Scholar™ search.

ID Code: 99287
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :25 Export Date: 5 September 2016 CODEN: JPACE Correspondence Address: Junkers, T.; Institute for Materials Research, Universiteit Hasselt, Polymer Reaction Design Group, Agoralaan, Gebouw D, B-3590 Diepenbeek, Belgium; email: thomas.junkers@uhasselt.be References: Matyjaszewski, K., Xia, J., (2001) Chem Rev, 101, pp. 2921-2990; Kamigaito, M., Ando, T., Sawamoto, M., (2001) Chem Rev, 101, pp. 3689-3746; Moad, G., Rizzardo, E., Thang, S.H., (2009) Aust J Chem, 62, pp. 1402-1472; Barner, L., Davis, T.P., Stenzel, M.H., Barner-Kowollik, C., (2007) Macromol Rapid Commun, 28, pp. 539-559; Hawker, C.J., Bosman, A.W., Harth, E., (2001) Chem Rev, 101, pp. 3661-3688; Versace, D.-L., Lalevee, J., Fouassier, J.-P., Gigmes, D., Guillaneuf, Y., Bertin, D., (2010) J Polym Sci Part A: Polym Chem, 48, pp. 2910-2915; Edeleva, M.V., Kirilyuk, I.A., Zubenko, D.P., Zhurko, I.F., Marque, S.R.A., Gigmes, D., Guillaneuf, Y., Bagryanskaya, E.G., (2009) J Polym Sci Part A: Polym Chem, 47, pp. 6579-6595; Sciannamea, V., Catala, J.-M., Jerome, R., Jerome, C., Detrembleur, C., (2009) J Polym Sci Part A: Polym Chem, 47, pp. 1085-1097; Coca, S., Jasieczek, C.B., Beers, K.L., Matyjaszewski, K., (1998) J Polym Sci Part A: Polym Chem, 36, pp. 1417-1424; Tsarevsky, N.V., Bencherif, S.A., Matyjaszewski, K., (2007) Macromolecules, 40, pp. 4439-4445; Becer, C.R., Babiuch, K., Pilz, D., Hornig, S., Henize, T., Gottschaldt, M., Schubert, U.S., (2009) Macromolecules, 42, pp. 2387-2394; Jochum, F.D., Forst, F.R., Theato, P., (2010) Macromol Rapid Commun, 31, pp. 1456-1461; Ting, S.R.S., Chen, G., Stenzel, M.H., (2010) Polym Chem, 1, pp. 1392-1412; Vinson, N., Gou, Y., Becer, C.R., Haddleton, D.M., Gibson, M.I., (2011) Polym Chem, 2, pp. 107-113; Pfeifer, S., Lutz, J.-F., (2008) Chem Eur J, 14, pp. 10949-10957; Coessens, V., Pintauer, T., Matyjaszewski, K., (2001) Prog Polym Sci, 26, pp. 337-377; Sinnwell, S., Inglis, A.J., Davis, T.P., Stenzel, M.H., Barner-Kowollik, C., (2008) Chem Commun, pp. 2052-2054; Mansfeld, U., Pietsch, C., Hoogenboom, R., Becer, C.R., Schubert, U.S., (2010) Polym Chem, 1, pp. 1560-1598; Quemener, D., Davis, T.P., Barner-Kowollik, C., Stenzel, M.H., (2006) Chem Commun, pp. 5051-5053; Dao, J., Benoit, D., Hawker, C.J., (1998) J Polym Sci Part A: Polym Chem, 36, pp. 2161-2167; Altintas, O., Hizal, G., Tunca, U., (2008) J Polym Sci Part A: Polym Chem, 46, pp. 1218-1228; Lutz, J.-F., (2010) Nat Chem, 2, pp. 84-85; Badi, N., Lutz, J.-F., (2009) Chem Soc Rev, 38, pp. 3383-3390; Pfeifer, S., Lutz, J.-F., (2007) J Am Chem Soc, 129, pp. 9542-9543; Wong, E.H.H., Boyer, C., Stenzel, M.H., Barner-Kowollik, C., Junkers, T., (2010) Chem Commun, 46, pp. 1959-1961; Debuigne, A., Jerome, C., Detrembleur, C., (2009) Angew Chem Int Ed, 48, pp. 1422-1424; Debuigne, A., Poli, R., De Winter, J., Laurent, P., Gerbaux, P., Dubois, P., Wathelet, J.-P., Detrembleur, C., (2010) Chem Eur J, 16, pp. 1799-1811; Fu, Q., Zhang, Z., Lin, W., Huang, J., (2009) Macromolecules, 42, pp. 4381-4383; Wong, E.H.H., Junkers, T., Barner-Kowollik, C., Polym Chem, , in press, DOI: 10.1039/C0PY00377H; Wong, E.H.H., Altintas, O., Stenzel, M.H., Barner-Kowollik, C., Junkers, T., Chem Commun, , submitted for publication; Wong, E.H.H., Stenzel, M.H., Junkers, T., Barner-Kowollik, C., (2010) Macromolecules, 43, pp. 3785-3793; Wong, E.H.H., Junkers, T., Barner-Kowollik, C., (2008) J Polym Sci Part A: Polym Chem, 46, pp. 7273-7279; Wong, E.H.H., Stenzel, M.H., Junkers, T., Barner-Kowollik, C., (2009) J Polym Sci Part A: Polym Chem, 47, pp. 1098-1107; Junkers, T., Wong, E.H.H., Stenzel, M.H., Barner-Kowollik, C., (2009) Macromolecules, 42, pp. 5027-5035; Zang, L., Wong, E.H.H., Barner-Kowollik, C., Junkers, T., (2010) Polymer, 51, pp. 3821-3825; Kolb, H.C., Finn, M.G., Sharpless, K.B., (2001) Angew Chem Int Ed, 40, pp. 2004-2021; Billet, L., Fournier, D., Du Prez, F., (2009) Polymer, 50, pp. 3877-3886; Barner-Kowollik, C., Inglis, A.J., (2009) Macromol Chem Phys, 210, pp. 987-992; Binder, W.H., Sachsenhofer, R., (2008) Macromol Rapid Commun, 29, pp. 952-981; Hoogenboom, R., (2010) Angew Chem Int Ed, 49, pp. 3415-3417; Konkolewicz, D., Poon, C.K., Gray-Weale, A., Perrier, S., (2010) Chem Commun, 47, pp. 239-241; Sarbu, T., Lin, K.-Y., Ell, J., Siegwart, D.J., Spanswick, J., Matyjaszewski, K., (2004) Macromolecules, 37, pp. 3120-3127; Zhang, C., Wang, Q., (2011) J Polym Sci Part A: Polym Chem, 49, pp. 612-618; Kulis, J., Bell, C.A., Micallef, A.S., Monteiro, M.J., (2010) Aust J Chem, 63, pp. 1227-1236; Nicolay, R., Marx, L., Hemery, P., Matyjaszewski, K., (2007) Macromolecules, 40, pp. 9217-9223; Janzen, E.G., Poyer, J.L., Schaefer, C.F., Downs, P.E., Dubose, C.M., (1995) J Biochem Biophys Methods, 30, pp. 239-247; Tsarevsky, N.V., Braunecker, W.A., Matyjaszewski, K., (2007) J Organomet Chem, 692, pp. 3212-3222; Gruendling, T., Junkers, T., Guilhaus, M., Barner-Kowollik, C., (2010) Macromol Chem Phys, 211, pp. 520-528
Keywords: ATRP, functionalization of polymers, nitrones, radical coupling reactions, radical spin traps, step-growth polymerization, thiol-yne, Acetylene, Free radical reactions, Functional groups, Functional polymers, Polymerization, Polymers, Atom transfer radical polymerization
DOI: 10.1002/pola.24639
ISSN: 0887624X
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 05 Oct 2016 02:06

Export: EndNote | Dublin Core | BibTeX

Repository Staff Only: item control page