Ambient Temperature Synthesis of a Versatile Macromolecular Building Block: Cyclopentadienyl-Capped Polymers

Inglis, A. J., Paulöhrl, T., & Barner-Kowollik, C. (2010) Ambient Temperature Synthesis of a Versatile Macromolecular Building Block: Cyclopentadienyl-Capped Polymers. Macromolecules, 43(1).

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The functionalization of poly styrene (PS) prepared by atom transfer radical polymerization (ATRP) and poly ethylene glycol monomethyl ether with sodium cyclopentadienyl (NaCp) through nucleophilic substitution of the respective bromide and tosylated end-groups was reported. PS, poly methyl methacrylate (PMMA), poly methyl acrylate (PMA), and polyisobornyl acrylate (PiBoA) were prepared through low conversion ATRP ensured high bromide functionality. The tributylphosphine was dissolved in anhydrous tetrahydrofuran (THF) under a nitrogen atmosphere and the NiCp2 was also added. The mixture was then passed through a short column of basic alumina and precipitated in an appropriate solvent at the end of the reaction. The results of 1H NMR spectroscopic analysis revealed that Cp functionality was imparted to the polymer chain by virtue of the appearance of characteristic signals at 6.6-5.8 and 2.9 ppm. The results show that that such functionalization would bring the concept of ambient temperature and catalystfree conjugation to a broader platform.

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39 citations in Web of Science®
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ID Code: 99246
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :44
Export Date: 5 September 2016
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76128 Karlsruhe, Germany; email:
References: Matyjaszewski, K., Xia, J.H., (2001) Chem. Rev, 101, pp. 2921-2990; Perrier, S., Takolpuckdee, P., (2005) J. Polym. Sci., Part A: Polym. Chem, 43, pp. 5347-5393; Der vaux, B., Van Camp, W., Van Renterghem, L., Du Prez, F.E., (2008) J. Polym. Sci., Part A: Polym. Chem, 46, pp. 1649-1661; Zhu, J., Zhu, X., Zhou, D., Chen, J., Wang, X., (2004) Eur. Polym. J, 40, pp. 743-749; Binder, W.H., Sachsenhofer, R., (2008) Macromol. Rapid Commun, 29, pp. 952-981; Coessens, V., Matyjaszewski, K., (1999) J. Macromol. Sci., Part A: Pure Appl. Chem, A36, pp. 661-619; Quemener, D., Davis, T.P., Barner-Kowollik, C., Stenzel, M.H., (2006) Chem. Commun, pp. 5051-5053; Campos, L.M., Killops, K.L., Sakai, R., Paulusse, J.M.J., Damiron, D., Drockenmuller, E., Messmore, B.W., Hawker, C.J., (2008) Macromolecules, 41, pp. 7063-7070; Li, M., De, P., Gondi, S.R., Sumerlin, B.S., (2008) J. Polym. Sci., Part A: Polym. Chem, 46, pp. 5093-5100; Gruendling, T., Dietrich, M., Barner-Kowollik, C., (2008) Aust. J. Chem, 62, pp. 806-812; Coessens, V., Matyjaszewski, K., (1999) Macromol. Rapid Commun, 20, pp. 127-134; Matyjaszewski, K., Nakagawa, Y., Gaynor, S.G., (1997) Macromol. Rapid Commun, 18, pp. 1057-1066; Lai, J.T., Filia, D., Shea, R., (2002) Macromolecules, 35, pp. 6754-6756; Inglis, A.J., Sinnwell, S., Stenzel, M.H., Barner-Kowollik, C., (2009) Angew. Chem., Int. Ed, 48, pp. 2411-2414; Inglis, A.J., Stenzel, M.H., Barner-Kowollik, C., (2009) Macromol. Rapid Commun, 30, pp. 1792-1798; Coolbaugh, T.S., Coots, R.J., Santarsiero, B.D., Grubbs, R.H., (1985) Inorg. Chim. Acta, 98, pp. 99-105; Ben Romdhane, H., Chaabouni, M.R., Grenier-Loustalot, M.F., Delolme, F., Mison, P., Sillion, B., (2000) Polymer, 41, pp. 3183-3191; Christie, S.D.R., Man, K.W., Whitby, R.J., Slawin, A.M.Z., (1999) Organometallics, 18, pp. 348-359; Liu, L., Zhang, W.-X., Wang, C., Wang, C., Xi, Z., (2009) Angew. Chem., Int. Ed, , DOI: 10.1002/anie.200904298; Sai, M., Sorneya, H., Yorimitsu, H., Oshima, K., (2008) Org. Lett, 10, pp. 2545-2547; Ge, Z.X., Duchamp, J.C., Cai, T., Gibson, H.W., Dorn, H.C., (2005) J. Am. Chem. Soc, 127, pp. 16292-16298; Nie, B., Rotello, V., (1996) J. Phys. Chem. Solids, 58, pp. 1897-1899; Stork, M., Koch, M., Klapper, M., Mullen, K., Gregorius, H., Rief, U., (1999) Macromol. Rapid Commun, 20, pp. 210-213; Nenov, N., Koch, M., Klapper, M., Müllen, K., (2002) Polym. Bull, 47, pp. 391-398; Dillmore, W.S., Yousaf, M.N., Mrksich, M., (2004) Langmuir, 20, pp. 7223-7231; Rausch, M.D., Hart, W.P., Macomber, D.W., (1981) J. Macromol. Sci., Chem, A16, pp. 243-250; Blankenbuehler, M.T., Selegue, J.P., (2002) J. Organomet. Chem, 642, pp. 268-274; Chajara, K., Ottosson, H., (2004) Tetrahedron Lett, 45, pp. 6741-6744; Ben Romdhane, H., Chaabouni, M.R., Grenier-Loustalot, M.F., Delolme, F., Mison, P., Sillion, B., (2000) Polymer, 41, pp. 1633-1639; Rufanov, K.A., Kazennova, N.B., Churakov, A.V., Lemenovskii, D.A., Kuzmina, L.G., (1995) J. Organomet. Chem, 485, pp. 173-178; Hughes, R.P., Trujillo, H.A., (1996) Organometallics, 15, pp. 286-294; Leadbeater, N.E., (2002) Tetrahedron Lett, 43, pp. 691-693; Gruendling, T., Guilhaus, M., Barner-Kowollik, C., (2009) Macromol. Rapid Commun, 30, pp. 589-597
Keywords: Ambient temperatures, Catalyst-free, Characteristic signal, Cyclopentadienyls, End-groups, Functionalizations, Macromolecular building blocks, Monomethyl ethers, Nitrogen atmospheres, NMR spectroscopic analysis, Nucleophilic substitutions, Poly methyl acrylate, Polymer chains, Short column, Tetrahydrofurans, Acrylic monomers, Dissolution, Esters, Ethers, Ethylene, Ethylene glycol, Free radical reactions, Functional polymers, Sodium, Spectroscopic analysis, Styrene, Synthesis (chemical), Temperature, Atom transfer radical polymerization
DOI: 10.1021/ma902464a
ISSN: 00249297
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: 07 Oct 2016 02:42

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