Cleaning the Click: A Simple Electrochemical Avenue for Copper Removal from Strongly Coordinating Macromolecules

Jasinski, N., Lauer, A., Stals, P.J.M., Behrens, S., Essig, S., Walther, A., Goldmann, A.S., & Barner-Kowollik, C. (2015) Cleaning the Click: A Simple Electrochemical Avenue for Copper Removal from Strongly Coordinating Macromolecules. ACS Macro Letters, 4(3).

View at publisher

Abstract

We introduce a novel electrochemical method for the purification of complex water-soluble functional polymers contaminated with copper salts originating from copper-catalyzed azide/alkyne ligation chemistry, for which no standard purification protocol is suitable. A triethylene glycol methyl ether methacrylate (TEGMA) star polymer with 2-ureido-4H-pyrimidone (UPy) end groups was prepared via an activator generated by electron transfer atom transfer radical polymerization (AGET ATRP) and copper-catalyzed azide/alkyne cycloaddition (CuAAc) and selected as a model system for electrolysis of an aqueous polymer solution. We systematically investigate the influence of sample concentration, voltage, and time of electrolysis on the quality of the purification. Atom emission spectroscopy (AES) reveals almost quantitative removal of copper, and size exclusion chromatography (SEC) as well as proton nuclear magnetic resonance spectroscopy (1H NMR) ensure the full integrity of the polymer under all selected conditions. (Figure Presented). © 2015 American Chemical Society.

Impact and interest:

6 citations in Scopus
Search Google Scholar™
5 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: 99435
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :2
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, Germany
References: Lutz, J.-F., (2007) Angew. Chem., Int. Ed., 46, p. 1018; Matyjaszewski, K., Xia, J., (2001) Chem. Rev., 101, p. 2921; Meldal, M., (2008) Macromol. Rapid Commun., 29, p. 1016; Binder, W.H., Sachsenhofer, R., (2007) Macromol. Rapid Commun., 28, p. 15; Gaetke, L.M., Chow, C.K., (2003) Toxicology, 189, p. 147; Usluer, Ö., Abbas, M., Wantz, G., Vignau, L., Hirsch, L., Grana, E., Brochon, C., Hadziioannou, G., (2014) ACS Macro Lett., 3, p. 1134; Baskin, J.M., Prescher, J.A., Laughlin, S.T., Agard, N.J., Chang, P.V., Miller, I.A., Lo, A., Bertozzi, C.R., (2007) Proc. Natl. Acad. Sci. U.S.A., 104, p. 16793; Pintauer, T., Matyjaszewski, K., (2008) Chem. Soc. Rev., 37, p. 1087; Jewett, J.C., Bertozzi, C.R., (2010) Chem. Soc. Rev., 39, p. 1272; Yang, Y., Hua, C., Dong, C.-M., (2009) Biomacromolecules, 10, p. 2310; Liu, H., Li, C., Liu, H., Liu, S., (2009) Langmuir, 25, p. 4724; Sugai, N., Yamamoto, T., Tezuka, Y., (2012) ACS Macro Lett., 1, p. 902; Isono, T., Otsuka, I., Suemasa, D., Rochas, C., Satoh, T., Borsali, R., Kakuchi, T., (2013) Macromolecules, 46, p. 8932; Nakagawa, A., Kamitakahara, H., Takano, T., (2012) Cellulose, 19, p. 1315; Bobade, S., Wang, Y., Mays, J., Baskaran, D., (2014) Macromolecules, 47, p. 5040; Isono, T., Kondo, Y., Otsuka, I., Nishiyama, Y., Borsali, R., Kakuchi, T., Satoh, T., (2013) Macromolecules, 46, p. 8509; Dong, X.-H., Van Horn, R., Chen, Z., Ni, B., Yu, X., Wurm, A., Schick, C., Cheng, S.Z.D., (2013) J. Phys. Chem. Lett., 4, p. 2356; Huan, X., Wang, D., Dong, R., Tu, C., Zhu, B., Yan, D., Zhu, X., (2012) Macromolecules, 45, p. 5941; Yan, Q., Yuan, J., Cai, Z., Xin, Y., Kang, Y., Yin, Y., (2010) J. Am. Chem. Soc., 132, p. 9268; Hosono, N., Gillissen, M.A.J., Li, Y., Sheiko, S.S., Palmans, A.R.A., Meijer, E.W., (2012) J. Am. Chem. Soc., 135, p. 501; Stals, P.J.M., Gillissen, M.A.J., Nicolay, R., Palmans, A.R.A., Meijer, E.W., (2013) Polym. Chem., 4, p. 2584; Feldman, K.E., Kade, M.J., De Greef, T.F.A., Meijer, E.W., Kramer, E.J., Hawker, C.J., (2008) Macromolecules, 41, p. 4694; Magenau, A.J.D., Strandwitz, N.C., Gennaro, A., Matyjaszewski, K., (2011) Science, 332, p. 81; Magenau, A.J.D., Bortolamei, N., Frick, E., Park, S., Gennaro, A., Matyjaszewski, K., (2013) Macromolecules, 46, p. 4346; Canturk, F., Karagoz, B., Bicak, N., (2011) J. Polym. Sci., Part A: Polym. Chem., 49, p. 3536; Nuhn, L., Schüll, C., Frey, H., Zentel, R., (2013) Macromolecules, 46, p. 2892
DOI: 10.1021/acsmacrolett.5b00046
ISSN: 21611653
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: 17 May 2017 00:28

Export: EndNote | Dublin Core | BibTeX

Repository Staff Only: item control page