Rapid bonding/debonding on demand: Reversibly cross-linked functional polymers via diels-alder chemistry

Inglis, A. J., Nebhani, L., Altintas, O., Schmidt, F. G., & Barner-Kowollik, C. (2010) Rapid bonding/debonding on demand: Reversibly cross-linked functional polymers via diels-alder chemistry. Macromolecules, 43(13).

View at publisher


The synthesis of a novel poly(methyl methacrylate) (PMMA) chain bearing Cp functionality at both chain ends and a trifunctional pyridinyldithioformate linker molecule, which are able to rapidly and reversibly cross-link on demand within a highly accessible temperature range was reported. The ATRP initiator 1,2-bis(bromoisobutyryloxy)ethane was synthesized. Methyl methacrylate was passed through a short column of basic alumina and stored at -19°C prior to use. Copper(I) bromide (Fluka) was purified by sequential washing with sulfurous acid, acetic acid, and ethanol, followed by drying under reduced pressure. 1H NMR spectroscopy was performed using a Bruker AM 250 spectrometer at 250 MHz for hydrogen nuclei and 100 MHz for carbon nuclei. Size exclusion chromatography measurements were performed on a Polymer Laboratories. It is observed that a sharp increase in the absorbance of the system occurs at around 80 °C, corresponding to the rapid onset of debonding.

Impact and interest:

76 citations in Scopus
74 citations in Web of Science®
Search Google Scholar™

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: 99245
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :62
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: christopher.barner-kowollik@kit.edu
References: Engle, L.P., Wagener, K.B., (1993) J. Macromol. Sci., Rev. Macromol. Chem. Phys., C33, pp. 239-257; Kloxin, C.J., Scott, T.F., Adzima, B.J., Bowman, C.N., (2010) Macro-molecules, 43, pp. 2643-2653; Furusho, Y., Oku, T., Hasegawa, T., Tsuboi, A., Kihara, N., Takata, T., (2003) Chem.-Eur. J., 9, pp. 2895-2903; Chen, Y., Chen, K.H., (1997) J. Polym. Sci., Part A: Polym. Chem., 35, pp. 613-624; Kamplain, J.W., Bielawski, C.W., (2006) Chem. Commun., pp. 1727-1729; Chang, J.Y., Do, S.K., Han, M., (2001) J. Polymer., 42, pp. 7589-7594; Themistou, E., Patrickios, C.S., (2006) Macromolecules, 39, pp. 73-80; Chen, X.X., Dam, M.A., Ono, K., Mal, A., Shen, H.B., Nutt, S.R., Sheran, K., Wudl, F., (2002) Science, 295, pp. 1698-1702; Gandini, A., Silvestre, A.J.D., Coelho, D., (2010) J. Polym. Sci., Part A: Polym. Chem., 48, pp. 2053-2056; Gheneim, R., Perez-Berumen, C., Gandini, A., (2002) Macromolecules, 35, pp. 7246-7253; Goiti, E., Heatley, F., Huglin, M.B., Rego, J.M., (2004) Eur. Polym. J., 40, pp. 1451-1460; Imai, Y., Itoh, H., Naka, K., Chujo, Y., (2000) Macromolecules, 33, pp. 4343-4346; Jones, J.R., Liotta, C.L., Collard, D.M., Schiraldi, D.A., (1999) Macromolecules, 32, pp. 5786-5792; Reinecke, M., Ritter, H., (1993) Makromol. Chem., 194, pp. 2385-2393; Aumsuwan, N., Urban, M.W., (2009) Polymer., 50, pp. 33-36; Syrett, J.A., Mantovani, G., Barton, W.R.S., Price, D., Haddleton, D.M., (2010) Polym. Chem., 1, pp. 102-106; 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; Nebhani, L., Gerstel, P., Atanasova, P., Bruns, M., Barner-Kowollik, C., (2009) J. Polym. Sci., Part A: Polym. Chem., 47, pp. 7090-7095; Nebhani, L., Schmiedl, D., Barner, L., Barner-Kowollik, C., (2010) Adv. Funct. Mater., , DOI: 10.1002/adfm 200902330; Inglis, A.J., Sinnwell, S., Davis, T.P., Barner-Kowollik, C., Stenzel, M.H., (2008) Macromolecules, 41, pp. 4120-4126; Sinnwell, S., Synatschke, C.V., Junkers, T., Stenzel, M.H., Barner-Kowollik, C., (2008) Macromolecules, 41, pp. 7904-7912; Paulöhrl, T., Inglis, A.J., Barner-Kowollik, C., (2010) Adv. Mater., , DOI: 10.1002/adma.201000361; Inglis, A.J., Paulöhrl, T., Barner-Kowollik, C., (2010) Macromolecules, 43, pp. 33-36; Karanam, S., Goossens, H., Klumperman, B., Lemstra, P., (2003) Macromolecules, 36, pp. 8304-8311; Gruendling, T., Guilhaus, M., Barner-Kowollik, C., (2008) Anal. Chem., 80, pp. 6915-6927; Abrunhosa, I., Gulea, M., Masson, S., (2004) Synthesis, pp. 928-934
Keywords: Absorbances, ATRP initiator, Chain bearings, Chain-ends, Copper bromide, Diels-Alder, H NMR spectroscopy, Hydrogen nuclei, Linker molecules, Methyl methacrylates, Reduced pressure, Sharp increase, Short column, Temperature range, Acids, Bromine compounds, Crosslinking, Esters, Ethane, Ethanol, Functional polymers, Nuclear magnetic resonance spectroscopy, Organic polymers, Synthesis (chemical), Size exclusion chromatography
DOI: 10.1021/ma100945b
ISSN: 00249297
Divisions: Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 28 Jun 2017 15:01

Export: EndNote | Dublin Core | BibTeX

Repository Staff Only: item control page