Hetero diels-alder chemistry for the functionalization of single-walled carbon nanotubes with cyclopentadienyl end-capped polymer strands

Zydziak, N., Preuss, C. M., Winkler, V., Bruns, M., Hübner, C., & Barner-Kowollik, C. (2013) Hetero diels-alder chemistry for the functionalization of single-walled carbon nanotubes with cyclopentadienyl end-capped polymer strands. Macromolecular Rapid Communications, 34(8).

View at publisher


Single-walled carbon nanotubes (SWCNTs) are pre-functionalized with a pyridinyl-based dithioester to undergo a hetero Diels-Alder (HDA) reaction with cyclopentadienyl end-capped poly(methyl)methacrylate (Mn = 2700 g mol-1, PDI = 1.14). Fourier transform infrared spectroscopy, thermogravimetric analysis, elemental analysis (EA), and X-ray photoelectron spectroscopy (XPS) evidence the success of the grafting process. The estimated resulting grafting density (from XPS and EA) via the HDA reaction increases by a factor of more than two (0.0774 chains·nm-2 via XPS) compared with typical values obtained via a direct cyclopentadiene driven Diels-Alder conjugation onto non-functional SWCNTs under similar conditions. Cyclopentadienyl end-capped polymer strands react at the surface of pre-functionalized single-walled carbon nanotubes with a pyridine-based dithioester through a hetero Diels-Alder reaction. Elemental analysis and X-ray photoelectron spectroscopy are employed to determine the grafting density. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Impact and interest:

8 citations in Scopus
8 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: 99372
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :7
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
Chemicals/CAS: poly(methyl methacrylate), 39320-98-4, 9008-29-1; pyridine, 110-86-1; thiol derivative, 13940-21-1; Cyclopentanes; Nanotubes, Carbon; Polymethyl Methacrylate, 9011-14-7; Pyridines; Sulfhydryl Compounds; pyridine, NH9L3PP67S
References: Binder, W.H., Sachsenhofer, R., (2007) Macromol. Rapid Commun., 28, p. 15; Binder, W.H., Sachsenhofer, R., (2008) Macromol. Rapid Commun., 29, p. 952; Evans, R.A., (2007) Aust. J. Chem., 60, p. 384; Kolb, H.C., Finn, M.G., Sharpless, K.B., (2001) Angew. Chem. Int. Ed., 40, p. 2004; Moses, J.E., Moorhouse, A.D., (2007) Chem. Soc. Rev., 36, p. 1249; Nicolaou, K.C., Snyder, S.A., Montagnon, T., Vassilikogiannakis, G., (2002) Angew. Chem. Int. Ed., 41, p. 1668; Bodnar, B.S., Miller, M.J., (2011) Angew. Chem. Int. Ed., 50, p. 5630; Barner-Kowollik, C., Du Prez, F.E., Espeel, P., Hawker, C.J., Junkers, T., Schlaad, H., Van Camp, W., (2011) Angew. Chem. Int. Ed., 50, p. 60; Tasdelen, M.A., (2011) Polym. Chem., 2, p. 2133; Kempe, K., Krieg, A., Becer, C.R., Schubert, U.S., (2012) Chem. Soc. Rev., 41, p. 176; Diels, O., Thiele, W.E., (1938) Ber. Dtsch. Chem. Ges. A/B, 71, p. 1173; Ikeda, M., Ochi, R., Kurita, Y.-S., Pochan, D.J., Hamachi, I., (2012) Chem. Eur. J., 18, p. 13091; Woodward, R.B., Hoffmann, R., (1965) J. Am. Chem. Soc., 87, p. 395; Johns, V.K., Shi, Z., Dang, W., McInnis, M.D., Weng, Y., Liao, Y., (2011) J. Phys. Chem. A, 28, p. 8093; Bapat, A.P., Ray, J.G., Savin, D.A., Hoff, E.A., Patton, D.L., Sumerlin, B.S., (2012) Polym. Chem., 3, p. 3112; Syrett, J.A., Mantovani, G., Barton, W.R.S., Pricec, D., Haddleton, D.M., (2010) Polym. Chem., 1, p. 102; Bartlett, P.D., Schueller, K.E., (1968) J. Am. Chem. Soc., 22, p. 6077; Diels, O., Alder, K., (1928) Ann., 460, p. 98; Woodward, R.B., Katz, T.J., (1959) Tetrahedron, 5, p. 70; Li, J.-L., Liu, T., Chen, Y.-C., (2012) Acc. Chem. Res., 45, p. 1491; Nebhani, L., Sinnwell, S., Lin, C.Y., Coote, M.L., Stenzel, M.H., Barner-Kowollik, C., (2009) J. Polym. Sci. - Polym. Chem, 47, p. 6053; Sinnwell, S., Inglis, A.J., Davis, T.P., Stenzel, M.H., Barner-Kowollik, C., (2008) Chem. Commun., p. 2052; Bousquet, A., Boyer, C., Davis, T.P., Stenzel, M.H., (2010) Polym. Chem., 1, p. 1186; Tischer, T., Goldmann, A.S., Linkert, K., Trouillet, V., Boerner, H.G., Barner-Kowollik, C., (2012) Adv. Funct. Mater., 22, p. 3853; Kaupp, M., Vogt, A.P., Natterodt, J.C., Trouillet, V., Gruendling, T., Hofe, T., Barner, L., Barner-Kowollik, C., (2012) Polym. Chem., 3, p. 2605; Zhang, L., Yang, J., Edwards, C.L., Alemany, L.B., Khabashesku, V.N., Barron, A.R., (2005) Chem. Commun., p. 3265; Priftis, D., Sakellariou, G., Baskaran, D., Mays, J.W., Hadjichristidis, N., (2009) Soft Matter, 5, p. 4272; Zydziak, N., Hübner, C., Bruns, M., Barner-Kowollik, C., (2011) Macromolecules, 44, p. 3374; Homenick, C.M., Sivasubramaniam, U., Adronov, A., (2008) Polym. Int., 57, p. 1007; Chadwick, R.C., Khan, U., Coleman, J.N., Adronov, A., (2013) Small, 4, p. 552; Hu, H., Zhao, B., Itkis, M.E., Haddon, R.C., (2003) J. Phys. Chem., 107, p. 13838; Tchoul, M.N., Ford, W.T., Lolli, G., Resasco, D.E., Arepalli, S., (2007) Chem. Mater., 19, p. 5765; Andersson, C.-H., Grennberg, H., (2009) Eur. J. Org., Chem., p. 4421; Lee, G.-W., Kumar, S., (2005) J. Phys. Chem. B, 109, p. 17128; Lee, G.-W., Jagannathan, S., Chae, H.G., Minus, M.L., Kumar, S., (2008) Polymer, 49, p. 1831; Marshall, M.W., Popa-Nita, S., Shapter, J.G., (2006) Carbon, 44, p. 1137; Špitalsky, Z., Krontiras, C.A., Georga, S.N., Galiotis, C., (2009) Compos. Part A-Appl. S., 40, p. 778; Pumera, M., Šmíd, B., Veltruská, K., (2009) J. Nanosci. Nanotechnol., 9, p. 2671; Inglis, A.J., Paulöhrl, T., Barner-Kowollik, C., (2010) Macromolecules, 43, p. 33; Lefrant, S., Baibarac, M., Baltog, I., (2009) J. Mater. Chem., 19, p. 5690; Kim, U., Liu, X., Furtado, C., Chen, G., Saito, R., Jiang, J., Dresselhaus, M., Eklund, P.C., (2005) Phys. Rev. Lett., 95, p. 157402; Estrade-Szwarckopf, H., (2004) Carbon, 42, p. 1713; Maldonado, S., Morin, S., Stevenson, K.J., (2006) Carbon, 44, p. 1429; Okpalugo, T.I.T., Papakonstantinou, P., Murphy, H., McLaughlin, J., Brown, N.M.D., (2005) Carbon, 43, p. 153; Pumera, M., Šmid, B., Veltruská, K., (2009) J. Nanosci. Nanotechnol., 9, p. 2671; Lee, W.H., Kim, S.J., Lee, W.J., Lee, J.G., Haddon, R.C., Reucroft, P.J., (2001) Appl. Surf. Sci., 181, p. 121; Martinez, M.T., Callejas, M.A., Benito, A.M., Cochet, M., Seeger, T., Anson, A., Schreiber, J., Maser, W.K., (2003) Carbon, 41, p. 2247; Lock, E.H., Petrovykh, D.Y., Mack, P., Carney, T., White, R.G., Walton, S.G., Fernsler, R.F., (2010) Langmuir, 26, p. 8857; Wang, L.-P., Wang, Y.-P., Yuan, K., Lei, Z.-Q., (2008) Polym. Adv. Techn., 19, p. 285; Gurbuz, N., Demirci, S., Yavuz, S., Caykara, T., (2011) J. Polym. Sci. Polym. Chem., 49, p. 423; Kvon, R.I., Il'Inich, G.N., Chuvilin, A.L., Likholobov, V.A., (2000) J. Mol. Catal. A- Chem., 158, p. 413; Zeng, X.M., Chan, C.M., Weng, L.T., Li, L., (2000) Polymer, 41, p. 8321
Keywords: cyclopentadiene, grafting density, hetero Diels-Alder reaction, poly(methyl)methacrylate, single-walled carbon nanotubes, Cyclopentadienes, Cyclopentadienyls, Functionalizations, Grafting densities, Grafting process, Polymer strands, Single-walled carbon nanotube (SWCNTs), Directive antennas, Fourier transform infrared spectroscopy, Olefins, Photoelectrons, Single-walled carbon nanotubes (SWCN), Thermogravimetric analysis, X ray photoelectron spectroscopy, Grafting (chemical), carbon nanotube, cyclopentane derivative, poly(methyl methacrylate), pyridine, pyridine derivative, thiol derivative, article, chemistry, cycloaddition, esterification, oxidation reduction reaction, Cycloaddition Reaction, Cyclopentanes, Nanotubes, Carbon, Oxidation-Reduction, Polymethyl Methacrylate, Pyridines, Sulfhydryl Compounds
DOI: 10.1002/marc.201300025
ISSN: 10221336
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 16:02

Export: EndNote | Dublin Core | BibTeX

Repository Staff Only: item control page