Fluorescent Covalently Cross-Linked Cellulose Networks via Light-Induced Ligation

Hufendiek, A., Carlmark, A., Meier, M. A. R., & Barner-Kowollik, C. (2016) Fluorescent Covalently Cross-Linked Cellulose Networks via Light-Induced Ligation. ACS Macro Letters, 5(1).

View at publisher


A facile light-induced procedure for the covalent cross-linking of cellulose at ambient conditions employing the nitrile imine mediated tetrazole-ene cycloaddition (NITEC) reaction is presented. Cellulose-tetrazoles with 2 degrees of substitution (0.14 and 0.23) were synthesized in a solution-based transesterification procedure in an ionic liquid. Two bismaleimides with either a trioxatridecane or a dithiodipropionyl backbone were used as cross-linkers to form fluorescent, covalently cross-linked cellulose networks and films, which were characterized by UV/vis spectroscopy, fluorescence spectroscopy, DSC, and TGA. The films showed a broad emission band from 500-700 nm and were thermally stable up to 200 °C. Using the bismaleimide with a disulfide moiety as the cross-linker, reductive degradation of the films can be induced. Finally, cellulose-tetrazole was cross-linked in a spatially resolved fashion, providing a strategy for the shaping of films based on renewable resources. © 2016 American Chemical Society.

Impact and interest:

5 citations in Scopus
3 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: 99465
Item Type: Journal Article
Refereed: Yes
Additional Information: Export Date: 5 September 2016
Correspondence Address: Meier, M.A.R.; Laboratory of Applied Chemistry, Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, Germany; email: m.a.r.meier@kit.edu
References: Klemm, D., Heublein, B., Fink, H.-P., Bohn, A., (2005) Angew. Chem., Int. Ed., 44, pp. 3358-3393; Puspasari, T., Pradeep, N., Peinemann, K.-V., (2015) J. Membr. Sci., 491, pp. 132-137; Kono, H., Fujita, S., (2012) Carbohydr. Polym., 87, pp. 2582-2588; Kabra, B.G., Gehrke, S.H., Spontak, R.J., (1998) Macromolecules, 31, pp. 2166-2173; Qiu, X., Tao, S., Ren, X., Hu, S., (2012) Carbohydr. Polym., 88, pp. 1272-1280; Hasani, M., Westman, G., (2011) Cellulose, 18, pp. 575-583; Freudenberg, U., Zimmermann, R., Schmidt, K., Behrens, S.H., Werner, C., (2007) J. Colloid Interface Sci., 309, pp. 360-365; Alvarez-Lorenzo, C., Blanco-Fernandez, B., Puga, A.M., Concheiro, A., (2013) Adv. Drug Delivery Rev., 65, pp. 1148-1171; Reza, A.T., Nicoll, S.B., (2010) Acta Biomater., 6, pp. 179-186; Shen, X., Kitajyo, Y., Duan, Q., Narumi, A., Kaga, H., Kaneko, N., Satoh, T., Kakuchi, T., (2006) Polym. Bull., 56, pp. 137-143; Kamath, M., Kincaid, J., Mandal, B.K., (1996) J. Appl. Polym. Sci., 59, pp. 45-50; Kuwabara, S., Kubota, H., (1996) J. Appl. Polym. Sci., 60, pp. 1965-1970; Lin, M.-S., Chen, A.-J., (1993) Polymer, 34, pp. 389-393; Wach, R.A., Rokita, B., Bartoszek, N., Katsumura, Y., Ulanski, P., Rosiak, J.M., (2014) Carbohydr. Polym., 112, pp. 412-415; Sawut, A., Yimit, M., Sun, W., Nurulla, I., (2014) Carbohydr. Polym., 101, pp. 231-239; Edgar, K.J., Buchanan, C.M., Debenham, J.S., Rundquist, P.A., Seiler, B.D., Shelton, M.C., Tindall, D., (2001) Prog. Polym. Sci., 26, pp. 1605-1688; Allahbash, S., Nicolai, T., Chassenieux, C., Tassin, J.-F., Benyahia, L., Weiss, P., Rethore, G., (2015) Carbohydr. Polym., 115, pp. 510-515; Memmi, A., Granet, R., Gahbiche, M.A., Fekih, A., Bakhrouf, A., Krausz, P., (2006) J. Appl. Polym. Sci., 101, pp. 751-755; Joly, N., Granet, R., Krausz, P., (2005) J. Polym. Sci., Part A: Polym. Chem., 43, pp. 407-418; Seufert, M., Fakirov, C., Wegner, G., (1995) Adv. Mater., 7, pp. 52-55; Faugeras, P.-A., Brouillette, F., Zerrouki, R., (2012) Carbohydr. Res., 356, pp. 247-251; Koschella, A., Hartlieb, M., Heinze, T., (2011) Carbohydr. Polym., 86, pp. 154-161; Zhang, J., Xu, X.-D., Wu, D.-Q., Zhang, X.-Z., Zhuo, R.-X., (2009) Carbohydr. Polym., 77, pp. 583-589; Redl, F.X., Köthe, O., Röckl, K., Bauer, W., Daub, J., (2000) Macromol. Chem. Phys., 201, pp. 2091-2100; Janko, M., Jocher, M., Boehm, A., Babel, L., Bump, S., Biesalski, M., Meckel, T., Stark, R.W., (2015) Biomacromolecules, 16, pp. 2179-2187; Wondraczek, H., Kotiaho, A., Fardim, P., Heinze, T., (2011) Carbohydr. Polym., 83, pp. 1048-1061; Fertier, L., Koleilat, H., Stemmelen, M., Giani, O., Joly-Duhamel, C., Lapinte, V., Robin, J.-J., (2013) Prog. Polym. Sci., 38, pp. 932-962; Tischer, T., Rodriguez-Emmenegger, C., Trouillet, V., Welle, A., Schueler, V., Mueller, J.O., Goldmann, A.S., Barner-Kowollik, C., (2014) Adv. Mater., 26, pp. 4087-4092; Hufendiek, A., Barner-Kowollik, C., Meier, M.A.R., (2015) Polym. Chem., 6, pp. 2188-2191; Mueller, J.O., Guimard, N.K., Oehlenschlaeger, K.K., Schmidt, F.G., Barner-Kowollik, C., (2014) Polym. Chem., 5, pp. 1447-1456; El Seoud, O.A., Koschella, A., Fidale, L.C., Dorn, S., Heinze, T., (2007) Biomacromolecules, 8, pp. 2629-2647; Gericke, M., Fardim, P., Heinze, T., (2012) Molecules, 17, pp. 7458-7502; Schenzel, A., Hufendiek, A., Barner-Kowollik, C., Meier, M.A.R., (2014) Green Chem., 16, pp. 3266-3271; Kim, Y.H., Stites, W.E., (2008) Biochemistry, 47, pp. 8804-8814; Mantovani, G., Lecolley, F., Tao, L., Haddleton, D.M., Clerx, J., Cornelissen, J.J.L.M., Velonia, K., (2005) J. Am. Chem. Soc., 127, pp. 2966-2973; Li, W., Wang, W., Yang, Y., Zhang, K., (2014) J. Mater. Chem. A, 2, pp. 13675-13681; Huisgen, R., Seidel, M., Wallbillich, G., Knupfer, H., (1962) Tetrahedron, 17, pp. 3-29; Willenbacher, J., Wuest, K.N.R., Mueller, J.O., Kaupp, M., Wagenknecht, H.-A., Barner-Kowollik, C., (2014) ACS Macro Lett., 3, pp. 574-579; Huisgen, R., Seidel, M., Sauer, J., McFarland, J., Wallbillich, G., (1959) J. Org. Chem., 24, pp. 892-893
DOI: 10.1021/acsmacrolett.5b00806
ISSN: 21611653
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 17:02

Export: EndNote | Dublin Core | BibTeX

Repository Staff Only: item control page