Biomimetic dopamine-diels-alder switches

Preuss, C. M., Goldmann, A. S., Trouillet, V., Walther, A., & Barner-Kowollik, C. (2013) Biomimetic dopamine-diels-alder switches. Macromolecular Rapid Communications, 34(8).

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Mussel adhesives function as tools for surface modifications of a wide variety of materials due to their remarkable adhesion properties. Herein, a combination of bioinspired mussel adhesives based on a dopamine derivative, polymer chemistry, and well-established Diels-Alder (DA) chemistry leads to a bioinspired switchable surface system that possesses the capability of attaching and detaching specific polymers on demand. A dopaminemaleimide compound, which has been attached to a gold surface under maritime conditions undergoes DA- and retro-DA-click-conjugations with cyclopentadiene-carrying PEG chains. The surface attachment and the subsequent DA/rDA cycles are evidenced via XPS analysis. Biomimetic switching: Mussel adhesives operate as tools for surface modification of a wide variety of materials due to their remarkable adhesion properties. Herein, a combination of biomimetic mussel adhesives, polymer chemistry, and well-established Diels-Alder chemistry leads to a biomimetic switch system on surfaces that possesses the capability of attaching and detaching specific polymers on demand. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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16 citations in Web of Science®

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ID Code: 99360
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :15 Export Date: 5 September 2016 CODEN: MRCOE Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76131 Karlsruhe, Germany; email: Chemicals/CAS: dopamine, 51-61-6, 62-31-7; gold, 7440-57-5; maleimide, 541-59-3; Adhesives; Gold, 7440-57-5; Maleimides; maleimide, 541-59-3 References: Barthlott, W., Koch, K., (2011) Beilstein J. Nanotechnol., 2, p. 135; Vincent, J.F.V., (2009) Proc. Inst. Mech. Eng. Part H.-J. Eng. Med., 223, p. 919; Bhushan, B., (2009) Phil. Trans. R. Soc. A: Math. Phys. Eng. Sci., 367, p. 1445; Coyne, K.J., Qin, X.-X., Waite, J.H., (1997) Science, 277, p. 1830; Lee, H., Dellatore, S.M., Miller, W.M., Messersmith, P.B., (2007) Science, 318, p. 426; Brubaker, C.E., Messersmith, P.B., (2011) Biomacromolecules, 12, p. 4326; Bilic, G., Brubaker, C., Messersmith, P.B., Mallik, A.S., Quinn, T.M., Haller, C., Done, E., Zisch, A.H., (2010) Am. J. Obstetrics Gynecology, 202, p. 85; Messersmith, P.B., (2008) Science, 319, p. 1767; Ryou, M.-H., Lee, Y.M., Park, J.-K., Choi, J.W., (2011) Adv. Mater., 23, p. 3066; Lee, Y.H., Lee, H., Kim, Y.B., Kim, J.Y., Hyeon, T., Park, H., Messersmith, P.B., Park, T.G., (2008) Adv. Mater., 20, p. 4154; Chen, Y., Zhu, H.Y., Lei, Y.H., Sun, W.W., Liu, Y.P., Chen, S.G., (2009) Multi-Functional Materials and Structures, Pts. 1 and 2, 7982, p. 2155. , (Eds: Y. S. Yin, X. Wang), Trans Tech Publications Ltd, Stafa-Zurich, p; Yu, M., Hwang, J., Deming, T.J., (1999) J. Am. Chem. Soc., 121, p. 5825; D'Ischia, M., Napolitano, A., Pezzella, A., Meredith, P., Sarna, T., (2009) Angew. Chem. Int. Ed., 48, p. 3914; Wang, J., Tahir, M.N., Kappl, M., Tremel, W., Metz, N., Barz, M., Theato, P., Butt, H.-J., (2008) Adv. Mater., 20, p. 3872; Pop-Georgievski, O., Popelka, S.T.P.N., Houska, M., Chvostová, D., Proks, V.R., Rypáček, F.E., (2011) Biomacromolecules, 12, p. 3232; Goldmann, A.S., Schödel, C., Walther, A., Yuan, J., Loos, K., Müller, A.H.E., (2010) Macromol. Rapid Commun., 31, p. 1608; Shultz, M.D., Reveles, J.U., Khanna, S.N., Carpenter, E.E., (2007) J. Am. Chem. Soc., 129, p. 2482; Xie, J., Xu, C., Kohler, N., Hou, Y., Sun, S., (2007) Adv. Mater., 19, p. 3163; Kolb, H.C., Finn, M.G., Sharpless, K.B., (2001) Angew. Chem. Int. Ed., 40, p. 2004; 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; Moses, J.E., Moorhouse, A.D., (2007) Chem. Soc. Rev., 36, p. 1249; 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; Blinco, J.P., Trouillet, V., Bruns, M., Gerstel, P., Gliemann, H., Barner-Kowollik, C., (2011) Adv. Mater., 23, p. 4435; Geiseler, B., Fruk, L., (2012) J. Mater. Chem., 22, p. 735; Sun, G., Hovestädt, M., Zhang, X., Hinrichs, K., Rosu, D.M., Lauermann, I., Zielke, C., Rappich, J., (2011) Surf. Interface Anal., 43, p. 1203
Keywords: biomimetic synthesis, Diels-Alder chemistry, dopamine, polymer chemistry, reversible click chemistry, Click chemistry, Diels-Alder, Adhesion, Adhesives, Amines, Biomimetic processes, Molluscs, Neurophysiology, Shellfish, Surface treatment, Functional polymers, adhesive agent, biomimetic material, gold, maleimide, maleimide derivative, article, chemistry, cycloaddition, polymerization, surface property, synthesis, X ray photoelectron spectroscopy, Biomimetic Materials, Cycloaddition Reaction, Maleimides, Photoelectron Spectroscopy, Surface Properties
DOI: 10.1002/marc.201300094
ISSN: 10221336
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: 30 Sep 2016 00:58

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