Fusing catechol-driven surface anchoring with rapid hetero diels-alder ligation

Preuss, C. M., Zieger, M. M., Rodriguez-Emmenegger, C., Zydziak, N., Trouillet, V., Goldmann, A. S., & Barner-Kowollik, C. (2014) Fusing catechol-driven surface anchoring with rapid hetero diels-alder ligation. ACS Macro Letters, 3(11).

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Abstract

We fuse the surface anchoring abilities of catechols with the rapid ligating nature of thiocarbonyl thio-based hetero-Diels-Alder (HDA) reactions via the synthesis of a new small molecule (HDA-DOPA-Cp) combining a HDA moiety with a catechol. Inspired by the mechanism of strong adhesion of marine mussels, we employed catechols as anchors to attach HDA ligation points to silicon wafers. The latter was exploited to generate a base for the HDA reactions on the surface employing α-cyclopentadiene (Cp) functional polymers such as poly(ethylene glycol)-Cp (PEG-Cp) and poly(trifluoro ethyl methacrylate)-Cp (PTFEMA-Cp) as dienes. By utilizing the fast and efficient HDA chemistry in combination with catechol anchoring groups, a new method for creating functional surfaces was developed. © 2014 American Chemical Society.

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ID Code: 99397
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :6
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: De Araújo, A.D., Palomo, J.M., Cramer, J., Köhn, M., Schröder, H., Wacker, R., Niemeyer, C., Waldmann, H., (2006) Angew. Chem., Int. Ed., 45, p. 296; Lin, P.-C., Weinrich, D., Waldmann, H., (2010) Macromol. Chem. Phys., 211, p. 136; Martinez, A.W., Phillips, S.T., Whitesides, G.M., Carrilho, E., (2010) Anal. Chem., 82, p. 3; Williams, D.F., (2009) Biomaterials, 30, p. 5897; Advincula, R.C., Brittain, W.J., Caster, K.C., Jürgen, R., (2004) Polymer Brushes: Synthesis, Characterization, Applications, , Wiley Interscience; Zou, Y.Q., Yeh, P.Y.J., Rossi, N.A.A., Brooks, D.E., Kizhakkedathu, J.N., (2010) Biomacromolecules, 11, p. 284; Blasco, E., Piñol, M., Oriol, L., Schmidt, B.V.K.J., Welle, A., Trouillet, V., Bruns, M., Barner-Kowollik, C., (2013) Adv. Funct. Mater., 23, p. 4011; Rodriguez-Emmenegger, C., Brynda, E., Riedel, T., Sedlakova, Z., Houska, M., Alles, A.B., (2009) Langmuir, 25, p. 6328; Rodriguez-Emmenegger, C., Hasan, E., Pop-Georgievski, O., Houska, M., Brynda, E., Alles, A.B., (2012) Macromol. Biosci., 12, p. 525; Fan, X., Lin, L., Dalsin, J.L., Messersmith, P.B., (2005) J. Am. Chem. Soc., 127, p. 15843; Xu, C., Xu, K., Gu, H., Zheng, R., Liu, H., Zhang, X., Guo, Z., Xu, B., (2004) J. Am. Chem. Soc., 126, p. 9938; Dalsin, J.L., Lin, L., Tosatti, S., Vörös, J., Textor, M., Messersmith, P.B., (2004) Langmuir, 21, p. 640; Hansson, S., Östmark, E., Carlmark, A., Malmström, E., (2009) ACS Appl. Mater. Interfaces, 1, p. 2651; Tischer, T., Claus, T.K., Oehlenschlaeger, K.K., Trouillet, V., Bruns, M., Welle, A., Linkert, K., Barner-Kowollik, C., (2014) Macromol. Rap. Commun., 35, p. 1121; Lee, H., Dellatore, S.M., Miller, W.M., Messersmith, P.B., (2007) Science, 318, p. 426; Lee, B.P., Messersmith, P.B., Israelachvili, J.N., Waite, J.H., (2011) Annu. Rev. Mater. Res., 41, p. 99; Preuss, C.M., Goldmann, A.S., Trouillet, V., Walther, A., Barner-Kowollik, C., (2013) Macromol. Rapid Commun., 34, p. 640; Preuss, C.M., Tischer, T., Rodriguez-Emmenegger, C., Zieger, M.M., Bruns, M., Goldmann, A.S., Barner-Kowollik, C., (2014) J. Mater. Chem. B, 2, p. 36; Rodriguez-Emmenegger, C., Preuss, C.M., Yameen, B., Pop-Georgievski, O., Bachmann, M., Mueller, J.O., Bruns, M., Barner-Kowollik, C., (2013) Adv. Mater., 25, p. 6123; Zdyrko, B., Luzinov, I., (2011) Macromol. Rapid Commun., 32, p. 859; Carlsson, L., Utsel, S., Wagberg, L., Malmstrom, E., Carlmark, A., (2012) Soft Matter, 8, p. 512; Duran, H., Yameen, B., Khan, H.U., Förch, R., Knoll, W., (2013) React. Funct. Polym., 73, p. 606; Zamfir, M., Rodriguez-Emmenegger, C., Bauer, S., Barner, L., Rosenhahn, A., Barner-Kowollik, C., (2013) J. Mater. Chem. B, 1, p. 6027; Ohno, K., Ma, Y., Huang, Y., Mori, C., Yahata, Y., Tsujii, Y., Maschmeyer, T., Perrier, S., (2011) Macromolecules, 44, p. 8944; Edlund, U., Rodriguez-Emmenegger, C., Brynda, E., Albersson, A.C., (2012) Polym. Chem., 3, p. 2920; Ding, S., Floyd, J.A., Walters, K.B., (2009) J. Polym. Sci. A Polym. Chem., 47, p. 6552; Pop-Georgievski, O., Verreault, D., Diesner, M.-O., Proks, V., Heissler, S., Rypáček, F., Koelsch, P., (2012) Langmuir, 28, p. 14273; Pop-Georgievski, O., Popelka, S.T.P.N., Houska, M., Chvostová, D., Proks, V.R., Rypáček, R.F., (2011) Biomacromolecules, 12, p. 3232; Zobrist, C.D., Sobocinski, J., Lyskawa, J.L., Fournier, D., Miri, V.R., Traisnel, M., Jimenez, M., Woisel, P., (2011) Macromolecules, 44, p. 5883; Ulman, A., (1996) Chem. Rev., 96, p. 1533; Paripovic, D., Klok, H.-A., (2011) Macromol. Chem. Phys., 212, p. 950; Tugulu, S., Klok, H.-A., (2008) Biomacromolecules, 9, p. 906; McGovern, M.E., Thompson, M., (1998) Anal. Commun., 35, p. 391; Kallury, K.M.R., Macdonald, P.M., Thompson, M., (1994) Langmuir, 10, p. 492; Fadeev, A.Y., McCarthy, T.J., (2000) Langmuir, 16, p. 7268; Kassam, A., Bremner, G., Clark, B., Ulibarri, G., Lennox, R.B., (2006) J. Am. Chem. Soc., 128, p. 3476; Lee, B.P., Messersmith, P.B., Israelachvili, J.N., Waite, J.H., (2011) Annu. Rev. Mater. Res., 41, p. 99; Waite, J.H., Tanzer, M.L., (1981) Science, 121, p. 1038; Lee, H., Scherer, N.F., Messersmith, P.B., (2006) Proc. Natl. Acad. Sci. USA PNAS, 103, p. 12999; Dalsin, J.L., Messersmith, P.B., (2005) Mater. Today, 8, p. 38; Sinnwell, S., Inglis, A.J., Davis, T.P., Stenzel, M.H., Barner-Kowollik, C., (2008) Chem. Commun., p. 2052; Inglis, A.J., Sinnwell, S., Davis, T.P., Barner-Kowollik, C., Stenzel, M.H., (2008) Macromolecules, 41, p. 4120; Inglis, A.J., Stenzel, M.H., Barner-Kowollik, C., (2009) Macromol. Rapid Commun., 30, p. 1792; Inglis, A.J., Sinnwell, S., Stenzel, M.H., Barner-Kowollik, C., (2009) Angew. Chem., Int. Ed., 48, p. 2411; Glassner, M., Delaittre, G., Kaupp, M., Blinco, J.P., Barner-Kowollik, C., (2012) J. Am. Chem. Soc., 134, p. 7274
DOI: 10.1021/mz5006469
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: 27 Sep 2016 04:54

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