Spatially controlled surface immobilization of nucleophiles via trapping of photo-generated thioaldehydes

Pauloehrl, T., Welle, A., Oehlenschlaeger, K. K., & Barner-Kowollik, C. (2013) Spatially controlled surface immobilization of nucleophiles via trapping of photo-generated thioaldehydes. Chemical Science, 4(9).

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Abstract

A novel and very simple photochemical strategy that utilizes light as a facile means to provide spatio-temporal control for the direct covalent immobilization of nucleophiles is presented. The concept is based upon the efficient trapping of photogenerated thioaldehydes by amines, hydroxylamines, and thiols. Surface patterns of polymers and small molecules bearing pendant amine-, hydroxylamine- or thiol moieties were successfully generated and imaged in a time-of-flight secondary-ion mass spectrometry (ToF-SIMS) investigation. © 2013 The Royal Society of Chemistry.

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ID Code: 99359
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :18
Export Date: 5 September 2016
CODEN: CSHCC
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstraße 18, 76128 Karlsruhe, Germany; email: christopher.barner-kowollik@kit.edu
References: Huo, F., Zheng, Z., Zheng, G., Giam, L.R., Zhang, H., Mirkin, C.A., (2008) Science, 321, p. 1658; Bochet, C.G., (2002) J. Chem. Soc., Perkin Trans. 1, p. 125; Cui, J., Miguel, V.S., Del Campo, A., (2013) Macromol. Rapid Commun., 34, p. 310; Klán, P., Šolomek, T., Bochet, C.G., Blanc, A., Givens, R., Rubina, M., Popik, V., Wirz, J., (2013) Chem. Rev., 113, p. 119; Orski, S.V., Poloukhtine, A.A., Arumugam, S., Mao, L., Popik, V.V., Locklin, J., (2010) J. Am. Chem. Soc., 132, p. 11024; McNitt, C.D., Popik, V.V., (2012) Org. Biomol. Chem., 10, p. 8200; Song, W., Wang, Y., Qu, J., Madden, M.M., Lin, Q., (2008) Angew. Chem., Int. Ed., 47, p. 2832; Wang, Y., Song, W., Hu, W.J., Lin, Q., (2009) Angew. Chem., Int. Ed., 48, p. 5330; Pauloehrl, T., Delaittre, G., Bruns, M., Meißler, M., Börner, H.G., Bastmeyer, M., Barner-Kowollik, C., (2012) Angew. Chem., Int. Ed., 51, p. 9181; Arumugam, S., Orski, S.V., Locklin, J., Popik, V.V., (2012) J. Am. Chem. Soc., 134, p. 179; Arumugam, S., Popik, V.V., (2009) J. Am. Chem. Soc., 131, p. 11892; Arumugam, S., Popik, V.V., (2012) J. Am. Chem. Soc., 134, p. 8408; Pauloehrl, T., Delaittre, G., Winkler, V., Welle, A., Bruns, M., Börner, H.G., Greiner, A.M., Barner-Kowollik, C., (2012) Angew. Chem., Int. Ed., 51, p. 1071; Oehlenschlaeger, K.K., Mueller, J.O., Heine, N.B., Glassner, M., Guimard, N.K., Delaittre, G., Schmidt, F.G., Barner-Kowollik, C., (2013) Angew. Chem., Int. Ed., 52, p. 762; Vedejs, E., Eberlein, T.H., Varie, D.L., (1982) J. Am. Chem. Soc., 104, p. 1445; Glassner, M., Oehlenschlaeger, K.K., Welle, A., Bruns, M., Barner-Kowollik, C., (2013) Chem. Commun., 49, p. 633; Zavarzin, I.V., Yarovenko, V.N., Shirokov, A.V., Smirnova, N.G., Es'Kov, A.A., Krayushkin, M.M., (2003) ARKIVOC, 8, p. 205; Duchenet, V., Vallee, Y., (1993) J. Chem. Soc., Chem. Commun., p. 806; Vedejs, E., Reid, J.G., (1984) J. Am. Chem. Soc., 106, p. 4617; Salter, T.L., Green, F.M., Gilmore, I.S., Seah, M.P., Stokes, P., (2011) Surf. Interface Anal., 43, p. 294; Benninghoven, A., (2011) Surf. Interface Anal., 43, p. 2; Benninghoven, A., (1994) Angew. Chem., Int. Ed. Engl., 33, p. 1023; Norrman, K., Papra, A., Kamounah, F.S., Gadegaard, N., Larsen, N.B., (2002) J. Mass Spectrom., 37, p. 699; Artel, V., Cohen, R., Aped, I., Ronen, M., Gerber, D., Sukenik, C.N., (2013) Langmuir, 29, p. 191; Dirksen, A., Hackeng, T.M., Dawson, P.E., (2006) Angew. Chem., 118, p. 7743; Meyer, C.D., Joiner, C.S., Stoddart, J.F., (2007) Chem. Soc. Rev., 36, p. 1705; Kalia, J., Raines, R.T., (2008) Angew. Chem., Int. Ed., 47, p. 7523
Keywords: Covalent immobilization, Pendant amines, Small molecules, Spatio-temporal, Surface immobilization, Surface pattern, Time of flight secondary ion mass spectrometry, Amines, Chemical compounds, Reaction kinetics, Secondary ion mass spectrometry, Nucleophiles
DOI: 10.1039/c3sc50815c
ISSN: 20416520
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 01:01

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