Surface modification of poly(divinylbenzene) microspheres via thiol-Ene chemistry and alkyne-azide click reactions

Goldmann, Anja S., Walther, Andreas, Nebhani, Leena, Joso, Raymond, Ernst, Dominique, Loos, Katja, Barner-Kowollik, Christopher, Barner, Leonie, & Mueller, Axel H.E. (2009) Surface modification of poly(divinylbenzene) microspheres via thiol-Ene chemistry and alkyne-azide click reactions. Macromolecules, 42(11), pp. 3707-3714.

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We report the functionalization of cross-linked poly(divinylbenzene) (pDVB) microspheres using both thiol-ene chemistry and azide-alkyne click reactions. The RAFT technique was carried out to synthesize SH-functionalized poly(N-isopropylacrylimide) (pNIPAAm) and utilized to generate pNIPAAm surface-modified microspheres via thiol-ene modification. The accessible double bonds on the surface of the microspheres allow the direct coupling with thiol-end functionalized pNIPAAm. In a second approach, pDVB microspheres were grafted with poly(2-hydroxyethyl methacrylate) (pHEMA). For this purpose, the residual double bonds on the microspheres surface were used to attach azide groups via the thiol-ene approach of 1-azido-undecane-11-thiol. In a second step, alkyne endfunctionalized pHEMA was used to graft pHEMA to the azide-modified surface via click-chemistry (Huisgen 1,3-dipolar cycloaddition). The surface-sensitive characterization methods X-ray photoelectron spectroscopy, scanning-electron microscopy and FT-IR transmission spectroscopy were employed to characterize the successful surface modification of the microspheres. In addition, fluorescence microscopy confirms the presence of grafted pHEMA chains after labeling with Rhodamine B.

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ID Code: 97490
Item Type: Journal Article
Refereed: Yes
DOI: 10.1021/ma900332d
ISSN: 1520-5835
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: 28 Jul 2016 23:00
Last Modified: 05 Aug 2016 02:47

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