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Issue 14, 2013
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UV-induced functionalization of poly(divinylbenzene) nanoparticles via efficient [2 + 2]-photocycloadditions

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Abstract

The efficient functionalization of poly(divinylbenzene) (polyDVB) nanoparticles via Paterno–Büchi type [2 + 2]-photocycloadditions is described. Initially polyDVB nanoparticles with high density of alkene groups on the surface are synthesized via radical miniemulsion polymerization. Subsequently, UV-induced [2 + 2]-photocycloadditions with different functionalized aldehydes have been performed on the surface under mild and catalyst-free conditions. In order to show the versatility and the accessibility towards incorporation of different functionalities with this strategy, surface modifications were carried out with ATRP initiators and NHS esters for bioconjugation, respectively. Finally, these photofunctionalized nanoparticles were grafted with poly(butyl acrylate) or with gold-labeled antibodies to prove the success of the reactions. PolyDVB nanoparticles before and after photofunctionalization are characterized by X-ray photoelectron spectroscopy (XPS), electron microscopy (SEM and TEM) and ATR-FTIR spectroscopy. Results show that the photoconjugation route is highly efficient and grafting densities of 4 to 5 molecules per nm2 on the entire surface of the particles are achieved.

Graphical abstract: UV-induced functionalization of poly(divinylbenzene) nanoparticles via efficient [2 + 2]-photocycloadditions

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Publication details

The article was received on 02 Apr 2013, accepted on 07 May 2013 and first published on 08 May 2013


Article type: Paper
DOI: 10.1039/C3PY00427A
Citation: Polym. Chem., 2013,4, 4010-4016
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    UV-induced functionalization of poly(divinylbenzene) nanoparticles via efficient [2 + 2]-photocycloadditions

    A. Ethirajan, L. Baeten, M. Conradi, K. Ranieri, B. Conings, H. Boyen and T. Junkers, Polym. Chem., 2013, 4, 4010
    DOI: 10.1039/C3PY00427A

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