A New Versatile Water‐Soluble Iniferter Platform for the Preparation of Molecularly Imprinted Nanoparticles by Photopolymerisation in Aqueous Media. Issue 29 (8th June 2016)

• Record Type: Journal Article
• Authors: Bonomi, Paolo; Attieh, Mira Daoud; Gonzato, Carlo; Haupt, Karsten
• Is Part Of: Chemistry. Volume 22:Issue 29(2016)
• Page Start: 10150
• Page End: 10154
• Publication Date: 2016-06-08
• Subjects: click chemistry -- imprinting -- iniferters -- nanoparticles -- polymerisation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201600750
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The multi‐step synthesis of a new water‐soluble dithiocarbamate iniferter platform for the preparation of nanoparticles and ‐gels in aqueous solvents by photoinduced living‐radical polymerisation is described herein. The water solubility of the dithiocarbamate iniferter was achieved by incorporating two unprotected glucose units into the iniferter structure by copper(I)‐catalysed azide–alkyne cycloaddition ("click chemistry"). Molecularly imprinted nanoparticles (MIPs) specific for 2, 4‐dichlorophenoxyacetic acid and the corresponding non‐imprinted particles (NIPs) were prepared in pure water by using the prepared iniferter as photoinitiator. Radioligand binding tests confirmed a high imprinting factor, and the living character of the iniferter was demonstrated by re‐initiating a second photochemical polymerisation on the NIP nanoparticles in water by using ethylene glycol methacrylate phosphate. Our newly synthesised structure is a promising tool for iniferter‐mediated photopolymerisations in aqueous media for the preparation of biocompatible nanomaterials with high potential for biomedical applications in a bottom‐up fashion. Abstract : Molecular imprinting : The synthesis of a new water‐soluble dithiocarbamate iniferter platform (see figure) for the preparation of molecularly imprinted polymer nanogels in aqueous solvents by photoinduced living‐radical polymerisation is described. Water solubility was achieved through the attachment, by click chemistry, of two hydrophilic moieties, namely unprotected glucose units.