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Synthesis and application of new photocrosslinkers for poly(ethylene glycol)

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Mehenni, Hakim [UCL] Pourcelle, Vincent [UCL] Gohy, Jean-François [UCL] Marchand-Brynaert, Jacqueline [UCL]

Photocrosslinking of polyethylene glycol (PEG) using exogenous agents is a convenient way to produce branched PEG from commercial sources thus avoiding the tricky synthesis of new reactive and functional polymers. In this study, we synthesized two series of new photocrosslinkers, i.e. bis-fluorophenyl azide and bis-trifluoromethyl diazirine, which under soft UV-irradiation produce reactive species (i.e. nitrene and carbene respectively) that insert into the CH bond of the polymer backbone, building new bridges between macromolecular chains. These photocrosslinkers are different in terms of behaviour under irradiation and affinity for the target substrate (i.e. PEG). Thus, practical conditions for photocrosslinking of a 10-kDa PEG were studied and followed by NMR and size-exclusion chromatography. In particular, we investigated irradiation in bulk or in solvent, at different irradiation times, with several concentrations of PEG and photolinkers. Finally, we were able to design a procedure to obtain soluble crosslinked PEGs of 300kDa. © 2012 CSIRO.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2012
Language Anglais
Journal information "Australian Journal of Chemistry" - Vol. 65, no. 2, p. 193-201 (2012)
Peer reviewed yes
Publisher CSIRO publishing
issn 0004-9425
e-issn 1445-0038
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Keywords C-H bond ; Polymer backbones ; Reactive species ; Target-substrate ; UV irradiation ; Functional polymers ; Irradiation ; Size exclusion chromatography ; Polyethylene glycols ; Carbenes ; Commercial sources ; Crosslinked ; Exogenous agents ; Macromolecular chain ; Nitrenes ; Photocross-linking ; Photolinkers
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Bibliographic reference Mehenni, Hakim ; Pourcelle, Vincent ; Gohy, Jean-François ; Marchand-Brynaert, Jacqueline. Synthesis and application of new photocrosslinkers for poly(ethylene glycol). In: Australian Journal of Chemistry, Vol. 65, no. 2, p. 193-201 (2012)
Permanent URL http://hdl.handle.net/2078.1/124524