[en] The allyl phosphoester group is shown to be a protecting group for the synthesis of anionic polyphosphodiesters. Our strategy relies on the synthesis of a cyclic phosphate monomer bearing a pendant allyl phosphoester group, its easy purification by fractional distillation, its organocatalyzed ring-opening polymerization by 1,8-diazobicyclo[5.4.0]undec-7-ene (DBU) and 1-[3,5-bis(trifluoromethyl)phenyl]-3-cyclohexyl-thiourea (TU). Finally, the deprotection of the allyl phosphoester group is carried out by reaction with sodium benzenethiolate in the absence of any detectable degradation.
Research Center/Unit :
Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Clément, Benoit; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Molin, Daniel G.; Maastricht University, BioMIMedics Interreg EMR IV-A Consortium: Lead Partner
Jérôme, Christine ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Lecomte, Philippe ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Synthesis of polyphosphodiesters by ring-opening polymerization of cyclic phosphates bearing allyl phosphoester protecting groups
Publication date :
15 November 2015
Journal title :
Journal of Polymer Science. Part A, Polymer Chemistry
ISSN :
0887-624X
eISSN :
1099-0518
Publisher :
Wiley Interscience, New York, United States - New York
Volume :
53
Issue :
22
Pages :
2642-2648
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
The Walloon Region and the European Union in the frame of the Interreg program BioMiMedics BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique F.R.S.-FNRS - Fonds de la Recherche Scientifique
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